RSS preview of Tim Ferriss

Cathy Lanier, NFL Chief Security Officer — From Food Stamps to the Super Bowl War Room

Additional podcast platforms

Listen to this episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

Tim Ferriss: Cathy, it is so lovely to see you, and thanks for making the time. Really nice to see you again.

Cathy Lanier: Glad to finally connect. It was nice to see you, too, Tim.

Tim Ferriss: And I was going back and forth on where to start this, and I think I’m just going to follow the tried and true and begin at the beginning here. And maybe we should start with Tuxedo and just give people sort of a snapshot of where you grew up, how you grew up, all those dreams of being in law enforcement. I’m partially kidding, of course, because I know a little bit of the backstory. But can you tell people about the beginning?

Cathy Lanier: It’s important, I think, for context about the choices I made in my life. Like everybody on this planet, the way you’re raised, your family, your environment has so much influence on the way you do things as an adult. So my parents married right after high school, first boyfriend, girlfriend. So right after high school, my father was a firefighter, went in the fire department. My mother was a secretary. She went to work for the federal government. Back in the ’50s, being married at 18 was perfectly normal. So they got married, bought a home, started having children. They had three kids. I’m the youngest of the three. After I was born, I think they realized that a secretary and a firefighter salary does not exactly cover childcare for three kids. So they couldn’t afford the childcare for three kids for both of them to work, so my mother took a leave of absence from work. She did eventually go back, but she took a 10-year leave of absence after I was born.

And then when I was two, my mother took us to my grandparents for the weekend, and when we came home, my father was gone, and left my mom with three kids and no income, literally, because she was not working at the time. So life changed pretty dramatically for us then. Again, I was two. I don’t remember a lot of detail early on. But I do remember as a child growing up over that next 10 years while mom was home with us, really just a wonderful childhood. My mother was always there. She helped with homework and she would take me to soccer practice and basketball practice and majorette practice. She was always with us and she was just a wonderful, loving, caring mom. And we didn’t have a lot. We lived on $350 a month. My father eventually paid child support. We had a lot of support from the church and from friends and family. But it was a fun childhood for me. I mean, my mom was with me, and I think she provided a lot of stability for my brothers and I.

And then when I was getting ready to go from — back then, this was back before middle school, so you went elementary school, junior high school, high school. So in sixth grade, you leave elementary school and you go to junior high school. So I was 12 years old, 13 years old, becoming a teenager. We were going to a new school. I was going to seventh grade. My mother went back to work. I was the youngest at the time at 13. She felt like we were old enough to be latchkey kids and come home and let us in, be home for a couple hours every day until she got home from work. So she went back to work in her same role working for her same boss that she left 10 years earlier, which is pretty amazing.

Tim Ferriss: That is amazing.

Cathy Lanier: In fact, that whole 10-year period while my mother was off, also important is how it frames my context of things, is during that 10 years when my mom was home, I remember her sitting in front of the TV and taking shorthand to the television. She would get our favorite records and she would write down in shorthand all the words. And then she would sit at the table and type them all up and give us the words so we could sing along with our songs. And I thought it was just Mom doing fun things for us, but it was her keeping her skills. My mom, when she went back to work after a 10-year break in service, she still took shorthand at 96 words a minute and still could type over 100 words a minute. So just a wonderful example of work ethic for us. She knew she needed to go back to work and wanted to go back to work as soon as possible and she wanted to be on her game.

So I mean, great childhood. But when I was moving to junior high school, my mom went back to work, so I kind of lost that guardian, that best friend at a critical time, right? I’m becoming a teenager, we were going to a new school. They were busing back in those days, so I was being bused into a really tough neighborhood in Washington, DC. So that’s where everything started —

Tim Ferriss: From Maryland to Washington, DC.

Cathy Lanier: From Maryland.

Tim Ferriss: Yeah.

Cathy Lanier: Right on the border of DC.

Tim Ferriss: Can I pause you for one second?

Cathy Lanier: Sure.

Tim Ferriss: I’m just trying to put myself, which is impossible for me to do, of course, in your mom’s shoes, right? You guys returned to the house, no car, dad’s gone, three kids. Have you spoken to her or do you have any best guesses as to the other things that helped her hold everything together in terms of resilience or support or anything else? I mean, I suppose that necessity is the mother of invention on some level, but have you ever spoken to her about that?

Cathy Lanier: I did. And it’s funny, my mother was very passive, sweet, just kind of a very quiet, internal person, and in my entire life, I never saw my mother cry. Never. Never. I mean, under any circumstances. I’m sure she did, but I never really saw my mother cry. And my grandmother was completely the opposite. My mom was an only child. Her mother was like a pistol, like hardcore — so my grandmother was very helpful, but my mother was a rock. I mean, she took care of us. When I tell people now, we lived on food stamps, welfare, the church brought us baskets of food for the holidays, but we didn’t have a car for many years. We finally got a car. It didn’t have heat. It used to break down every time we went out in it. The hot water spigot in our bathroom used to squirt scalding hot water over you if you weren’t careful because it needed a washer, and there was nobody to come and fix that washer.

But we had a wonderful childhood. My mother was just solid. She loved her kids, and she was a beautiful, beautiful woman. And I always ask her why she didn’t ever date, and she’s like, “My kids were my life, and I didn’t want anybody around my children that didn’t think of them as the same priority that I thought of them.” So I think her resilience was really just steady for her family. I think her family was her motivation, and nothing was going to disrupt her commitment there.

Tim Ferriss: Yeah, the singular focus. So I interrupted you. You were saying —

Cathy Lanier: That’s okay.

Tim Ferriss: — there’s this transition point, you’re busing in to Washington, DC, and you’ve sort of lost your guardian in a sense at that point. So if you wouldn’t mind picking up there.

Cathy Lanier: So, again, we were being bused into a neighborhood. The idea at the time was to racially integrate neighborhoods. I lived in a very small industrial neighborhood, like an industrial park, right on the border of Washington, DC. Literally, there was a train that ran right behind my house in the backyard. On the other side of that train tracks was Washington, DC. We were on the Maryland side. So they were busing us to a school on the border of Northeast Washington to racially integrate the schools.

So each day when our bus would pick us up and take us to school, when our bus would pull up in front of the school — everything in most big cities, I would say, but in Washington for sure, is very neighborhood-based. So when our bus would pull up in front of the school and we would get out as the Maryland kids coming to the school, as soon as we’d get off the bus, we’d get jumped. Every day there was a fight. It was a terrible change. All the way through school, I was in the talented and gifted program, straight-A student, loved school, and now I’m being bused into a school where the kids that we were going to school with hated us. It was very racially charged. It was agonizing to go to school because you had to fight just to get from the bus to the classroom.

So my mom would go — her bus would — it’s funny now. It wasn’t funny then. But her bus would pick her up on the corner at 7:00 in the morning, and my bus would pick me up on the other corner at 7:15. So we’d both go out to the bus stop together in the morning, and she would wait for her bus, I’d wait for my bus. She’d get on her bus and she’d ride by me, and I’d wave, and then one of my older friends who had a car would come and pick me up and we would go skip school for the day. I at least would skip the first half. I would skip the first few periods so I didn’t have to go through that agonizing fight every morning.

Tim Ferriss: Entry, rough entry. Mm-hmm.

Cathy Lanier: So I went from a talented and gifted student with straight As to failing literally every subject the first quarter of seventh grade. I was chronically truant. I think I was averaging 19 days a quarter that I was actually showing up for school. My mother didn’t know because the school never notified her, and by the time she got home from work at 6:00 p.m., we were all sitting around pretending to do our homework. So my poor mother had no idea until about midway through the eighth grade I was so chronically truant that I was failing all of my major subjects.

So meanwhile, while I’m skipping school, I’m hanging out with the wrong people, much older crowd, friends of my older brother and just an older crowd and just getting in trouble. And I fall in love with a much older boyfriend at the time, think I’m in love, and we want to get married and run away and get married. And so by the time I was in the ninth grade, I’m 14 years old, found myself pregnant. My boyfriend at the time had given me a diamond ring. We were engaged, we’re going to get married, so we run away. He was 26 at the time. I was 14. My mother, when she finds out, was going to have him arrested. She was going to put him in jail. So I run away from home and think, “Well, we’ve got this. We’re going to get married and we’re going to have the baby and everything’s going to be great.” The mind of a 14-year-old. Obviously things didn’t work out that way.

Interestingly, I went to my father who had been out of the picture most of my life and asked for him to sign for me to get married. Because of my age, one of my parents had to legally sign over my legal guardianship to my husband. So they literally signed over my legal guardianship to my husband. So my dad, thinking he would have one less child to pay child support for, because once he signed over my guardianship, he —

Tim Ferriss: Right, cuts the child support bill.

Cathy Lanier: — paid $100 less a month in child support. So he signed over my legal guardianship to my husband. We got married the day after my 15th birthday. I was eight months pregnant at the time.

So I guess fast-forward a little bit, a year and a half later, I was back at home. My mother was taking me to GED classes at night. I was sneaking to go to GED classes when I was still married. My husband didn’t approve of me going to school. So once we separated, my mom made sure I stayed in school, got my GED. And she would bring her typewriter home from work and she taught me how to type on the kitchen table. So she taught me how to type and take a little shorthand, and I went and got a job as a secretary. I lied about my age. I got a job as a secretary when I was 16, so started working as secretary and then worked as a waitress in the evening in a bar. Also lied about my age to work in a bar. That was the only option up in the area where I was working. So for the next several years, I worked two jobs as a secretary and a waitress.

And my motivation really was my son. It was kind of a significant moment for me, and I’ve had a few in my life. When my son was born, I had never babysat before, I’d never held a baby. I didn’t know anything about babies or children. And when he was born, he was such a good baby. His crib was at the end of my bed in my bedroom. And I’d wake up in the morning, and he’d be awake and he’d just be looking at me, waiting for me to wake up. Not crying, nothing. He would just be looking at me. So about three weeks into this —

Tim Ferriss: That is remarkable. Yeah.

Cathy Lanier: Yeah, about three weeks into this experiment, I’m looking at him one morning, and it just dawns on me for the first time that I’m a parent and that that helpless little baby was completely reliant on me. And my mother always stressed the importance of education and work to us, and here I was, my husband didn’t allow me to go to school, I would never be able to get a job, and I’m looking at this poor little innocent baby and I’m thinking his whole life depends on me, and what am I going to be able to provide with a ninth grade education? Not much. So that was a aha moment.

Tim Ferriss: I’m going to resist the temptation to ask 300 questions about the last few minutes that you shared because we’ll end up spending all of our time there if I do that. But I am curious for you, I’m trying to put myself in your shoes at that young age, when you — and we don’t need to get into the details unless you’d like to share, but when you separated from your then-husband, when that happened, what did you think was going to become of you? What did you envision your path would be at that point? I have to imagine that it would have just been incredibly challenging. I don’t know. You can’t believe everything you read on the internet, but I read that when you were a young girl, you dreamed of being a lawyer. I don’t know if that’s true or not.

Cathy Lanier: Mm-hmm.

Tim Ferriss: And then flash-forward, you go through this entire tumultuous experience and you land back at home. Where did you think your life was headed? Where did you think you were headed at that point?

Cathy Lanier: Well, I knew that with a ninth grade education and a single mom that I had zero chance of being able to do what I thought was most important in the world, and that’s take care of my son. And when I first moved back home, I got my GED, but I still was not able to easily find a job at my age. It was 16, almost 17. I had to wait till I was 16 and nine months to take the test to get the GED. Interestingly, you needed 255 to pass the test. I got 256. I passed it by one point.

Tim Ferriss: Oh my God. Talk about —

Cathy Lanier: There’s another little footnote of my life.

Tim Ferriss: — these Sliding Door moments. Holy cow, right? Okay.

Cathy Lanier: So I knew that my mother had always stressed the importance of education and work, so I knew I had to go back to school, and I wanted to go to college. I didn’t want my son to be subject to the same crappy neighborhoods and the same crappy schools that I went to. I wanted him to have a real chance, and I knew if I was going to do that, I had to go back to school and get a college education. If I didn’t do that, I was standing in the same food stamp line my mother stood in with me. I remember the first day I went to get food stamps, going to the big white building by Prince George’s Plaza right near my home and standing in the same line with my son that I stood in with my mom when I was a kid, and I was like, “This is not my path. This can’t be my path.”

And so when I got my job as a secretary, they offered tuition reimbursement to go to college, so I started at community college. I just started taking one class a semester, and that’s where it started, one class a semester. And they reimbursed me for it.

Tim Ferriss: I mean, for people who don’t have context, we’ve been trying to schedule this for a while, and understandably you got a lot of balls to juggle. And I remember hearing just pieces of your story. This was, God, it has to be, what, more than a year ago now, I’m sure. Time flies. But it’s been a long while. And I just remember thinking to myself, “God, I hope someday that we can have this conversation on the podcast,” so I want to thank you again for doing it.

How do you then go from there — what is the connective tissue, sort of the catalyzing events that ultimately get you into law enforcement? What are the first few dominoes that get tipped over that start to push you in that direction?

Cathy Lanier: So to be fair, my family’s a public service family. My father was a firefighter. My oldest brother had become a firefighter right out of high school. My other brother was a police officer. I was working as a secretary. I was taking that one class a semester working as a secretary, trying to get my son in private school. I wanted him in private school. I did not want him going to those schools. I was still living in the same crappy neighborhood, but I wanted my son in a good school.

And I saw an ad — I was 23 years old. I saw an ad in the Washington Post for the Metropolitan Police Department; they were hiring. And what caught my attention — it’s a full page ad in the Post. Half of the page said tuition reimbursement. I’m like, “Oh my God, tuition reimbursement. I’m paying for one class a semester. Going to take me 30 years to get a degree.”

So I went with a friend, and we went and stood in line. They were hiring a thousand cops. This was during the crack cocaine wars in Washington, early 1990. 500 murders a year. DC was known as the murder capital of the world at the time. So I just went and stood in line with a thousand other people, went and took the test, and I came out — I want to say I came out like 60 out of a thousand people on that test. So they called me right away. I was the only white female in the room. This is back in the early ’90s. Washington DC was about 89% African American.

So I mean, I felt the same drive my mother felt taking care of us is that I have a son that needs me, he needs me to provide for him, and the only way I’m going to do this is get a good job, government job, not a bad option, and go back to school and get my degree. So I got hired by the Metropolitan Police in 1990, started walking a footbeat. My first day out of the academy was the Mount Pleasant riots. So my first day out of the academy, I went to work and didn’t come home for five days. It was great.

Tim Ferriss: Okay, we’re going to double-click on that and come right back to Mount Pleasant, but before we do, I want to know what the entrance exam or qualification exam was like, right? Because you mentioned the GED, and just by the skin of your teeth getting in, passing the hurdle. And then it sounds like you’ve, not a very technical term, but kind of crushed the examination that you took that ultimately placed you at 60 out of a thousand. What was that test like?

Cathy Lanier: So remember, now when I started taking classes at Prince George’s Community College, my goal was to be a lawyer. I wanted to be an attorney. I started out wanting to be a secretary like my mom. Then once I got into the workplace, I realized I wanted bigger, better things, so I wanted to be an attorney. So I was taking political science, philosophy, a lot of those kind of courses, getting all my generals out of the way at community college. So by the time I got to the Metropolitan Police Department at 23, I had three years of college courses. But the exam for entry into policing, now back in those days, they only required a high school diploma or an equivalent. You didn’t need college.

So the entry exam was a lot of things that you would expect for law enforcement. You do a lot of multiple choice questions. You have to be able to read and comprehend well, so reading comprehension was a big part of it. You have to do some basic math, so you have to understand math. But there was a lot of problem-solving type questions. So they flash a photo in front of you and then they say — there’s a photo inside of a department store, and then, okay, you’ve just walked into this department store and there’s been a robbery. What is it you noticed in that quick three seconds you had to look at that photo? What do you remember? What time was it on the clock? What color was the lady’s shoes that was standing at the register? So there was reading comprehension, math, problem-solving, and then a good bit of, are you paying attention? Do you have the detail to pay attention to do the things that you need to do as a police officer, much of which you learn as a cop.

Tim Ferriss: Mm-hmm. But it seems like you had either developed or innately possessed — and maybe I’m reaching, but I mean, maybe not. I mean, was there anything in that test that highlighted, for lack of a better descriptor, superpowers, strengths of yours, that came into full fruition later where you’re like, “Okay, if I look at the recipe, some of the ingredients of the recipe that ultimately contributed to my success,” were any of them sort of revealed in that test in any way or not really?

Cathy Lanier: Yeah.

Tim Ferriss: And I won’t — okay.

Cathy Lanier: Actually, great question. Actually, it’s a very good question. I don’t get a lot of interviews to ask the types of question you’re asking. I think it’s an excellent question. So I would say the two things that have helped me in that exam and that have helped me most of my law enforcement career, my grandmother instilled in me — she spent a lot of time with us growing up as well — two things, problem-solving being a big part of that. You never make excuses. When bad things happen, don’t make excuses. You put yourself in that position. You found yourself here. It is nobody else’s fault but yours. I’m not an excuse person. I don’t make excuses. If I find myself in a bad situation, I did something to get myself here and I’m going to get myself out. And that was the way she taught us. You get yourself in, you get yourself out. And the other thing she taught me was, she’s like, “You’re going to be damned if you do and damned if you don’t. You better be damned for doing.” So you act. You always act. You don’t let your circumstances dictate for you. You act and you take action and you do. You don’t wait for somebody else to do for you.

And those things were really part of that problem-solving exercise when you’re coming on the police department, and it’s certainly your problem-solving exercise every day you’re on the police department. It certainly was for the next 27 years for me. Look, you can’t avoid consequences. There’s consequences for everything that happens. Every decision you make has consequences. You can’t avoid consequences. But you can choose what you do after those things happen.

Tim Ferriss: Yeah. I imagine you’ve probably not met him, but I interviewed someone named Jocko Willink, who’s a former Navy SEAL commander, many years ago. It was the first time he ever did a public interview. And he wrote a book called Extreme Ownership. And I feel like your grandmother and what she instilled in you is in a nutshell exactly the type of high-agency thinking that Jocko talks about. It’s the same thing. Wow.

Cathy Lanier: My grandma would say there’s two types of people in the world, excuse people and people who are accountable, and I’m going to be the accountable.

Tim Ferriss: So let’s come back to Mount Pleasant. For people who don’t have the historical context, what were the Mount Pleasant riots? And you said right before I asked about the test, you said it was great. And if that is actually not a sarcastic statement, but a real statement of how you felt, I want to know why that was the case. But let’s start with just a little bit of history for people who aren’t familiar, I certainly wasn’t, with the Mount Pleasant riots.

Cathy Lanier: Well, when I said it was great, in terms of being a rookie right out of the academy and understanding what you’ve got yourself into, it was, “Here’s what you’ve got yourself into. You went to work today and you’re not going home for five days.”

So the night before my first day out of the academy, there was a pair of police officers walking a foot patrol in our patrol district. They tried to place a gentleman under arrest for drinking in public. He was a Latino male, didn’t speak English. We had a big problem in our city back in those days. We had very few people on the department that spoke Spanish. We had a huge Latino population. There was a big gap in our community. So it’s really difficult to do any kind of effective policing if you’re not communicating with the people in the community, and we were not. So when this officer was trying to place this person under arrest, during the handcuffing the subject, after one handcuff was on, he turned around, pulled a knife on the officer, and the officer shot, so he was shot with one handcuff on. So the partner of the officer shot, rolled him over, put the other handcuff on, took the knife away, called paramedics. All’s the people saw was a handcuffed person who had been shot. So the Latino community in that neighborhood immediately began gathering on the street, large crowd. This all happened around 11:30 at night so by the time I got into the station for 5:30 roll call, I show up at 5:30 in the morning, the riot had broken out around 1:00 a.m. They had burned several police cars. There was stores that were looted and on fire. There was a big, big deal down in Mount Pleasant. So when I got to work my first day, I walked into the station, said, “Hi, I’m Cathy Lanier. I’m the new rookie from the academy.” And they threw me a gas mask and they told me to go out and get in the van. And he said, “Hop over the counter, go out the back door and get in that van.” And I was like, “Okay.” So I hopped over the counter and went and got in that van.

I was sitting with 15 other cops with gas masks on and big riot sticks. And they took us down and they dumped us off on the corner of Mount Pleasant Park Road and it was fully engulfed in fires and looting. And people were throwing bottles and bricks and stones at us. We had little helmets they had given us as we were hopping out of the van. And I didn’t have a radio because rookies weren’t allowed to have radios at the time. I had not been trained how to use the radio. So my partner had the radio. So my lifeline was on my partner, but we stood there online and literally got pelted with bricks and bottles. And I mean, over the course of five days, it was trial by fire for sure. But it was a big learning experience for me because I understood the frustration.

I understood the frustration. That whole community in Mount Pleasant were all Latino. They didn’t speak English. The cops didn’t speak to them very well. I mean, nobody could really communicate with — but the cops were pushing people around and there was no way to try and get the story straight and really no effort to get the story straight, to understand the frustration. So it was a big learning experience for me as I worked my way up the ranks to understand how important inclusion is in the community. If you’re a police officer and you are not embedding yourself in that community and understanding who the people are in that community and what their needs are and how to communicate, you’re really not going to be successful.

Tim Ferriss: We’re going to, I imagine, revisit that at some point because it seems to be a consistent thread through a lot of the work that you’ve done, but I want to spend a little bit more time on Mount Pleasant. I am curious, I suppose, yet again, what that maybe showed you about yourself or just highlighted about you constitutionally or personality wise, right? Because I would imagine some people could get dropped in that environment after they just signed up, they’re like, “Hey, I’m just here for tuition reimbursement. Holy shit, I’m getting hit with bricks. This is not exactly what I thought my first day was going to be,” and they’re out. I have to imagine that there are some people who would be closer to that.

Maybe they didn’t quit, but they were probably closer to that end of the spectrum. And do you thrive in particular in intense environments? I wonder, right? Because in my case, constitutionally out of the box, little things, especially interpersonal things, bother me that are trivial, frankly. I get all wound up about very stupid things, but in crisis situations, the car accident in front of me, some guy’s got his leg blown apart or whatever. I actually do really very well in those environments. I don’t know why that is. I really have no idea, but was there anything that you noticed about yourself in that type of environment, in those types of circumstances?

Cathy Lanier: I think the thing for me that I thrive on is as we’re dropped out down there and they’re giving us the riot sticks and the helmets and the gas mask and they’re shooting canisters of gas into the crowd and knowing what started this and how this all blew up, I’m thinking to myself, we’re not going about this the right way. I was a rookie. I know nothing about policing other than what I was taught in the academy so by no means did I think I was smarter than the guy making the command decisions, right? But I’m just looking at it from my perspective and going, “This is just not the right way to do this. We’re not going to win here. This is not a win situation. This should be done differently.” And I just always felt like from the minute I hit the ground, watching [inaudible] analyze the way that we were doing things and thinking, why are we doing this this way?

There’s a better way to do these things. And so that’s the way I felt in Mount Pleasant. My first day on the job, really hard to explain, I just felt like there’s a problem to be solved here and we’re not going about it in a problem solving manner. We’re going about it with brute force. Brute force doesn’t always work. And so it intrigued me and every day after that, once the riots were over, I started walking a foot beat in the city. Every single day I went to work, I got to problem solve. For six, seven, eight times a day, calls for service, 911 calls, you respond to people who are in crisis, people who need help and you get to try and help think through that, help solve the problem. And that’s what I enjoyed doing. It’s frustrating when you’re at the bottom of the totem pole and you’re the line officer. You’re in a chain of command, you can’t make certain decisions. But I did feel like every single day I went to work, I made a difference in someone’s life, no matter how small.

Tim Ferriss: Yeah. And this was around, tell me if I’m getting this wrong, but around 1990 or early ’90s?

Cathy Lanier: 1990.

Tim Ferriss: 1990.

Cathy Lanier: Yep. 1990.

Tim Ferriss: And you were working your way up the ranks. When did you first, and we’ll certainly talk about the good, the bad, and the ugly of that timeframe in some respects, but when did your first real mentor show up? I have different names from doing homework in front of me. I’ve got, if I’m saying it correctly, Sonya Proctor, I’ve got Charles Ramsey, who might show up a little bit later. I’m not sure exactly on the chronology, but were there any critical figures in the first few years who were helpful to you? Or was it really just executing, getting the job done, delivering and working your way up? I’m wondering when your first mentor of sorts or — I don’t want to say guardian, it might not be the right word — but influential figure showed up in policing.

Cathy Lanier: So I was an officer and I loved my job. Once I worked my way up, I was foot patrol the first several months. And then I went to motorcycle school and I got trained to ride a motor and then I was on a motorcycle. I wanted to be mobile so I could get around and I love the adrenaline, 911 calls, getting out there, being first on the scene. And then I got moved up a little bit more in seniority and I was in a patrol car. And I used to get on the radio and I’m like, “All right, Dispatcher, I’m in service. Stack me up. Give me all the calls you got pending that’s been sitting there waiting. I’ll take them off.” So I had a lieutenant who, he was like a SWAT team commander guy who got promoted to lieutenant and they sent him out to patrol, which is like a slap in the face to a SWAT guy, right?

Tim Ferriss: For sure.

Cathy Lanier: They hate the call stuff. But he had come to my district and he called me in his office one day. He’s like, “I hear you on the radio out there.” He’s like, “You’re really humping.” I was like, “Yeah, I love this job. This is great. It’s fun.” And he’s like, “You’re coming up on three years, you’re going to be eligible for sergeant. You should take that sergeant’s test.” And I was like, “Why’d I want to do that? I like my job. I like what I’m doing. If I take a sergeant test I’m going to get moved somewhere,” he’s like, “No, no, you need to take the sergeant’s test.” I’m like, “Well, why would I want to do that?” And he’s like, “Well, you want to make more money, right?”

And I’m like, “That’s a good point.” And he said, “And once you start taking these promotional exams, it gives you more opportunities to influence the things. I hear you, you’re trying to change some things, why don’t you take that exam?” So he pushed me pretty hard. And when the test announcement came out, he said, “Come on, I’m going to give you a ride. Let’s go pick up your books. You have an eight-month window to study.” He’s like, “Let’s go pick up your books.” So I was like, “All right.” I was a little intimidated. I’m like, okay. So I took that sergeant’s test. I was eligible for sergeant at three years. I took the first sergeants to test. There was 890 people that were eligible that we took the test altogether.

After the written exam, you go to an assessment phase where you do a bunch of oral interviews and exercises and paper exercises. And I ended up coming out number 13 out of 890 for that. So I got promoted right away, a very young sergeant, 26 years old, three years on the job. I had a master patrol officer working for me that had more years on the job than I was old. He had 26 years on the job, I was 26 years old. So that was the first mentor. And he had remained a mentor for me for most of my career.

Tim Ferriss: What was his name?

Cathy Lanier: Donny Exum.

Tim Ferriss: I mean, man, these stories are so critical because whenever — I mean, people are self-made in many respects and at the same time, you just have to wonder sometimes, right? If you didn’t have these intervening figures, nothing like your experience, but I had a pretty miserable public school experience when I was growing up and ultimately hadn’t even thought of private school. And there was one math teacher who was basically like, “You need to get the hell out of here.” And I was like, “Yeah, yeah, yeah, out of here to where?” And he just kept harping on me. And then there was one other person who chimed in. Then I had two people and I was like, “Oh, okay, maybe I should take a look at this.” And it was just like, if that had not happened, who knows? It’s just a lot of question marks.

Cathy Lanier: Critical. Those mentors are critical.

Tim Ferriss: Yeah. What does a sergeant do? I’m embarrassed to admit that I have no idea. What does a sergeant do?

Cathy Lanier: So this is one of the things that police departments do right. Now that I’m in the private sector, I wish the private sector had a similar structure. So once you make sergeant, you start as a first line supervisor. So they’ll give you eight people, eight to 10 people that you’re responsible for. So you’re the squad sergeant. You have a squad that’s assigned to you, those eight to 10 people, they report to you. So I’m responsible for making sure when we pop at a roll call and we hit the street that my squad of eight is doing what they’re supposed to do. They’re clearing their calls, they’re taking reports like they’re supposed to. If they get in a situation where they don’t know what to do, they go over the radio call for me, I go down and help them work through that situation and I help teach them how to manage these situations.

So you’re first line supervision, you’re right there every day on the street with the 911 responders and you’re helping them manage those calls and you’re helping them manage how to solve those problems. You’re signing arrest paperwork. If you make an arrest, “Wait a minute, let me look at all of the probable cause you have here before we put this person in handcuffs.” Or if you’ve got the person in handcuffs when I get on the scene, “Let’s review what you got here before we take somebody to jail. Let’s make sure we’ve met the DC code, we know that you’ve got a legitimate arrest here.” So you start managing a small group and then the next level is manager. Then you become a lieutenant and then they give you like 40 people to manage and you start making little bigger decisions. Now you’re scheduling, you’re assigning, you’re working through warrants and things like that. So it’s a very gradual progression.

Tim Ferriss: In that timeframe, early 90s or just 90s, I suppose, writ large, what was it like being a woman in the police force?

Cathy Lanier: It was a really tough environment when I first got there. There were a few days in the very beginning when I was an officer that — the good thing about the officer, when I got there, the department was 85 probably percent African American. The city was largely 89% African American. So largely African American, certainly very few white females. It was very few females. So I would think we were about 11% women on the department of 5,000, 5,200, I think, when I came on, the size of our department. So very few women, very few white women, little bit — this was a very — it’s hard to think back to 1990. Sexual harassment was commonplace. Nobody talked about it. Nobody cared about it. It wasn’t an issue. It happened every day and you work through it. I grew up with two older brothers, so I knew how to navigate it a little bit.

Listen, my brothers gave me advice on how to deal with some of this. The good thing is as an officer, you very quickly establish yourself. And I established myself as an officer early on as a worker. I came to work, I did my job. I don’t need anybody to do me any favors. You don’t need to look out for me. I don’t need a partner. I can ride by myself, I’m good. Once I made sergeant though, the harassment got worse. I mean, I had a lieutenant that was really, really sexually harassing. I mean, not just me, but several women, physical harassment. I mean, getting you on a midnight shift in a sergeant’s office and closing the door and putting hands on you and things like that. And I remember saying to my boyfriend at the time, I was like, “You know what? I got real thick skin. I can take all kinds of comments. I don’t mind any of that stuff, but I’m not going to let people put their hands on me. That’s just not going to happen.” So the harassment was pretty intense. It was a really tough environment.

Tim Ferriss: So what happened?

Cathy Lanier: So had a lieutenant, when I made sergeant, I was sent over to Southeast Washington. I was patrolling in Southeast. I had really a good squad. I worked nights, permanent nights. So I had a lieutenant that was harassing me and some other women, but me pretty intensely, calling me on the radio, forcing me to drive him around, putting me in his cruiser with them, making me drive him around, just not letting me do my job. Constant harassment, calling me on the radio, bringing me to the office, making me drive him somewhere, things like that. And so I finally, after several times of asking him to leave me alone, I finally filed a sexual harassment complaint. He had put his hands on me several times. So I filed a complaint, and I remember going down to the EEO office and filing this complaint, and they asked me to write a list of anybody who had ever — well, first of all, before I went down, my partner, one of my fellow sergeants, who was a Black male officer, said to me one day, we were out riding together.

The lieutenant had called me in and my partner said to me, the other sergeant said, “How long are you going to let this keep going on before you do something about it?” And I was like, “What are you talking about?” He’s like, “I hope you’re writing this stuff down. I hope you’re going to say something to somebody because this can’t go on like this.” So the first, again, a man, not a woman, another male police officer basically said to me, “If you’re not going to stand up for yourself, nobody else is going to stand up for you.” And so when he said that, it clicked. He’s trying to say either you’re going to allow this to keep happening or you don’t want it to happen and you do something about it. So after that conversation, I filed this complaint, I list all the people who had witnessed because my harasser made no effort to hide it.

He made horrible comments and grabbed women in front of others all the time. So I listed 17 different witnesses and they did the investigation. And literally I left the EEO office, I went to court, I had court that day and I was in court 20 minutes after I left the EEO office from filing my complaint, my harasser, the lieutenant, texted me on my beeper, we had beepers back then and said, “I know what you’re doing and you’re not going to get away with this.” So it was supposed to be confidential, but within 20 minutes of leaving the office, the person who was doing my investigation called him and told him that I had made a complaint.

Tim Ferriss: Gross.

Cathy Lanier: So I had to go back to work in that environment, one of the most violent areas of Washington DC. From that day forward, he prohibited me from partnering with anybody. He refused to allow me to ride with anybody else. He continued the harassment. He came into my office the next day, shut the door and said, “Look, I know that what you’re doing. You need to back down. You need to withdraw this complaint. You’re not going to win.” Anyway, long story short, they sustained the complaint. So the investigation, all the witnesses I listed, they were all men. I didn’t think any of them would tell the truth. Nobody wants to go against a higher ranking person, and every single one of them told the truth. They all wrote down what they saw. They all not only talked about what they saw him doing to me, but what they saw him doing to other women.

And I was just shocked. I always say to women, you don’t realize when you’re in these scenarios, decent men that observe these things going on, they don’t like it either. They don’t like it either. And those other men that I was working with, they didn’t like it either. And some of them, this guy had harassed their girlfriends or their wives, you know what I mean? So that really made an impression on me, that so many of the men that I work with stood up and did the right thing there. When it was time for him to be disciplined for this, when we got to trial board, I walk into trial board for the discipline to come down and they told me they had to drop the whole case and throw it out. And I’m like, “Why? What happened?” And they said, “Well, we missed the 90 days. In the District of Columbia, you have to bring discipline within 90 days of the day that you knew or should have known about the misconduct.” They sat on this investigation till day 91 and then turned it in.

So literally after all of that, they threw the case out and they said, “Well, we’ll just transfer you. Where do you want to be transferred to?” And I was like, “I don’t want to be transferred. I didn’t do anything wrong. Don’t transfer me. Transfer him. I didn’t do anything.” He later had several other complaints come forward and eventually was terminated for a severe case with multiple other subordinates later on.

But I will tell you this, now everything above the rank of captain in the police department is appointed. You civil service exam for sergeant, lieutenant, and captain. After captain, it’s appointed by the chief of police. You’re an appointed rank and you’re also at will so you can get appointed to inspector or commander, but you also can get demoted with no cause either.

So I remember one of my mentors, another mentor, a lieutenant, there was a captain and a lieutenant that were both good mentors to me there. The captain of the two mentors I had there pulled me aside after this complaint and said, “You did the right thing. He’s been harassing women here for years and somebody needed to stand up so you did the right thing.” He said, “But just know you’ll never make it past the rank of captain.” Because that lieutenant was very well-connected at the time to the chief of police, so very friendly with the chief of police that whole administration. So I said, “That’s fine. That’s fine.” I wasn’t thinking long-term longevity and promotion.

Tim Ferriss: So that actually ties into what I was going to ask you because it strikes me as an incredibly brave thing to do. I imagine not everyone in your situation would’ve done that. I mean, in fact, they didn’t. I mean, I imagine there’s a lot of fear around, there could be a lot of fear around the political or job, professional repercussions of voicing something like that, especially during a period when that was not common.

