2026-08-04 21:02:53
👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Podcast | Lennybot | How I AI | Become an AI-Native Builder and other favorite AI/PM courses
P.S. Get a full free year of Cursor, Notion, Replit, Lovable, Factory, Wispr Flow, Linear, ElevenLabs, PostHog, Brain.fm, Waking Up, and more, by becoming an Insider subscriber (while supplies last). Learn more.
Molly Graham’s first guest post, The Waterline Model, quickly rose to be my 7th most popular post of all time—extra impressive for not being about AI. I suspect this post will rise even faster.
Below, Molly introduces the concept of emergence as an alternative to conventional career advice. What she describes is exactly what my career path has looked like, and it’s a pattern I’ve seen across most of the successful people I know. If you’re worried about not having a plan for your career, or if your plan isn’t going according to plan, you’ll feel better after reading this post.
If you’re not familiar with Molly, she’s . . . incredible. She was an early employee at Google and Facebook, COO at Quip (working closely with Bret Taylor), helped build the Chan Zuckerberg Initiative (working closely with Priscilla Chan and Mark Zuckerberg), co-founder of Glue Club, co-founder of The Guild, and most recently, host of TED’s WorkLife podcast (taking over for Adam Grant). At 22, she was leading 75-day wilderness expeditions in Patagonia and Alaska for the National Outdoor Leadership School. Tl;dr, she’s seen and done a lot.
Let’s get into it.
Sheryl Sandberg once told me that everyone should have a two-year plan and a 20-year plan. The first, I could figure out; 20 always looked fuzzy.
I’ve never had a career plan. And I’ve always felt a little broken because of it.
We’re taught that careers should look like a set of stairs—you decide where you want to end up and march upward. When you look at many successful people, their careers can often appear like that from the outside.
My resume includes jobs at some big-name companies, C-level titles, and fun-looking solo ventures, but I have always wondered if it suffered from lack of design or clear destination in mind. At times, it has felt more like a game of chutes and ladders than any kind of stairs.
But recently, a conversation with Mark Rober completely changed how I think about my career. Don’t know Mark? Ask any 8-year-old who he is. He is one of the most popular creators on YouTube—76 million followers, 16 billion views—and he’s built that audience by making science genuinely fun and accessible. He’s put out one video a month on YouTube for 15 years, with remarkable consistency.
I asked him how he’s stayed grounded across a career on a platform with its own relentless pressures. Mark said he’s never had a long-term plan. Fifteen years of consistency, and none of it was by design. Instead, he has a clear set of principles that guide him, and he focuses only on the next step in front of him. And then, according to Mark, “good shit’s gonna happen.”
Then Mark introduced me to the scientific concept of emergence, a process that occurs in nature when multiple parts come together to form a complex whole without a clear plan or intention. I had a strange feeling when I heard him talk about how he trusts an emergent philosophy to guide his own career. He was describing something I’d already been doing for years, without ever having a name for it.
Emergence tells us there’s a different way to build a career: not by optimizing toward a destination but by getting really clear on your principles, learning to follow your energy, and trusting that the path will reveal itself. In some ways, an emergent career is harder to manage than having a plan and staying loyal to it. There are moments of real uncertainty, and stretches where you can’t see where you’re going. But all of that uncertainty (and all of that faith) is exactly what creates room for the opportunities you couldn’t have seen coming—which, in my experience, are the ones that matter most to a career that works for you.
A murmuration of starlings—thousands of birds moving