Cathy Lanier: Well, remember, my driver in life, Tim, if you think about this, and harassers work this way, my goal in life is to take care of my son. I’m a single mom and after he knew I made a complaint, he was threatening my job. He was really making it very difficult for me to come to work. It was terrifying to come to work. And I was fighting for my job, I can’t lose my job. I have a son to take care of and I’m not going to lose my job because somebody wants to be a bully. And that’s the motivation. It was terrible. I was sick to my stomach every day. I was going in the bathroom and throwing up. I mean, when I got to work and just every time I heard his voice on the radio, it was terrible for me, but I also couldn’t afford to lose my job. I was not going to let somebody force me out of my goal. And I had a son to take care of, so I couldn’t afford that. I was going to fight until I knew that I was safe.

Tim Ferriss: Yeah. I mean, it’s a focusing, forcing function, right? I mean, having that singular priority. So it seems like, I mean, the predictions about you never rising above the rank of, what was it, captain?

Cathy Lanier: Captain.

Tim Ferriss: Seems like that fellow wasn’t exactly the Nostradamus of predicting the future. So could you walk us through how things progressed and why were you able to continue to excel? Did his prediction just turn out to be completely false.

Cathy Lanier: I think it would have been accurate. I tell you what, the stars aligned for me. So I took sergeant test at three years. I was eligible for lieutenant at five. I took the lieutenant’s test at five years. I came in number one on that test. I took the captain’s test, seven years, I came in number three on that test. So I got promoted bang, bang, bang, three years, five years, seven years. I was a captain in seven years. I would have never gone past the rank of captain in that current administration. And then Marion Barry gets arrested, our mayor, Marion Barry is taken out and replaced by the control board. The control board comes in 1998. I’m a captain at the time. Marion Barry is now taken out of play. The control board takes over. They bring in Chuck Ramsey, an outsider who knows nobody in the department.

He doesn’t know anybody. He’s got no clique. He’s got no boys. Everybody’s fresh. So he comes in as I’m a lieutenant just making captain, takes over the police department as a complete outsider and is doing his assessment of what officials, what command level officials he wanted to have on his team. And he appointed me from the rank of captain to be an inspector to take over major narcotics branch with less than eight years on the job. I was 29, I think.

Tim Ferriss: All right. Then Chuck makes his appearance. Right. Okay. Charles Ramsey.

Cathy Lanier: He’s the next big mentor.

Tim Ferriss: Yes. Okay. So just for honestly, my personal curiosity, because I really know nothing about how police structures work. What is a captain doing? And then what does an inspector do, if you don’t mind?

Cathy Lanier: So again, this is where I think the police department gets right. You spend three years as a patrol officer, you make sergeant, you study really hard, you take the test, you make sergeant, you go through some schools. After you make sergeant, you manage a small group, then you make lieutenant two years later, you go through the exam process, you go through some schools after that, and then you manage a platoon of 40. When I was a lieutenant, I had narcotics officers, I had detectives, and I had patrol.

Tim Ferriss: How are those 40 people determined? Is it based on neighborhood or some type of geographic area?

Cathy Lanier: So at that time, it’s done differently and over the course of the years, it’s changed, but at that time it was geographically. So I had a patrol district, and of that patrol district, I had one third of that patrol district, and I managed every resource for that part of the district. So all three shifts. I had day work, midnights, evening shift, all three shifts. Those officers are split across those three shifts, and they covered all the policing. So not just the 911 responders, the guys in uniform going to 911 calls, but also your narcotics officers and your detectives that follow up and investigate crimes.

Tim Ferriss: This is lieutenant.

Cathy Lanier: That’s lieutenant.

Tim Ferriss: Okay. So lieutenant, is that the first time where you’re getting the decathlete’s exposure to all of these different things?

Cathy Lanier: Yes. And you’re also getting exposure to administration. So part of that promotional exam is studying administration. You have to learn administration. So if there are municipal regulations that need to be changed, and I’m managing a large part of the portion of the District of Columbia, I see a municipal regulation needs to be changed, I need to know the process to petition to change that municipal regulation. How do I go about changing that law? Because I’m seeing firsthand the impact it’s having in our neighborhoods, so police administration starts to become more and more important there. I also now can start influencing policy. I can influence policy for my little piece of the world. I decide what my drug enforcement tactics are going to be. I decide how we’re going to work in terms of doing warrant service and things like that. So that’s where you first start to get a better understanding of influencing how policing actually is carried out.

Tim Ferriss: Not to minimize the prior steps, but it sounds like the lieutenant role is a very dense learning opportunity based on the description.

Cathy Lanier: And I think the best role, the best rank on the police department for me was lieutenant. I was able to still go out on the street, support my troops, back up my sergeants, have fun policing and do the policing that I enjoyed, but I also had the ability to change the environment for them, help them, and also influence how we were policing our community.

After captain, it gets — the captain is more — you’re strapped to your desk a lot more.

Tim Ferriss: Yeah, I was going to say more behind the desk.

Cathy Lanier: You’re reviewing bad arrests, that a sergeant didn’t do the right thing and review the paperwork. Now you’ve got a bad arrest that’s got to be detention journaled. So you’ve got to review and make that decision. You’ve got to set things up at the courts. You’ve got to look at all the disciplinary investigations that come in. Officers getting disciplined for things. You’ve got to make decisions about that. You sit on trial boards. Who’s going to get disciplined? Who’s going to get terminated? It’s very administrative. You’re helping the commander make decisions, community meetings, deployment decisions, and it’s not as much fun.

Tim Ferriss: Yeah. I know a few people in law enforcement, but mostly military, former military guys. And I mean, very similar. Some of these guys, they just love being in the field and they’re like, “I got promoted.” It’s like, “I just don’t know how I feel about it.” There’s very mixed excuses.

Cathy Lanier: Well, here’s the big key. When I went to go change my uniform, so you go to property division, when you get promoted, you walk off the stage, you get your birds or whatever you’re getting, your clusters or whatever for your new rank. You go to the property division, you get your new rank insignia. When I made captain and I went over to property division to get my new rank insignia, they said, “Turn in your handcuffs.”

And I was like, “What? Turn in my handcuffs? What are you talking about?”

“Well, you don’t need those anymore.”

I’m like, “You’re not taking my handcuffs. I’m going to keep my handcuffs. Right here. Right here.”

I kept my gun belt. I kept my gun belt, my handcuffs, my extra magazines, all those things that the administrative captains used to turn in. I’m like, “No, I’m keeping this stuff.”

Tim Ferriss: So let’s come back to Chuck. And because I’m so unfamiliar with the internal workings, it’s hard for me to pick the next sort of flashpoint, maybe a seminal moment for you. I mean, there’s a lot to pick from. I’m not sure how to put them in order, not that they have to be in order, but maybe tell me if there’s something that we just talked about before this. But you mentioned Chuck, pushing you to take tough assignments. Is special operations division, is that a sensible place to hop to next? Or what do you think? Are we skipping some important steps in between?

Cathy Lanier: When Chuck came in and he initially put me in charge, I’d only been a captain, I want to say four or five months, and he kind of did a clean out at the top. A lot of that old boy network that was there when he got there, they were all people that were long past retirement. So he pushed a lot of the command staff out. So that made him push people up pretty young in their career. So he pushed me up to be the commander of major narcotics branch as an inspector, like I said, just under eight years on. So I was very young and I had a major role —

Tim Ferriss: Let’s see. I’m trying to do the math. How old were you then at that point?

Cathy Lanier: So I want to say I was 30-ish, 30, 31. I made the narcotics branch.

Tim Ferriss: Man, that’s amazing. That is a lot of responsibility. Yeah.

Cathy Lanier: And so, I went to major narcotics branch. I was there for — so I had major narcotics branch and vehicular homicide. So I managed all the vehicular homicide investigative units there for just under two years. And then he promoted me again to commander. And I took over a patrol district, the fourth district where Mount Pleasant sits. The patrol district I started in, I went back now and I was the commander of that patrol district. It was the largest residential area in the city of Washington. So I took over that district. I ran that for two years, and then Chuck got a way. He called me down to his office and he says, “I’m thinking I’m going to send you to SOD.” It was 9/11 happens. The Friday after 9/11, he says, “I think I’m going to send you to special operations division.”

I was like, “You know what? I love being the district commander. I love working in 4D. My goal was to retire as the commander of 4D. Thanks, but I really like where I am.”

And he’s like, “Oh, okay.” And then two days later, a teletype came out transferring me to SOD. So it wasn’t really asking me. He’s like, “Oh, okay.”

Tim Ferriss: He’s like, “That’s a great story. Thank you for that.”

Cathy Lanier: Yeah, funny. Right. “Glad to hear it.”

So I took over special ops. Now, special operations division had never had a woman in charge. So that in itself was a little intimidating. But the one thing that when you talk about mentors, and I know you probably have experienced this like many others, is what a mentor does for you is they lend you confidence that you don’t have. Chuck recognized that I didn’t have the confidence. I was intimidated by this SOD thing. I was like, yeah, no. Never had a woman in charge. It’s a predominantly male. I always say the most testosterone in the police departments in SOD. It’s the bomb squad, the SWAT team, Harbor, the Marine Unit, the helicopter unit, aviation, horse-mounted unit, K-9, civil disturbance unit, the presidential protection unit. So it’s like nine or 10 different units, your high-end stuff. So anyway, he recognized that I was intimidated by that. And he’s like, “Mm-mm, you’re going to go and you’re going to do it.”

He sent me off to a bunch of schools. I went to EOD schools, bombing schools, so I learned how to manage a bomb squad. I learned how to manage a SWAT team and the people there were great. That was my best assignment in my entire career. I spent six years there after 9/11, recreating our special operations division and turning it into a Homeland Security and counterterrorism unit.

Tim Ferriss: What made it so good for you, that particular role?

Cathy Lanier: Well, it was the most complex role I’d ever held. Most of the units I managed, I had to manage three or four different type of specialties. I had to manage nine different specialties, and they were highly special. These were highly trying — sniper teams on the SWAT teams, negotiations unit, the bomb squad. We were just after 9/11 and we were trying to evolve our department from a pre 9/11 police department in the nation’s Capitol to a post 9/11 police department in the nation’s Capitol. We got caught flatfooted on 9/11 and we should not have been. We didn’t have the skills, training, equipment, and things that we should have had. I always say Timothy McVeigh was, that Oklahoma City bombing was the wake-up call. That’s when we should have started changing the way we train and prepare our police officers, but we didn’t.

And then there’s the first World Trade Center bombing. That was another wake-up call. We didn’t respond to that. It was not until 9/11 that the nation’s police departments and the largest cities really realized that we have to be prepared for this type of asymmetric threat that we’re now facing. So when Chuck put me in charge of SOD, he said, “I want you to create the homeland security capabilities that we need, not just in SOD, but across the whole department.”

So he gave me a blank check to create a brand new police philosophy in the Metropolitan Police Department. So we created the Homeland Security Counterterrorism Bureau. We created CBR&E. My first year, we got $17 million in funding to buy level A suits to send our people down to Anniston, Alabama. I went down to Anniston, Alabama. I trained in Sarin and VX, live Sarin and VX gas. We were trained to do rescues in hot zones. We went down to Nevada and trained on rad environments, radiological environments. We trained with — I was one of the few people that was fortunate enough to train with Ken Alibek and Bill Patrick, two bioweapons scientists, one from Russia and one from the US, taught my bioweapons class, how to respond to biological threats, anthrax, right? We had anthrax in Washington, DC. These are all things that I was on the front end of creating, and I got to go through all of that training and all of that experience with my whole team. And the Metropolitan Police Department, when we were finished that six years of evolution, was a completely different place.

Tim Ferriss: This is a good time to, I think, come back to something I kind of promised to listeners that we would revisit, and it goes all the way back. We’re not going to go all the way back to Mount Pleasant, but when you were first day on the job, five days, and you’re looking at it, and you’re thinking to yourself, “We’re not doing this the right way. We can’t even communicate with these community members. Furthermore, we’re not even trying to set the message straight.”

And then if we flash forward, I have notes that are a bit scattered here, but I have notes on embracing technology. So this is from governing.com. I want to give credit where credit is due. So this relates to looking for new ways to connect the community to the police, in the case of the police. So the creation of an anonymous text tip line, cleverly named 50 411. Am I saying that the right way?

Cathy Lanier: Give the 5-0, the 411, right?

Tim Ferriss: The 5-0. I’m such an idiot.

Cathy Lanier: We are the 5-0, like the cop, you know, they used to call us the 5-0 back in the old days and 411, you know 411.

Tim Ferriss: Yeah, right. So in 2008, it received 292 tips. By the end of 2011, that number jumped to 1200.

Cathy Lanier: 1200. Yeah. We got up to about 2800.

Tim Ferriss: 2800. Right. And there are many examples of how that ended up being valuable. And then there’s a whole separate topic, which is maybe related but different, which is cultivating sources, right? So like developing sources, getting to know people, and this is quoting from the same piece, but you treat people with respect, you establish relationships. And God, I’m trying to think of some of these examples that I read about separately, but this seems to all probably feed into a lot of what you were doing in that overhaul later, right?

Cathy Lanier: Yes.

Tim Ferriss: And I’m just wondering if you have any other examples of sort of cultivating a access to helpful information, right? Not just drowning in noise. I’m wondering how you even thought about that. Because I imagine one of the challenges at that time, probably even still today, but especially post 9/11 in the wake of that, that there’s kind of a good news, bad news situation. If you want more information or tips, there’s probably going to be an overwhelming amount depending on how you solicit and how you search for it. So how did you think of separating signal from noise?

Cathy Lanier: So for me, it was pretty simple and it does go back to Mount Pleasant. Again, pretty intuitive on your part not having been in policing. So when I became the chief of police, a couple of commitments I made to myself and to the community was that we had a tendency to place higher value on some neighborhoods and some crimes than others. And our job is to protect all of the community and every crime should be equally important to us. If we’re not preventing crimes, we’re not being successful, making arrests. We used to publish our arrest stats every year and go, “Oh, look, we made 50,000 arrests last year. Look how successful we are.”

Well, that’s 50,000 times. We didn’t do our job because we didn’t prevent those crimes from happening. So to me, arrest stats are not a good measure of success for a police department. Now, I don’t have a stat that can tell you what I prevented, but the goal should be to try and prevent. So for me, what was very clear is, so when I first took over as chief, I promised I was going to go on the scene of every single homicide. Why? Because I wanted people in the communities to know it didn’t matter what neighborhood you lived in or what the circumstances of that homicide was, that homicide’s just as important to us as every other homicide. So homicide in Georgetown, in the very expensive, wealthy neighborhood, if there was a homicide there, it would get news coverage for weeks and police were all over it. And almost always those crimes would be closed. But if there was a homicide in a public housing project, it got little to no news coverage. Three people shot last night in Southeast.

That was it. That’s all you hear. And nothing about those people or what happened with those crimes. And they very rarely got closed. So I put an emphasis on trying to cultivate those relationships in the community. And it was clear to me two things. People didn’t trust us, they didn’t trust the police, and we didn’t close these homicides, because witnesses wouldn’t come forward. They wouldn’t come forward, because they didn’t trust us. And so, we had to change that. So I had a great example. I was out, we did a crime initiative during the summer called All Hands on Deck. So I was out on all hands on deck. I’m walking through a public housing complex and there’s two middle-aged women sitting on a wall outside in the summer. They’re drinking. They got open containers of alcohol, which is illegal. They could have been — in the old days when I was policing, we would just walk over and handcuff them, lock them up, take them to the station.

That’s open container alcohol. So I go over and I sit down, start talking to them. There had been a series of shootings in this complex and I said, “Hey.”

She’s like, “I don’t know why you guys are here. You don’t care about us.”

Kind of giving me the lip. And I said, “Okay, well, I’ll tell you what, here’s my business card. My cell phone number’s on here.” First of all, they had no idea it was a chief. I’m just the cop. They don’t watch the local news. They don’t know that I’m the chief. “Here’s my business card. If you have any information and you want to talk to me about anything that’s going on here, and tell me who’s out here shooting in the middle of the night, hit these kids that are on the tennis court, on the basketball court, please let me know.”

And when I walk over to the two ladies, they kind of take their beer and stick it behind the wall. I was like, “You know you’re not supposed to be drinking out here, but I’m going to pretend I didn’t see that.”

So I give them my business card. I give them that respect. Yes, ma’am. No, ma’am. Talk to them with a little respect. I give them my business card, my cell phone number’s on there. About two weeks later, I get a call at one o’clock in the morning, and it was a woman’s voice. Don’t know if it was those women, can’t prove it, don’t know to this day. But I get a call about one o’clock in the morning. There was a shooting in that neighborhood, and the woman’s voice said to me, “Tell your officers that the gun is behind the white Escalade.”

And I’m like, “What are you talking about?”

She says, “On Cloud Street…” She gave me the address on Cloud Street. She said, “There’s a white Escalade. The gun is there.”

So I turn on my police radio half asleep, switch to the sixth district where that address is, and sure enough, they’re working a shooting. And I went over the radio, I said, “Cruiser one, who’s the on scene official? Have him call me.” He calls me and I said, “Look, I just got a tip from somebody that there’s a gun involved in this case and this is where the gun is.”

Sure enough, that’s where the gun was. They recovered that gun. From that recovery of that gun, they were able to start working this case and actually get information. So I always tie that back to, I strongly believe that the fact that I walked over to those women, I showed them a little respect. I sat on the wall with them. I didn’t lock them up for the open container of alcohol. They weren’t hurting anybody. I sat and chatted with them. I gave them my cell number and said, “Look, I want to help, but if you don’t give me information, I can’t help.”

So that’s the philosophy that I wanted all of my cops to have. That’s the way I wanted all of us to lease our communities. I wanted people to see that you give me information, you’ll see results. You tell me who’s involved in shooting up the neighborhood. We’ll go after them. We will make arrests. So we started doing, instead of just putting posters up when a homicide occurred, when we made an arrest for the homicide, we went back and put posters up saying the case is closed. Reverse canvas. Instead of just telling you when something bad happens, we’re going to tell you when we close it. So now people know that we’ve taken that person off the street and those little things matter.

Tim Ferriss: Yeah. Matter a lot. I want to please confirm or deny this, but I am in the course of speaking with you and certainly in the course of doing homework for this conversation, impressed with your attention to detail, which comes back also to my signal versus noise, because I am dazzled by your ability to manage all of these details. And tell me if this is a complete dead end, but it seems like you demonstrated this really, really early on. And we’ll come back to where we were in the timeline, but this is how you had a job at 16 as a secretary at a commercial real estate firm. Am I getting that right? And you handled —

Cathy Lanier: That’s Eisinger Kilbane.

Tim Ferriss: You handled tenant billing, right?

Cathy Lanier: Yeah.

Tim Ferriss: And it seems like you’ve practiced this or just had this ability that you’ve honed over time. Thousands of pieces of correspondence come through the police department every day, but you’re also talking about learning, I think at that job to never let anything that’s got your name on it be imperfect. And it’s just like, how come —

Cathy Lanier: Sound familiar, Tim?

Tim Ferriss: Yeah. Well, yes, there’s that also. My incredibly helpful slash —

Cathy Lanier: OCD?

Tim Ferriss: Yeah, brain damage too, saying OCD. But as you have a job that increases in scope upon scope, upon scope, upon scope, and how do you build systems that help you to keep track of these things, right? Because not everyone is going to have necessarily your eye for detail or capacity to remember the details in that photograph that flash for a fraction of time that you then need to recall. So it seems like ultimately, and I am cheating a little bit, because when you sent and we asked for some notes in advance of this conversation, I’ll just read one thing here, because —

Cathy Lanier: I don’t remember now, so you’re going to get me on this.

Tim Ferriss: Great. Yeah, no, it’s good. It just says, “No hacks for me. I try to focus on systems or strategies that will hold up over time.”

And I’m wondering, for instance, whether it’s in your current role or where we left off in terms of your timeline, as you’re soliciting information from the community and they’re offering more, because you’re showing not just the announcement of the bad thing, but that you actually took action related to their help that closed cases, et cetera, et cetera. How do you ensure that the department or the organization that you’re a part of is equipped to digest that? And I’m not sure that’s an easy question to answer, but I’ll just leave it there.

Cathy Lanier: No, it’s not an easy question to answer, but I would say this — I pushed technology very, very hard once I became the chief. When I took over as a chief, we had Teletubby pagers. We didn’t even have cell phones, and I wanted everybody to have smartphones. The early smartphones, the first one we got was a Trio. We had Palm Pilots and Trios, right? If you remember that far back.

Tim Ferriss: Sure, I do.

Cathy Lanier: And then we pushed putting computers in the cars and we pushed the technology, gunshot detection technology, cameras, integrating those gunshot detection technology cameras, all those things together. I really wanted technology to be those systems, right? Taking all this great technology that’s coming out, make us more effective and more efficient as police officers. Instead of spending three hours handwriting an accident report, we could pull up on the scene of an accident report, have a iPad or a laptop in the cruiser that GPS drops the intersection on a police report and all’s I got to do is plink a little car down there and my police report now takes 10 minutes instead of two hours.

So I brought all this technology, the systems that made us better, it made us more effective. And I relied a lot on people. I mean, everything I did, I learned from the people that work for me and the people in the community. I made it a point to go out and talk to people and listen. Everything I learned about fighting crime that was effective, I got it from walking around the community and giving my cell phone number out, listening to what people had to say. Because if you listen to people, they will tell you what to do.

And my officers, my detectives, my sergeants, my lieutenants, those guys, when I did my strategic planning sessions, I would bring in from all of those groups and brainstorm with them. What are the things we need? How can we do better? What do you need that you don’t have? What are the crime trends that you’re seeing? But when I witnessed this evolution of technology and crime, and we had to get our police department to adjust to meet that evolution. We hire cops for a 25-year career. And when this technological crime evolution was happening, we had detectives that didn’t know how to manage a crime scene with seven different cameras they had to download to get video of the crime scene. They didn’t know how to mobily, forensically dump a phone. You arrest a guy who just did some armed robberies. And the biggest case, and I’m sure in your research, you saw this Thomas Maslin case.

There was a case that really kind of set this in stone for me. There’s this poor gentleman who was robbed for his cell phone one night, he’s beaten with a baseball bat. They crush his skull, they take his phone. Those same suspects, we find Mr. Maslin the next day with his skull crushed, barely alive, no cell phone. We don’t know where his cell phone is. He’s in the hospital. Well, what we don’t know is that same night right after they robbed him, that same group of kids went to Adams Morgan, another neighborhood, and they robbed three more people and they were arrested. And when they were arrested, they had multiple cell phones on them. They were robbing people for their cell phones, because they were going to go and turn those phones in and make money. And all those cell phones were recovered as evidence and put on the books, but nobody knew that Thomas Maslin’s phone was in that books, because we didn’t have anybody that had the digital forensic skill to dump those phones and figure out whose phones they were.

And when we finally did figure that out months later, I said, “This is never going to happen again. We need to have people that are trained to have that skill. And if we can’t train our detectives to do it or they don’t have the bandwidth to do it, then we’re going to hire civilians to do it, but we’re going to have that skill and we’re going to have it out on the street daily.”

And so we did. We hired criminal research specialists, we hired some other civilians for digital forensics. And so, we went through this evolution and it is building systems that will endure over time and policing was not designed that way. So we had to really change the way we do policing. And now police departments are doing much better at keeping pace with technology.

Tim Ferriss: Before we get to maybe the differences between your experience in law enforcement and everything that preceded the NFL and the NFL, could you just give people an idea of the scope of your responsibilities at the NFL? What are you responsible for?

Cathy Lanier: Everything related to security. So executive protection, I set the standards for physical security and cybersecurity at the stadiums. So all of the stadiums, the 30 stadiums across the US and our international stadiums, a little bit of variation on the international, but across all the US stadiums, we set the requirements for security that they have to meet. So once we set that standard, we update it annually. We do the audits and red teaming and we make sure that they are meeting those standards. So physical security, cybersecurity, both. We also have investigative responsibilities. So violations of the personal conduct policy. Those are all investigations that are done by my team. We have game integrity, so management of the game integrity program. So making sure that we are maintaining the integrity of this game. There’s a lot involved in that.

If it’s got anything to do with security, it falls on us. Individually, the league office has full responsibility for Super Bowl, Pro Bowl, Combine, Draft, and all the international series games. So when I say we have nine international games this year, the reason scheduling this is so hard, each one of those international games, I will take a team out and advance at least two trips, if not three. And we’ve got nine international games this year. And I’m also working on, we plan Super Bowl about 18 months out in advance ’cause that’s 10 days of events over 20 some venues and then Draft. So Draft, I’m leaving for Pittsburgh on Sunday to go manage the Draft for the next seven or eight days. So special events, tentpole events, that’s a big, big part of it.

Tim Ferriss: Yeah. So tons of free time.

Cathy Lanier: Tons of free time. 170 days on the road last year.

Tim Ferriss: Oh my Lordy. So red teaming is a really critical concept that I want people to understand. Some folks may recognize it within the context of say tech, given the types of people that I’ve interviewed before in terms of paying people to try to break into your systems, let’s just say, or to take down your service or to fill in the blank, but they’re on your side. And I wonder where red teaming, I should know this, comes from. It’s probably from hiring people —

Cathy Lanier: Military.

Tim Ferriss: Military —

Cathy Lanier: Military.

Tim Ferriss: — pretending to be the Soviets, right. Probably.

Cathy Lanier: It’s the military. I mean, it was a military concept initially. And think about it this way. You’ve got to look at it a little differently. I think on the tech side, it is a little different, but I think of red teaming as we set a standard, like, we think use of magnetometers to screen for weapons. We think use of a perimeter to make sure everybody goes through screening. All these standards we put in place of security. I can go and audit you and you have all those standards in place, but what a red team operation does is it’s quality assurance. Are those standards working? Did I tell you to do something that didn’t necessarily work? So it tells you if the standards that you were using are effective or not. It may be that you put them in place, but you didn’t execute them properly, so they’re not effective.

So if you’re not properly doing secondary screening, it’s not that the magnetometers didn’t work, it’s that your guard didn’t respond properly to an alert. So it’s a quality assurance. It’s a quality assurance test to see if the standards that you are employing or you’re requiring are being used properly and are they effective? That’s the key. It’s not a gotcha. It’s like, is what we’re doing effective? And if it’s not effective, how can we make it effective?

Tim Ferriss: How are your responsibilities or your job with the NFL most different from what you did beforehand? I’m just imagining there might be new constraints on what you can or can’t do, even though you’re coordinating with federal, state and local law entities. I mean, just imagining what that entails with 32 clubs makes my head spin. But how is it most different from what you did before?

Cathy Lanier: I’d say it’s most different in terms of its diversity. So I thought coming from 27 years in the nation’s capital, managing SOD, I managed every large event protest, demonstration. We had about 2,300 a year that I was responsible for when I was there. So I thought, and then presidential inaugurations, I was like, “This is easy. I can come to the NFL, this Super Bowl thing’s going to be nothing. This is going to be a walk in the park.” And the diversity here is, the complexity here is so much more. It’s so much more complex and the diversity. So I’m not only setting up the equivalent of a presidential inauguration that I did every four years before, every year it’s Super Bowl, but the Super Bowl is more complex. It’s spread over 10 days, over 26 venues, and it moves every year. So it’s in a different place.

So I’ve got to build all those relationships. I’ve got to learn all those new venues. I’ve got to figure out security in a completely different climate. And in Minneapolis, it was 25 below zero. Guess what? Some technology doesn’t work in that 25 below zero. Some of the things that we do in Arizona’s not going to work in Minneapolis. And then now with international, we try and go and implement our full suite of security standards in Madrid and Sao Paulo and Australia and Munich. But when we get there, 20% of what we do is going to have to be adapted to the local environment. There’s laws and regulations and things that are different in different countries. Things that we do here, you can’t do there. Things they do there, we can’t do here. So the complexity of what I do now is far more complicated and it’s far more diverse than what I used to do.

Tim Ferriss: And by diverse, you just mean constantly shifting, like you mentioned, these different locations with —

Cathy Lanier: There’s no template. I can’t say, “Hey, it’s inauguration. This is what we do for the inauguration.” The ball sites are all the same. We do the same things. We know what to do with the inauguration. This is, every time it’s like you just take the old plan and throw it away, start all over. Pretty much, not completely, but pretty much.

Tim Ferriss: Yeah, yeah, yeah. Well, no shortage of learning —

Cathy Lanier: You don’t want to start with any assumptions. No assumptions, that’s for sure.

Tim Ferriss: I’m going to shift gears just a little bit. I’m wondering if, are there any books that you recommend or resources? This doesn’t have to be within the context of the NFL, but when I imagine you get approached by people who are hoping to learn from you in one way or another, or you are just mentoring people, whether that was in policing or within the NFL or in other contexts, are there any books that you recommend frequently to other people? It doesn’t need to be nonfiction, could be anything.

Cathy Lanier: So I’d say my favorite book of all times, and I made it mandatory reading for my command staff when I took over as the chief, which was a hoot because nobody ever made our command staff read anything before. And I also did a book club. I also used this book and did a book club with the community, The Tipping Point, Malcolm Gladwell. One of my all time favorite reads, because it forces you to understand that no matter what your challenge and no matter what your problem is, it goes back to problem solving. Whatever the problem is you’re trying to solve, there is a tipping point. You just have to know what that tipping point is. And I love that book. I’ve read it three times, I think. It’s a great book, so that’s one of my favorites. It just makes you think differently.

Tim Ferriss: What did you hope people reading it would take away to apply? How might that change how they act on the job or think and then therefore act on the job?

Cathy Lanier: Well, it doesn’t matter what you’re doing, what your profession is. If you read The Tipping Point, the key point is that you can turn around any situation, you can solve any problem if you’re paying close enough attention to the details that you can hit that tipping point. What is the tipping point to turn around high levels of violence in a community? What is the tipping point to turn around whatever your problem is?

I would also say Blink. Blink is another one that I only read because I liked Malcolm Gladwell, but Blink, for people in high-paced professions, Blink is one that helps you really evaluate how you make decisions, how you rely on your instinct and your experience and how much that matters. So those are two of my favorites. And then the only thing I read, Tim, is stuff about my job. I read work stuff, so nothing really fun.

Tim Ferriss: Well, let me come back to the — I suppose this all relates, everything relates to making decisions, but especially performing under extreme and sustained pressure. And I would imagine that, of course, part of the hiring process for a lot of the people who report to you, let’s just say, or within your organization, you’re already vetting for people who can operate at a high level with sustained pressure, where they also have to be very good at improvising when conditions change and so on. But if you were teaching a class to, could be high school students, college students on sort of resilience and handling pressure, right, some people buckle and sometimes you learn by buckling and then you figure out how to approach it next time. What would you tell them about making decisions under pressure and acting under pressure as opposed to becoming paralyzed? How would you even begin to talk to them about that?

Cathy Lanier: I would say it’s — I don’t care who you are. It’s not 100% instinct, right. It is, your body’s going to react in a crisis to what it knows. So if it’s a situation where you have trained for it or you’ve thought about it or you’ve prepared for it, in your mind, you’ve walked through it, you’re going to be in a lot better position than if it’s something that’s never crossed your mind. This is where kind of preparedness crosses that line. And this is why we try and encourage people to be prepared. Know when you walk into a building, what are the two different ways you can get out, not just the way you came in. Is there other ways you can get out of this building? Right. So everybody’s going to freeze initially. I think to a certain extent, if you have no experience, nothing in your brain that your brain can go back to have you act.

But in terms of being in a workplace or a professional environment and making decisions as a leader, if you have the knowledge that you need, you’ve done your homework, you’ve read everything that there is to read, you’ve got your education, you’ve got experience, decision making becomes easy. Each time you go up at a different level of rank, as a sergeant, when I first made sergeant, making decisions was a little tough at first because I was still pretty inexperienced myself. So my job was to be more well-read, understand the DC code a little better than the patrol officer, know what case law says. So if I didn’t read that stuff and I didn’t study, I would be uncomfortable making decisions and I would hesitate to make decisions. We had a lot of people that don’t like to make decisions. But the more you read, the more you learn, the more you invest in your knowledge, the easier it is to make decisions.

To me, decisions now with all of the years I’m in 36 years in this business, and now again, I have two master’s degrees, I’ve studied, I’ve got all this experience, decisions for me like boom, boom, boom, boom. So it comes with experience. It comes with investment of time. It comes with preparing yourself to be able to make a decision. And of course people will throw things at me that I’ve never experienced before, but because I have all those other things to rely on, I can make a decision and I feel good about it.

Tim Ferriss: Well, I have to imagine also, this is true in a lot of contexts outside of security or law enforcement. Certainly applies to military, but it kind of applies everywhere, which is making decisions in the face of incomplete information. And so I’m wondering what you have learned about that, making decisions, biasing towards action when you have incomplete information. How do you think about that?

Cathy Lanier: It happens. It happens a lot, especially in first responder communities and military. Like you said, it happens a lot. You’re not always going to have a complete picture. Again, I think your comfort level with being able to make those decisions is going to fall back on, are you qualified to make that decision? If you feel qualified to make the decision, sometimes I got to make decisions without all the information. There’s two things that go along with that. One is, do the best you can based on what you know at the time, but know a decision has to be made. And then if you make the wrong decision, undo it, change it, fix it. Don’t just stick with it because you’ve got to be the boss. And this is what I said. Admit you’re wrong. Change course, go another direction. That’s where people get tripped up, right.

When I’m making a decision and I don’t have full information, I’m thinking to myself as I’m making this decision, “I can either go this way or I can go that way. If I go this way, what can go wrong? If I go this way, what can go wrong?” Okay, now I’m going to go this way. If one of those things goes wrong, consequence thinking, right. “If one of those things goes wrong, what’s my course of action then?” So if I’m making a decision with incomplete information, as I’m making that decision and giving that command, I’m thinking about how I’m going to deal with the collateral damage if that was the wrong decision ’cause that’s next. You make a bad decision, you can’t just go, “Oh shoot. Wow, darn.”

Tim Ferriss: Tough look. Yeah.

Cathy Lanier: You’ve got to — right, fix it, fix it, fix it, fix it. What are you going to do about it now? How are you going to fix it?

Tim Ferriss: So just a few more questions and then let you get back to your very busy day. If you could put, this is metaphorically speaking, like a message on a billboard or have a reminder on your desk that everybody sees when they come in. It could be a quote, could be a mantra, could be anything. If you could put it on a billboard for millions of people to see, what might that be? I mean, is there anything that comes to mind? Could be someone else’s quote, could be something that you try to live your life by, could be something you want everybody who’s within your organization to be reminded of, or it could be something else entirely. Does anything come to mind?

Cathy Lanier: I mean, I tell people all the time, bad things happen to everybody. Bad things happen to everybody. And a lot of times it’s we do it to ourself. We make bad decisions, bad things happen to us because of ourselves. Bad things happen to everybody. It’s not about the bad decision you made or the bad thing that happened to you; it’s what you do after that. So it’s easy to have some tragedy or some terrible thing happen to you and sit around and feel sorry for yourself or become a victim or let it define you. It’s your attitude and your effort that you put into how you recover. So it’s not what happens to you. It’s not the bad thing.

It’s how you handle those things that really matter in life because you can have one of two attitudes every time something bad happens, which attitude are you going to pick? For me, it’s going to be, I wish that never had happened. I wish I’d never made that decision. I wish that had never happened, but you know what, I’m going to fix it. I’m going to not let it define me. I’m not going to let it take me down.

Tim Ferriss: Well, Cathy, I mean, I think that’s a pretty strong way to land this plane. I’m so —

Cathy Lanier: You have the coolest job, by the way.

Tim Ferriss: It’s so fun.

Cathy Lanier: I can’t imagine how much you get to learn talking to so many people and you must have an encyclopedia in your brain.

Tim Ferriss: It’s the best job. And it didn’t come from some big long-term plan. It was kind of zigging and zagging with, frankly, I mean, tying into what you said, some really — in retrospect, with the information I had at the time, there were good decisions about various things, starting books, but made some terrible decisions on deadlines where there were kind of suicide missions and ultimately just adapted and tried to make the best of a sequence of, I would say, in retrospect, kind of poor decisions led to one of the best decisions, which I never thought would become this. And here we are. And thanks for —

Cathy Lanier: Good for you.

Tim Ferriss: Thanks for being willing to do the dance and play some improv jazz in this conversation. Is there anything else you’d like to say or add, suggest to people, request of people, anything at all before we wind to a close?

Cathy Lanier: No, just was a fascinating couple of hours with you. I’m an avid follower and really enjoyed my time here, so thank you for including me.

Tim Ferriss: Oh, definitely. Cathy, thank you so much. I hope we get to see each other at some point. Who knows? Might get to your neck of the world. Probably will, actually.

Cathy Lanier: Please let me know if you do. New York or DC, look me up.

Tim Ferriss: I’m in both. So I’ll keep you posted. Thank you again for the time.

Cathy Lanier: Okay. All right.Tim Ferriss: And for everybody listening, we’ll have show notes, links to everything that we talked about at tim.blog/podcast as per usual. Just search for Cathy and you will find this episode. Until next time, be just a bit kinder than is necessary to others, but also to yourself. Thanks for tuning in.

DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:

WHAT YOU’RE WELCOME TO DO: You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the tim.blog/podcast URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.

WHAT IS NOT ALLOWED: No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on tim.blog or (obviously) license photos of Tim Ferriss from Getty Images, etc.

The post The Tim Ferriss Show Transcripts: Cathy Lanier, NFL Chief Security Officer — From Food Stamps to the Super Bowl War Room (#862) appeared first on The Blog of Author Tim Ferriss.

Cathy Lanier, NFL Chief Security Officer — From Food Stamps to the Super Bowl War Room (#862)

2026-04-24 05:21:33

Cathy Lanier serves as the chief security officer (CSO) for the National Football League (NFL). As the league’s CSO, she supervises all operations and activities of the NFL Security Department—overseeing coordination with the league office and all 32 clubs and working with federal, state, and local law entities to ensure the security of the NFL’s venues, fans, players, staff, and infrastructure.

Prior to her work at the NFL, Cathy served as chief of police with the Washington, D.C., Metropolitan Police Department (MPD) from 2007 to 2016, becoming the first female police chief of the nation’s capital, the first commanding officer of Homeland Security and Counter-Terrorism for D.C. Police, and the longest serving chief on the D.C. force. Her innovative strategies were credited with reducing violent crime in Washington by 21 percent from 2007 to 2015, while the city’s population grew by 15 percent.

Cathy is a graduate of the FBI National Academy and the United States Drug Enforcement Administration’s Drug Unit Commanders Academy. She holds bachelor’s and master’s degrees in management from Johns Hopkins University and a master’s degree in national security studies from the Naval Postgraduate School in Monterey, California.

Please enjoy!

This episode is brought to you by:

Eight Sleep Pod Cover 5 sleeping solution for dynamic cooling and heating: EightSleep.com/Tim
Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: Shopify.com/Tim
Helix Sleep premium mattresses: HelixSleep.com/Tim
Wealthfront high-yield cash account: Wealthfront.com/Tim

Books, people, tools, and resources mentioned in the interview

Cathy Lanier, NFL Chief Security Officer — From Food Stamps to the Super Bowl War Room

Additional podcast platforms

Listen to this episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

Transcripts

SELECTED LINKS FROM THE EPISODE

Connect with Cathy Lanier:

Books

Biohazard: The Chilling True Story of the Largest Covert Biological Weapons Program in the World—Told from Inside by the Man Who Ran It by Ken Alibek and Stephen Handelman
Blink: The Power of Thinking Without Thinking by Malcolm Gladwell
Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink and Leif Babin
The Tipping Point: How Little Things Can Make a Big Difference by Malcolm Gladwell

People

Companies, Institutions, & Organizations

Center for Domestic Preparedness (FEMA)
FBI National Academy (FBI)
Johns Hopkins University (JHU)
Metropolitan Police Department of the District of Columbia (MPDC)
National Football League (NFL)
Naval Postgraduate School (NPS)
Nevada National Security Site (NNSS)
Prince George’s Community College (PGCC)
Promark Partners
US Drug Enforcement Administration (DEA)

Events & Cases

Tools, Technologies, & Chemical/Biological Agents Referenced

Palm Treo
PalmPilot
Sarin
Text the Police: 50411 | Metropolitan Police Department of DC
VX (Nerve Agent)

Concepts

Timestamps

[00:00] Start.
[01:38] Cathy Lanier: from Tuxedo to the top.
[03:22] Dad vanishes; Mom holds the line (and takes shorthand to the TV).
[08:08] Bused into DC: straight-A student turns chronic truant.
[10:37] Married at 15, signed over for $100 off child support.
[12:54] The baby-in-the-crib wake-up call.
[16:37] GED by a single point; secretary by day, waitress by night.
[20:18] The Washington Post ad that changed everything.
[20:39] 1990 MPD: into the crack cocaine wars.
[23:46] Grandma’s gospel: no excuses, damned for doing.
[26:23] Mount Pleasant riots: trial by brick, and a better-way epiphany.
[33:23] Donny Exum’s nudge — and sergeant at 26.
[38:56] Being a woman on the ’90s force: harassment and the 90-day dodge.
[49:38] Marion Barry exits, Chuck Ramsey enters.
[51:08] Lieutenant: the sweet spot. Captain: the desk (but keep the cuffs).
[56:58] 9/11 and the surprise transfer to Special Ops.
[58:07] Mentors lend confidence — and a counterterrorism bureau built from scratch.
[1:00:14] Live Sarin, VX, and training with bioweapons legends.
[1:02:22] Text the 50, get the 411: the tip line gambit.
[1:03:36] Cultivating sources: the white Escalade payoff.
[1:09:02] Attention to detail: OCD as a superpower.
[1:10:43] Teletubby pagers to smartphones — and the Thomas Maslin reckoning.
[1:15:14] NFL security: the scope of “everything.”
[1:17:10] Red teaming, explained.
[1:18:53] NFL vs. MPD: diversity and complexity that goes to 11.
[1:21:24] The book club: The Tipping Point and Blink.
[1:23:32] Decisions under pressure — and with incomplete information.
[1:28:34] Billboard wisdom: it’s not what happens; it’s what you do.
[1:30:08] Parting thoughts.

CATHY LANIER QUOTES FROM THE INTERVIEW

“You’re going to be damned if you do and damned if you don’t. You better be damned for doing.”

— Cathy Lanier

“I’m not an excuse person. I don’t make excuses. If I find myself in a bad situation, I did something to get myself here and I’m going to get myself out.”

— Cathy Lanier

“What a mentor does for you is they lend you confidence that you don’t have.”

— Cathy Lanier

“To me, arrest stats are not a good measure of success for a police department.”

— Cathy Lanier

“Effective communication, both verbal and written, is critical for professional success. And it is a skill that develops over time, the listening part of it more importantly than the communicating part.”

— Cathy Lanier

“Bad things happen to everybody. It’s not about the bad decision you made or the bad thing that happened to you; it’s what you do after that.”

— Cathy Lanier

This episode is brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. Go to Shopify.com/Tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting Shopify.com/Tim.

This episode is brought to you by Helix Sleep! Helix was selected as the best overall mattress of 2025 by Forbes and Wired magazines and best in category by Good Housekeeping, GQ, and many others. With Helix, there’s a specific mattress to meet each and every body’s unique comfort needs. Just take their quiz—only two minutes to complete—that matches your body type and sleep preferences to the perfect mattress for you. They have a 10-year warranty, and you get to try it out for a hundred nights, risk-free. They’ll even pick it up from you if you don’t love it. And now, Helix is offering listeners 20% off all mattress orders for a limited time at HelixSleep.com/Tim.

This episode is brought to you by Eight Sleep. Temperature is one of the main causes of poor sleep, and heat is my personal nemesis. But a few years ago, I started using the Pod Cover, and it has transformed my sleep. Eight Sleep has launched their newest generation of the Pod: Pod 5 Ultra. It cools, it heats, and now it elevates, automatically. With the best temperature performance to date, Pod 5 Ultra ensures you and your partner stay cool in the heat and cozy warm in the cold. And now, listeners of The Tim Ferriss Show can get $350 off of the Pod 5 Ultra for a limited time! Click here to claim this deal and unlock your full potential through optimal sleep.

This episode is brought to you by Wealthfront! Wealthfront is a financial services platform that offers services to help you save and invest your money. Right now, your cash can earn 3.30% APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account from its network of program banks. That’s 8 times more interest than a typical savings account at a bank, according to FDIC.gov as of 1/22/2026 (Wealthfront’s 3.30% APY vs. 0.39% average savings rate). Right now, for a limited time, Wealthfront is offering new clients that use my sign-up link an additional 0.75% boost over the base rate for three months, meaning you can get up to 4.05% APY, limited to $150,000 in deposits. Terms & Conditions apply. Visit Wealthfront.com/Tim to get started.

The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC (“WFB”), member FINRA/SIPC. Wealthfront Brokerage is not a bank. The 3.30% Base APY on cash deposits is as of January 30, 2026, is representative, subject to change, and requires no minimum balance. The overall boosted rate is subject to change if the base rate decreases during the three-month promotional period. Tim Ferriss, who’s not a client, receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage LLC, which creates an incentive that results in a conflict of interest. Tim expresses his own opinions and Wealthfront does not endorse, sponsor, or promote them. This ad may not reflect the experience of other Cash Account clients, and similar outcomes are not guaranteed. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, not bank-guaranteed or FDIC-insured, and may lose value. See full disclosures here.

Want to hear another episode with the author whose books became required reading for Cathy’s command staff? Listen to my conversation with best-selling author Malcolm Gladwell, in which we discussed the ideas behind The Tipping Point, Blink, and Outliers, creative “recipes” for storytelling, his years at The Washington Post, lessons from Revisionist History, taking and organizing notes, the advantages of disadvantages, flaws that turned into strengths, writing in noisy public places, and much more.

The post Cathy Lanier, NFL Chief Security Officer — From Food Stamps to the Super Bowl War Room (#862) appeared first on The Blog of Author Tim Ferriss.

The Tim Ferriss Show Transcripts: 4-Hour Workweek Success Story Brian Dean — From Dad’s Basement to Selling Two Companies (#861)

2026-04-17 02:12:09

Welcome to another episode featuring a 4-Hour Workweek case study—a conversation with someone who has read the book, applied it, and built a life and a businesses I never could have imagined. In this episode, we have Brian Dean, the founder of Backlinko and Exploding Topics, both acquired by Semrush, which itself was recently acquired by Adobe for $1.9 billion. We cover geoarbitrage, testing assumptions cheaply, building a muse, automating income, and—the chapter almost everyone skips—Filling the Void.

Full introduction

Legal conditions/copyright information

4-Hour Workweek Success Story, Brian Dean — From Dad’s Basement to Selling Two Companies

Additional podcast platforms

Listen to this episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

Tim Ferriss: Brian, nice to meet you finally. Thank you for taking the time.

Brian Dean: Hey, great to be here.

Tim Ferriss: Brian, where should we begin? I’m thinking maybe because the impetus for this is somewhat around the connective tissue of The 4-Hour Workweek, should we just begin with how on earth you and The 4-Hour Workweek intersected? Maybe we start there?

Brian Dean: So it intersected at a really weird and sort of low time in my life where I had just started a PhD program at Purdue and I basically hated it. It was just overall not great experience. I went in gung ho, “I’m going to be a scientist,” and all this stuff. And then the hard reality of pipetting in a lab and having an advisor, breathing down your neck was like, “I can’t do this anymore. I’m out.” So my plan was to get a job because I had a degree. I was like, “Let me get a job as a dietician.” Unfortunately, that didn’t really work out and I ended up in my dad’s basement.

Tim Ferriss: What was the timing of this? This was what year, roughly?

Brian Dean: This was 2008. So I think the book was relatively new then.

Tim Ferriss: Yeah. 2008, that would’ve been a year after publication, let’s just say. And also not exactly the hottest job market for people who may not recall. It was a tough time overall because of the financial crisis.

Brian Dean: Totally unbeknownst to me as going to graduate school, spending most of my time at bars, drinking, the great financial crisis was over my head. Never heard of it until I started to get a job. And suddenly it became very real, very fast. So basically I was in my dad’s basement, broke, no girlfriend obviously, no real prospects. I’m just kind of lazily applying for jobs every morning and just sitting around and watching Jerry Springer in the afternoon. That’s pretty much my day.

And then one day I have an idea. I’m like, “I should start something.” I don’t know where this came from. I’m like, “I should start a search engine for nutrition questions. When people ask how much vitamin C is in a carrot, it’ll just give them the answers.” This is basically what an LLM would do way before and someone that’s not remotely qualified to come up with something like this.

So I was like, “How do I start a business?” It’d never crossed my mind before. I literally thought starting a business was like in The Office when Michael Scott gives this lecture and he’s like, “First, you need a building.” So I’m thinking this is this huge undertaking I’m about to do. So I go to the bookstore to find a book to help me get started. And I basically saw The 4-Hour Workweek, grabbed it, and it just sort of spoke to me.

Tim Ferriss: What happened after that?

Brian Dean: It blew my mind. I read the book. I’m like, “Well, I could start a business.” It was just a crazy, mind-blowing concept that someone has no experience was totally broke, could start something, not necessarily be a smash hit, but you could start something. So basically I just followed the book exactly as it was written. I mean, I literally had notes in the margins. You had those little Q&As at the end or little steps at the end. I would make sure I wouldn’t go past that page until I did everything. I was like, “I’m not going to…”

Tim Ferriss: My dream reader.

Brian Dean: I was like, “I’m not going to go to the next page until I’m good and ready.” So basically I followed the plan and then created an ebook about nutrition, how to help your back pain with nutrition.

Tim Ferriss: And we have so much to cover. I know I’m cheating a little bit, but I think it’s fair to say that your first attempt did not turn into the mega hit that you might’ve hoped.

Turns out it’s hard to get traffic, right? Or it can be hard to get traffic. And if you don’t have a budget for paid ads, well, I guess necessity is the mother of invention or at least learning. And just I want to add a sidebar here, which is this is so fucking common. It is incredibly common that you basically have your sort of first love/relationship. Seldom works out, right?

Brian Dean: Yeah.

Tim Ferriss: But you learn a lot and that leads to something else. But tell us about what you learned and how you adapted to that first experience.

Brian Dean: I spent all this time on creating a product that I thought was helpful, I thought was good. And then it was like, “Now what? How do you get people to actually see this thing?” And like you said, Tim, there’s paid ads, which wasn’t really something that I could do considering I was broke in my dad’s basement, having Dinty Moore beef stew for dinner every night, or so called free traffic, which I was like, “What? Free traffic? How does that work?” So of course I went all in on that and eventually sort of stumbled on this thing called “Search Engine Optimization,” which was like, you can rank in Google and people who are searching for what you sell, you can get in front of them. And I was like, “Oh, I’ve used Google.” And I never really understood that there was this whole world behind the scenes, figuring out how it works, trying to game the algorithm and stuff. And that sent me down the path of learning this thing called SEO.

Tim Ferriss: Also, I would say, just to paint a picture for folks, because I remember looking at this when I started my first, let’s call it real business, also out of necessity when everybody at the startup I joined got fired in 2000, 2001, not a great time for most dot com companies. So I was working off of my soon to expire COBRA healthcare in California and eating also microwave dinners. Or I remember I had a couple of favorites at Jack in the Box, which was in the parking lot of a Safeway. So that was my nutritional intake. Very similar, it sounds like, right? But slowly figuring out the mechanics behind these things that we use every day, right? And you took it certainly a lot further than I ever did. And it’s the Wild West, right? I mean, SEO can be, especially those days, kind of the Wild West.

So you built up a huge kind of portfolio of domains, it seems like, something like close to 200 or over 200. What was the game plan? When you started getting into SEO and then flashing forward, what was the sort of plan in terms of revenue generation?

Brian Dean: The idea was you’d have these one-page websites rank and then you’d have AdSense display ads on each of those. And back then, it was sort of a loophole that if you had a domain that matched the keyword exactly, then it was a massive advantage in the search results. So I would have lorealshampoo.org and I would just write a thousand words about why L’Oreal shampoo is great, which I obviously don’t really know a lot about.

Tim Ferriss: For those who can’t see the video, we are both completely bald. Yeah.

Brian Dean: And then putting AdSense ads on the pages times 200, and the idea is that you scale up enough and take a few steps later, you’ve got a private island or something.

Tim Ferriss: Yeah, right.

Brian Dean: That was the plan.

Tim Ferriss: Right. ABC dot dot dot M and then private island. So let’s backstep for a second because we can talk about the business and the business experiments and adventures, which we will, and misadventures, a.k.a. Panda Death, which we’ll probably get to. But if we’re looking back to your reading of the book, there are a couple of different directions as a choose your own adventure map that you can take. And part of that oftentimes is figuring out your target monthly income, doing exercises like Dreamlining, which people can find for free to figure out exactly what it is that you are building as a lifestyle and the things you want to do, et cetera. And you come up with this very precise, not necessarily accurate, but it’s a starting point number, right? Where were you when you’re going through all of this? Because you can build a business for the sake of building a business and generating all this cash, but then the question is, what do you do with that?

How does it inform your life? Were you thinking about that stuff at the time or was it just get out of the basement, and eat something besides the Dinty Moore stew?

Brian Dean: Have a proper meal. Yeah, exactly. Have a meal that’s not out of a can. So I just wrote that in the whole dreamlining section that was basically what I wrote. It changed. It morphed a little bit. At first it was that. And then during this building the 200 websites at some point, I was in Asia backpacking and then my whole world changed to 3k a month. I was like, “If you can get 3k a month in Thailand, you can live like a king.” So my whole goal just became to get 3k a month passive income. That was my entire focus. So it sort of shifted once I had sort of a lifestyle that I tried and liked, I was like, “Oh, I could live like a backpacker. I can do this.” So then it just became 3k a month for a long time. For, like, a year.

Tim Ferriss: For a year. Did you hit the 3k a month before the Google slap, which may be one and the same as the Panda update, I’m not sure. Maybe those are two separate things entirely, but where were you before things got pretty strongly corrected?

Brian Dean: Yeah, it was maybe a 3k a month around there for like a couple months. Had a good ride and then it kind of got slapped. Didn’t last long.

The first was a Panda update, as you mentioned, which was a very content-focused update. That was where —

Tim Ferriss: By Google.

Brian Dean: By Google. It was an update that basically was, “If your content is thin or repetitive or not helpful, we’re going to wipe you out.” And it was like one day they push a button and thousands of websites get completely obliterated, including mine.

Tim Ferriss: That’s a rough — where were you when this happened? Do you remember when you got the news?

Brian Dean: That first one… I got slapped twice. The first time didn’t scare me straight enough. So I went back to the — I was like, “Oh, I’ll just do a different type of black hat SEO and I’ll get away with it.” It didn’t work. So that one, I think I was in Thailand when it happened.

Tim Ferriss: So let’s then go to, you get scared straight as you put it, and you build your first, as I think you’ve put it, real site, right? Which isn’t L’Orealshampoo.org. It’s something else. When you decided to hop to the white hat side of things, what did you end up doing and why?

Brian Dean: So there was that first update and then a second update where I was in Spain and Granada and I went to my hostel, I checked the laptop and it was like, again, it was like a repeat of the Thailand experience. Everything dropped. This was a different set of websites that got knocked out. And I was like, “You know what? This is crazy. Why am I doing this? This is an insane way to live.” So then I was like, “I’m going to build this one real website.” And I was kind of inspired because there were these forums at the time with these marketing people and they were basically like, “Spam, spam, spam.” And there were a couple voices in there of people who were like, “Guys, build a real business. What are you guys doing? Build something real that’s durable, that’s not 100 percent reliant on Google.” And I kind of ignored those people.

And then once I got hit that second time, I was like, “Okay, it’s time to build something real.” So I basically built a sort of real site in the personal finance space, wrote real blog content, didn’t do any shady spammy stuff and tried to keep it on the up and up.

Tim Ferriss: And what is the bridge or what happens between that and then building Backlinko? How do you end up segueing? I mean, I guess this could be a very fast montage in the sort of fictionalized movie of your life, but what happened to go from there to Backlinko, which ultimately you ended up getting acquired? What transpired between those two?

Brian Dean: So once a site started to get a little bit of traction, I was like, “Wow, this is a whole world I didn’t know about. Real marketing, white hat SEO.” And it was fun. It was working and it was more enjoyable because I didn’t have to look over my shoulder that I was going to get hit with an update next week. And it was cool because I’m reaching out to other websites and they’re like, “Oh, this is really helpful,” And they’re linking to me. I’m not paying for links. They’re just naturally doing it. And I’m like, “How do I learn more about this?” This whole world opened up. I’m like, “How do I get better at this?” And all the advice that I read on all these white hat SEO blogs were basically vague advice, create great content, build relationships with other people, market your site in a — yeah.

What do you do with that?

Tim Ferriss: Lead with integrity. You’re like, “Okay, what’s my next step?” Very unclear.

Brian Dean: Exactly.

Tim Ferriss: All right.

Brian Dean: It was as vague as you could imagine.

Tim Ferriss: Then Backlinko is a case of sort of creating the thing that you couldn’t find?

Brian Dean: Exactly.

Tim Ferriss: Is that a fair way to put it?

Brian Dean: Yep.

Tim Ferriss: One thing that I saw here in the prep notes, which I was like, “Oh, that’s so smart,” and I wanted to highlight it is — there are a number of things, obviously, that you ended up doing really well that seemed to have set the stage for a lot of things that came. One of them was digging through Google Patents and engineer statements. And I’ll come back and expand on why this is smart, but it’ll probably become very obvious once you explain why you did it. Why were you digging through Google Patents and then engineer statements, are those part of the patents or are those something separate?

Brian Dean: Separate.

Tim Ferriss: Okay. So could you explain what you were doing?

Brian Dean: When I launched Backlinko, I was like, “There must be other people like me who are getting into this whole world of white hat SEO. They want to learn more about it and they’re disappointed about what’s out there.” And it turns out there was. I just didn’t know how to reach them at first. So I basically followed the same advice that I read for starting a blog, which was, you need to publish every week or every other day, and that’s how you build an audience. You just publish and pray that people come. So that’s what I did.

Tim Ferriss: People still give that advice. Publish and pray. Yeah, exactly.

Brian Dean: So yeah, I did that and banged my head against the wall. And I was like, “You know what?” I came up with an actually creative idea for a post that would be really special instead of just the stuff I was putting out every week, which was good. It was definitely actually decent to give myself some credit, but it wasn’t anything that’s going to grab you by the shirt and be like, “I need to read this.” It was just slightly above average and what was out there. I was really going on that consistency play. “If I do this consistently over time, there’ll be like a secret society that will just send me traffic as a reward for being so consistent.” I didn’t really have the whole thing planned out, to be honest. I just knew consistency equaled traffic at some point, and it honestly didn’t for me.

So I had this idea for a post, which was Google recently had said that there’s 200 ranking factors in the algorithm. So I was like, “Let’s just try to find them.” Obviously a lot of it’s going to be conjecture and guessing and speculation, but let’s just do a list of 200 instead of the list of 10 or 20 that I’d seen out there. And then I got to like 55 and I’m like, “Man, you have to really dig to find some of these.” And that’s when I went through the Google Patents and also people would interview Google engineers or they would give statements about, they’d be at a conference and they would give a talk and one of the slides would mention a ranking factor that they’re considering. So it took a lot of digging. It took like 20 to 25 hours to complete. this single post.

And that’s really why I was digging into all this stuff.

Tim Ferriss: And I just want to add an addendum to that, which is people who have not heard of this approach, for some folks they’ll be like, “Oh, I or someone else has done that.” But it is incredible what you can learn through reviewing patents and looking at very niche events, industry events for videos and transcripts of presentations. This was incredibly valuable when I was getting started as well, mostly looking at kind of closed door or very small event presentations and things like that. All right. So I guess that was sort of a massive post that you really invested in. I mean, 25 hours is not trivial, right? I mean, that’s a lot more presumably than you’re putting into the kind of publish and pray consistent approach to just sliding a plate with content salad out the door and hoping that leprechaun’s going to show up and trade for a pot of gold, right?

So what was the response to that post?

Brian Dean: Massive traffic and controversy, kind of everything you want in a piece of content, to be honest. I mean, you had the traffic, you had people, the wow factor, and then you had the controversy, which is like, “Those aren’t Google’s 200 ranking factors, no one knows those.” And then people saying, “Well, this is at least trying to come up with something,” and then people saying, “Well, they shouldn’t do it.” So there’s a perfect little debate around it that was pretty lightweight. It’s not anything super controversial, but just enough to get people’s attention. So yeah, brought in, I mean, I would say I was probably getting 150 visitors a month, that probably brought in a couple thousand when I first put it out. It’s brought in a million since then.

Tim Ferriss: What did you then follow that up with in terms of lessons learned, coming up with new rules for yourself in terms of how you were going to approach the business? How did that inform things going forward once you saw that response?

Brian Dean: I just threw out the whole playbook I was doing. I was using this consistency thing. I would even have on Fridays, I would have like a Q&A, I would just put five questions and answer them. And of course I wasn’t getting any questions, so I just completely made them up and then answer my own questions, just to have something to put out there. And I’m reading it. I’m like, “Why would anyone want to read this?” So then I just scrapped the whole thing and was like, “I’m just going to put out something once a month and it’s going to be the best thing on that topic that’s ever been written by 10x.” And that was sort of how I totally changed my content focus to quality over quantity.

Tim Ferriss: So you had a fun YouTube video on ultimately the acquisition of Backlinko. And I guess the original email you got was like, “Hey, we’d love to connect to collaborate.” And you’re like, “Well, that smells like every bullshit spam email I’ve ever received.” So you just ignored it, right?

Brian Dean: Yep.

Tim Ferriss: As I remember. And we won’t spend a ton of time on this, but what is Semrush? This is the acquirer ultimately, but for people who don’t know, what is Semrush?

Brian Dean: They’re essentially a marketing platform that help you get better results from SEO, pay-per-click, and also now AI search.

Tim Ferriss: And are they private, publicly traded? They’re publicly traded, right? Yeah. It looks like on the New York Stock Exchange.

Brian Dean: They got acquired by Adobe last year, so they will be part of Adobe, I think, sometime this year when everything goes through.

Tim Ferriss: Got it. And they acquired you ultimately while they were public, right?

Brian Dean: Yes.

Tim Ferriss: I mean, there’s so many good aspects to this, but do you want to tell the story about flying to Boston? I mean, eventually this contact, I can’t remember his name, but since you ignored the first email he wrote and they basically said, “Hey, look, we might be interested in buying your company. Let me be direct.” And you’re like, “Okay, I’ll reply to that one.” But can you tell the story of flying to Boston? I think it’s pretty funny. I also liked in your video when you said, “Up to that point, I hadn’t sold anything, except for maybe a used car.” I think you said something like that. I was like, “That’s a pretty good line.” Okay. So the first Boston trip, what happens there or what’s in your mind?

Brian Dean: In my mind, I’m like, “We’re going to close this thing. Let’s go to Boston.” It was really a meet and greet where the executive team just wanted to meet me and chat about, see how it could help them, how Backlinko could fit into their platform and their business. And so I spend the day with them in the office and then afterwards we all go out to drinks to celebrate the deal, and I’m shitting myself. I’m like, “What? We’re celebrating the deal now. I never saw a contract or an agreement or anything.” I’m like, “We’re going to sign it tonight.”

So we go out and we’re at Legal Sea Foods just taking shots, “Yeah, this is great, Brian. This is going to be the best thing ever.” And I’m thinking, “Where’s the contract? When are we going to sign?” I really thought right there they’re going to buy this company —

Tim Ferriss: “Did I miss something? Did I black out? What happened?”

Brian Dean: Exactly. I’m like, “Did I agree? Is a verbal agreement enough for a deal like this?” So yeah, that was definitely — I was way off on that. It took two more months of due diligence after that meeting for the deal to actually close.

Tim Ferriss: You said two months?

Brian Dean: Yeah.

Tim Ferriss: Which, for people who have never gone through it, it can be very challenging if you don’t have your ducks in a row, which almost nobody does unless they’ve kind of been through this before or are venture backed and they have people overseeing all this stuff. Two months is pretty good, right? It’s painful, but man, due diligence can go on forever. For people who are starting a company, maybe they never intend to sell it, but hey, you had not gone into Backlinko thinking that you were going to sell it, right? But they want to preserve the optionality.

I remember coming across, and I haven’t read it in a long time, but a book by John Warrillow called Built to Sell, which talks a bit about this. And I thought it was actually very good, a very kind of, I don’t want to say basic, but pretty sort of foundational primer for some of this stuff. But what advice would you give to folks? I mean, one comes to mind, which I have also had to learn the hard way about independent contractors, but what are some of the tenets or sort of commandments of like, “Hey, just in case one day you want to sell this thing, here are a couple of things that I learned.”? Anything come to mind?

Brian Dean: Independent contractors, for sure. Maybe you can expand on that, Tim, because you have experience with that.

Tim Ferriss: Look, if you ever want to sell something, the acquiring party is going to want to know with some assurance, and they’ll have reps and warranties in the agreement that basically say, “Hey, if you miss something or you’re not telling us the truth, there’s going to be a world of trouble and we’ll probably be able to back out of the deal and take all the money back.” But they want to know that everything they’re buying is free and clear, right? So if you’ve had, as I have and as you have in some cases, well, I’ll just speak personally, always maintained a very small full-time team, but have used dozens and probably hundreds, certainly hundreds of contractors over the span of decades. And if you’re building something and they want to see, they meaning the acquiring company, every single contract to make sure that someone isn’t going to come out of the woodwork and say, “Hey, I own a part of that. Hey, I contributed to this and therefore I am entitled to a piece of equity. Yada, yada, yada, yada.” Which if the deal’s big enough, come out of the woodwork no matter what. You see this with a lot of tech IPOs and stuff. As soon as they file the S1 getting ready to IPO, then some rando comes out of the woodwork and says, “I’m the seventh co-founder.” And you’re like, “What? No one’s ever heard of this person.” And they just want nuisance money to go away.

So that’s the relatively short and sweet on independent contractors. This is going to be true also with pretty much any agreement or contract, right? You just want to document, document, document, make everything formal. No verbal, no handshake. If you want to preserve the option to cleanly and hopefully relatively quickly sell a company later. Anything else that you would add to that, Brian?

Brian Dean: If you don’t have your finances in order, like you don’t get P&Ls, that is something they obviously will care a lot about. And I was good. Luckily I had a good accountant that did that stuff, so that wasn’t a big deal. The number one time sink for me was the independent contractors. I mean, I’m like you, I hired so many people that did one, like created a blog post image or something or like a social media image once for like 10 bucks and I had to go try to find them. Basically I have to hire, almost like a private investigator to find these people because you don’t even barely remember them. And even people that ghosted me. I had people that I paid a deposit for work and they never even replied. They totally, they ghosted me.

And I still had to reach out to those people. Of course, they’re not going to reply, but you have to show that you tried. And then obviously since this experience, every contractor that gets hired signs an ironclad agreement that says, “You don’t own any of this work. Once you’re paid, it’s a property of blah, blah, blah.” And yeah, that made things a lot easier the second time, but I had no idea this independent contractor thing was so important to the acquirer, but absolutely is.

Tim Ferriss: Yeah. And so we won’t spend a ton of time on sort of what followed, but there was one funny anecdote about the public announcement. Could you just explain that given the time zone differences? I thought that one was great.

Brian Dean: Time zone differences and I’m like early to bed kind of person. So they told me that, “Hey, Brian, we’re going to announce this tomorrow and we’re going to announce it at 5: 00 p.m. Eastern.” And I’m like, “Oh man, I don’t know. Is it possible to send it earlier? That’s like 10: 00 p.m. here. I’m already kind of getting ready for bed.” Basically say, “I’m in my PJs at that point. Is it possible to push this earlier?” And they said, “No, because it’s a public company due to SEC rules, we have to make these announcements after the market’s closed.” Yeah, I was so embarrassed. I was like, “Oh yeah, right. I forgot the league I’m playing in here.”

Tim Ferriss: So you sell the company, presumably there’s some type of earnout or period of time for which you’re required to still work on Backlinko, right? Who knows what the exact terms are of that, but for people who’ve never gone through it, right, you can have a vesting period, you can have an earnout where you get X percentage of the total purchase price based on hitting or exceeding X, Y, and Z metrics or whatever, right? So there’s a period of time like that. Post acquisition, let’s just say, because I know that was very stressful and you started grinding your teeth and that kind of evaporated as soon as the deal was done. Let’s just flash forward two or three months after the acquisition. What does your life look like? What does a week look like for you?

Brian Dean: It’s honestly not that different because I had another startup that I was already working on. So I was basically running on a treadmill and then I just hopped onto another treadmill that was right next to it and just kept going. So there wasn’t a whole lot of downtime to really reflect or analyze. That one day that the announcement was made, especially the next day, because it was late here. So the next day was really when I was sending messages to people and stuff and getting congratulations and whatnot. But after that day, I was pretty much back working on the next thing, like, didn’t reflect too much on it. So my life was more or less the same one day after. Yeah.

Tim Ferriss: Looking back, are you basically like, “Hey, I’m a border collie. I need to work or I’m going to go crazy. So I’m glad I did that.” Do you wish you had approached it differently?

Brian Dean: I kind of wish I approached it differently. Yeah. And looking back, I wish I took some time off. It was just tricky because you know how it is. When you have a startup, it’s kind of a strange situation. I had a new company that was growing. I had this old company that I sold and it felt weird to say to the new team like, “Hey guys, I need to reflect about how great my life is. I need to chill out. You guys still work though. You work your assess off. I’m going to sit on the beach for a while.” So it felt a little weird. I felt like I kind of had to go back into the trenches with them right away, almost even more so to prove like, look, I’m not done. I’m not going to rest in my laurels. We’re still in it to win it.

Tim Ferriss: Financially at that point, were you focused on the new company, Exploding Topics, because you wanted to get to that sort of big pot of gold at the end of the rainbow? What was the driver behind that? I don’t know to what extent you were sort of financially stable, had savings. We don’t have to get into all the nitty-gritty if you don’t want to, but I’m just curious, what was driving the involvement in the new company for you?

Brian Dean: It wasn’t really a hundred percent financial. When I sold Backlinko, before then I was probably okay for most of my life. Then when I sold Backlinko, it was like, okay, I’m probably good forever. And then I wouldn’t have probably started something else right away if I hadn’t already. So, towards the end of Backlinko’s, when I was involved with it before I sold, I was honestly getting a little bit bored with it. I was bored talking about the same things, writing about the same things, doing the whole course launch thing, and I kind of wanted something new. And I saw an opportunity where there were more trends than ever, but I couldn’t find a good tool for curating them that was like, here are all the trends in this space right now. There was Google Trends, which is fantastic if you know about a topic and you want to see how it’s trending, but what about a trend you’ve never even heard of?

And that’s sort of where I realized the opportunity was. So it wasn’t really purely financial. It was more like, this is kind of exciting and new. I think it’s a good opportunity as well, and it’ll give me something to do between these sessions with Backlinko, which was, it was also boring because it was so optimized. I work three hours a week. It was like 4-Hour Workweek, honestly, at the end. It was getting so much traffic on autopilot. The launches were really easy to do. Even courses were easier to create at the end because I just had it all down to a science. Even if it was a totally different topic, I knew exactly how to create a course. So the challenge wasn’t really there. And this was like, okay, new challenge, new space. And that’s basically, it wasn’t so much financial, it was more just to freshen things up and to try something new.

Tim Ferriss: Yeah. And you’d also already committed to other people, right, with this new startup. So it makes a lot of sense. When you had, with Backlinko, so much on autopilot, the three hours per week, right, what were you doing with the rest of that time? Because the most, and we don’t have to dig into the book too much here, but if I had to point to one chapter that people pay no attention to, because typically they’re like, “Oh yeah, that’d be a nice problem to have,” and they forget about it, is the “Filling the Void” chapter.

Brian Dean: Yeah.

Tim Ferriss: “Filling the Void” chapter, 4-Hour Workweek is really important so you don’t go into psychological free fall, among other reasons. But what were you doing with the rest of your time if Backlinko at one point, right, when the flywheel was really spinning, was only occupying or requiring three hours a week?

Brian Dean: Yeah, I was bored, honestly. I wasn’t filling it well. I wasn’t filling the void. I was basically going to the gym, reading books, playing video games, nothing, and I think that was part of this and we, this boredom was I needed to reread that chapter essentially and fill this with something meaningful. And I think that’s why I was seeking another startup project because I’m like —

Tim Ferriss: Yeah, 100 percent. Yeah.

Brian Dean: It was like, I need to work. I need to build something. I’m not building this. I’m just maintaining it. And so that’s really what got me into Exploding Topics. So honestly, the filling the void chapter, the whole filling the void concept, I really only took seriously recently, but before then I basically filled it with sort of nonsense to be honest, and then started another startup.

Tim Ferriss: What were some of the things you did differently with Exploding Topics after all of the experience with Backlinko? And maybe things that in retrospect you’re like, “Wow, that was a really smart decision and change.” And maybe somewhere you’re like, “Hmm, okay, lesson learned. Right. Would probably, if I were starting from scratch with Exploding Topics, I would’ve done it differently.” Anything come to mind in terms of good and quote, unquote bad decisions?

Brian Dean: Yeah, we can start with the bad one, which was how to monetize this site. I had this very strange idea that we’re going to create this awesome free resource that anyone can visit and just see trends right away. They can filter, they can go by category and you think, “Oh, how are you going to monetize that?” Logically, you think SaaS, an upgraded version of what they’re seeing for free. And for some reason, I was like, “A paid newsletter. Let’s create a paid newsletter.” So we created this paid newsletter that was, granted, helpful in objective terms, but not necessarily for that person who wants to see trends in their particular niche. So we would send them a trend on some sort of face cream and then on a car and then a battery and then a tech startup and they would be like, “What is this?” People were like, “I want just trends about e-commerce. I just want trends about this one thing. Why are you sending me all this stuff?”

And then people would also sign up thinking it’s SaaS, even though we said everywhere, like paid newsletter, paid newsletter, and they’d be like, “I thought this was SaaS. I thought it was SaaS.” That was our number one complaint. And yeah, sometimes you just need to get that beaten over your head because I was like, “Oh, SaaS is so complicated.” I mean, my co-founder was a coder, but I’m still like, “Oh, we’re going to have to hire developers and I don’t know anything about this whole world. UI…”

Tim Ferriss: And for people who may be listening who don’t recognize the term, a lot of people will, but Software as a Service, right, think about Dropbox, maybe not the best example, but I mean, Dropbox is a great example, but with a lot of these products, there’s a freemium version. There’s a version that you get to use for free. And then if you want a bunch of additional storage or features or access, whatever it might be, then you pay 9.99 a month or whatever. And there’s the basic, intermediate, advanced version, enterprise, et cetera, that’s SaaS. Sorry to interrupt. I just wanted to define that.

Brian Dean: Yep. Yeah. But if you had told me that before we started, I would’ve been like, “Oh, logically, then we should have the premium advanced enterprise version in the backend instead of the paid newsletter idea.” So that didn’t really go well until we ultimately shifted to what we should have been in the first place. So that was sort of the bad decision. The good decision was definitely investing in this data, publishing data early on. So with Backlinko, this is something I only discovered after five years of running the site. And then with Exploding Topics, I was like, “Day one, we’re going to publish tons of data. We’re going to be the source.” That’s another strategy, like be the source of information on technology, software, e-commerce trends, anything trend related, we’re going to be the source. We’re going to have the latest data, we’re going to have the best visuals, and we’re just going to be the source for that information. As opposed to writing how-to content, we’re really focused on data-driven content.

Tim Ferriss: Did it work right out of the gate or was there a formula that you realized worked after you had a particular well-received publication of data?

Brian Dean: Yeah, it did. It took a while to get going. A lot of mistakes, a lot of posts that weren’t great, or the topic wasn’t a good choice. What really helped us, what was sort of the smash hit were these very specific stats that people look for. So what I discovered through this process was this stats page idea is nothing new. People write the biggest stats around the fitness industry or LinkedIn stats or whatever, and those are fine, but usually journalists aren’t looking for LinkedIn stats or TikTok stats. Some of them are, and that’s fine, but most of them look into something very specific like how many users does TikTok have or how many people use LinkedIn every day, like daily active users, or how many posts are on LinkedIn every day. It’s super specific. So if you’re able to find a credible stat around that, then you can crush it.

Even if you’re not the one that developed it. A lot of times these are also buried in PDFs or white papers or again, interviews that you have to pull out. One of our biggest smash hits in this area was how many users that ChatGPT have? Granted, we publish this early. That’s another thing that can help a lot. If you publish one of the first or the first specific stats page, then you get into this virtuous cycle where you’re very visible when someone’s searching for that topic, then they link to you, they mention you, makes you more visible, and then you just are in this massive flywheel. So one of our best pieces was how many users does ChatGPT have? And every once in a while, Sam Altman will give a talk and he’ll mention it, or when they raise a round, they’ll mention it. And all we did was just document their user growth based on these statements that they made.

The initial post probably costs, hiring a freelancer like 200 bucks, and then to update it every couple months is another 50, and it’s been referenced like 3,000 times. It’s absolutely insane. The effort to reward ratio is nuts on that. And of course it’s just like, part of it is some pieces do better than others, but we’ve noticed that that formula tends to work well. If you can find a trending specific stat that bloggers or journalists are looking for when they write about that topic, they’re very likely to reference you.

Tim Ferriss: So I read, I’ll give credit here. This is on growthmanifesto.com, found this doing research. You were interviewed. Towards the end of that interview by Alex, he asked you what the best piece of business advice was that you’ve ever received. Now this may have changed and there’s probably more, but it was Noah Kagan advising you to double down on what works. Could you expand on that? And then I’m wondering if there are any other sort of mantras or short pieces of advice that you would also put on the Mount Rushmore of your best advice that you’ve received.

Brian Dean: It sounds so simple, but it’s one of those pieces of advice that’s simple but hard to follow because when you’re running a business, there’s like a million things to worry about, to focus on. There’s new opportunities, new challenges, other competitors, you have an employee that’s sick. It’s hard to really focus on that little thing that works. But I think this is especially important when you’re first starting out, because when you’re first starting out, nothing’s working almost by definition. You’re starting something new. At least in my experience, when I’m starting something new, I don’t know, nothing’s working. And then when something does, most people are like, “Okay, that works. Now let’s go with something else.” But instead, you should just take that niche. It’s almost like a little niche when you’re rock climbing. Just take that niche and just double down, triple down, quadruple. It should really be like 10X down on what works, but it’s so rare that you find something that works. And honestly, in most businesses, if you can find one thing that works and scale it up, that can get you pretty far.

Tim Ferriss: Aside from The 4-Hour Workweek, which was, I suppose, a catalyst of sorts in the beginning, have there been any other books that stand out or resources when someone comes to you and they’re like, “I’m thinking about starting a business. I’d like to start a business” — are there any books or resources that you tend to recommend frequently?

Brian Dean: Yes. For people that are just like, “I want to start a business,” and they’re like, “I don’t know what to do, how to do it,” they’re totally green, then Ready, Fire, Aim is usually the book that I recommend. Are you familiar with that one?

Tim Ferriss: I’ve heard of it.

Brian Dean: Michael Masterson.

Tim Ferriss: What leads you to recommend this book?

Brian Dean: It gets people into the action mindset, leaning towards action instead of analysis. I was guilty of this when I first started, like doing a lot of spreadsheets and analysis and business cards, registering your company, all those things that you can do later that don’t really matter. This gets you going on the most important things. And then later, you can always change course. If you can start — but the key is really starting, starting, starting, or like Paul Graham says, “Action produces information.” So this book basically will hopefully give people a kick in the butt to get started instead of analyzing and then being like, “Okay, now I’m ready.” Just be like, “Start today and then change as you go.”

I feel like that book is almost a litmus test. If you read that book and at the end you don’t do anything, then you’re probably not ready.

Tim Ferriss: Yeah. Yeah, right?

Brian Dean: The book, the whole point is to get started and it gives you advice on how to know you’ve got traction and what to do once you get traction. So I feel like if you just read the book and you’re like, “Okay, what’s the next book to read?” It’s probably not the best approach. So that book is hopefully the kick in the butt that someone needs.

Tim Ferriss: This might be a tough question to answer, but how would you define the startup costs for Backlinko and Exploding Topics? In the first three months of those two companies existing, how much money was invested in each of those? How much money was required/invested?

Brian Dean: Yeah, I would say for Backlinko’s case, a few hundred bucks at the most. It was domain, WordPress. I probably hired someone to create a basic blog design theme for WordPress. Don’t remember how much, but if I spent a thousand, I would say that’s a lot. It was probably more like 500 bucks because it’s a blog. I mean, really, at the end of the day, there shouldn’t be a lot of costs involved with that.

Exploding Topics was a lot different because I acquired a prototype version from someone for 75,000 to start with and hire them and that was part of their pay package as well. So just on day one, I was in with that much. And then it was a redesign and a rebrand, adding more trends, hiring a couple of people to do some basic things. So that was probably more like 90,000, something in that range. But it was a unique situation because it wasn’t built from scratch. It was acquiring someone and then that was also paying for some of their time. It was like hiring them as part of the acquisition and that was paid out over the course of a few months. So I’m not exactly sure how much would be in that first couple months, but it was in that range.

Tim Ferriss: Why did you acquire something and what was the deal structure of the acquisition?

Brian Dean: So I acquired it because I was trying to build this exact thing myself and just stumbling and stubbing my toe over and over again. So I knew that there was an opportunity for this trend. I couldn’t even describe it very well. It was just basically, you want to go to a website and it just shows you trends in whatever niche you’re interested in. And that sounds so simple, but nothing existed like that, believe it or not.

And I hired someone to build something like that and it was horrible. It used Reddit. So we’d look at Subreddits and we would see how many times a word was mentioned or something, and we found nothing valuable. The signal-to-noise ratio was completely backwards. It was like for every 200 hits, one was decent. And then one day someone forwarded me this random site this guy started and I’m like, “No, this, this is exactly what I want,” but it was even better than I had imagined.

So then I reached out to him, and then the deal structure was essentially buy it 100 percent, straight up. Part of the acquisition costs will be — you’ll get paid that. And then on top of that, if it goes well over the first, I think, couple months, then we can set up some sort of part-time deal. And if that goes well, we can do full-time. And if it goes well, then —

Tim Ferriss: And he would be helping you throughout that entire period of time to help you determine if it’s going well or not?

Brian Dean: Exactly. And he was the coder and developer behind the original version. So he was best qualified to continue to work on it and improve it. Rather than hiring someone random to come in, it was his vision to start with. And then I said, basically, “If it goes well with full-time for, I think another month or so, we’ll basically be co-founders on this thing. The only rub will be if you want a lot of equity, then you’re going to have to put money in to fund this thing, or if you prefer that you get more cash, then you can just get a proper salary and then I’ll own most of the business.” So that’s basically what we did. He chose more money and then he owned part as equity in Exploding Topics.

Tim Ferriss: How did you end up in Europe?

Brian Dean: I mean, love, to be honest.

Tim Ferriss: Yeah, that’ll do it.

Brian Dean: Yeah. I mean, my wife, we met in Thailand many years ago, and then we moved to Berlin, this is actually a funny story, partially from The 4-Hour Workweek because you mentioned Berlin as this cheap place.

So we’re in Thailand looking at Craigslist and looking at all these apartments that are like palaces for 300 euros a month. And we’re like, “Tim was right. This is amazing. You can live like a king in Berlin for nothing.” So we start replying to all this. So as we’re flying there, we send out all these emails.

Tim Ferriss: Uh-oh.

Brian Dean: And of course, they’re all scams. It’s like, “I’m lost. Oh, I’m out of town and I lost my passport, but if you leave this money in this Western Union.” I’m like, “No!”

Tim Ferriss: Oh, no.

Brian Dean: We show up to Berlin. We’re in a hostel for like eight euros a night in a 12-bed hostel while we realize that this whole thing, all these ads we’re applying to is a scam. No one uses Craigslist in Germany. So then we eventually found an apartment, lived in Germany, and she’s Portuguese. So we visited Portugal a number of times where we lived there and eventually it was like, “We could freeze our asses off or we could live in the sun, so let’s look at the sun.” So that’s basically how we ended up here.

Tim Ferriss: Yeah. The thing about The 4-Hour Workweek, the principles and frameworks all still work. Obviously some of the tech tools, since they were last updated in 2009, most of them are completely irrelevant. Probably not going to use GoToMyPC at this point to access your home computer remotely to do the work you need to do. But the pricing examples, obviously, have changed since it was first written in 2007, 2009.

So the principle, the idea of geoarbitrage and applying that to what you earn and how you pay contractors, employees, and then your sort of living expenses, it applies. But definitely for anybody who ends up picking it up, if you read that doing something in Buenos Aires costs A, B, and C, I would go online and fact-check that because it’s probably changed a little bit.

Looking at all the questions I could possibly ask, what are other sort of lessons learned or things that you would like to share with folks? Could be about your journey, could be about mistakes along the way, really anything at all. Because part of the value of these conversations is that we can get into a lot of specifics that are omitted in the magazine and profiles of people that end up reading like a list of highlights, right? And there’s obviously a survivorship bias to begin with if people appear on magazine covers. I know that’s an antiquated example to use, but what else would you like to share with folks or anything else you’d like to add just about the journey? Because it’s not over, it still goes.

Brian Dean: Yeah. One thing was that I wanted to share would be actually filling the void. I felt the void after selling Exploding Topics and how I was able to fill the void.

Tim Ferriss: Yeah, please.

Brian Dean: So yeah, so set the stage for you. I sold Backlinko, and then about two years later sold Exploding Topics and was just going full-time. Not super crazy working all the time because I was fairly efficient, but still working all the time. And then went from that to basically stop, to zero. And a lot of people, I think they have this feeling of listlessness, no direction, maybe a bit of depression. For me, the symptom was stress. I think I was wired for stress, not only just in general, but also because of the sale process is stressful. And then just because the sale is done, your body and I think part of your reptilian brain doesn’t really recognize that, and it’s looking for threats and it’s looking for opportunities and it’s just not chilled out.

So I struggled for two months with stress. On my Oura Ring, my stress was like 2X baseline from after I sold. And you’d think it’d be the opposite. You’re like, “This is great. I sold two companies. I’m good for the rest of my life. What is there to be stressed about?” And then I realized what I needed was a hard reset.

That was the first step. We went on a trip, got away from the environment, got away from the day-to-day life, and then it somehow was able to hack my brain to be like, “Okay, you’re safe,” or, “things are chill now.” So when I went back home, the stress was gone. It was back to baseline or below baseline.

Then I got a little bit more —

Tim Ferriss: What was the trip? What was the extra —

Brian Dean: It was a trip to the south of Portugal, to The Algarve.

Tim Ferriss: Yeah, it’s a nice spot.

Brian Dean: So went to the beach.

Tim Ferriss: Nice oranges. Toasty.

Brian Dean: Yeah. Yeah, good oranges.

Tim Ferriss: Depending —

Brian Dean: Good oranges, yeah. Yeah, so spent some time down there and that was just the hard reset. I think it’s just to get you to get out of your environment.

But then when I got back, it was like stress is gone, but now feeling a little bit bored. That boredom was coming back. And I was tempted to start another startup. And I read this — someone sent me this, another friend who had a big acquisition. He sent me this thing by, I think it was Yale School of Management, and it was basically they interviewed founders that had just exited and they asked them their advice. “What was it like? What were the good ups and the downs?” And they basically said,” When you sell, there are psychological dangers that can occur. One is that you lose your sense of structure. The other is you lose your sense of purpose and you lose your sense of connection with your team. It all goes away. You have it and then one day you literally don’t.”

So different people react to it in different ways, but they warn that — a lot of case studies in this paper were saying people that started companies within a year of selling usually regretted it. So it was basically, “Take a year and don’t make any major commitments whatsoever.” So that’s what I did. It kept me from starting these. I had all these ideas, “I’m going to start a startup,” and then I’d be like, “no, wait a year, wait a year, wait a year.” And then by the time a year came around, I didn’t really want to because I was able to fill the void largely with tennis.

For me, tennis has been — one activity fills almost all of these boxes or checks all of the boxes and fills this void. It’s amazing, man, because if you think about it, if you want to have fun, you play video games or watch TV or something. If you want to socialize, you go out drinking. If you want to exercise, you go to the gym. If you want to get fresh air, you go for a walk. Tennis does all of these things in one activity. And if you want a community, you need to — whatever, I don’t know. I actually don’t even know how to do that outside of tennis. That was the thing that changed was I joined a tennis club and there’s a lot of other entrepreneurs there. A lot of Americans, man. It’s like the 51st state over there, to be honest. It’s getting a little crazy.

But anyway, so yeah, I filled the void with this community of people that are playing tennis, trying to improve, obsessed with the game, watching YouTube videos, reading about it, practicing all the time. And now I don’t have that same sense of wanting to start something new.

Tim Ferriss: I love that. And just a few observations since, as you would imagine, since the book came out in 2007, I’ve had the opportunity to vicariously watch a lot of people grapple with this. And having worked with so many startups and angel investing, granted in a venture-backed environment, but a lot of the challenges are the same, right?

Brian Dean: Yep.

Tim Ferriss: Whether you’re coming out of, for instance, I know guys in special operations, if you’re coming out of running a company, if you’re coming out of starting and running a company, when you lose, as you put it, and I really liked the categories you mentioned, when you lose the structure, when you lose, in a sense, the identity, when you lose the connection to team, you can end up with a severe degree of vertigo and a very precarious paradox of choice. And something like tennis — and some people listening might think like, “What? Tennis?”

Brian Dean: Probably.

Tim Ferriss: Even if it’s not the forever solution and the end-all, be-all, what it does, just like getting your recommended daily allowance of essential amino acids and vitamins and so on, you’re getting just enough that it provides you with the psycho-emotional health and space to think about things more clearly instead of being reactive. You know what I mean?

Brian Dean: Yep.

Tim Ferriss: You’re getting enough of all of those things and it provides you with a buffer and a certain equilibrium that allows you to think about things more clearly. And furthermore, this is not necessarily a problem you have to solve after everything vanishes. You can think about this in advance and experiment with things so that when you have a real phase shift, which in the context of The 4-Hour Workweek isn’t necessarily selling a company, it’s just like once you get it to a high degree of automation where it requires two, three hours a week, if that, to manage, which is more common than people might think, what you do with the rest of the time is a tremendously big question.

Brian Dean: Yep.

Tim Ferriss: So I love that. It makes me want to go back to The Algarve also. It can get a little toasty.

Brian Dean: Could be worse. Let’s put it that way.

Tim Ferriss: Yeah. It’s a good country for tennis.

Brian, this has been super fun. Where would you like people to find you online, if anywhere?

Brian Dean: So let’s start with YouTube. So that would be the first place, and then LinkedIn. @BrianDean on YouTube and @BrianEDean on LinkedIn.

Tim Ferriss: Perfect.

Brian Dean: The other Brian must have grabbed that one. I don’t know.

Tim Ferriss: Brian, is there anything else you would like to say before we wind to a close?

Brian Dean: Oh, this has been great. That’s it.

Tim Ferriss: Yeah. Thanks, man. I know it’s late, several time zones away, and I appreciate being flexible on the timing. So thanks so much for taking the time.

Everybody listening or watching, we will link to everything we discussed in the show notes as usual at tim.blog/podcast. And until next time, as always, be just a bit kinder than is necessary to others and also to yourself. Thanks for tuning in.

DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:

The post The Tim Ferriss Show Transcripts: 4-Hour Workweek Success Story Brian Dean — From Dad’s Basement to Selling Two Companies (#861) appeared first on The Blog of Author Tim Ferriss.

4-Hour Workweek Success Story Brian Dean — From Dad’s Basement to Selling Two Companies (#861)

2026-04-16 19:36:34

Welcome to another episode of The Tim Ferriss Show.

This is a shorter episode and by request. Many of you have requested more 4-Hour Workweek Case Studies—conversations with people who have read the book, applied it, and built lives and businesses I never could have imagined.

Brian Dean—today’s guest—has a story that starts exactly where a lot of great stories start: broke, directionless, and eating canned beef stew in his dad’s basement during the 2008 financial crisis.

He picked up a copy of The 4-Hour Workweek and took action. As is nearly always the case, his path wasn’t a straight line, but a series of winding turns, all fed by experiments. Today’s episode covers geoarbitrage, testing assumptions cheaply, building a muse, automating income, and—the chapter almost everyone skips—filling the void. His journey includes failures, two successful exits, and a hard-won answer to the question most people never think to ask: what do you actually do with your freedom once you have it?

But who is Brian?

Brian Dean is the founder of Backlinko and Exploding Topics, both acquired by Semrush, which itself was recently acquired by Adobe for $1.9 billion.

P.S. A special thank you to Elaine Pofeldt for getting Brian’s story on my radar. Elaine is the author of The Million-Dollar, One-Person Business and more recently, Tiny Business, Big Money.

Please enjoy!

This episode is brought to you by:

Fin, powerful AI Agent for all your customer service: Fin.Ai/Tim
Incogni, which automatically removes your personal data from the web, helping shield you from fraud, scams, and identity theft: https://incogni.com/Tim

Books, people, tools, and resources mentioned in the interview

4-Hour Workweek Success Story, Brian Dean — From Dad’s Basement to Selling Two Companies

Additional podcast platforms

Listen to this episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

Transcripts

SELECTED LINKS FROM THE EPISODE

Connect with Brian Dean:

YouTube | LinkedIn

People

Companies & Tools

Concepts & Frameworks

“Action Produces Information” (Attributed to Paul Graham)
Black Hat vs. White Hat SEO
“Double Down on What Works” (Noah Kagan Advice)
Dreamlining (from The 4-Hour Workweek)
Dreamlining Worksheet Excel File (from The 4-Hour Workweek)
Due Diligence / Earnout / Vesting (M&A Terms)
Exact Match Domain (EMD)
“Filling the Void” Chapter (The 4-Hour Workweek)
Geoarbitrage (from The 4-Hour Workweek)
Google Panda Update (February 2011)
Mergers and Acquisitions (M&A)
Profit and Loss Statement (P&L)
Sample Dreamline PDF (from The 4-Hour Workweek)
Search Engine Optimization (SEO)
Software as a Service (SaaS)

TIMESTAMPS

[00:00:00] Start.
[00:02:53] From PhD pipettes to Dad’s basement to Jerry Springer.
[00:04:38] The 4-Hour Workweek finds its dream reader — marginal notes and all.
[00:06:04] First product flops, free traffic beckons, and SEO.
[00:07:40] The 200-domain AdSense empire.
[00:09:40] Dreamlining: From “escape the basement” to “3k a month in Thailand.”
[00:11:27] When Google’s Panda update slapped the internet (and Brian’s empire).
[00:12:32] Scared straight: Black hat to white hat via a hostel in Spain.
[00:17:55] Backlinko is born.
[00:19:50] The 200 ranking factors post: 25 hours of patent-digging, a million visitors.
[00:22:13] New rule: One post a month, 10x better than anything out there.
[00:23:02] Semrush comes knocking to buy his company — Brian ignores the email.
[00:24:02] Taking celebratory shots at Legal Sea Foods while wondering where the contract is.
[00:25:32] Due diligence hell: Hunting down ghosted freelancers and the contractor commandments.
[00:29:25] SEC market-close rules vs. Brian’s 10 p.m. bedtime.
[00:30:16] Post-acquisition: Hopping from one treadmill to the next.
[00:34:19] Backlinko on autopilot, boredom on full blast, and the chapter everyone skips.
[00:35:42] Exploding Topics: The paid newsletter mistake vs. the obvious SaaS play.
[00:38:41] Data-driven content and the ChatGPT user stats flywheel.
[00:41:00] Noah Kagan’s advice: Double down on what works — then 10x down.
[00:42:26] Ready, Fire, Aim — the litmus test for would-be founders.
[00:44:06] Startup costs: $500 for Backlinko vs. $90k to acquire Exploding Topics.
[00:47:29] How love and a Craigslist apartment scam in Berlin landed Brian in Portugal.
[00:48:48] Geoarbitrage still works — just don’t trust the 2007 pricing.
[00:50:20] Post-exit stress: Oura Ring at 2x baseline and the Algarve hard reset.
[00:52:21] Why founders who launch within a year of selling usually regret it.
[00:53:30] Tennis as the ultimate void-filler: Fun, fitness, community, and fresh air in one sport.
[00:54:31] The paradox of choice after exit: Structure, identity, and vertigo.
[00:56:52] Parting thoughts.

BRIAN DEAN QUOTES FROM THE INTERVIEW

“So, I go to the bookstore to find a book to help me get started. And I basically saw The 4-Hour Workweek, grabbed it, and it just sort of spoke to me … It blew my mind. I read the book. I’m like, ‘Well, I could start a business.’ It was just a crazy, mind-blowing concept that someone who has no experience, was totally broke, could start something, not necessarily be a smash hit, but you could start something.”

— Brian Dean

“I feel like [Ready, Fire, Aim] is almost a litmus test. If you read that book and at the end you don’t do anything, then you’re probably not ready.”

— Brian Dean

“When you sell [your company], there are psychological dangers that can occur. One is that you lose your sense of structure. The other is you lose your sense of purpose and you lose your sense of connection with your team. It all goes away. You have it and then one day you literally don’t.”

— Brian Dean

“Tennis … fills almost all of these boxes or checks all of the boxes and fills this void. It’s amazing because, if you think about it, if you want to have fun, you play video games or watch TV or something. If you want to socialize, you go out drinking. If you want to exercise, you go to the gym. If you want to get fresh air, you go for a walk. Tennis does all of these things in one activity.”

— Brian Dean

This episode is brought to you by Fin! Fin is an AI agent that delivers high-quality answers and helps resolve complex queries that your customers may have. Rapidly-growing companies like Anthropic (the AI lab behind Claude) rely on Fin to deliver accurate and thoughtful customer support to millions. Fin is built using custom models trained on thousands of customer interactions, and it understands the complexity and nuance of customer service like no other agent. You feed Fin your internal knowledge and policies, it learns your rules, and it can start supporting your overstretched support team. And because every business runs things differently, Fin is fully self-manageable. See the difference Fin can make for your business with a free trial at Fin.ai/Tim.

This episode is brought to you by Incogni: erase your personal data from the web and prevent scams, fraud, and identity theft! Incogni automatically removes your information across 420+ data brokers (1,000+ additional sites covered in their Unlimited plan), and they keep it scrubbed automatically. Deloitte has independently verified the headline numbers (245M+ removal requests), and the company adheres to AICPA SOC security standards, with an A+ rating from the BBB. And with their Unlimited plan, if you find your info on a site they don’t automatically monitor, just send them the link, and their privacy team will handle it. Protect yourself now with Incogni. Go to Incogni.com/Tim to get 60% off their annual plan.

Want to hear an episode with the person who gave Brian his best piece of business advice? Listen to my conversation with serial entrepreneur and AppSumo founder Noah Kagan, in which we discussed launching a million-dollar business in a weekend, the 48-hour money challenge, finding your first customers before you build anything, the LOT (listen, options, transition) sales framework, the “coffee challenge” as a training wheel for asking, geoarbitrage from Austin to Barcelona, why most business ideas die of “idea constipation,” and much more.

The post 4-Hour Workweek Success Story Brian Dean — From Dad’s Basement to Selling Two Companies (#861) appeared first on The Blog of Author Tim Ferriss.

The Tim Ferriss Show Transcripts: Daredevil Michelle Khare — How to Become a YouTube Superstar, Open Impossible Doors (FBI, Secret Service, etc.), Craft Jedi-Level Cold Emails, and Use Fear-Setting to Change Your Life (#860)

2026-04-08 15:28:19

Please enjoy this transcript of my interview with daredevil Michelle Khare. Michelle lives life to the extreme in Challenge Accepted, amassing more than 6 million followers and more than 1 billion views. Michelle hopes to prove that with enough dedication and failure, anything is possible. In 2025, Challenge Accepted made history successfully petitioning to join the Primetime Emmy® ballot. Michelle was named a TIME100 honoree for her impact as a creator and storyteller.

Michelle’s full bio

Legal conditions/copyright information

Daredevil Michelle Khare — How to Become a YouTube Superstar, Open Impossible Doors (FBI, Secret Service, etc.), Craft Jedi-Level Cold Emails, and Use Fear-Setting to Change Your Life

Additional podcast platforms

Listen to this episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

Tim Ferriss: Michelle, at long last, here we are.

Michelle Khare: Here we are, Tim.

Tim Ferriss: So nice to meet you in person.

Michelle Khare: It’s so nice to meet you too. This is so exciting and surreal for me. So thank you for letting me infiltrate your podcast studio today.

Tim Ferriss: Absolutely, I am thrilled. It looks like about three years ago that I first put you and your channel in my newsletter, 5-Bullet Friday, and I think it was probably even before that, that one of our mutual friends, Adam Grant, had been telling me repeatedly, “You have to have Michelle on the show.” And the reason that I was so excited to put you in the newsletter — I don’t even remember the line, I went back and I looked at what I said exactly. And one of the things I said was, “I’m so happy that someone finally cracked this premise and did it right.” But since people probably have no idea what I’m talking about, although I would have already said something in the intro, what’s the logline, so to speak, for —

Michelle Khare: Of Challenge Accepted?

Tim Ferriss: Of Challenge Accepted. What is it?

Michelle Khare: Challenge Accepted is a show where I attempt the world’s toughest stunts and professions, and that can range from learning and attempting Harry Houdini’s deadliest trick, the water torture cell, to training with the Secret Service for a week, to most recently, I recreated Tom Cruise’s stunt from Mission: Impossible, where I was hanging off the side of a military aircraft as it was taking off.

Tim Ferriss: And you have more than six million followers, more than a billion views, and I’m going to read — you know what? We’ll probably just skip the intro because I’m basically getting into it anyway.

Michelle Khare: Okay.

Tim Ferriss: “Michelle hopes to prove that, with enough dedication and failure, anything is possible”. And that’s one of the characteristics that I most appreciate about the show, is if you have a breakdown, if you’re flat on your back, if you stumble and fall, it’s in there, right? That’s a feature and not a bug.

Michelle Khare: Exactly.

Tim Ferriss: So it’s not just the highlights, it’s also the low lights. And since we’re already getting into it, I’m just going to read this paragraph. All right. “Michelle’s work has earned multiple Streamy awards, including Show of the Year, has been featured in The New York Times, Forbes, Vogue India, and more. In 2025, Challenge Accepted made history — congratulations — successfully petitioning to join the primetime Emmy ballot. Michelle was named a Time100 honoree for her impact as a creator and storyteller.” Let’s rewind way back. We were chatting a little bit before we got started about Shreveport, Louisiana.

Michelle Khare: Oh, yes. Shout out Shreveport.

Tim Ferriss: And I mentioned I had been there and you were like, “Oh, I’m so sorry.”

Michelle Khare: Yes, there’s not much there.

Tim Ferriss: Why was I there? Why had I been there? And why does that tie into your background a little bit, your history growing up? Well, I was just saying, if you want to hop into it, because I’ll, I suppose, answer my own question, which is the reason I was in Shreveport is because they have very compelling tax incentives and other incentives for filming. So what was your first exposure to “the business,” broadly speaking?

Michelle Khare: My very first exposure to the business was my dad is a big, big movie and television lover. He actually learned English after immigrating from India by watching films, even on the plane from India to America. And so, growing up, because there’s not much to do in Shreveport, every Friday night we were at the movies. It didn’t matter if it was a blockbuster or a very low-rated Rotten Tomatoes B-side movie, I saw everything. Kids’ movies, PG13 up, we saw it all. And then we would go to a pizza shop and talk about the movie afterwards. Again, there’s nothing to do in Shreveport, so this was like the pinnacle of entertainment.

And so, just naturally, I started experiencing a homegrown little film school, if that makes sense. We printed out the AFI Top 100 Movies, and had them in our living room, and we would check them off as we watched them, me and my dad. And what was special is as I got a little older, all these tax incentives started happening, bringing films to New Orleans and to Shreveport. We got a lot of Twilight knockoff movies, I think one of the Scary Movies was shot in Shreveport. And so our town experienced this little economic art renaissance, which was really exciting. And so, all of our friends and family members were becoming extras in movies and TV shows, and feeling very excited about all of that. And so, one of my first jobs was I had an internship on a movie starring The Rock, it was a movie called Snitch.

It came out in 2013. And I think I was like so low on the call sheet, I was like, it was after all the PAs, it was PA intern. It was the last person on the call sheet was me, and I was just getting coffee for people and learning. And it was an incredible experience, and I loved that because I got a window into the traditional scope of what it could take to tell a story at a higher Hollywood level. And that’s what I hope to bring a lot of to what we do, even on Challenge Accepted today, is this midpoint of digital freedom, ownership, but structure and understanding and respect of the history of where our visual storytelling medium has come from.

Tim Ferriss: Part of the reason I said I’m so glad somebody finally cracked this is, you’ll know this, some people may not, there are basically two reasons why I’m doing this podcast, or the catalysts that led to this podcast, and they both relate to ownership in a sense. The first was The 4-Hour Chef, which was basically just a suicide mission of a deadline, a book that should have taken three years was done in a year, and that’s just physically effectively impossible. So, ran myself into the ground with that.

Michelle Khare: Because you are self-testing all of these things.

Tim Ferriss: Yeah, exactly. I was doing everything in the book, full of experiments, and somehow thought it would be a good idea to try to learn photography, to do hundreds of photographs in the book myself, which turns out to be a craft in and of itself that takes a lot of time, if you want to be even halfway decent.

Michelle Khare: Yeah, I agree.

Tim Ferriss: And what ended up happening in that case was distribution got hamstrung. I expected some of it because it was a book, it was the largest title that had been acquired by the then very nascent Amazon Publishing, and because people, in some ways, rightly fear Amazon as this omnipowerful, omnipotent entity that controls all of these different aspects of, in most cases, distribution, but now Amazon Publishing was going to be competing with the big publishing houses for author talent, and this scared the hell out of everybody. So, I expected that there would be, say, boycotts by Barnes & Noble, I did not anticipate it would include all of the big box retailers and much more.

So, the book basically, I don’t want to say it died on the vine because it did as well as it could have, but at the same time, roughly — this is the part I haven’t talked as much about. I had been filming and then debuted in 2013, The Tim Ferriss Experiment, right? And The Tim Ferriss Experiment had me doing these experiments, as you might expect, on a weekly basis. And that was through a startup within Turner broadcasting, called Upwave. But there were all of these problems internally at Upwave, ultimately, that got shut down. There was a regime change, and then what happens? The catalog of episodes, if it succeeds, the new leadership’s not going to get any credit, and if it goes poorly, they’re going to get all the blame. So it just got locked up.

And it took me two years or three years to get back the rights and then “self-publish” on Apple, and it did very well at the time. But what you just said is so important, I want to underscore it for people. Because I’ve heard you discuss, and I want to give a shout-out to Colin and Samir, two of the best interviewers out there, in my opinion, especially when it comes to creator economy, and the nuts and bolts of making things in this modern era, I really want to give them due credit. When you’ve had conversations — and I’m going to talk for a second, I apologize.

But when you’ve had conversations with some of these larger, let’s call it traditional outlets or platforms, and you start to talk about your production schedule, they’re like, “Well, wait a second, it takes you six months or a year, or — fill in the blank, in their mind, excessively long period of time, could we compress it into a week?” And you have figured out very artfully how to have largely complete editorial control — there are some constraints, depending on how you want to go about it, with partners and sponsors and things like that. But largely you control your schedule, your direction. Actually, you do completely, right? You’re choosing positive constraints, depending on your objectives. But what ended up happening with The Tim Ferriss Experiment is like, okay, we have a week for each one.

Michelle Khare: Right.

Tim Ferriss: And so I would be in compression pants and putting on DMSO and all this crap because I had a ton of injuries from one episode, but we were already going into post, and then we’d have a day of travel, and then I’m starting the next episode, and it was impossible. It was just physically, I’m still contending with injuries from that. We might talk about that with respect to some of the stuff that you’re doing, I want to hear about it. But there were two issues, right? There was the production side control problem, and then ultimately, didn’t control distribution. And for those reasons, those two straws that broke the camel’s back, I was like, fuck this. And I’d used podcasts to launch The 4-Hour Chef, and I thought to myself, you know what? I like RSS feeds. I like this idea of being able to do whatever I want, be myself.

If I want to curse, I can curse. Not that that’s ultimately — I suppose it can be an art form in and of itself, depending on where you grow up. And that’s how we ended up here today, right?

Michelle Khare: Just so I understand, you were human guinea pigging 4-Hour Chef and shooting Tim Ferriss Experiment at the same time?

Tim Ferriss: They were basically back to back, and there was probably some overlap. So I was doing pre-production while I was finishing The 4-Hour Chef because I’m a glutton for punishment.

Michelle Khare: Oh, my God.

Tim Ferriss: For people who haven’t seen that, it’s my first four-color book, it’s something like 600, 700 pages, cut down from like 1,000 probably. And the biggest difference, I’d say the absolute biggest difference between The 4-Hour Chef and the books that came before it, The 4-Hour Workweek and The 4-Hour Body, is that in the case of The 4-Hour Body, I did all of the experiments, then digested it all, combed through everything, and compiled the book. In the case of The 4-Hour Chef, I was still, because of the deadline, doing a lot of the experiments as I was already beginning to write the earlier sections of the book, which is a very risky gambit.

And then, on top of that, because I did not know — and I thought this was actually a good idea, although there were a lot of pitfalls. Because The 4-Hour Chef was a huge gamble, particularly from a distribution perspective, I expected I was going to get kneecapped in certain ways. And I was like, well, if this doesn’t work out the way I want it to, I still have the benefit of the doubt and the eyes of most people, and I can use the success of the prior book, and the blog at that time — remember blogs, people? To parlay that into the television. So, I was like, let me get the deal before The 4-Hour Chef fully comes out so that I have the leverage that might become a question mark once it’s published.

Michelle Khare: Oh, my gosh. Okay. So, for those of you, I feel like there are so few people in the world who can truly empathize with what you put yourself through. I’m thinking of Morgan Spurlock, the true pioneer of whatever it is we’re doing.

Tim Ferriss: Yeah, rest in peace, Morgan.

Michelle Khare: And rest in peace, my gosh. David Blaine is another that comes to mind. And I think what people don’t realize when they watch your content or even mine is that it’s not filmed in a vacuum. Life is happening. As you mentioned, you’re not just going to Japan to learn Yabusame for five days, you’re struggling with the jet lag, and then you’re also probably answering questions and emails about what next week’s episode is going to entail. And that is a level of professional athlete that is so unappreciated.

Tim Ferriss: Well, thank you.

Michelle Khare: I much empathize with that.

Tim Ferriss: Yeah, I really appreciate that.

Michelle Khare: We were talking about decisions.

Tim Ferriss: Decisions, yeah. So, decisions, and then we’re going to go back chronologically.

Michelle Khare: Okay.

Tim Ferriss: And thank you for saying all that. And I was also building initially the writing side of things based on, in some ways, models from, let’s call it experiential journalism who came before me. And there were quite a few. Usually it was done with some type of satirical or humor twist, like A.J. Jacobs would be a great example for people who don’t know, The Year of Living Biblically, I think, is an amazing, amazing book.

Michelle Khare: Incredible. I met him a couple months ago and I said, “You need to do that again and make it a YouTube video, it would bang.”

Tim Ferriss: He’s such a sweetheart. He is such a sweet guy. Morgan Spurlock, for people who might not have recognized the name immediately, Supersize Me, really a sort of a genre breaking, category redefining, experiment, and many more who came earlier from a writing perspective, but questions.

Tim Ferriss: So, what I would love to know, and this is going to get in the weeds a bit, guys, but we’re going to zoom out and get the genesis story as well. But part of what I’m so curious about is you have in some ways the dizziness of freedom, right? You have a paradox of choice challenge, where having complete lack of constraints can be almost as bad if you don’t have a framework for figuring it out as having too many constraints.

So, when you have things running concurrently, you might, as I understand it, be working on two or three challenges at the same time, right? You’re doing post-production for one, maybe you’re doing planning for another, and you’re in the middle of a third. First of all, how far in advance do you plan your editorial calendar?

Michelle Khare: The editorial calendar for Challenge Accepted can be anywhere from 12 to 15 months out from idea to upload. And an example of concurrent things happening would be, there was one day where I had to do astronaut training for a NASA episode. So, naturally, I began my day by going up in a fighter jet in the middle of nowhere in California, flying around, having no idea what I was getting myself into.

Tim Ferriss: Hope you took your Zofran.

Michelle Khare: Yeah. I threw up while —

Tim Ferriss: Yeah. There we go. There we go.

Michelle Khare: I exited the plane, we finished filming that, I got in my car, drove three hours back to Los Angeles, and had a ballet lesson. I think that is just a good window into what one day of life is like, and often training for multiple things at once. But when you have a situation, and a privilege, honestly, of the gift of choice and getting to choose how you use your time, I like to maximize my output for each year, as far as, it really comes down to something that I learned early, which is the more milestone memories you experience, the longer life feels.

Tim Ferriss: For sure.

Michelle Khare: And I’ve realized that that goes hand in hand with my business. The more milestone memories I create and can capture and turn into stories, it actually is a better episode. It leads to more revenue, more opportunities. And so, I’ve merged those together. But it comes from, I am an athlete, I am a person who operates in an environment where you give me a coach, you give me a training plan, I’ll follow it. I’ll do exactly what you tell me to, and I really thrive in that environment. And being a business owner is such an oppositional to that, because now you are both the coach and the athlete at the same time. And so, what I’ve had to do is, and I’m stealing this term from one of my other friends, is put a Formula One team around myself.

A Formula One team, we love Max Verstappen, he’s an incredible driver, and he’s not able to do what he does without the support of all of the mechanics and engineers. So, what I have done at every step in my life is try to find who are the best people to put around myself to continually challenge me, whether it’s business, personal, relationships, content, story, and assembling that team is really important to me. Those are the people who help me decide, how do I spend each minute of a calendar day?

Tim Ferriss: We’re going to double click on a few things here and we’re going to go all over the place, folks, so —

Michelle Khare: Buckle up.

Tim Ferriss: Buckle up. Right. It’s not quite going to be the vomit comet for astronaut training.

Michelle Khare: Okay.

Tim Ferriss: Hopefully it’ll be a little —

Michelle Khare: Yes.

Tim Ferriss: It’ll be more like a tour through the countryside with lots of interesting sites and vistas. But a few things come to mind that I want to mention and then ask about. The first is that, and Colin and Samir made this point, you exemplify something that I hope continues to gain traction, which is a focus on quality over quantity.

Michelle Khare: Thank you.

Tim Ferriss: Because there was a point where it’s like, hey, you have to post 50 times a day, you have to do this, you have to do that, you have to vlog 20 minutes every 12 hours, no matter what you do.

And you’re borrowing a lot of the best storytelling techniques and production quality of “traditional,” right? But also applying it to this digital native environment, which has a lot of its own upsides and also potentially long-term damaging temptations, which you have to be aware of, and I think you very much are. And when you’re publishing fewer videos, however, in a sense, not in all senses, but in some senses, you’re fighting the drive of the algorithm. And there are economic incentives that drive the frequency with which a lot of people publish.

So, when you’re doing less, and again, hat tip to Colin and Samir, it’s like you are — I want you to modify this because it’s been a minute since you spoke with them. But you can keep the lights on to some extent with AdSense, and the ad revenue from that, then you’ve got brand partners, right? And that’s part of the reason why it seems like it’s helpful to have an editorial calendar out for a period of time, right?

Michelle Khare: Yes.

Tim Ferriss: Because you can have some type of, I don’t want to call it sales process, but you have sort of forward looking thematic opportunities to look for those types of deals. And then you’ve got your app among other things. And I’d like to hear you talk about that. But when you’re going to break a mold and you’re trying to do something that people say can’t be done, like traditional TV on the internet or whatever it might be, you may have to find a new approach to financing what you want to do.

And so I’d love to hear you speak for just a moment about kind of what you have had to build and how you’ve had to think differently in order to do what you want to do. And then I do want to return to, and you can mention this in your answer if you want, but when you have certain episodes that take a day to film, right? Some that take a week, some that take six months, some that take a year to set up, how the hell do you create like a Gantt chart or whatever to actually do that? And my understanding is like production is one of your superpowers, right? So that is a very gigantic half page question.

But yeah, if you could speak to basically how you make it work.

Michelle Khare: How we make it work.

Tim Ferriss: Right. Because a lot of creators, I think, are succumbing to the culture of cortisol drive where they feel like they have to keep up, keep up, keep up often in terms of just frequency. And I think that’s a really dangerous game to play for a lot of reasons. Somebody else is always going to be able to sacrifice or be willing to sacrifice their entire lives to publish more frequently. So that can’t be your sole metric, right? So how do you do what you do? And how do you have to think differently, operate differently?

Michelle Khare: How do we operate differently? Our business is super antithetical to what most creators are doing. And I started in that place that you’re referring to, uploading multiple long form videos a week. I mean, I was uploading before TikTok existed, so it was all long form. Then of course, short form came along. But what happened at the beginning of my career was I was trying to grow my channel to create financial and personal stability. I had taken a big risk by leaving my job. And as a part of that, the first entry point was stability in some sense.

So I was making videos about anything I thought would perform well, and still with my own lens, of course. But I would have this strategy of, I’m going to do three videos a month for the studio, if you will, which is a term from traditional TV and film where a big director will do a big blockbuster movie and then the studio will allow them to do their passion project. So I would do that for myself where once a month I would do a passion project. And at the beginning of my channel, it was, I would DM stunt performers like Tom Holland’s stunt double, and asked them, “Would you train with me for a week? And can we make a video together?”

And it was cool because we were targeting communities that were undervalued and unseen often. I mean, many stunt performers aren’t allowed to share their work. And so giving them an opportunity to highlight their work was helpful to them and exciting for them and exciting for me selfishly, because I want to learn how to do all these incredible stunts and make an amazing story about it. And I saw a market opportunity because when you see BTS stuff from movies, it’s very —

Tim Ferriss: Behind the scenes.

Michelle Khare: Yeah, behind the scenes. My apologies.

When you see behind the scenes content from big Marvel movies, it’s very manicured and very short, and I really wanted to give space and breathability to this experimental process. And what ended up happening is those passion projects started outperforming the things I expected to just perform well. And it got to this point where I was limited resource wise, just like my own time even, of being able to do more of that passion thing. And I just decided, we decided as a team, we’re only going to focus on Challenge Accepted. Let’s just try that for a few months.

Tim Ferriss: And when did it get named Challenge Accepted?

Michelle Khare: It got named Challenge Accepted after Challenge Accepted existed. So when you go back and look at season one of Challenge Accepted, which is a while ago now, I think we went back and named it that because we’re like, “Oh, yeah, this was the beginning of this show,” which is so funny. But we were doing many things on the channel and we decided to strip away everything and only go in on that. And that is where a true inflection point came on the channel.

I would honestly say, Tim, you were asking earlier about key decisions, I think a lot of the inflection points of my life have happened when my back has been against the wall. Not in a place of “I get to make a decision,” but more like, “I have to make a decision because everything’s going to break if I don’t.” And this was a risky decision to make, to go all in on a show where I am physically committing myself for up to months at a time. At this point in 2026, 2025, we released eight to 10 episodes per year, that’s my upload cadence. And so every opportunity is a big bet. But what I have found is that when I did that, something even more special happened. It created something unique. And I have found that defining something unique can be even more valuable than consistency or mass viewership.

We’re very blessed that Challenge Accepted does get a lot of views and we feel strong about the bets that we make on these episodes. But, I have found that creating something special attracts even more people to want to support it. And so now what we ironically have on the channel is a scarcity mindset for advertisers that if you want to be in an episode of Challenge Accepted, there are 10. The train’s going. Are you getting on or are you getting off? Because we only have so much inventory to sell, we’re able to sell it at a premium, and it makes what we’re doing so one of one. And that’s always been my big thesis is whatever we do has to be one of one.

Tim Ferriss: Yeah. A few things come to mind as you’re talking. One is the importance of owning or creating, even better yet, a category. So this category of one idea, Blue Ocean Strategy, I think, is a good — at least at the time I read it, which was a long time ago, 10 years ago, pretty good exploration of this. But separately, as I look at the landscape now, I’ve had a lot of people ask me about podcasting. “If you were to start now, what would you do?” And I could throw out sort of examples of what I might do, but just from a broader kind of meta level, I say, I think it would be very difficult for me to do now or start now what I started in 2014, which was kind of a broad exploration of deconstructing world-class performers in an interview format. Now there are 600 of those.

And if you want something that is sustainable, and this is not exactly the right way to frame it, but premium from a partnership perspective, from a CPM perspective, from a whatever perspective, the best examples that I would try to model are shows like yours. Although I’m not really — I’m kind of shy with video, so I probably wouldn’t do video first, but it would be a show like yours. I mean, if I were 20 right now, I’d be like, “That’s what I want to do.” If I could have a job, it would be Michelle’s job.

Michelle Khare: Oh, my God.

Tim Ferriss: I mean, honestly, it would be — but if you want to look at some other examples where I probably wouldn’t pursue it, but they’re doing excellent jobs. Acquired, for instance, Founders, David Senra, highly focused, long form, very hard to replicate because there’s so much God damn work, right?

Michelle Khare: Yes.

Tim Ferriss: Which is true with yours also. It’s like, “Oh, you want to spend six months making a video?”

Michelle Khare: Exactly.

Tim Ferriss: Let’s see. It’s a lot easier to publish frequently without thinking as hard about the lead time of doing something that’s very complex.

Michelle Khare: Right. And that was part of the strategy with Challenge Accepted too, is you see many people copying one another online, in any form of art, people are copying constantly. And part of our defensive strategy was how do we do something that is so crazy? No one would be crazy enough, I don’t think, to run seven marathons on all seven continents in one single week and make a documentary about it and go through all of the production headache of that, or call the FAA 300 times to get permission to hang off the side of a military plane to recreate the Mission: Impossible stunt.

Tim Ferriss: Right.

Michelle Khare: It’s almost like the things that feel so untouchable instantly become opportunities for story, because it’s a great story to try and overcome that. And also the second mover scenario will at least take them so long to catch up to us to get there.

Tim Ferriss: Right, because you’re going to be the comp. They’re going to say, “Oh, it’s like Challenge Accepted, but dot, dot, dot.” And that is going to be very difficult for other people to overcome. And I want to explore this a little bit more because it’s, I think, so critical and you see it in a lot of different places, sometimes the hard thing is the easier thing long term. Meaning, if you solve a very hard problem upfront, it makes your life a little easier or a lot easier long term. And this applies everywhere.

There’s an amazing, amazing guy. You should meet him at some point. Jerzy Gregorek and his wife, Aniela Gregorek, they’re Polish emigres. They immigrated to the US with like 10 or 100 bucks in their pocket. They were political refugees, landed in California, and still to this day, they both have multiple world records in Olympic weightlifting. And I would say they’re both around mid-60s and Jerzy can get on an Indo Board like a balance board with a fully loaded barbell and do a perfect Olympic snatch, like ass to heels and then drop the weight and repeat while balancing on a board. He’s got to be at least 65 now.

His wife, Aniela, who also, as I mentioned, has a bunch of world records can — her daughter’s, I guess, ball got caught in a tree a few years ago and she just ran up the tree and got it and came down. I mean, they are incredible physical specimens. They take no prescription medications. And the reason I’m bringing them up is that Jerzy has this expression, which is, “Hard choice is easy life. Easy choice is hard life.” And so it applies in physical training and health. It applies in creation, broadly speaking. It’s like with what you’re doing, you’re creating a moat that is very defensible in a lot of ways. It applies to startups where it’s like, okay, sure. Yeah, you can vibe code and create something in 20 minutes. And that’s interesting and you should experiment with that. And the barrier to entry has been lowered dramatically on the production of say an app, but the barrier to attention has never been higher.

Therefore, there is actually something to be said for the hard startup being the easier startup where if you’re solving a hard problem that requires a really good team, like hardware and this, that and the other thing, most people are never going to attempt it. Therefore, you actually have a margin of safety in some respect if you can execute. So I just wanted to mention that because I see this all over the place where if you spend the time to work on something hard upfront, it buys you a lot of safety is at least one way that I think about it.

And you’ve talked about assembling this Formula One team, but let’s rewind because I’m sure some people are like, “Well, if I don’t have any money and I’m just getting started, how do you afford to hire the Formula One team? That sounds expensive.” So let’s go back a little bit. Before you became active on YouTube, what were you doing?

Michelle Khare: What was I doing?

Tim Ferriss: Yeah.

Michelle Khare: Gosh, so I grew up in Shreveport, got my first taste of the film industry there. I went to college at Dartmouth, and then while I was in college —

Tim Ferriss: Good school.

Michelle Khare: Yeah, it was great. And while I was in college, I did some internships in the industry, but I also did an internship at Google. And so there I sort of saw the behind the scenes of the platform I guess I upload to now, which was really interesting. And as I was mentioning to you, Tim, a lot of things that have driven key moments in my life have been moments when my back has been against the wall. And one of those moments for me was when you do a Google internship, at the end of the summer, like many big internships, you find out if you get the job. You can go into your senior year of college like, “Oh, my gosh, I’m rocking. I got the job. I’m set. I can chill out the last year.”

And there was one day where they called everybody from my internship class, letting them know if they got the job and we’re all in a big text chain together and everyone’s like, “I got it. See you next year, blah, blah, blah.” I get my phone call —

Tim Ferriss: Sounds stressful.

Michelle Khare: I didn’t get the job. And I would say that this was pivotal and ironic now that I’m so embedded in YouTube in a completely different way. But what it forced me to do was my whole life had been about, as an athlete, finding a coach, doing exactly what they tell me to do. In school, it was, “Here are all the books to do while on the SAT. I will do them. I will wake up at five in the morning over the summer and memorize everything and do it.” Because that’s the formula to success.

Tim Ferriss: Executing to plan on the formula.

Michelle Khare: Exactly. And I think it’s part of the immigrant mentality of the holy trinity of doctoral lawyer engineer is because those are systems for safety. And also from my family, like with many immigrant families, they know so intimately what instability feels like. And so that led me on the course that eventually led me to BuzzFeed, which was in many ways sort of the first creative risk I had taken on myself. And at the time it was the fastest growing YouTube channel in the world.

Tim Ferriss: What was the job that you had at BuzzFeed?

Michelle Khare: So I started as an intern again, And eventually I became a producer at BuzzFeed. And producer is such a strange term, even in traditional, but what it meant at BuzzFeed was doing everything. So I was responsible for everything from ideation to filming, editing, uploading, and I didn’t have any of those skills. Even though my homegrown Shreveport, Louisiana, shout out Vivek Khare, my dad putting on his little AFI film school in our house, it did not cut it for what we needed to do. But what I loved about that was you had to learn every part of the process. Unlike when I interned on a traditional film set, it’s very specialized. There are unions. You don’t even touch equipment from a department that’s not yours.

Tim Ferriss: I’ve seen that. You get yelled at.

Michelle Khare: And you do get yelled at, and there are great reasons for that. But the learning environment was so important for me to learn, when you ingest footage, you can accidentally delete it all. That sucks. I needed to learn all of those processes because even today, now, we have an amazing team, a massive production team, and it helps me as a leader to be able to empathetically chat with each department. We’ve all been at companies or on film sets where the director or CEO has never done the jobs of anyone that they’re asking to do a job for. And I like being able to talk to the sound person in my basic understanding of what are the frequencies we’re on. Is there anything we need to adjust about this set that is disruptive to the way you have the boompole set up? I like knowing all of the details and being able to think critically about each department so everyone can succeed.

Tim Ferriss: So this is going to be a leading question, but I’m going to try it anyway. Do you think it’s fair to say that if you had not had the BuzzFeed job and you’d gone straight from not getting the gig at Google to YouTube, that the outcome would have been very different?

Michelle Khare: Exponentially different. Yeah. I don’t think I would have succeeded.

Tim Ferriss: So I want to spend a second on this simply to say, because I get asked about starting companies all the time. And someone’s like, “I’m graduating and I’m going to start my company.” And I think they’re sometimes surprised and a lot of professors disagree with me on this, which is fine because I think that makes for interesting conversations. But my default recommendation is do not start a company right after school. Go get an MBA or a master’s degree in X where you get to do every job where someone else is paying you for it.

Michelle Khare: Exactly. It’s a little, paid graduate school.

Tim Ferriss: So that you are learning to learn, make all your dumb mistakes or make your first massive round of dumb mistakes on someone else’s dime. And if you immediately start your own company, you’re also not necessarily going to get the breadth of experience in a more mature — and that by mature, that could be 10 or 20 or 30 employees, it doesn’t have to be a gigantic company. But get that experience first and then increase the odds of your own success at that point by going and starting your own gig.

Michelle Khare: Right.

Tim Ferriss: I’m curious if you think that still applies, for instance, in the world of, and I know this is painting with the broad brush, but YouTube. If somebody came to you and they said, “I want to get really good at…” The world has changed so quickly in terms of video and entertainment and visual storytelling. With a startup, I would still tell someone, “Hey, if you can…” I know we’re all painting this dystopian picture of Mad Max in 10 years. Let’s just, for the time being, for planning purposes, assume that’s not going to be the case, work at a startup first, then start your own startup.

But in the world of visual storytelling, would you suggest people get a job kind of working at a place like a BuzzFeed or something like that before making the leap into YouTube now? Or is there a better way to learn the skills necessary to do in-depth, long-form stuff?

Michelle Khare: I definitely think having experience working for someone else in the field that you want to be a part of is so educational, not just to be in the mail room and see how things work, but also to define a core tenet list of what you enjoy about the company and all the little things you don’t like. When I left my job, I had a very clear list of, “This worked great for this company, but at my company, I’m never going to do X, Y, or Z.” And that was super, super helpful to define company culture, to ensure people’s voices are heard, to keep employee retention high. And I think that’s why with Challenge Accepted, our sets operate so differently, that everybody has a digital mind of we need to shoot it this way because it will perform well, or we’re thinking critically about retention and the intro and whatnot, but we’re also thinking about storytelling as a medium has been solved. Traditional Hollywood, they clearly did something right, and let’s learn from that.

It’s as simple as breaking for lunch every six hours. It’s as simple as making sure we have enough pre-production meetings. And those are the things that were pain points for me at prior jobs, and I’m able to apply them in this really special space where we have an amazing, amazing culture and work environment where people can hopefully feel that they’re able to express themselves artistically, experiment, and learn at the same time.

Tim Ferriss: So I’m trying to figure out where to go next because I think it’s probably going to be fear-setting just because I want to hear how that factors into things. Why don’t we just go there because I’ve read about the whiteboard of fears and other things. I’m sure we’ll spend a second on cycling also.

But the way that this interview ultimately happened was because of an X exchange. I put up a post about YouTube channels. Are there any YouTube channels out there that have some type of intersection with The 4-Hour Workweek. Or anything in it? And that’s how we ultimately personally connected.

How does fear-setting fit into the story?

Michelle Khare: Well, well, Tim, it fits into the story in a few ways. Challenge Accepted at its core originally began by me taking a whiteboard and writing all of my fears out and then connecting each fear to a circumstance that would cause me to address it, not just as a personal self-help type of thing, because I am a very anxious person internally, but more specifically because it makes for a better story.

We realized very early on showing the vulnerability, showing the fear, that’s a key part of Snyder’s beats of storytelling. So starting with the all is lost moment of the story led us to unlock really, really fascinating episodes and we would structure the thesis of each of like, “I want to be a firefighter, but I’m not brave enough.” Okay, that’s an interesting story and we’re thinking about that in every piece of the edit, every piece of the pre-production. And that is the climax of the emotional core of when I finally go in a burning building, why we care so much. It’s the same in the Mission: Impossible project. I would love to be in a Mission: Impossible movie, but am I actually brave enough to strap myself to the side of a plane like icon Tom Cruise? Okay, I’ve got to do that first.

But I actually brought something, Tim.

Tim Ferriss: You brought something?

Michelle Khare: I brought something to help demonstrate fear-setting.

Tim Ferriss: Okay.

Michelle Khare: I’m going to bring it out now.

Tim Ferriss: Yeah, let’s do it.

Michelle Khare: I’ll describe it for the audio listeners.

Tim Ferriss: Oh. I recognize the colors.

Michelle Khare: This is not a plug. Unfortunately, you are dealing with a fan in the chair opposite from you, but reading The 4-Hour Workweek changed my life. This is the original copy I have from 2016. I was a bit young when it came out in 2007, so I didn’t have that version, so this might be slightly revised. But I went back into my archives and I found this email. The date is, what is today? March 31st, 2026. The date of this email — I’m not making this up. March 18th, 2016. It has been exactly 10 years since I sent this email.

Tim Ferriss: Wow. Okay.

Michelle Khare: I have to shout out my therapist, Jody, because she’s the one who told me to read your book. And I wanted to read a section of my fear-setting to you.

Tim Ferriss: Oh, my God. Amazing.

Michelle Khare: Now, as you know, because these are your memories and your brain, this was prior to the define, prevent, repair chart of your 2017 TED Talk.

Tim Ferriss: TED Talk.

Michelle Khare: So this isn’t even in a chart. These are just a couple of questions that you had. But I wrote here, this is so crazy, “My dream is to leave my job, start a YouTube channel, somehow succeed, own my ideas, and start a company where I can grow as a storyteller and help other storytellers grow without traditional barriers to entry.”

Number one, define your nightmare. I’m just going to read a few of the highlights.

Tim Ferriss: Yeah, please. Oh, yeah. No, take your time.

Michelle Khare: Define my nightmare was going broke. Never figuring out what I’m best at since I find the most joy in trying everything rather than specializing. People not thinking I’m funny. And the last one is actually not being funny. And of course, I went through the steps of repairing the damage.

Tim Ferriss: Well, do you have any examples there?

Michelle Khare: Yeah, of course.

Tim Ferriss: Yeah. Because, I want to give a quick —

Michelle Khare: Oh, do your spiel.

Tim Ferriss: No, no, not spiel. Just like a quick context trapper. So fear-setting is a pretty straightforward thing. It’s basically borrowed from the stoics. I’m not the first person to look at this. I just tried to systematize it for myself. It was in The 4-Hour Workweek. And it’s like goal setting, but it’s identifying your fears very specifically and then making them as concrete as possible, then talking about what you might do to prevent them and/or repair them if they inevitably happened. And the objective here is to, in a sense, demystify and take your fears from being this nebulous cloud of anxiety to something that you can put under a microscope to test.

Michelle Khare: Yes. So the first part is defining the nightmare. The second is what steps would you take to repair the damage even temporarily? And here I had using my savings from my Google internship.

Tim Ferriss: Yeah.

Michelle Khare: So I did have savings from that. And then making sure that my resume or LinkedIn was ready for other jobs in the industry. Number four. Oh, this is number three. If you were fired from your job today, how would you get things under financial control? And I said that I would temporarily use my savings and if that didn’t work out, aggressively apply for other jobs and listed some other companies I would reach out to. This is where it gets very intense.

What are you putting off out of fear? I’m putting off quitting my job. I’m putting off reaching out to all the people I need to make this dream a reality because it means I have to say it out loud. I’ve reached out to some people, but I know I can do better. What is it costing you financially, emotionally, physically to postpone action? I’m under emotional, high stress. I want to tell stories that really resonate with other people. I want to be around people who share creative joy in the same values of quality that I do. I am unhappy in an environment where I feel like people feel the opposite.

What are you waiting for? So this is the last section. I’m waiting for a false sense of security to inspire me to take a leap, a brand offering to collaborate, someone else offering financial stability, et cetera. But I’m actually being challenged and invited to create my own security for the first time. I have — oh, this is crazy to read. I’ve continually found success in other people’s rubric of success, but I’ve actually never found happiness. I’ve never designed my own rubric of success. And that’s because I don’t trust myself to define success. I’m scared to assume that responsibility.

That was my fear-setting chart. It’s a very personal process.

Tim Ferriss: It is.

Michelle Khare: I know you and anyone listening who have actually done it can empathize with that. I’m a very emotional person, as you can see from my videos. It’s real. Anyways, I was so excited to share that with you.

Tim Ferriss: I’m so moved by you sharing that, and I really appreciate you bringing that.

Michelle Khare: Yeah, of course.

Tim Ferriss: And you fucking did it. Awesome. Right?

Michelle Khare: God, that’s crazy. Guys, it works. It actually works. Wait, I didn’t tell you the funniest part of this. Here was the funniest part. So this has obviously been on my bookshelf for 10 years at this point. And I am a copious, like you, hand writer, note taker. I beat up my books. I write in the margins and proof. I mean, you can see the wear and tear on this thing. But when I opened this, there was absolutely no annotation. And I was like, why is this? And I felt stumped on it. And it wasn’t until I found this email where it was revealed.

Okay, this is how I wrote to my therapist with the chart. OMG, all caps. I am obsessed with The 4-Hour Workweek, several exclamation points. I just got the book on Monday from my coworker and I’ve been reading it incessantly every night. Here’s my fear-setting exercise. I stole this book apparently. And I said, I called my therapist last night before the recording. I was like, “Who would I have borrowed this book from? I have no idea whose book is in my lap right now, but it’s been on my shelf for 10 years. Whoever it is, I’m so sorry.”

By the way, I did buy all of your other books, so I did contribute to that economy, but I have a stolen Tim Ferriss book.

Tim Ferriss: That’s amazing.

Michelle Khare: I can contribute to the cycle and donate it to a library or something, but —

Tim Ferriss: Oh, my God. That is so good.

Michelle Khare: It’s so funny because the person from my job who let me borrow and steal this has no idea how much they impact me because I don’t even remember who it was. I mean, we were all in a bullpen with 30 desks. I probably just borrowed it from someone who sat next to me, but —

Tim Ferriss: So here’s a follow-up question on the fear-setting. And this isn’t a trick question because when people experience any ambitious or scary journey for themselves, often the same thing, it’s not a straightforward line-up into the right. It’s a bumpy path.

Michelle Khare: No.

Tim Ferriss: After doing that, when did you take action towards realizing the dream? And what was — it could have been a very small thing, I don’t know, but what was the kind of defining first step that kind of set you on the actual path to realizing what you laid out?

Michelle Khare: I took action pretty immediately, but it took me a year to quit my job. And I’ll define what the difference is. I took action immediately by, this might be crazy, this was a Tim Ferriss experiment. I really resonated with what you wrote about coming to terms with the worst possible outcome. And so I decided I’m going to train myself for the worst possible outcome.

Tim Ferriss: I love it. Yeah.

Michelle Khare: So I moved into a studio apartment with a roommate. I cut — financially stripped down. I mean, I didn’t have much anyways, but stripped as much as I could to simulate. If I’m truly failing at this and having to live in a Hollywood apartment with a bunch of roommates, I’m just going to get used to that. I’m going to get used to it right now. I’m going to cancel all of my memberships and figure out how to stay healthy with just myself, just myself in this small place.

I am also going to commit to working on my own stories after work, on the weekends, because if I can’t do it now with stability, I need to prove to myself that I actually give a shit about this, really. And I did that for an entire year, growing a little bit of a personal savings, but also growing mental and physical stamina towards — I’m already in — it’s still a place of safety, of course, but I am in a situation where I think I can handle this. I got this.

LinkedIn is up-to-date, little resume is up-to-date. I am so ready. I have defined, prevent, and hopefully we don’t got to go to that third column repair. And so then a year later, exactly, I quit my job. And when I quit, I had two months of videos backlogged, ready to go. Also, legally, for the record, on my own machine, not company resources. All of that was ready to go.

And I knew what my first big project would be, the training with the stunt doubles. I had a shoot date ready. I had taken — I only had like three months of savings at that point, and I had allocated this is going to be for the dream project. My first risk on my channel, nothing will touch that. The rest is for operating daily life expenses. And I said, “I got three months to make this work.” And like you said, like we’ve been talking about, sometimes you got to put your back against a wall and go.

Tim Ferriss: Yeah. I love this. So this is, I feel like we were separated at birth. So a few things. I’ll say number one to try to, I’m not a paragon of self-awareness, but I will say that I, for different reasons, have a certain hypervigilance focus on safety and security, which might sound strange to people listening, but I’m always trying to risk mitigate, right? I’m actually, I don’t view myself as a big risk-taker.

I have done a few things that have ended up with me accumulating injuries that maybe in retrospect shouldn’t have done, but broadly speaking, I’m always trying to mitigate risk, which underscores this entire fear-setting exercise, right? Because it’s not just about convincing yourself. It’s also, in my mind, completely intertwined with what you did, which is preparing and training yourself and your circumstances, right? So when I flash back to starting my first company, it’s like, how did I start the first company?

I started my first company during lunch hours, evenings and weekends, basically, while still doing my other job and doing my other job well, but I wanted to have a head start so that I wasn’t beginning from scratch after quitting a job, right? So I did that. By the way, you’re simultaneously developing skills as you’re doing that and proving that you don’t need the crutch or the training wheels of your company to enable you to do those things, right?

So the moonlighting aspect, this is another thing that, at least in my mind, maybe conflicts with how some listeners might think about me, but there’s a difference between — I’d be curious to hear you speak to this. There’s a difference between putting your back against a wall. In other words, like highly pushing yourself to make a decision and like burning all the ships and burning all the bridges.

And the way I would frame the difference is when like a year to the day almost, right? You quit your job and you’re setting up this groundwork and you have some videos ready to go and you were in — where were you at the time? This was in —

Michelle Khare: In L.A.

Tim Ferriss: — in L.A. So you’ve got probably COBRA, right? You might have some residual healthcare after you quit. I’m not sure how it was set up benefit wise, but like in my company, I knew I had at least like a handful of months where I wasn’t going to have to pay for my own healthcare. And in that case, right, as you’re thinking about what could I do if this fails, right? If it doesn’t work out, what could I do? You’ve got your LinkedIn and resume ready to go, right?

And in my fear-setting, and for a lot of people, it’s like, well, I could get like a temp waitering job. I could bartend. I could sell a bunch of my furniture. I could sell my piece of shit used car and take public transport. I could whatever, right? Sleep on an air mattress in a friend’s room. So in a sense, you’ve proven to yourself that the permanent irreversible risk is actually low, right? While at the same time propelling yourself towards this defining decision, which is like taking the leap.

Michelle Khare: And I think the emotional stability of that decision is important. You want to be able to brainstorm, what should I do in the worst case scenario from a place of safety, which is what I had at the job still. So I was able to be creative about thinking about solutions without being panicked at the same time in that situation.

Tim Ferriss: Yeah, exactly. What an amazing story. What fun. And it’s a recipe, right? It’s replicable. It’s going to be different for every person, but it is actually, it’s a formula that works, like a lot of things. And I want to also mention a few things that come to mind just to draw some parallels. So you mentioned BuzzFeed where you learn to do all of these different jobs, right?

And there’s a benefit to that above and beyond the expertise of say spot checking your team’s work or something like that. Your team will also respect you more because they know you have done the thing you are asking them to do, which you did kind of mention in passing, but it’s really important. I think of, I have some PTSD memories of this book, but The 4-Hour Chef, which confusingly is a book about accelerated learning, actually tried to do a lot with that book, but very proud of it.

I think it worked. But the reason I bring it up is there’s a chef who’s profiled in that named Grant Achatz who was basically one of two superheroes in a sense. I mean, they both have super powers, right? You had Grant Achatz, the chef wunderkind genius, and then you have Nick Kokonas, who I’ve become very close friends with, who is a former genius options trader in Chicago who then decides to get in touch with Grant. He’s magical at cold emailing, which I want to talk to you about, very good at cold emailing.

And they got together and Nick is from a business kind of challenging and redesigning of systems perspective, incredible. But the reason I bring it up is that Grant can work every station in the restaurant better than everybody else, which is not to say automatically that I or you can do that with all of our team members, but he’s, at the very least, incredibly good at each of the stations so that he can when need be, improve systems, change things.

He can also teach and coach. He can give feedback. And if he gives feedback, people take it seriously because they know he’s done it himself and he knows what he’s talking about, right? So there’s a huge advantage to that and it makes your mistakes, later, less expensive, also, and it allows you to hire more effectively, whether that hiring is a contractor or full-time. Okay. I just wrote this down and I have to mention it because basically I’m like living vicariously through you now —

Michelle Khare: Oh, my God.

Tim Ferriss: — in a sense because your channel’s like, “Oh, my God.” If I could have sort of self-authored a path to doing that, like, oh, man, what an amazing thing.

Michelle Khare: Oh, my gosh. Thank you.

Tim Ferriss: I know there’s a lot under the hood and behind the scenes that I’m sure is very difficult, which we’ll talk about. But if you have not connected, and maybe you’ve graduated on from the stunt work and so on, but Damien Walters, have you seen Damien Walters?

Michelle Khare: No.

Tim Ferriss: Okay. I don’t know if he’s still in the game, but Damien Walters, he’s a former high-level British gymnast who then entered the world of stunt work and just has the most insane yearly highlight videos that he put out for a while. This is an older vintage, right? But he’s been doing it a long time. But in any case, I thought he could be incredibly fun to connect with at some point.

Michelle Khare: That’s awesome.

Tim Ferriss: I’ve never really interacted with him, so I can’t —

Michelle Khare: I have so much love and heart for the stunt community. That’s really where the channel started. And even the stunt coordinator that I work with today, his name is Steve Brown, and this is how crazy the world is, right? Back in 2016, so a few months after I sent this email, I went to a kebab shop in L.A., sat down at the counter, and was just eating dinner by myself. And I remember I was really critically thinking about this decision of going off on my own and applying this.

And this guy comes in, sits next to me, we just start talking, have a nice conversation, go our separate ways. I go on to start my channel and do what I’m doing. He goes on to choreograph and do stunts and lead stunts for Logan, several Marvel projects, and most recently, all of the Avatar films. That guy also does all of the stunt coordination on our channel.

Tim Ferriss: That’s incredible.

Michelle Khare: And it’s amazing that when you meet people who are passionate, you know when you meet a flavor of a person before they have hit their peak moment, it’s special to connect with them and rise together. And that’s what’s been awesome about Steve is between his Avatar movies, he’ll come over and strap me to the side of a plane or throw me in the Houdini tank and make sure that everything’s okay because we have that kebab friendship.

Tim Ferriss: Well, this speaks also to putting yourself in the center of the action, right? And I’ve had very famous investor named Bill Gurley on the show before sat where you’re sitting right now, legendary investor and he talks about this a lot, which is putting yourself where the action is, right? So if you want to have those types of connections, it’s less likely to happen in a small town in Montana than it is in Los Angeles, right?

Michelle Khare: Right.

Tim Ferriss: Similarly, depending on your industry, IRL still matters a lot, right? As much as we would like to think it doesn’t, it’s like if you want to be in certain games in tech and you want to have access to the talent, et cetera, still to this day, in a lot of instances, you have to be in San Francisco or somewhere near San Francisco. That’s just where you have to be.

Michelle Khare: And this is coming from the virtual guy.

Tim Ferriss: It is. It is. And yet, if you look at what the virtual guy did, because I was trying and wanted to get involved in tech and then ultimately angel investing, where was I? I was in the Bay Area for 17 years. If I had not done that, I think my success would have had a 0% likelihood. I mean, literally 0%. If I look at how a lot of the ultimately best advising or investing relationships came together, they almost all started with chance encounters at the equivalent of a kebab shop, right?

I go to a barbecue at someone’s house and accidentally bump into someone and spill their drink and start a conversation and then boom, that turns into one of the most — ends up defining 30% of my net worth. And sure, there’s luck involved, but you have to provide a, and I’m borrowing this term from someone else, but surface area for luck, right?

Michelle Khare: So what have we learned? Barbecue, kebab, spilling drinks, key to success. 30% of Tim’s network.

Tim Ferriss: Chapter one. Chapter one. Bump into people. Actually, it really could be. The other thing I wanted to mention is you talked about, in a sense, and this is not the most elegant way to put it, but like practicing poverty, right? That was one of your fears, right? It was like running out of money. So you move into the apartment where you’re sharing a studio with someone else or multiple people and you get rid of your memberships and so on and you prove to yourself, number one, you can certainly survive. Number two, probably it’s not that bad. You can figure it out.

And sure, maybe if you’re depending on the roommate, I mean, you might want to get rid of said roommate, but it reminded me of, not to belabor this, but since the genesis of fear-setting is stoic philosophy and the stoics, Seneca the Younger talks about practicing in this way. A very close friend of mine, Kevin Kelly, who was the founding editor of Wired magazine and fascinating person on all levels. Also has a big Amish beard and has spent time with the Amish to study how they accept or reject technology, et cetera, et cetera. Really interesting guy.

But he also, I don’t know if he does it anymore, he’s got to be mid-70s now, but he used to routinely spend periods of time, I want to say every year where he would just camp out in his living room in a sleeping bag and have like instant coffee and instant oatmeal and just do that for like a week and he’s like, “Oh, yeah, great. Yeah, I don’t really need that much.” And by doing that, it gives you courage, which I think is a practiced skill, right? Your subconscious has to believe that you can do something. You can’t just read books and suddenly have confidence in all situations. And I mean, you’re, I think, a walking example of how you can do that.

So my question for you, Formula One team. All right. Formula One is expensive, right? It’s like these cars in some cases are like what? $250 million when you start to add everything in, pricey. Yes, very high performance. But when you quit your job and you’re like, “I have three months.” How did you assemble or enroll the help that you needed in the early days, the first three to six months after quitting your job, or did you just do everything yourself? I don’t know. So what did it look like in the early days?

Because once you get some momentum, I’m sure you get some money coming in. Okay, you can start to add, you can start to upgrade, you can start to do various things, but in the beginning you’re very capital constrained, right?

Michelle Khare: Yes.

Tim Ferriss: What do you do? How did you assemble the help that you needed or enlisted?

Michelle Khare: I think — this is a strategy I employ for every challenge I take on now. And hindsight is 2020. And with that 2020 hindsight, I think it comes down to having three people on your Formula One team, and it doesn’t need to be fancy. It’s really a coach, a mentor, and a cheerleader.

Tim Ferriss: Okay.

Michelle Khare: What does that mean?

Tim Ferriss: Yep.

Michelle Khare: In a specific episode of Challenge Accepted, the coach is the most important person that I want to find before we pursue an episode. In a recent episode, I attempted to get a black belt in taekwondo in only 90 days. And in martial arts, that’s a somewhat controversial thing to even attempt to do. And so I knew I could only do it with the blessing of a really respected master. So objective number one was to find the best master and coach in the world. And I think it’s important to find someone. And again, I’ll give an example for what I did in that specific situation, but that’s number one for me because this is the person I’m going to be spending all of this time with and learning from them.

The second person is a mentor who is different from the coach. This is a person who has most recently done the thing you’re trying to do. So for me, that’s other students in the black belt class. They’re my mentors. They have gone through this process. They know what it feels like to break a brick with their hands and get through that. And it’s important that it’s different from the coach because coaching is a different skillset and art form from mentoring.

Tim Ferriss: Also, it’s harder for the coach to put themselves in your shoes because so much of what they do is second nature and they’re probably decades removed from the experience you’re about to have.

Michelle Khare: You want someone who has the experience of leading somebody to that finish line of greatness, and you also want someone who knows what it feels like to be the man in the arena. And then the third person is a cheerleader, which is someone who is completely detached from the outcome. So for me, that’s my best friend, Olivia. It could be a sibling, friend, family member, someone who is going to root for you and love you no matter whether you succeed or fail.

So that’s how I approach every single challenge on the channel. Meta-wise at the beginning of the channel, what was that for me? It was the mentor figure or figures for me were other people who had recently started channels and were just a few steps ahead of me in the process. Maybe they had 50,000 subscribers, maybe they had 100,000 subscribers. They were people I met at little meetups at, rest in peace, the YouTube Space, which doesn’t exist anymore, but those peer groups were really special and important to me to keep me motivated and to just reach out to people.

Even today, reaching out to other creators, “What do you guys think of this thumbnail? What do you think of these titles?” Having people who are just a couple steps ahead of you or on similar playing fields can be so, so helpful in that process. The cheerleader for me at that time was my sister, Madeline, who was one of the only people I told I was going to quit my job and fully believed in me. And then the mentor, sorry, the coach figure for me when I was starting from ground zero was cold emailing people I respected.

Now that’s not the same as having a coach who’s with you every day in the way Master Ree is training taekwondo with me every day, but I saw those as coaching opportunities because they were people light years ahead who had the mentorship component of, not the — the teaching component, I should say, of being able to advise even in small doses.

Tim Ferriss: What did those emails look like?

Michelle Khare: Okay. I love a great email. You mentioned that you have an amazing cold emailer. I need to see their art and their work because I love comparing notes on emails. I personally believe that a really well-written email can open any door and —

Tim Ferriss: I agree, by the way. I mean, assuming the person sees it, right? There’s some friction, but people underestimate what they can do.

Michelle Khare: I agree. And there’s something about an email that’s different from an Instagram DM or — I don’t know. I love an email. I love a Google Calendar. This is where we’re talking about true passions to emails. So at the beginning of my channel, when we didn’t have millions of subscribers and we wanted to collaborate with institutions like the FBI and the Secret Service, and ultimately we became some of the first YouTube channels to ever do that. Came from not a producer, not a friend of a friend sending email, but me sending a cold email.

And an example of that is I wanted to do a video with the FBI, so I went on fbi.gov. I called the 1-800 number of the FBI, which by the way, is for crime tips, which I didn’t realize. And I pitched them this idea over the phone and they’re like, “So I’m here to receive crime tips, but I can connect you to someone else.” And I wasn’t anticipating that. I thought it would kind of be a dead end.

Tim Ferriss: So I just want to pause here for the specifics. Ring, ring, hello, FBI 800 number. What are you saying?

Michelle Khare: Hi, my name is Michelle Khare. I know this might come off as a little strange or unexpected, but I was trying to contact someone in your department who might work with film and television. I’m a content creator online. We have several hundred thousand subscribers and I was hoping to talk about a collaboration.

Tim Ferriss: All right, great.

Michelle Khare: And usually they’re like, “YouTube, what?” But this person was generous enough to connect me to someone else and we kind of got kicked down a few different routes, but we ended up connecting with someone called The Hollywood Guy. This is a job at the FBI.

Tim Ferriss: He’s just like, “How did I get stuck in this department every email that comes over the transom about some kind of film, television thing.”

Michelle Khare: It’s The Hollywood guy. And now this is the person within the Federal Bureau of Investigation who is assigned to documentaries or even scripted shows to ensure that the seal of the FBI is accurately and not displayed, not misrepresented, or shown in a derogatory manner. This is the guy who did the McDonald’s Monopoly HBO documentary. He was the FBI’s representative for that. Amazing docuseries.

Tim Ferriss: I’m sorry. I’m not familiar with this. Monopoly, like the game Monopoly?

Michelle Khare: Oh, my God, you’re not familiar. What is this called? Oh, the documentary. It’s called McMillion$.

Tim Ferriss: Okay.

Michelle Khare: Have you heard of this doc?

Tim Ferriss: I mean, what is it about Happy Meals or something?

Michelle Khare: Riveting documentary series.

Tim Ferriss: McMillion$? Okay.

Michelle Khare: Oh, Tim, you’re going to love it.

Tim Ferriss: All right.

Tim Ferriss: I got it. So there’s probably some fraud involved and the FBI gets involved. Who knows?

Michelle Khare: Okay. Do you remember in the ’90s, 2000s, there was the Monopoly game at McDonald’s where you could peel off the sticker and see if you won a vacation or a bunch of money. Turns out all of the winners of that were all related in some way.

Tim Ferriss: Oh, they figured out how to game the system.

Michelle Khare: They’re all family relatives or friends of friends or people within this group of people that they hired to win. I don’t want to reveal how they did it because it’s riveting, but the documentary tells the story from the perspective of the FBI agents who uncovered it.

Tim Ferriss: Right. So Hollywood guy gets an email. Hey.

Michelle Khare: So this guy just did McMillion$, an incredible docuseries for HBO, gets an email from me, YouTuber. And effectively what happened was he was like, “Well, I’m retiring in a couple months. Let’s try it out.”

Tim Ferriss: It’s so —

Michelle Khare: “Let’s try it out.”

Tim Ferriss: — wild how these things work out sometimes.

Michelle Khare: It’s amazing.

Tim Ferriss: Now, so that, again, this surface area for luck, right? You have to have some pinballs in the pinball machine —

Michelle Khare: Yes.

Tim Ferriss: — for the possibility of something like that happening. Is there anything else in your email or communication with the Hollywood Guy that you think increased the likelihood of him saying yes?

Michelle Khare: I do. I do. I think a great email, and a cold email, specifically, has to have some key components. The first is the subject line needs to show your value to the reader. For me, right now, it would look, like, something, I’ll be totally honest, “Collaboration with Michelle Khare (this many followers).”

In the beginning, that was a small number for me, but I still put it in the subject line. It could be a number of views, it could be collaborated with X, Y, and Z institutions. It just needs to be enough for the reader to see some value in what you’re doing.

Then the body of the email is three paragraphs. Very short paragraphs. In fact, three blocks of two sentences each. I wouldn’t even call it a paragraph. The first paragraph is one sentence about who you are, and your legitimacy. It has to be encompassed in one sentence. “Hi. My name is Michelle Khare. I’m a content creator with this many followers, and I’ve done this, this, and this.” Very succinctly proving your value.

Second sentence of that first paragraph, what are you asking for or offering to the other person? And, ideally, you’re doing both, you’re offering something. The second sentence of that email to the FBI would be, “I’m reaching out to inquire about an opportunity to film a collaboration for my channels.” What you’re offering there is access to our audience. “In the eyes of many of the people we collaborate with, it’s a marketing opportunity potentially.”

Tim Ferriss: Recruiting opportunity.

Michelle Khare: Right. Something like that. Paragraph two is two sentences or less of what you want to do. This would be the details of, “We’re hoping to do a shoot following just a few days of the academy embedding in existing activities, ultimately, leading up to a final scenario as follows academy protocol.”

So, that second paragraph is about a window into the vision you hope to come to together. And a peek at some of the resources you might be asking for. And, ideally, you do it in such a way that you show you’ve done your homework. I’m not just cold emailing the FBI hoping to do a video with them. I know very clearly I’ve watched everything I can online about what does the academy take to do? What are the activities? What are the ones that are best for camera? So, you’re showing your — it’s an opportunity to flatter them, and to put them at ease. We speak the same language. So, there’s that.

Paragraph three is the call to action. Two sentences or less. “Would love to hop on the phone. Let me know a good time. Here’s my phone number. Text me any time.” I think that’s, honestly, potentially, the most important part. “Here’s my phone number. Text me any time.” This is an anti-Tim Ferriss tactic potentially.

Tim Ferriss: Not when I’m sending cold emails —

Michelle Khare: Okay.

Tim Ferriss: — to people who are very busy that I want to —

Michelle Khare: Yeah.

Tim Ferriss: — connect with.

Michelle Khare: And what that does is say, “I’m available. I don’t know you, but here’s my phone number.” It exhibits, “I’m trusting you.” And it says, “You don’t have to respond with a crazy detailed formal email back to me. Hit me up anytime. We can talk on the phone.” It removes the barrier to entry for them to have to come back to you.

And then have a nice email signature.

Tim Ferriss: What is a nice email signature?

Michelle Khare: Just in a sans serif font. Maybe add a little color.

Tim Ferriss: With no Comic Sans? I’m kidding.

Michelle Khare: No Comic Sans, no Times New Roman. Tim, it’s not 2007 anymore.

Tim Ferriss: No. I saw this photograph — I have a lot of friends who work at Google.

Michelle Khare: Okay.

Tim Ferriss: And there was this big printed out sign to employees talking about snacks or things in refrigerators, and it was in Comic Sans. And then someone else took a marker and wrote on it, they were like, “This is Google, and it is a serious place of work. Please do not use Comic Sans.”

Michelle Khare: Wow.

Tim Ferriss: I just thought it was pretty funny, because there are a lot of people with high IQ at Google who may not have the social graces. But I have to agree on Comic Sans.

So, let me say a few things about this email.

Michelle Khare: Okay.

Tim Ferriss: I, in some ways, owe my entire career as it is to cold emails. And what you learn in crafting cold emails is directly translatable to in person and talking to people. In a way, it’s the same thing. There are some differences, but I want to highlight a couple things that you just said. Number one, including your cellphone. I am shocked by how many emails I get that are actually somewhat interesting that get surfaced by my team, because I have people who triage my email, that do not have a phone number.

And I’m like, “I don’t have time to have a bunch of…” My team does not have time to do a bunch of back and forth to figure out a time to talk, even though, you didn’t even offer a time to talk, and, blah, blah, blah. Archive. I just don’t have time for it. Like, this seems interesting, but it’s not definitively interesting. If you gave a cellphone, I would figure out a way to maybe call you, and in five minutes, I’d be like, “Hey. I have three quick questions. Interesting, but this is it, five minutes.” And in a friendly way, obviously. If it’s important to you, include your cellphone.

Michelle Khare: And I think it’s important to include it, this is just me personally, as the final sentence of the email, not tucked under your name.

Tim Ferriss: No.

Michelle Khare: You want to —

Tim Ferriss: Yes.

Michelle Khare: — truly invite them.

Tim Ferriss: Make it explicit. 100% agree.

Michelle Khare: Yeah.

Tim Ferriss: So, I want to just mention a couple of direct parallels between what you just mentioned as this formula — and if you’re open to it, maybe we could share a few examples or a template of —

Michelle Khare: Ooh, a downloadable PDF on Tim.blog.

Tim Ferriss: Exactly. PDF or a blog post or show notes.

Michelle Khare: Yeah.

Tim Ferriss: Just, so, people can actually see it.

Michelle Khare: Yes. Of course.

Tim Ferriss: And I will just draw a few parallels. So, number one, you need credibility upfront. And one way to think about this, and I always — if I’m thinking about reaching out to someone who is above my pay grade, and, trust me, there are plenty of people who are way above my pay grade, the first thing in the subject line —

I’ll give a tip that I sometimes use. So, let’s just say that — who knows? All right. Somebody knows Mr. Beast or Tom Cruise, or whoever it might be. Now, practically speaking, everything is going to have to get routed through someone else for Tom Cruise, and if you do get their personal information, they’re going to be very annoyed.

But where I’ll start with the subject line is one of two places or both. So, you mentioned the credibility indicator in the subject. Right?

Michelle Khare: Yes.

Tim Ferriss: I’ll use that, but if we actually have someone in common who actually recommended I connect —

Michelle Khare: Yes.

Tim Ferriss: — but they haven’t made the intro, I will say, for instance — it would be, again, just to use the Tom Cruise example, who I think would make an amazing interview, but like, “For Tom Cruise via mutual connection” —

Michelle Khare: Ooh.

Tim Ferriss: — “Tim Ferriss,” whatever the credibility indicator is. Right? So, I will mention the mutual connection first, because subject lines often get truncated on mobile or elsewhere. So, if they just see, “For Tom Cruise from Tim Ferriss,” he’s going to be like, “Who the fuck is Tim Ferriss? Archive.” But if it’s —

Michelle Khare: See the name data.

Tim Ferriss: If it’s, “For Tom,” or, “For Tom Cruise via” person who actually made the suggestion, and then my name, you —

Michelle Khare: I love that.

Tim Ferriss: — have a huge advantage, because chances are it’s going to get truncated, or —

Michelle Khare: I love the via.

Tim Ferriss: Yeah.

Michelle Khare: I’ve done, “Referral from X.”

Tim Ferriss: Yeah.

Michelle Khare: And then my stuff after.

Tim Ferriss: Yeah.

Michelle Khare: But I like the via, because it doesn’t necessarily mean that they’re going to have to vet, and call that person up. You know?

Tim Ferriss: Yeah. Yeah. Exactly. Well, that brings up another point, which is if you’re going to mention mutual connections, and I’m shocked by how many people violate this, you better actually know — assume the person you’re emailing is going to immediately text those people.

Michelle Khare: And they will.

Tim Ferriss: And I, certainly, will. And I would say nine times out of 10, that person is like, “Either I have no idea who that person is,” or, “I met that person once and we shook hands at a party. I don’t know them at all.” And I’m like, “You’re gone. You just misrepresented,” implicitly or explicitly.

But when I’m writing an email. Right? I’ll have that subject line. If there is a via, I’ll include that name. And in the subject line, I’ll keep it short as possible. Then always default to Mr. or Mrs. or Ms. Something. Like, something that I really appreciate about you, because it doesn’t cost anything is you are very default polite, and, even though, it makes me feel like an old bastard, you were like, “Yes, sir.” And you used sir with me a couple times when we came in.

And, no. No. But you’re always better off being on the safe side. And so, I am consistently surprised, and maybe this just makes me a salty, crotchety old bastard, but when people are like, “Hey, Tim. Yo, bro. Yo, Ferriss,” or whatever. I’m just like, “Did we go to PE” —

Michelle Khare: Someone says, “Yo, Ferriss?”

Tim Ferriss: I’ve got so many guys, it’s always guys, who think that that —

Michelle Khare: Like, founder bro type?

Tim Ferriss: It could be anything, but think that, like, shoulder slapping, immediate camaraderie is helpful. I will say that’s a very risky gambit. Maybe it works one out of 10 times. In my case, I’m just like, “This is a liability.” Right?

Michelle Khare: Right.

Tim Ferriss: Because here’s how I think about is I’m like, “Well, even if it doesn’t bother me that shows a general lack of awareness, and if they’re going to ask me to connect them with someone, or they’re going to work with anyone who I care about, and they pull that, it’s going to put…” It’s a reputational risk.

And so, most of the time that’s going to be an auto archive. It’s going to be like, “You know what?” The people you’re reaching out to, if they’re really busy, and if they’re well-known enough that you think to email them, have more opportunities than they can even look at.

So, your job number one is don’t do anything stupid.

Michelle Khare: Right.

Tim Ferriss: Don’t do anything that’s going to disqualify your email. Right?

Michelle Khare: And the, “Yo, Ferriss” of it all, emotionally, feels as if a stranger is coming up to you at the airport and giving you a hug. “Whoa. Wait. Who are you?”

Tim Ferriss: Yeah.

Michelle Khare: “What?” Like, that’s what it feels like.

Tim Ferriss: Yeah. Just another pro-tip, because we’re in Austin, and this is man bun, baggy pants/bitcoin, ayahuasca, CrossFit central is don’t just walk up to someone you don’t know and say, after they offer a hand, “Oh, I’m a hugger,” and just go for the hug. Don’t do that. Just really don’t do that.

Michelle Khare: Right. Right.

Tim Ferriss: Assume you’re in Japan and they’re going to strike you down with a sword if you do that. The person who wants the most distance wins that conversation. It’s like skiing in the back country with an avalanche risk, or something. Whoever is the most concerned gets to veto.

But let’s come back to the cold email. So, we’ve got the subject line, different subject lines for different purposes. In the first line, it’s going to be a credibility indicator. All right. A couple of points on this. Right? So, you’ve got your credibility indicator in the subject line, potentially, which I will also do, be like, “For interview (1 billion plus downloads).” Right? In the case of the podcast. Right? Something like that.

Michelle Khare: Right. And I’ll note for if you don’t have a billion downloads, or millions of followers, in the beginning for me it was examples of the work.

Tim Ferriss: Yeah.

Michelle Khare: That would, at least, show I’ve done my homework, no one’s watched this, but it looks really, really good and it’s beautifully edited.

Tim Ferriss: Yup. So, I am going to come back and ask you about, just to plant the seed, the mentors in the very early days when you didn’t really have much. Right? Like, what that email looked like. We’re going to come back to that.

Michelle Khare: Okay.

Tim Ferriss: I’ll give my example. When I first got to Silicon Valley, I volunteered for organizations that had name cache. So, I volunteered for, for instance, TiE, The IndUS Entrepreneur. Last time, I’m sure people checked, I’m not Indian, but TiE, super well-known at the time, maybe still, entrepreneurial organization. Like, the per capita density in the Indian diaspora in Silicon Valley with talent was fucking bananas.

Michelle Khare: Shout out.

Tim Ferriss: Yeah.

Michelle Khare: Those are my people.

Tim Ferriss: Exactly. And so, I volunteered there. And then I could say, “I’m emailing someone in tech,” and it would be for so-and-so via TiE or The IndUS Entrepreneur. And I wouldn’t even put my name, because who the hell am I? And that gets the email open. So, I would volunteer and then do things on behalf of the nonprofit as a way of establishing some kind of relationship. Ideally, inviting them to speak or something like that. All for free, by the way. Right? Like, some of the highest paying jobs you’ll ever get, you don’t get paid for in the beginning, in my opinion.

Michelle Khare: I love that.

Tim Ferriss: Yeah.

Michelle Khare: It does pay in dividends —

Tim Ferriss: Oh, my God.

Michelle Khare: — in ways you don’t expect.

Tim Ferriss: Yeah. I did that, and, ultimately, had, for instance, Jack Canfield, who co-created Chicken Soup for the Soul, which has sold hundreds and hundreds of millions of copies, and then they, ultimately, sold as a franchise, but I met him through an email like that from the Silicon Valley Association of Startup Entrepreneurs. And we are still friends to this day, 25 years later, or whatever it is, and he’s the one who introduced me to the agent who, ultimately, sold The 4-Hour Workweek after, like, 26 rejections.

So, long-term greedy, not short-term greedy. Right? Like, you don’t need to be paid upfront for something that will, ultimately, be very, very important to your life.

Right. To the email. For the credibility indicator, and, guys, we’ll give some templates just, so, you don’t have to piece this together in a Memento fashion, but I like to, and I suggest, include some text that establishes who you are. If someone says, “Hey. Here I am,” link, and sketchy attachment, I’m like, “I don’t have time to go on some scavenger hunt to figure out who you are.” Right?

So, include a line or two on who the hell you are. Do you know what I mean?

Michelle Khare: Yes.

Tim Ferriss: Don’t require them to click through and find this, this, and this, and this, and this.

Michelle Khare: A hyperlink to here. Uh-uh.

Tim Ferriss: It’s not enough.

Michelle Khare: You know what I mean? When it’s, like, “Click here.” No. It should be, “And I’ve done this thing,” hyperlink the, “And I’ve done this thing.”

Tim Ferriss: Yeah. Exactly.

Michelle Khare: So, if I want to learn more —

Tim Ferriss: Yeah. And just to give people some intel on that, one reason for that is that it just takes more time for someone, and you need to remove the reasons for them to say no. And you might think to yourself like, “Who the hell doesn’t have 30 seconds or a minute to click through,” and I’m like, “Somebody who gets 1,000 emails a day.” That’s answer number one.

And number two, anyone who is reasonably well-known has a lot of phishing attacks. Like, they have people from different vectors, who are trying to get them to click on links that are very dangerous and intended to steal information, or set the team up for social engineering.

Michelle Khare: I have been a recipient of a false, “You’re invited to the Tim Ferriss Podcast” email.

Tim Ferriss: Oh, yeah. Those. That’s a very clever scam. Do you know how that works?

Michelle Khare: No.

Tim Ferriss: Okay. So, how that works, because these are still going around, I think the jig is up, because people have realized most of these are fake, but — so I’m guessing the email was like, “We place people,” or, “We’re inviting you on the show” either if they’re not very sophisticated, they’ll be like, “It costs this much to go on the show,” and then anyone who knows me should be like, “Well, that doesn’t sound right.” But there’s this pay-for-play thing, which most people will sniff out.

The other one is, “Let’s get on a Zoom call, and discuss.” And what happens is you get on a Zoom call, and they somehow figure out a way to get you to provide, basically, screen access, not just sharing screen, but screen access, and they’ll take you to your Facebook page, or something like that, and they will hijack your Facebook page, then use it to promote a crypto scam on a large page, and then hold that for ransom also to get money from you.

So, this is just a way of saying —

Michelle Khare: Wow.

Tim Ferriss: — “Guys, include some fucking text.”

Michelle Khare: Yeah.

Tim Ferriss: Right? And then, to your point again, be very clear about the ask. The number of emails I get that it’s, like, even if they establish, “Hey. I’m credible,” but I’m not a president or the CEO of a Fortune 50 company. It’s, like, “Okay. This might be kind of interesting.” Right? If it’s, like, Rick Rubin, who I did his first interview on a podcast ever in Asana, but if you’re like, “Oh, it’s fucking Rick Rubin,” and he’s like, “Hey. Let’s jump on the phone,” you’re like, “Yeah. Okay. Fine. As long as I can confirm that’s who the person is.”

Michelle Khare: Right.

Tim Ferriss: But otherwise, assuming that you, who is cold emailing is not Rick Rubin, which is likely, then be clear about your ask. Right? If it’s like, “Would love to discuss something vague, let’s hop on the phone to discuss. How’s next Tuesday at 2 P.M.?” I’m never going to respond to that. Right?

Because if you can’t write a professional first cold email, I’m skeptical of everything that’s going to follow.

Michelle Khare: Right.

Tim Ferriss: Right? You’re not placing a value on the recipient’s time that you’ve thought through. Does that make sense? So, it’s, like, be really clear in the ask. And then when I close, again, to your point — right? Make yourself — and, by the way, you can use a burner, or you can use Google Voice, you can spin up a Google Voice number very easily from any G Suite, et cetera, et cetera. But have a number. Right? Where somebody can reach you. Do not just bury it in your signature. Make it explicitly clear. “Feel free to text me anytime.” Right? “We can schedule or just feel free to hop on the phone. I promise it will not take more than 10 minutes.” By the way, if you say that, do not go over 10 minutes.

Michelle Khare: Yeah.

Tim Ferriss: And then I almost always say, “If you’ve read this far, I really appreciate it. And if you’re too busy to get back to me, I totally understand.”

Michelle Khare: Okay. That’s a great learning. I’m going to add that.

Tim Ferriss: Yeah.

Michelle Khare: Love that.

Tim Ferriss: And by displaying as little or zero entitlement as possible, you get a much higher response rate. Why? Because your cold email is an audition for everything else to come. So, if you’re like, “Here’s this vague email. How about next Tuesday or Thursday at 2 P.M.”, it’s like, “Bro, slow down. You’re humping my leg already. We haven’t even established who you are, or what you want.” And that reflects a certain lack of awareness, and business savvy that is going to be a problem later. Right?

Michelle Khare: Mm-hmm.

Tim Ferriss: That’s how the train of thought goes. And that’s it. Here’s another pro-tip, if you send that email, do not follow up two days later with, “Bumping this up,” and then do that two days later, “Bumping this up.” You get to do that once. Right?

Michelle Khare: I think it’s got to be, at least, a week.

Tim Ferriss: Yeah. You’ve got to wait, and you’re allowed to do it once, and then just assume they’re not interested. And that’s okay. Move on. The world is full of great people, and if people are not responding to your email, it’s probably, common denominator, a problem with the email.

Michelle Khare: Yeah.

Tim Ferriss: You know what I mean? So, in the beginning, when you were reaching out to mentors, you just quit your job —

Michelle Khare: Yes.

Tim Ferriss: — what are you saying in the email?

Michelle Khare: Here’s an example, I sent a cold email to Hank Green, who is just —

Tim Ferriss: Yes.

Michelle Khare: — one of the great people.

Tim Ferriss: Describe who Hank Green is.

Michelle Khare: Hank Green is if sunshine, and joy, and a human encyclopedia were bundled into one person. Just one of the smartest, coolest, groundbreaking people, especially, in the YouTube world, ever. He came and gave a talk at Buzzfeed once when I worked there. And maybe this while I was still working there, or shortly after I left, I sent him an email — and this is actually counter to everything we’ve discussed. I wasn’t explicitly reaching out about a business idea, or anything, or trying to get something from him.

But I wanted to get to know him. And so, I sent him an email saying that, “I’m learning as I consider pursuing my own creative endeavor, and I’m curious what was the most formative pinpoint for you as a child to pursue this profession?”

And it’s just a fun question, honestly. There’s not much strategy here. And he sent back a multi-page answer. And I think he —

Tim Ferriss: What was your subject line? Do you remember —

Michelle Khare: What was the subject line?

Tim Ferriss: — roughly or what might —

Michelle Khare: The subject line was, “Hello from Michelle Khare,” or, “Hello from Michelle Khare (Buzzfeed)”.

Tim Ferriss: Yeah. Yeah.

Michelle Khare: So, using the title of some form of legitimacy. But he sent me this multi-page response. And at the end said, “Thanks for the thoughtful question. No one’s asked me before.” And so, sometimes I find that people are excited to share themselves. And, of course, in him sharing that story I learned a lot about how I could find creative inspiration, or even find parallels with someone who, externally, I don’t have a lot of overlap with. And I think that was awesome.

And now, today, where I know him in a more friendly capacity as peers in the space, it’s really special to have those email — like, these emails like this are so crazy to go back on. So, even if you send a cold email, and never hear back, it might make for a great story later.

Tim Ferriss: And guess what? You’re practicing your ability to craft emails, and your ability to communicate. And this would be, like, I interviewed Brandon Sanderson, one of the most legendary fantasy —

Michelle Khare: Oh, gosh.

Tim Ferriss: — writers in the world, who is prolific. And I think he wrote I think it was five books before he even attempted to publish one.

Michelle Khare: He, intentionally, said, “I’m not publishing my first several books” —

Tim Ferriss: That’s right.

Michelle Khare: Isn’t that right?

Tim Ferriss: That’s right. And I did just a huge romp with him. Met up at his HQ in Utah. Fascinating, brilliant guy. But the point is maybe your first five to 10 cold emails are just to improve getting better at cold emails.

And, by the way, something I did also is I would ask people who I had not sent those cold emails, but who are better-known folks, I would be like, “Hey. Would you mind taking a look at…” I would do this at events. Sometimes I’d be like, “This is going to seem like a weird request. Don’t worry. It’s not anything super bizarre, but would you be willing to critique this email? I’ve sent this to a couple of people. I haven’t gotten a response,” or, “I only got one response. How would you change this?”

And that is a very concrete question, and it’s also not clearly a question that’s just setting up the thing you actually want. You know what I mean? Because sometimes people do that via email. They’ll be like, “Hey. I loved your sweater. How did you train your dog?” And then five seconds after I reply to that, they’re like, “So, anyway, I was thinking of having myself on your podcast.” I’m just like, “You asshole. Clearly, you’re just setting it up.” So, just be aware of that.

Michelle Khare: [inaudible 02:01:07]. You got clickbaited.

Tim Ferriss: I got clickbaited. So, a few things. Hank Green, I don’t know him personally, but I remember seeing him at VidCon once. And there are two things I want to say. One is just, “What a sweet guy. Seems like a really sweet human being.” Number two is you reached out with, let’s say, a mentoring question to someone who already has demonstrated that they mentor. Does that make sense?

Michelle Khare: Yes.

Tim Ferriss: Right? So, that will make your life easier in the beginning when you’re sending out these cold emails. The other thing is if you do get a response from somebody, treat it like you’re not at a sex party, you are dating someone in the 1800s. Right? This is like Downton Abbey. Do not reply five seconds later with, like, “Oh, great. Now here are 10 more questions.” Don’t do that. Right?

Michelle Khare: Right.

Tim Ferriss: Be patient. Life is —

Michelle Khare: And thoughtful.

Tim Ferriss: And thoughtful. Life is long. If you want these relationships — I’ll also say, “You do not need to have 100 relationships with people who are steps ahead of you.” If you actually develop genuine, mutually respectful communication with a few people, you, in most cases, in a lot of cases, you are set. Right? So, it’s, like, “Don’t be greedy. Don’t be a greedy little piglet. Don’t be in a rush.” And I’ve, certainly, had to learn that by fucking that up over and over again, because I’m constitutionally very impatient. I want to get stuff done very quickly, and some things do not lend themselves to that.

You mentioned Snyder’s Beats of Storytelling I think.

Michelle Khare: Don’t quiz me on that.

Tim Ferriss: I won’t quiz you on it, but as far as storytelling goes, as far as developing narrative arcs, it does not need to be a book, but it could be, are there any particular resources you would point people to? Where you’re like, “Okay” —

Michelle Khare: Oh, gosh.

Tim Ferriss: — “I know there’s being in the trenches and working on it, and testing, and split testing, and using warm audiences in the beginning,” et cetera, but if you’re like, “All right. Look, if you want to do something analogous to what I’m doing on YouTube…” Right? And there are other examples of people who put out very few videos. Right? For this, sort of, longer form, narrative arc storytelling. If you were teaching a class on that, what’s the syllabus? What do you tell people to read or watch?

Michelle Khare: A challenge — like, reality —

Tim Ferriss: Yeah.

Michelle Khare: — docu, class — okay. Welcome to my class. On the syllabus, we’re going to be studying a few things. First of all, I’m going to make everyone watch Survivor, and every week we’re going to discuss it. First of all, because it’s the best ever. I’m obsessed with Jeff Probst. And I think that part of reality doc, in particular — Survivor is a reality competition show, but there’s a lot that can be learned in doing your own vlogs, or self-filmed, human stories. They do an excellent job at taking hundreds of hours of footage, and pulling out the story beats that make sense. You watch an episode of Survivor, it might feel like things are just happening, and they are, but they’re also curated from thousands and thousands of moments, storylines that were left on the floor.

And so, I think Survivor is an amazing lesson in, first of all, hosting. And, second of all, killing your babies in a way. We know on that island they’re out there for a month and a half. A lot’s going to happen that’s not going to make the edit. But why have the producers chosen this storyline to tell? Why is it engaging? Why is this the act break for the commercial?

I think that’s number one, selfishly. Probst is the GOAT.

Tim Ferriss: Also, sidebar, Probst is an excellent example also of creating defensible IP. Right? Which a lot of people don’t realize.

Michelle Khare: Yes.

Tim Ferriss: They’re like, “Oh, isn’t he just the host guy?” It’s like, “No. No. No. No.”

Michelle Khare: No. He’s the Einstein of that operation.

Tim Ferriss: Yeah.

Michelle Khare: It’s amazing. And when you watch his hosting, it’s so masterful, because he is a fan, and also a researcher of the people on the show. You see him at tribal council. He is recounting things that have happened decades ago. He knows the details of the contestants’ life, and he asks a question, not as a leading question, but as a way for the contestant to open up. I think that is incredible interviewing.

And it’s something that I studied too. I did a show called Karma on HBO, which was a kids’ survival show produced by J.D. Roth, which another huge reality legend, and, again, I think people watch these shows and think the hosts are just there to say lines and deliver information to the audience, but there is a massive amount of research. You have a binder of every kids’ head shot, where they’re from, your family, you’re taking notes, you’re sitting in MCR, which is this trailer with hundreds of video feeds as it’s happening live. So, that when you go to meet with the contestants what things to ask, and how long to sit with them.

So, I think that’s just masterful story — not from just a great host, but also a producer.

Tim Ferriss: Okay. So, on the syllabus, you’ve got —

Michelle Khare: We got, “We’re watching some reality shows.”

Tim Ferriss: Yup. This is, like, Robert McKee, I guess, the story seminar with Casablanca. He’s like —

Michelle Khare: Nice.

Tim Ferriss: “We’re going to walk by this second by second.”

Michelle Khare: Exactly.

Tim Ferriss: “And look at what’s going on.” All right. So, we got Survivor as one part of the syllabus.

Michelle Khare: Survivor is one part of the syllabus. Part two is we are going to study Snyder’s Beats, and we’re going to study the Save The Cat of it all.

Tim Ferriss: Those two books are so good.

Michelle Khare: Yes.

Tim Ferriss: And I have some screenwriter friends who are like, “Yeah. They are really good,” and others who are like, “Please, no. Don’t suggest it.” I haven’t practiced as much as you have, or other folks, but I’m like, “These make it very tangible.” Right? And, I guess, not to interrupt.

Michelle Khare: Right. I think it’s important to understand the bones of a story. What are the hills and the valleys? What is the all is lost? And I think a lot of people look at that material, and think it only applies to scripted content, but it is so important in any piece.

Tim Ferriss: It’s storytelling.

Michelle Khare: It’s storytelling.

Tim Ferriss: It applies to books. It applies to all of it.

Michelle Khare: Yes, exactly. I would even go as far to say that a five-second vine hits all of the piece — if it performs well, hits all of the pieces of a story arc in just a few seconds. It sets a premise, it upends it, and there’s a resolution where the character is changed by the end. Even a video of a cat leaping off something and doing something crazy has a beginning, middle, and end where the cat is different at the beginning and the end of that, America’s Funniest Home video clip. That’s why we like it. That’s why we laugh. That’s why we engage with it. I think it’s really important to understand that. Part three of the syllabus, let’s see. I feel like if we have to have three parts of the syllabus. The third part of the syllabus would be an area of the class where everyone brings a piece of work released online within the last week that impacted them.

This would be the assess and dissect portion of the class. Why did this YouTube video speak to you? Oh, well, I just Googled, I wanted to learn about how the coronavirus spread originally, and I saw this video on Chris God. Okay, but let’s break it down. What was interesting? What was the title? What was the thumbnail? Why did this TikTok speak to you? Why did it stand out? I would want people to bring things that performed well or didn’t, so we can understand resonance. Resonance, as you mentioned earlier, attention is such a very, very valuable and finite and rare resource these days that I would want a discussion component of the class to talk about relevant impact in recent media. That would be the wackiest class ever, but that’s what we’d be doing.

Tim Ferriss: If you had, and I know we’re doing this on the fly, but let’s just say project assignments, right? I’ll buy you some time because I’m going to — I know this is on the spot, but the most formative writing class that I took, and I really only took one seminar ever focused on writing. I got very lucky in college, but there were two components to the class. There were these once weekly lectures, two or three hours long, pretty long, on writing with a tremendous focus on structure, primarily. Then there were reviews of work that we had already submitted. Each week we had a writing assignment and typically in the range, like 3 to 10 pages, but let’s just call it three to five pages. You would write your piece, then you would submit it at the beginning of the lecture.

Then you would have a one-on-one with the professor, in this case, John McPhee. If people haven’t read John McPhee, they should. Just tremendous. If you want to read something short, Levels of the Game, it’s incredible. He’s won one or two Pulitzer Prizes, just a phenomenal writer, can make anything interesting. Wrote an entire book on oranges, for instance. Another one on hand-carved wooden canoes and another one on the geology and nature of Alaska.

Michelle Khare: Wow.

Tim Ferriss: It’s just incredible. The Levels of the Game is about basically the entire game of tennis, but told through the lens of one match involving Arthur Ash. But coming back to the story, so we had the lecture, then we have these writing assignments. You turn in whatever your new assignment is at the beginning of each of the lectures. Then you have your one-on-one with Professor McPhee. He gives you back your printed out writing, which typically will have, at least in the first few weeks, more red ink from his edits and notes than what you put on the page. It is brutal, brutal, but incredibly helpful. Okay? You’ve got these writing assignments and the writing assignments are all over the place, but it might be something as seemingly simple/difficult as find a sculpture on campus and write three to five pages on it. We’re like, “Ah, can you give us any more direction?” He’s like, “No.” So everybody would take a slightly different approach because you’re like, “Wait a second, should I write about the history? Should I write about the subjective experience? Should I write about — “Mm-mm. Oh, oh.”

But no matter what I do, I have to think about structure and some of the points that he’s made in class. Then at the end of the seminar lecture, we would share our work. We would actually read out loud some of our work, and then —

Michelle Khare: After the revisions have been applied from it?

Tim Ferriss: No. This would be — I guess I’m probably screwing up the chronology a little bit in the lecture. We would read something that has not yet been corrected and then subject it to peer review and get his comments. There were a couple of different ingredients, and he’s taught this. He doesn’t teach it any longer, but taught it for 15, 20 years, very infrequently, like once every year or two. I got very lucky. This is a very roundabout way of asking if there were like an assignment component where people are doing their own work, what are perhaps some of the things you would have them do?

Michelle Khare: The assignment component of the class would be making the content?

Tim Ferriss: Yeah.

Michelle Khare: I would require all of the students to make an account if they don’t already have one on some platform. At the beginning of the class, I would want them to set and define the type of content. I would want them to define, why is this uniquely yours? How is this different from what other people have done? Then at the same time, how is this data backed by what other people have done? Then from there it would require them to actually make and produce videos. If the purpose of the class is become a YouTuber, let’s say. I would ask them to make and produce the videos weekly and actually post them so that we could do some peer review of course, but then actually see how does it play live in the world. I would also want them to do data analysis at the end and try to make educated guesses on why something did or didn’t perform well and receive critique and feedback, not just on the data and performance, but specifically the work itself. Why did this introduction work or not work? How could the technique be improved next time?

Tim Ferriss: You know what I was thinking could also be fun, you’d have to have a pretty small class to make this work, but assuming the videos are short and they’re doing it weekly, have them show the videos in class and then make predictions. What is your hypothesis? Do you know what I mean?

Michelle Khare: Like you can invest in videos.

Tim Ferriss: Yeah. Yeah. It’s like, what are your — then they can choose to modify the video or not based on feedback or your thoughts or something. You obviously want to let them learn their own lessons, but I think that would be a good way of refining the thinking process.

Michelle Khare: Someone’s got to teach this class.

Tim Ferriss: You are infinitely — you actually made this whole format work, so I think it’s you.

Michelle Khare: Only if you’re a guest lecturer.

Tim Ferriss: Sure. I mean, yes. The guest lecture is all the fun with none of the heavy lifting.

Michelle Khare: Exactly.

Tim Ferriss: I’m very much into that. Are you still — I want to mention two books, and I’m curious if they’re still relevant, because they came up in doing research for this conversation, Radical Candor by Kim Scott and the Six Thinking Hats by Edward de Bono. Do either of these ring a bell?

Michelle Khare: Yeah, of course.

Tim Ferriss: Okay. All right, got it.

Michelle Khare: My boy, Edward, with his hats.

Tim Ferriss: Yeah, there you go. How did these both factor in? Because these were basically the two books that I was able to find mentioned by title. Some of them I think were mentioned by people you work with and not directly by —

Michelle Khare: But maybe Garrett mentioned one of the hats.

Tim Ferriss: It was Garrett.

Michelle Khare: The Six Thinking Hats, I don’t even remember where I learned or heard of this concept or — oh, I actually think this was Jody. Shout out, Jody.

Tim Ferriss: Your therapist.

Michelle Khare: Jody puts me on all the great books. I was coming to her talking about just various problems I was facing, and she told me of this concept of the Six Thinking Hats. Effectively, I might butcher this, but it is a way of looking at a problem by filtering only by thinking type. For example, we’re going to put on a yellow hat and look at this potential idea, and the yellow hat means we’re only going to say things that could go well by pursuing this idea versus when we put on our black hat, that is we’re saying all of the things that could go completely wrong. It’s six different techniques of being able to assess and determine if an idea is good or how to solve a problem.

That thinking was really helpful to me as someone who often, prior to understanding this, would immediately go to black hat. This is coming from the mentality of everything’s going to go wrong. I’m going to fail at everything. I’m a person who, growing up, always defaulted to black hat. No, no, no, no, no. It’s not going to work. That doesn’t inspire creativity. That does not inspire entrepreneurship. It also gives an unfair shot to an idea that Respun may provide a new idea altogether.

I think this is also something I learned from a design thinking class. I might be crossing my wires here, but another class I took at Dartmouth was design thinking were similar to your writing class. It was an engineering class where every week we would have some wacky assignment, like the professor would give us each a sheet of poster board and say, “Next weekend you come to class, it has to be a chair. Turn this poster board into a chair that supports your body type. You can’t use any glue, any scissors, any other structural components. You can make cuts to it and shape it, but that’s it, and it has to support your body weight.” That class taught me a ton about myself before that class would look at that and say, “Not possible. Why am I even trying it?” Professor Roby really forced us to think critically through how could something be possible. That concept of the six hats is really, really impactful to me.

Tim Ferriss: Let’s pause there for a second because this book, believe it or not, was incredibly helpful to me in my first few years of building my first business and trying to figure out what I might be good at. But also as a solo operator effectively. Had lots of contractors, but as a solo operator, for the most part, effectively turning myself into a virtual board of directors with different perspectives by using these different hats, because I also default to black hat, which I think has its place, right? Part of the genius of this approach is you’re not saying, “Oh, that’s negative thinking, shame on you. Let’s only look at the bright side.” No, you have to realize it. It’s saying there’s a place for that, but there’s going to be a set time for it, and we’re going to go through each of these six. I haven’t read it in decades, but Edward de Bono, Six Thinking Hats, he also had, I believe, a book called Lateral Thinking, which I found helpful.

I don’t know how those would age for me if I read them now. Sometimes I’m like, “Oh, God, have you haven’t seen this movie? I haven’t seen 20 years. Let’s watch it.” Within 10 minutes, I’m like, “Oh, God, this is not as good as I remember.” There are definitely others. Well, it’s very NPC, but airplane and others that actually do age shockingly.

Michelle Khare: Well. I wonder what other hats are. I haven’t looked at this in such a long time, because I feel like we just —

Tim Ferriss: I can’t recall what the specifics are. I mean, if I had to guess, I’m imagining one is analytical by the numbers. One is emotional. I mean, I’m imagining there’s probably some version of that, but it stuck out to me because I was like, “That’s really interesting that this book which not a lot of people reference actually also popped up in both of our timelines professionally.” That’s super interesting. All right. Radical Candor.

Michelle Khare: Okay. Kim Scott. It’s like Tim, Adam Grant, Kim Scott, these are Mount Rushmore for me. Kim Scott is just phenomenal. I mean, I thought Radical Candor, and I know many of these works have been critiqued and refreshed in many ways, but her quad chart of how to provide feedback to people was really instrumental to me because effectively what happened was I quit my job when I was 23. I’d never made it to a — I mean 23, a managerial position in a corporate setting. I never had any manager training.

Tim Ferriss: Could you give an example of how Kim’s teaching or frameworks look when applied for an example?

Michelle Khare: Kim talks about four types of management and giving feedback to people. The quadrant I identify with the most is ruinous empathy, which is the idea of you are so nice to everyone around you that when you need to give critical feedback to someone, they might leave the meeting feeling like, “Wait, am I actually doing great? I don’t know, because you’re sandwiching compliments or downplaying the critique and you’re not direct enough.” And so transforming that into radical candor is about being more direct with feedback. Some of the things that Kim has helped me very applicably work through are workshopping, giving critical feedback to people, and hearing live feedback from her on, “Cut off that sentence, that’s fluff.” That is so, so amazing. I think an applicable setting here or an example of this would be…

Let’s say we have a collaborator on set who’s very, very good at what they do but they don’t compliment or uplift other people when they do a great job.

Tim Ferriss: Got it. Good at execution, maybe a little prickly around the edges.

Michelle Khare: Just a little prickly or they don’t — internally, they’re thinking that person is doing a great job, but they’re not vocalizing it.

Tim Ferriss: I see. Got it.

Michelle Khare: And so, it creates an environment on set where everyone’s like, “Oh, does this person not like what I’m doing?” Stepping in as a manager of the feedback, it’s a tough piece of feedback because how do you say, “Dude, I just need you to go out of your way and provide positive feedback to people.” It can be as simple as that. But what Kim, for example, taught me in this specific situation is communication exists on two wavelengths. It is, first of all, the wavelength of communicating the need, the tactical information, but there’s another wavelength that’s equally as important, which is the emotional component. And so, being able to define that with that person and say, “Hey, you’re doing a great job communicating, but there’s an emotional side you’re completely missing that’s actually really important to that communication,” was really helpful because it provided necessary value to that action for that person rather than just like, “I got to tell people they’re doing a good job. I got to take an hour out of my day and send nice emails.”

Tim Ferriss: Giving them the why as opposed to [inaudible 02:27:16].

Michelle Khare: Exactly. Exactly.

Tim Ferriss: This could include full-time and contractors, what does your org chart look like, so to speak? What is the team?

Michelle Khare: I mean, I remember reading 4-Hour Workweek and the whole virtual assistant chapter blew my mind. We do have someone in Singapore, which is funny. Our internal team full-time is intentionally tight. It’s seven full-time staff. That is myself, Garrett, who’s the chief creative officer, Nick, head of production, three editors, and an assistant for me. But we have what I call a slinky operation where that’s where it is when it’s tight. But when we get ready to do a big project, it balloons up very quickly. But what’s cool is all of the people that are on the internal team are department heads. When it’s time to recreate the Mission: Impossible stunt, each of us know how to staff up a camera team of seven people, stunt team of six people, and build that out to a team of 50 who come in to do that one specific project, and then we slink you back down.

Tim Ferriss: Your head of production would be responsible for the scoping and finding and hiring of those people?

Michelle Khare: Sometimes. Also, just within our entire team, we’re all very connected and embedded in the industry. The team I just mentioned is pretty much half people from the traditional entertainment world. Nick, for example, the head of production, came from working at Broadway video under Lorne Michaels and did Taco Bell Super Bowl commercials, so he understands feature film, high budget commercial world. Then people like myself or our editor, Ryan Gonzalez, we come from the digital-first world. Our training was at a content studio where it was fast output, but you know how to do everything. Bringing those worlds together is a really special and cool environment, intentionally set, because that is exactly the midpoint I want to occupy, is the bridge between the two worlds.

Tim Ferriss: Right. I’m curious how you — the context by my question is how you separate responsibilities in a sense. With the understanding that on a small team, you’re going to end up wearing a lot of hats, not to be confused with Edward de Bono, but when shit needs getting done, people are going to roll up their sleeves, and I imagine at that size, do whatever. But for instance, you could pick the episode, right? It could be any episode, but where do your responsibilities — say, how are they different from chief creative officer as one example?

Michelle Khare: We have a giant spreadsheet called the Areas of Responsibility Chart, which I learned from a book called The Great CEO Within. Again, I’m trying to learn all this Silicon Valley management stuff on my own. I even called my YouTube partner manager and I was like, “Can I please sit in on the YouTube corporate management training the next time it happens?” She said I couldn’t. I’m trying to piecemeal it all for myself and learn from people like you and Kim. But in that book, it details actually making a giant chart that outlines every single action that the company takes. This can go from, in our case, something as big as decides if brand deal is worth taking, all the way down to takes out the trash. Who is going to be doing all these things? This is, I think, hundreds of responsibilities.

Tim Ferriss: What would be some, just so I understand? Because it’s not a role that I’m familiar with, like chief creative officer.

Michelle Khare: For chief creative officer in this chart, for Garrett, that includes — Garrett’s role as a whole within the company is to define the creative tone and thesis of everything that we do? He is overseeing the story for each of the episodes, he’s directing the episodes and post, but he’s also making sure that if we’re updating our brand book or we’re having our Emmys four-year consideration event in a couple weeks, he is going through all of the marketing materials and confirming, yes, this fits the tone and the style of Challenge Accepted. This tells one cohesive story. What we don’t want is a channel or a show that is chaotic or unpredictable.

Tim Ferriss: Yeah, disjointed or —

Michelle Khare: Exactly. We [inaudible 02:37:37] wanted to hit a certain level of quality of storytelling. For Garrett, that means on a macro level, overseeing those decisions, but also on a micro level, approving edits and directing edits to make sure the stories we’re telling hit that bar of excellence too. He’s like chief creative officer and chief storyteller in a way.

Tim Ferriss: Then head of production, what percentage of the time for head of production is spent on in production episodes versus planning beforehand and post-production, would you say?

Michelle Khare: Oh, that’s hard. I would need to ask Nick exactly, but Nick primarily spends — when we green light an episode and we’re now in preparation to go shoot it, a lot of his time is spent assembling the crew, getting insurance permissions. In the case of the Seven Marathons project we did where we ran seven marathons on all seven continents in one week, he was handling all the logistics of the local crews we were working with.

Tim Ferriss: I love how you say that as we, the royal we.

Michelle Khare: Shit, I mean, it was a team effort. It was a team effort. Many people did it besides me, but —

Tim Ferriss: Of course. There is a certain level of physical brutality.

Michelle Khare: I did it with the help of an amazing team. He’s also figuring out permissions and cash flow working with our branded partners. He’s sort of touching many things, more like including head of ops in a way, I would say. The physical operation of the company itself.

Tim Ferriss: When you look out three or five years, and I imagine you’ve thought about this because to the best I can tell, you do like planning and spreadsheets and editorial calendars. I imagine that you’ve given this some thought, but it strikes me that this — I mean, this is a very demanding job that you have. And the company can — and the kind of strategic vision and where you go can go in a lot of different directions. So three to five years from now, what would you be happy with in terms of what your life and the channel looks like? And maybe the channel is too constraining. But I’m just wondering, three, five years out, understanding a lot of things can change technologically and otherwise, but what does it look like?

Michelle Khare: What does it look like?

Tim Ferriss: Yeah. You have a magic wand, and you’re like, “Okay…”

Michelle Khare: I have a magic wand.

Tim Ferriss: “…to some extent, I want to preserve the option that it’ll turn out this way.” Bing.

Michelle Khare: Ooh. It’s worth noting that I’m so privileged to be happy now. I love what I do. I love how our industry is evolving. I love being a part of that evolution of when you hear the word content creator, what that means and the social expectation of what that profession is. I’m really, really proud of, and excited for, the future of the evolution of that. And the convergence specifically of traditional and digital. A future for myself, first of all, I want to be doing this as long as I possibly can. I look to people like Tom Cruise, David Blaine, Jeff Probst again. They’re in their 50s and 60s and they have just decided they’re going to keep going. Richard Branson, he going out there. And I find that exciting and inspiring.

And also, I look forward to a world where the names of the people that I just mentioned are all men. And I look forward to helping lengthen the list of women who have longevity and careers like this too. So I think a future for me, external to the channel, is participating in that bridge. Supporting legacy studios and companies in understanding our world, and helping burgeoning creators find inspiration and solace and a path forward in a very seemingly nebulous career.

I love sharing with other creators the wins and the learnings and, “Don’t do what I did. Here’s my Google Excel spreadsheet. Skip all of the stuff I had to learn.” And so that mentorship component of giving trajectory and systems to younger creators is really, really important to me, and something I’m passionate about. In addition to having to lead by example and practicing what I preach, I look forward to the next three to five years because I know that’s the sphere of where I’m headed. That’s where our arrow is headed. I don’t know where the arrow’s going to land very specifically, but I am so excited about the ride.

Tim Ferriss: All right. I’m going to be the detective here for a second.

Michelle Khare: Oh, do you have a magnifying glass?

Tim Ferriss: Not in a spooky way. Well, I do have my brand new fancy spectacles. But part of the reason I’m asking is that you have to make decisions around how many episodes you pursue, how much they overlap. And for instance, against my, quote, unquote, “better financial interest,” there was a point where I had decided, well, in my best interest, I had realized pretty quickly, well, I make X amount per episode of the podcast, especially during the golden era of 2020 COVID and the two or three years that was just an absurd embarrassment of riches for anyone who was doing something reasonably defensible.

At that point, I was like, “Well, four is pretty easy for me to do per month.” If I want to increase the annual revenue of this thing, which is very high profit margins to do things with the foundation and my employees and blah, blah, blah, blah, blah, blah, I could just do two more episodes a month, easy, right? And if I wanted to double it, I can do eight. There are other ways you can double it. And I’ve looked at those levers too. But suffice to say, it was very self-evident to me at the time that it was going to be very easy to grow if I so wanted it to grow.

So I ended up at different points doing six, seven, eight episodes a month or doing different types of batch recording. And then a few things happened. About two or three months into doing this, yes, there were more financial resources to bring to bear on the funding science through the foundation and many other things. We could do fancy off-sites for the team and fly to these very far-flung, fun, exotic places, yes, which we can still do. But what I started to notice is there was this very subtle, energetic change. I wasn’t exhausted, but I started maybe dragging my feet a little bit. I started to feel, I noticed when I put a fine point on it, that it was becoming a job in the unpleasant sense. Does that make sense?

And it’s very, very easy for this to happen in people who have small operations that are not dependent on — or in some cases like venture financing or something like that. And I also recognized that I could make it work by, in my case, batching these episodes together, but when I batched them together, I didn’t actually get to retain and study and use and apply what I was learning from these people in these conversations.

Michelle Khare: That’s a really fatiguing day.

Tim Ferriss: Yeah. Yeah. Or week, right? And so I decided that I would step back to four or five a month. And I’m in a fortunate financial position to be able to make that type of decision, but it was really important for not just the longevity of the podcast, which is now 11 years or 12 years, whatever it is, but my enjoyment of it. And I’m just curious how you think about what drives the actual work product of the show. Because your priorities may change, I have no idea. For some people, if they’re thinking about family, then you have family consideration, you also have the professional motivations. You can end up getting driven by your team in some cases where it’s like you want to offer them the opportunity for advancement and increase scope and so on, but that can end up steering the ship sometimes.

So there are a lot of pitfalls that are hard to spot because they are gradual in terms of their onset. So I’m curious how you think about the actual work schedule, the number of episodes, the amount you take on, because I hear all the top level priorities, which are awesome, and the vision for three to five years, I think you can do all of those things.

Michelle Khare: Oh, thank God.

Tim Ferriss: But —

Michelle Khare: Tell me if you don’t think it’s possible.

Tim Ferriss: Well, I don’t think it’s possible if the show ends up taking on lots of features and obligations and scope creep —

Michelle Khare: I agree.

Tim Ferriss: — and splintering, that just removes the time and energy required to do those things.

Michelle Khare: I have a lot of empathy with what you’re saying about, “Oh, I can just fit in one more recording. I can fit in one more shoot day.” I mean, even separate of the channel, this didn’t impact the channel, but last year I was on a plane 73 times. Maybe not that high for many of the guests who have been in this chair. It was a record for me, at least.

Tim Ferriss: That’s a lot of flights.

Michelle Khare: It was a lot of flights. And I told Kim this, and she said, “How many vacations did you go on?” And I couldn’t answer it. I’d think that’s a sign. I went on — I did a couple things, but she gave me some advice at the beginning of this year. She’s like, “The next time you’re sent abroad, your assignment is…” And I need someone to say your assignment is for me to take it seriously. “Your assignment is you need to take at least six hours of a day. You don’t have to stay an entire extra day, take six hours of a day to do something for yourself.” And I did this last week. I was in Italy for a speaking engagement and my friend Olivia and I took six hours and we saw the whole city, and it was incredible.

And I think that avoiding the scope creep is something we’ve had to be very, very precise about. As you mentioned, there are so many shiny objects around. Oh, you should just do this collab and start a merch line. Or even, in our world, there’s a temptation of promote this product and big check comes in. Well, I don’t know if I agree with this product and maybe I won’t do it. And I think being really brutal about, if I don’t protect this, all of it falls apart. Not in a way of fragility, but in a sense of, if I take the brand deal for a lot of money, for the thing I’m not 100% on, it fractures trustworthiness. That, as we both know, is something that cannot be bought back. It’s so precious to what we’re doing. Or even the idea of we’ve had so many people come to us say, “We’ll license the Challenge Accepted brand and we’ll start a kids channel and we’ll run the whole thing for you.”

And these pitches sound great on paper when I know I’m not going to like the first few things you do. I’m going to have to get in the weeds. I’m going to have to be giving feedback. And you know what? I don’t have time for that. I have to remain really focused on the tip of the spear, which is making Challenge Accepted the best show it possibly can for all of the reasons that are emotionally important to me, financially important to the team, and socially important to our industry. So we’ve had to say no a lot, which I know you’ve been writing a lot about recently. But the saying of no is something I’m still learning how to do. And I think that has been why the show has lasted so long.

I have never — I’m literally knocking on wood, I don’t even know if this is real wood. I’m knocking on wood right now. I’ve never experienced creator burnout in the way that many of my colleagues have. Many of my colleagues have had a time where they hit the wall and have to take months off entirely. That’s never happened to me because all along the way, it’s been a fast growth, but still slow and steady. You can look at the growth of our channel and it’s not like I blew up on TikTok overnight. It’s been slow and steady. And for that, I feel fortunate because I’ve had the slowness to be able to make those adjustments, to acknowledge scope creep, where I’m being asked for more things and still learning how to practice that better.

Tim Ferriss: So few thoughts pop into my head. The first is that more so than with most, I actually have — I’m very confident that you’ll figure it out. And I’ll tell you why.

Michelle Khare: Oh, my God.

Tim Ferriss: The first is that — not that I’m like — who the fuck am I? I’m just saying, there’ve been a lot of people in that chair and I’ve met with a lot of creators and writers and so on, of different types. Number one is that you have an inbuilt novelty in the format of the show. So a lot of the YouTubers I run into who are just crashing and burning, they have a few things stacked against them. One, they chose something that was interesting to them five or 10 years ago, but it is a fairly narrow lane. And at some point, they get tired of being that person, or they pretended to be something in the beginning and they got a lot of positive feedback and they’re —

Michelle Khare: But it’s not who they are, yeah.

Tim Ferriss: — fatigued because they’re wearing a mask.

Michelle Khare: Yes.

Tim Ferriss: And there’s more to it. There’s audience capture issues and other things. But you have an inbuilt novelty in the nature of the show itself.

Michelle Khare: Every episode, my whole life changes.

Tim Ferriss: Yeah.

Michelle Khare: Right now, I’m training for Taekwondo Nationals. I’m going to take a flight back to L.A. and go to taekwondo training for three hours tonight. Every day is different and varied and interesting. And I feel lucky that my life changes frequently, to adjust for that.

Tim Ferriss: So this is something I wanted to take a moment to point out because willpower, discipline, all these things, yes, they sound great. And I agree with a lot of folks that ultimately systems beat certainly dreams and even goals. I mean, you have to have an idea of where you want to head, but inherent to what you chose to do, there’s a kind of cycling and rejuvenation to it, right?

Michelle Khare: Yeah.

Tim Ferriss: So I just wanted to highlight that because it’s a feature —

Michelle Khare: Thank you.

Tim Ferriss: — of what you chose to do. It’s not just something you have to fit in in the empty pockets with something that is uniform from start to finish. So I think that’s one thing I wanted to mention.

And then separately, just as an anecdote, guest lecturing, you mentioned. So the guest lectures at Princeton High-Tech Entrepreneurship that turned into The 4-Hour Workweek, the notes from that class, was based on a talk initially called Drug Dealing for Fun and Profit, because my first company was sports nutrition. The through-line of that lecture from start to finish, because I was one of the few entrepreneurs my professor invited, maybe the only one who bootstrapped. Everyone else was venture-backed. And that’s why it was interesting to him. Because I was like, “Ed,” who’s Ed Zschau, amazing guy I’ve had him on the podcast, said, “I don’t think I have anything to offer. I’m only a few years out of college. I’m bootstrapping this thing. It’s a lot smaller than any of the other companies that get highlighted by these CEOs who are taking companies public, et cetera.” And he said, “Well, that’s kind of the point.”

Michelle Khare: Wow.

Tim Ferriss: “You’re closer to the students, so they can see emulating or borrowing from what you’re doing more easily than they can someone who’s 20 years older and has taken four companies public.” But the —

Michelle Khare: And aligned with your through-line of owning everything you do.

Tim Ferriss: Yeah.

Michelle Khare: That’s a really special component.

Tim Ferriss: Owning, yeah, exactly. And there are times where like debt and venture and all that stuff, I’m just constitutionally allergic to it. It doesn’t make me feel safe and pleasant.

Michelle Khare: Same.

Tim Ferriss: So I generally avoid those things.

Michelle Khare: Yeah.

Tim Ferriss: I didn’t even have a credit card until a few years after college because I thought, foolishly, that if you have no debt, you’re going to have good credit. That’s just not how it works. So I had to get credit cards. But I have never carried a balance except for like a very short period. The reason I bring that up though is that in my class, it changed over time, this two-times-per-year guest lecture, it kind of followed what I was learning. The one thing that never changed was how I started it.

And how I started it every time is I’d say, “How many people here want to be a salesperson?” And this is Princeton, right? It’s in an electrical engineering operations research finance class, and no one raises their hand. They’re like, “Salespeople? Yuck.” And I’m like, “Okay, how many people here want to be good at negotiating?” Every hand goes up. I’m like, “Okay, how many people here want to be good deal-makers?” Almost every hand goes up. I’m like, “Guess what? They’re all the same thing.”

Michelle Khare: Yeah.

Tim Ferriss: Good news, bad news. You’re all going to have to be salespeople.

Michelle Khare: It’s true. It’s true.

Tim Ferriss: Whether you’re selling a position, whether you are selling yourself as a romantic partner, whether you are trying to persuade someone of anything and everything, the skillset is the same. And because you have that ability and you also have the — you’ve honed the ability to communicate with the cold emails and everything else, you have a lot of practice with that. And you have someone like Kim Scott in your corner on the honesty — you can take it too far, but honesty above people-pleasing, right?

Michelle Khare: Oh, yeah.

Tim Ferriss: This — what did you call it? It was the, not insidious empathy, but something close.

Michelle Khare: Ruinous empathy.

Tim Ferriss: Ruinous sympathy.

Tim Ferriss: That is where I tend to lean also, or have historically. And if you are trapped in that quadrant and you start to see the ship heading towards this iceberg of burnout for you personally or overall, you’re kind of fucked. Like, that’s not the time to learn how to steer the ship, which means these other quadrants, right?

Michelle Khare: And you write about that in your upcoming book too, about how when you say yes to everything, you become resentful towards other people when it’s actually you creating the problem.

Tim Ferriss: Yeah, exactly. Yeah. I’m going to be diving back into the — it’s a placeholder name, but The No Book, 850 pages, that’s going to get hacked down. It’s going to be, just as a teaser, it makes me so happy. I literally just got a text about this two days ago. I’ve had quite a few test readers read that book and it’s rough around the edges, but they read this book like six months ago, a year ago, and they text me to be like, “Look at how I am still using this stuff.” So I’m excited to get it out because it’s super — as we were talking about, template emails and so on, it’s really tactical. It’s not just hand-wavy stuff. So I’m excited about it, but you have sort of these —

Michelle Khare: And I promise I’ll buy it, I won’t steal it on accident.

Tim Ferriss: I’m okay with stealing my books. Well, I mean, it’s not okay because you’re stealing it from someone else, but —

Michelle Khare: Correct. It was not stolen from a Barnes & Noble.

Tim Ferriss: Yeah.

Michelle Khare: It was stolen from the desk of a coworker.

Tim Ferriss: Yeah. So I have confidence you’ll figure it out because you have the toolkit for correction. And I think part of what a lot of folks miss about saying no, it’s not like — saying no is a lot like working out. It’s not like you figure it out and you do it for a week or two and then your problems are solved.

Michelle Khare: It’s a practice.

Tim Ferriss: It’s a practice. It’s not only a practice, but 99.9% of the population, sure, there are a few exceptions, but are going to fall off the wagon occasionally. So the question is, how do you get back on the wagon? So in the case of say a book on no, a lot of the book is case studies of people and their toolkits for renegotiating. It’s like, if you’re reading the book, it probably means you say yes to too much stuff and over-commit.

You’re probably still going to do that. It’s kind of like AA and alcoholics. Once an addict, always an addict. You’re probably going to do that again. So the question isn’t, how do I avoid it permanently from this point forward? It’s, how do you actually correct it and how do you renegotiate commitments? How do you cancel things? And really —

Michelle Khare: Which is arguably harder than saying no out the gate. Once you’ve committed to something —

Tim Ferriss: It is. It’s basically signing up for long-term pain instead of short-term pain. But you’re going to deal with both.

Michelle Khare: Okay.

Tim Ferriss: Which is why Kim Scott is, and Kim’s teachings, are so valuable. I have to recommend — I don’t know if it was with respect to Kim specifically, but A.J. Jacobs, who I mentioned earlier —

Michelle Khare: I love him.

Tim Ferriss: — wrote this long Esquire piece called, and his poor wife, but the title of it is called “I Think You’re Fat,” and it’s like 30 days of experimentation with radical honesty or something like that.

Michelle Khare: Oh, yeah, yeah. I saw him give a presentation last fall and he included this anecdote.

Tim Ferriss: Yeah. And “I Think You’re Fat” is like — when his wife was like, “How do I look in this dress?” And also, the point is, his wife has put up with so much with his experiments, but she’s like, “Are you even listening to me?” And he’s like, “No. Honestly, I stopped listening five minutes ago and I’m thinking about A, B, and C.” Oh, what a saint his wife is, but also makes for pretty good reading because everything in excess kind of becomes its opposite.

I want to kind of talk about wishlist stuff —

Michelle Khare: Oh, my God.

Tim Ferriss: — because you never know who’s listening to this podcast. You just never know.

Michelle Khare: Okay, okay.

Tim Ferriss: I am constantly surprised. Maybe you can give some backstory, but have you met Mindy Kaling yet?

Michelle Khare: I have not met our Lord and Savior, Mindy Kaling yet. Okay.

Tim Ferriss: All right. Why did I even come across this? Yeah.

Michelle Khare: I know why you came across this, and it is because my first Twitter handle was @MindyKalingFan, I think. It’s since changed to my name. It’s normal now. I think I’ve deleted all the tweets, maybe. I would love to meet Mindy Kaling one day, when we’re talking about wishlist items for a few reasons. I feel like we have sort of traveled the same path in different flavors. We went to the same college. I obviously admire her work. We’re both Indian women in entertainment. And seeing someone like her on a show like The Office was instrumental to me as someone from Shreveport, Louisiana, who didn’t see someone like me on Disney Channel.

And I think that’s why the mentality I had of approaching a job like this was so black hat, if we’re going to go back to that. I was very negative on the idea of doing something in entertainment because I didn’t see a path or an example forward for someone like me. And factually, that’s incorrect. I mean, there’s a very thriving industry of Bollywood and there are many, many amazing women in entertainment. But something shifted for me when I saw her success, and felt that parallel path of, we’re going to the same school. And seeing how she took her opportunity at The Office and spun it into her own production company and new shows that continued to uplift and elevate female-centered stories, I think is incredible, and something that I look up to often when I think about how I started at a media company and am now doing my own thing and hoping to shift culture and expectation of what it means to be an Indian woman in entertainment and also what it means to be a content creator on the internet.

I love upending people’s expectations. It’s one of my secret favorite things to do. I love when people hear that I’m a YouTuber and then they go watch Challenge Accepted and are pleasantly, hopefully, pleasantly surprised by what they see, and wouldn’t expect that maybe from someone on the platform. And I think about how she and Shonda Rhimes and other incredible showrunners have done that.

Tim Ferriss: All right. Mindy, if you’re listening.

Michelle Khare: Mindy, yo.

Tim Ferriss: And there are definitely a few people on, or who have been on this podcast, like B.J. Novak who know Mindy. So if you guys are listening.

Michelle Khare: Oh, my God. I’m obsessed with both of them, as a unit. They’re amazing.

Tim Ferriss: Yeah, B.J. is incredible. B.J. is also incredible. I mean, The Office, I mean there are a few examples like this, but it’s kind of like the PayPal Mafia where you’re like, “How did all these people come out of this?”

Michelle Khare: The PayPal Mafia.

Tim Ferriss: How is it even possible that this density of talent was in one place at the same time? It was crazy. All right. Well, let me ask a question, right? Let’s just say Mindy’s listening and she’s like, “Maybe I’ll check her out.” Which episode should she start with?

Michelle Khare: Okay. Let me think.

Tim Ferriss: And that applies more broadly to people listening.

Michelle Khare: More broadly.

Tim Ferriss: But where should Mindy go?

Michelle Khare: This is a really tough question. For Mindy specifically, I’m going to recommend “I Try Tom Cruise’s Deadliest Stunt” because Mindy is in the Hollywood world, and I think that’s the most Hollywood episode we’ve done. It’s an episode where I strapped myself to the side of a C-130 to become the first person to recreate the stunt that Tom did for the Mission: Impossible franchise. And I truly am hanging off the side of a plane. And what’s interesting about that story is not just the stunt, which is cool, of course, but it’s an amazing story of being an underdog. The only people who have accomplished this previously are literally Tom Cruise and Paramount Studio.

And so to come at it from our angle was me sending more crazy cold emails. It was calling foreign militaries at three in the morning asking if they would lend us a plane. Those are the phone calls I’m making. And additionally, when you’re doing something that’s only been done once before, or in some cases has never been done before, you have to get really creative with the training and testing, which maybe you experienced in all of your work too. How do you prepare your body to do something like that? And it led us to training in wind tunnels. But even more interestingly, I had to go to a specialized optometrist who fabricated custom scleral contact lenses for me to wear, because for this stunt, you don’t wear goggles. And so there was a dedicated person on set called a lens technician, and his only job was to insert and remove these massive contact lenses that went over my eyes.

Tim Ferriss: That sounds so uncomfortable.

Michelle Khare: Because when you’re up there at multi-hundred mile per hour winds, even just a tiny pebble could blind you.

Tim Ferriss: Oh, yeah.

Michelle Khare: So I think it’s a really cool story of being a little bit of an underdog and accomplishing something great in an unexpected way. So I hope you watch it, Mindy.

Tim Ferriss: Amazing. All right. This is going to sound, it’s a non-sequitur/sequitur, but people should study, take a look at peregrine falcons and how their eyes and noses and nostrils are evolved. It’s fucking wild. And aircraft have actually been designed based on peregrine falcon evolved —

Michelle Khare: Why do I feel like —

Tim Ferriss: — form.

Michelle Khare: — you’ve spent a week in Mongolia training falconry?

Tim Ferriss: I would love to do that. I had my first experience with falconry on New Year’s Day this year, so it’s fresh in my mind.

Michelle Khare: Wow.

Tim Ferriss: Got to work with some amazing hawks. There are different birds that are appropriate for different levels of training, and it’s not necessarily the easiest bird. In some cases, they’re going to give you slightly more stubborn or difficult birds because if you have a very easy bird, you don’t actually develop the trainer technique that you need to use for a spectrum of birds. It would be kind of like giving, if you give everyone a really intrinsically motivated, high-energy dog, like a Belgian Malinois to train, that is like bred for being very, very, very, very trainable, you’re going to develop a false sense of confidence around your ability to do that with other breeds.

Michelle Khare: I see.

Tim Ferriss: So yes, I’m interested in falconry.

Michelle Khare: Have you seen that meme that went viral recently that’s like, “You hit at a certain age and all of a sudden you’re obsessed with birds”?

Tim Ferriss: That’s really funny. Maybe that’s what’s going on. Next thing you know, I’ll just like smoking a pipe on a porch talking about World War II all the time. I don’t know.

Michelle Khare: There you go. That’s in your future, Tim.

Tim Ferriss: Worse things could happen. All right. So here’s — I’m going to ask more, I want to ask more episode questions, but before we do that, anyone else that you’d like to sort of invoke?

Michelle Khare: I’m going to invoke.

Tim Ferriss: Are there any other partners, companies, people, anything that you’d like to check out your work?

Michelle Khare: This is such a special opportunity to do that. There are many people I would love to meet. And generally, as we move into this really exciting new chapter for the company and content creators in general, I’m excited to meet with anyone from traditional media who is excited to join forces. So that’s just a general statement. But if I have one shout-out, here’s the shout-out I’m going to ask for, The Royal Nanny School in England. We have been wanting —

Tim Ferriss: You’ve been working on this one for a while.

Michelle Khare: — the Norland College, we’re your biggest fans. We’ve been wanting to collaborate for years. If you see this, hit me up.

Tim Ferriss: Incredible. Perfect.

Michelle Khare: Okay. Let me tell you about the Norland nannies. You’re going to appreciate this, Tim.

Tim Ferriss: All right. I’m ready.

Michelle Khare: You know Mary Poppins, the silhouette with the pleated skirt and the little hat. It is based off of a real school called the Norland College where these are the nannies that are trained to serve billionaires and royal families. So when you look at — and they wear that outfit. So you look at footage from this school, and it’s literally they’re wearing this outfit and hat pushing a pram stroller while also wielding a gun because they have to protect the kids. So they know defensive driving. It’s like Secret Service meets Butler Academy, which you shouted out in the 5-Bullet Friday. So it’s two amazing worlds coming together. I think more people need to know about it. So I’m very passionate about it.

Tim Ferriss: And I imagine the fact that they’re like, “No, thank you. We don’t need that,” makes you just want it that much more.

Michelle Khare: Of course it does, Tim.

Tim Ferriss: Yeah.

Michelle Khare: But also, I respect it. What have we been talking about? Saying no. So I have to respect when someone else says no too. But also, I’m just letting you know, we’re still available, still interested and excited. Love you guys from afar, big fan.

Tim Ferriss: Of your episodes, when you look back, and you can’t say all of them, that’s disallowed, that answer is no good, no fly, if you did not have a YouTube channel, but you had a thriving career, so you had some money, which of those, you can pick two or three, of the experiences that you would pay to have looking back?

Michelle Khare: That I would do again in a heartbeat?

Tim Ferriss: Yeah, do again or you’re like, “Okay, I only get to pick two or three, but I would absolutely pay for these if I had to.”

Michelle Khare: I would pick, first of all, the black belt challenge. So this video, I had 90 days to try and get a black belt in taekwondo. Part of this came from a personal passion of having done all of these stunts and working with a lot of stunt performers, all of them come from world-class martial arts backgrounds. And I realized I had never actually taken the time to learn a martial art from the ground up. And that it was lacking in my performance and mental fortitude and I wanted to experience that. So what do I do? I make it a challenge so that I can devote my whole life to it.

And that experience changed me. When I look at clear before and after, from having put your body through a lot, there are moments when you have a photo before and after, my body changed. But there are moments in life when you as a person change before and after, and that can’t be captured by a photo always. That was one of those for me.

Getting to study with Grand Master Simon Rhee, one of the greatest martial artists on Planet Earth, took me under his wing, and did what most instructors would have never done, which is believe in me and push me to try and actually get a black belt in 90 days.

And we were talking about politeness, I think martial arts has taught me all of that. When you bow to the mat before you step on. When you yes sir, yes, ma’am, everything. It might sound gimmicky to someone on the outside, but it does become a practice and an automation and a way of life. And that’s something I’m really proud of as a now black belt and grateful for it. I would pay to do that again.

And in fact, I am because we’re doing a sequel. So I am paying to do it again. I’m trying to qualify for nationals this year with Master Rhee. So I’m very excited about it. I would recommend it to anybody.

Michelle Khare: The other one I was going to say that I would pay to do again, for the experience I had ultimately, not when I was going through it, is the Houdini challenge. So for that, I had six weeks to learn how to hold my breath and pick locks to attempt Houdini’s water torture cell. Which famously is hanging upside down in a glass box filled to the brim with water, escaping a series of lock picks with one breath of air. And that I would say is probably among the most physically challenging challenges I’ve done.

Tim Ferriss: I’m sure.

Michelle Khare: Free diving, breath holding is a level of athleticism that is so bizarre to me. Because when you’re in a workout class and it gets hard, they say, “Keep breathing.” This is the one time you can’t do that. You’re holding your breath.

So I was having to learn how to push through that. Having breath hold, a time of — ultimately, I got to 3:30. And most Navy Seals, two, three minutes is pretty good. Houdini’s best time was also 3:30.

But on the production side, it was a really fascinating challenge because it was the first time we creatively designed our own obstacle and solution. So in the beginning, we spent months trying to connect with other magicians on Earth who own a water torture cell. There are not many.

And ultimately, we came to the conclusion of designing our own, which was really, really incredible and creatively challenging. How do you create a glass box that can be filled with so many gallons of water and maintain the structural integrity when there’s a person inside? And function with all the locks and the hinges with water as an involved substance? It was a huge, huge engineering challenge for our team.

And I’m really, really proud of the final result. Because both of those things are things I would have never guessed that 2016 me would have been able to do. First of all, holding my breath that long. Second of all, taking the creative liberty to design something that was inspired by a work of history, but also our own.

Tim Ferriss: Next question. So this one you may not want to answer.I would understand why. I have a little bit more freedom in answering this for myself, so I can also go first and buy some time.

Michelle Khare: Challenge accepted. Let’s hear it.

Tim Ferriss: Yeah. So which one would you pay not to do again?

Michelle Khare: Oh, gosh.

Tim Ferriss: One or two. And the one I would say, for me, just to offer it up is, and holy shit, did I make a mistake, this was episode one of the Tim Ferriss Experiment, in terms of filming. And keep in mind, we had, I think it was 11 or 13 episodes or 10 or 13 episodes that we filmed in that number of weeks. So I mean, it was every week we were filming.

Michelle Khare: As a viewer, I never realized that it was 13 consecutive weeks.

Tim Ferriss: It was consecutive weeks.

Michelle Khare: That’s crazy.

Tim Ferriss: And the first one was parkour. And there were a couple of inherent problems with that. Number one, even if you tried to prepare your body for it, the impact of falling onto hard surfaces is very hard to train your body for. Even over the course of, say, a year with proper technique because of the connective tissue adaptations and sort of ligament and tendon adaptations that need to take place, which required quite a bit of time.

Secondly, the promise of the show was I haven’t cheated. So it’s like I can’t pre-prepare for it if I’m showing what it’s like to start from zero. And I am still contending with injuries from that week to this day. 12/13 weeks later.

Michelle Khare: No way. Wow. You guys shot that at Tempest, right?

Tim Ferriss: What was that?

Michelle Khare: Tempest?

Tim Ferriss: Yeah. Amazing gym.

Michelle Khare: Incredible.

Tim Ferriss: I mean, those guys are amazing. Tempest free running, check it out, it’s incredible.

Michelle Khare: Yeah. But I will say I have dropped from the monkey bars and pulled my back. It’s crazy.

Tim Ferriss: Yeah. I mean, I ended up tearing multiple heads of the quadricep in both legs.

Michelle Khare: And then you continued filming for 12 weeks after?

Tim Ferriss: For 12 more weeks. So you can imagine —

Michelle Khare: And that included the Yabusame episode. That’s different?

Tim Ferriss: No, the Yabusame episode is actually from a totally different TV show, a pilot of which was filmed right after the first book came out, it might’ve even been before. I think it was right after the first book came out. So that was a completely separate thing with a production company in Singapore. It was kind of wonky to be honest.

Michelle Khare: Oh, wow.

Tim Ferriss: But the Yabusame was way earlier. Back when I had hair or a little bit of hair. I was white knuckling.

Michelle Khare: Okay. Because all of my experience, transparently, of the show has been in online rips because many of this material is no longer available.

Tim Ferriss: All of the Tim Ferriss Experiment stuff, I got the rights back for a launch on iTunes, as it was called back then. And it was the number one nonfiction show when it launched for a while, which I was very happy about. Although it was excruciating, you can imagine, talking about negotiating with a big behemoth where you just don’t really have any leverage whatsoever. And they were helpful, but a lot of employee changes and so on that made it difficult. And then ultimately getting the rights back completely so I could just release it for free on YouTube.

But which would you pay not to do, any come to mind?

Michelle Khare: What would I pay not to do? I have a few answers for this actually. First one is chess. And again, I recognize the people who have sat in this chair, I feel like 99.9% of people in the Tim Ferriss sphere, everybody plays chess. Everybody is on chess.com. When you go to these entrepreneur events, there’s always a chess board. Everyone loves chess. So I feel a little shameful saying this. Chess was very challenging for me.

Tim Ferriss: There are plenty of people on this show who don’t like chess, including people who used to be professional players.

Michelle Khare: Really? Oh, my goodness. Now, I loved many aspects of it, but the challenge for that was originally I had one month to prepare for a competition. And I did the month of training. I got to the competition. I didn’t do as well as I had wanted. And something about the episode just felt empty.

And I think, you and I both know this, you know when you haven’t gone the distance with something, you haven’t given it your all. And I knew that deep down. So I continued training for nine more months, 10 months in total I believe, to achieve this goal of my Elo rating. And finally did it. And I was like, “I’m good.” I am so good on the London system, all this stuff. I was studying so hard. And I’m so glad I did it, but I’m good to be a casual chess player. Good to be a casual chess player.

I think the other one I don’t think I’ll do again is one that hasn’t come out yet. Which makes it interesting I suppose. The most challenging physical thing I’ve ever done is the seven marathons on seven continents in one week. Which is going to be coming out this April, a three part series on the channel. We’re so excited about it. Specifically within that, the Antarctica marathon is —

Tim Ferriss: Sounds terrible.

Michelle Khare: — something I probably won’t do again. People got frostbite when we were out there. It was insane.

Tim Ferriss: I’m sure they did.

Michelle Khare: But the sneaky sleeper marathon is — most people think Antarctica is the worst when they hear about this challenge. But the sneaky one is marathon number six, which is in Colombia. And the reason this one is so crazy is because historically people have gone to the hospital from heat exposure. It’s marathon number six, so you have five other marathons in your body that you have done in the five previous days before. And they actually schedule this marathon to happen overnight to try and avoid the sun. But because our flight was slightly delayed, we started around 3:00 AM. And that meant we were literally racing against the sunrise. And the slower you go, the more heat exposure you have. So it was 100% humidity. It’s so hot. And psychologically, you feel like you’re at the finish line because tomorrow’s the finale, tomorrow’s Miami, tomorrow’s race number seven. But really number six is the unexpected one.

Tim Ferriss: Yeah, that sounds brutal.

Michelle Khare: What’s crazy about that is there are the most unexpected people who do this marathon. Okay. There was a guy, you’re not going to believe this, there was a guy named Adrian, for whom his first marathon he ever ran was marathon one of that week. He knew some of the race organizers and just decided to come along. And originally he was going to run half-marathons and just decided, “I’m going to go for the full.” That’s crazy to do your very first marathon in a week where you’re going to do seven. Yeah. So that was nuts.

Tim Ferriss: Yeah. There are sort of breeds and then there are breeds also. I mean, there are mutants for each of these disciplines. There are mutants for all these disciplines we have discussed. And you meet some folks, and you mentioned stunt work on Avatar, but I remember, I’ve met people who are professional high jumpers. And I’m just looking at them and I’m like, “We are not the same species.”

Michelle Khare: No.

Tim Ferriss: Just like your attachment points and where your Achilles is.

Michelle Khare: Built different.

Tim Ferriss: Everything is different. I mean, that’s true for every discipline, including chess of course.

Michelle Khare: There’s an 83-year-old man named Dan Little who does this event. It was his fourth time doing it.

Tim Ferriss: The seven in seven?

Michelle Khare: Seven in seven. He’s done it four times. He’s 83 years old. He’s this guy named Dan from Oklahoma. And just the most incredible person you’ll ever meet. So joyful and excited. And he’s the last person on course every day. He takes seven or eight hours to do the full marathon. And he is smiling the whole time. I think that’s one of the coolest things about our job, our jobs, is perspective, the people you meet. It really redials your compass.

Tim Ferriss: Yeah, for sure. Yeah. I mean, if you’re the average of the people you spend the most time with, choose those people really carefully.

Michelle Khare: Gosh. Yeah.

Tim Ferriss: And I mean, the older I get, it’s not that surprising, but the more I enjoy spending time with people who are doing things like that, not necessarily in that much of an extreme. But it could be like Arthur Brooks, who we were just talking about, because there was some footage from a prior interview of mine up there. He’s a busy guy. Or Adam Grant. But they take fantastic care of themselves. And particularly with each passing year it seems as you get older, the sort of entropy that leads people to gather and just complain about their new aches and pains or how little time they have or how busy they are with the kids, whatever it might be, increases.

And I try, and I’ve succeeded fortunately, I have a lot of friends who are counter examples, and I’m like, “Okay, if there’s only one counter example in the world, okay. Well, maybe it’s just inevitable.” And I’m like, “If I’ve gathered five to 10 close friends who are all counter examples, that’s something you can do.” Because all of these people, from a personality perspective, from a life perspective, from a financial perspective, very different. Which means if you want it badly enough, you can be the counter example. And I find that super uplifting.

Michelle Khare: I love that.

Tim Ferriss: Let me ask a couple of very quick questions and then we’ll land this plane.

Michelle Khare: Okay. This has been so fun.

Tim Ferriss: Yeah. I’m really happy to spend time together. You mentioned McMillion$. Other favorite documentaries? I know you like documentaries. Are there any other documentaries that stand out to you?

Michelle Khare: My favorite one is Free Solo.

Tim Ferriss: Free Solo, that’s so good.

Michelle Khare: So good. Alex Honnold, what you doing? Talking about counter examples here. I am just endlessly inspired by him as a person. And I think Jimmy Chin’s work, directing, filming, it’s just outstanding given the care and the sensitivity of the subject nature.

Tim Ferriss: Terrifying.

Michelle Khare: And how he executed it.

Tim Ferriss: Yeah. So for people who maybe watched the recent live Netflix climbing of Taipei.

Michelle Khare: Taipei.

Tim Ferriss: Go watch Free Solo if you haven’t seen it. And fun fact, I actually interviewed Alex about six months before he did his Free Solo ascent of El Cap.

Michelle Khare: I just got chills.

Tim Ferriss: And he was in that white van that is in the movie. And freaked me out because he parked outside of my house. And I was like, “Who’s in this creepy van with no windows parked in front of my house?” And it’s also before he got media training. So if you want to see pre-polish Alex.

And I want to give a nod also, Free Solo is an amazing movie, to Chai Vasarhelyi. So Chai is married to Jimmy Chin. She is, I mean, in a lot of ways, the filmmaker. And Jimmy obviously, without his expertise and these crazy complicated rigs and the ability to climb and actually be suspended around Alex and so on, I won’t ruin anything with spoilers, there are a lot of adjustments that needed to be made with that, but that is a fantastic one.

I think it was The Dive, they’ve also had some follow-up films that are just incredible.

Michelle Khare: I remember seeing a tweet when Alex did the Taipei climb that was like, “Everyone’s freaking out about this. What if I told you this is actually not the craziest thing he’s ever done.” Referring to Free Solo.

Tim Ferriss: I mean, it is so far not the craziest thing in the sense that, watch the El Cap climb, it is infinitely hard. To any really, really seasoned climber, yes, it’s risky to climb with no ropes. Yes, the tower is dangerous if you make a mistake. From a technical perspective, from a technical perspective, it’s actually not that difficult. Doing what he did on El Cap is very much in the death defying category.

Michelle Khare: Yeah. I’m out. I’m sure people ask you this too, but people are always like, “What’s something you wouldn’t do?” I’m like, “I’m going to let Alex Honnold own the category of whatever it is he’s doing.” I think that category is well covered.

Tim Ferriss: The category of things I wouldn’t do is pretty broad. And it gets broader every day. After a few very scary avalanche experiences with back country skiing and heli-skiing where people have gotten really injured and could have been buried. I’m done. Avalanche risk, if there’s any real avalanche risk, I’m out.

Michelle Khare: So you’re out from Everest?

Tim Ferriss: Oh, there are many reasons I’m out from Everest.

Michelle Khare: Okay. There are many reasons I’m out from Everest too.

Tim Ferriss: Yeah, no, there are a lot of reasons I’m out from Everest.

Michelle Khare: Yeah. People ask me all the time —

Tim Ferriss: Not the least of which is plenty of people have already done it, why would I?

Michelle Khare: Exactly. I think the story’s been told.

Tim Ferriss: Yeah. Why would I risk my life for something that’s not even going to be a notable footnote for anything or anyone?

Michelle Khare: There you go.

Tim Ferriss: Book or books you’ve given most as a gift or recommended a lot, any books come to mind?

Michelle Khare: have recommended Radical Candor to pretty much everybody I know who’s a content creator trying to figure out their business. The other one is The Great CEO Within, which is a really fast and easy read. And for anyone who didn’t start in Silicon Valley or a startup culture or a startup of any kind, was really helpful to me to just understand here’s what a company is and how it works. And then I’ve given Adam Grant’s Originals to a few people too.

Tim Ferriss: Dig it. All right.

Michelle Khare: I would say this, but I feel like that’s cheating, so I’ve tried to exclude it from my answer.

Tim Ferriss: Yeah, yeah, no, that’s fine.

Michelle Khare: So I can’t say that, but obviously I talk about it all the time.

Tim Ferriss: If you could have one giant billboard anywhere, obviously this is metaphorically speaking, with anything on it, it could be a quote, nothing commercial, but could be a mantra, quote from someone else, a picture, anything, question, what might you put on that?

Michelle Khare: I feel like this one has been overused at this point, but one that was really helpful for me starting my channel was, “Everything you want is on the other side of fear.” Very simple. Again, overused at this point. But I love that one because it’s what I return to when things are hard in any aspect of life and especially when I’m doing a challenge. It’s a way for me to remind myself, this is the struggle I asked for to make myself better at the thing I want to be better at. And it’s also a reminder to move forward through it and not shy away from it.

As we talked about, Challenge Accepted was born out of writing my fears on a whiteboard. And so for me, I have a very intimate connection with that sentiment. And I think about it even in an exterior capacity when I get nervous about something, personal life, business, whatever, exterior to the challenge itself, I return to that often.

Tim Ferriss: Yeah. I have quotes related to that.

Michelle Khare: Let me hear them.

Tim Ferriss: Etched onto driftwood, ranging from Anaïs Nin to others all over my house.

I think I’ve done enough talking today, so I’m going to keep the focus on you. Michelle, where can people find you, where would you like to point people to?

Michelle Khare: You can follow me @michellekhare on everything. And the three-part series of my experience attempting seven marathons on all seven continents in one single week will be coming out on my YouTube channel in three consecutive weeks throughout April and May. And we’re going for a primetime Emmy this year, which I’m really excited about.

Tim Ferriss: So exciting.

Michelle Khare: We’re on the ballot for Outstanding Hosted Nonfiction Series or Special. It’s a very long title for a category. And I’m excited about it for a lot of reasons, most of which is I want to be a part of a future where it’s not unheard of that a YouTube channel is going for something like this. And that’s why I’m excited about it for myself and other creators.

Tim Ferriss: I’m excited for you.

Michelle Khare: Thank you. So if you’re a voter, please vote for me.

Tim Ferriss: I’d vote for you. I’d vote for you. And just for people who may miss this, Khare, K-H-A-R-E.

Michelle Khare: Oh, yeah, yeah. M-I-C-H-E-L-L-E K-H-A-R-E.

Tim Ferriss: Michelle, is there anything else you’d like to say, any parting words, anything you’d like to add before we wind to a close?

Michelle Khare: I want to say thank you, Tim. It was really special to go back through the archives and realize that your impact in my life started 10 years ago. And to almost to the date be meeting you 10 years later is really full circle and affirming for me. And I hope that anyone listening can hear the very grassroots fear-setting chart that I had for myself in the beginning. And I think it’s a special moment for me to reflect on the length of time it takes to do something special. And how that commitment can lead you somewhere unexpected.

Tim Ferriss: Thank you for that. And I have to say, it makes me so deeply happy, I mean, joy is probably a better word, I get so much joy out of the fact that you exist and you’re doing what you’re doing. Because it tests a lot of assumptions about a direction that I would view as pretty dystopian about online content creation. You’re putting out long form, positive, life affirming, nonfiction where you show that failure is not a terminal sentence, it’s just feedback along the path. And I just love that you’re doing what you’re doing. And I’m such a fan of your work, such a fan of Challenge Accepted. And I hope you keep doing it for a super long time.

Michelle Khare: Me too. Thank you, Tim.

Tim Ferriss: Yeah. All right, everybody, until next time, we’re going to put show notes, including some template emails for people, in the show notes at tim.blog/podcast. I assure you if you search K-H-A-R-E, there will be only one response. And until next time, be just a bit kinder than is necessary to others, but also to yourself. And thanks for tuning in.

DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:

The post The Tim Ferriss Show Transcripts: Daredevil Michelle Khare — How to Become a YouTube Superstar, Open Impossible Doors (FBI, Secret Service, etc.), Craft Jedi-Level Cold Emails, and Use Fear-Setting to Change Your Life (#860) appeared first on The Blog of Author Tim Ferriss.

Daredevil Michelle Khare — How to Become a YouTube Superstar, Open Impossible Doors (FBI, Secret Service, etc.), Craft Jedi-Level Cold Emails, and Use Fear-Setting to Change Your Life (#860)

2026-04-08 05:53:07

Daredevil Michelle Khare lives life to the extreme in Challenge Accepted, amassing more than 6 million followers and more than 1 billion views. Across the show, you’ll see Michelle attempt everything from Tom Cruise’s Deadliest stunt to Harry Houdini’s water torture cell to trying to earn a black belt in taekwondo in only 90 days. Michelle hopes to prove that with enough dedication and failure, anything is possible.

Michelle’s work has earned multiple Streamy Awards, including Show of the Year, and has been featured in The New York Times, Forbes,Vogue India, and more. In 2025, Challenge Accepted made history successfully petitioning to join the Primetime Emmy® ballot. Michelle was named a TIME100 honoree for her impact as a creator and storyteller.

Please enjoy!

This episode is brought to you by:

Fin powerful AI Agent for all your customer service: Fin.Ai/Tim
Monarch track, budget, plan, and do more with your money: Monarch.com/Tim
Momentous Fiber+ 3-in-1 formula with soluble fiber, insoluble fiber, and Solnul® resistant starch: LiveMomentous.com/Tim
AG1 all-in-one nutritional supplement: DrinkAG1.com/Tim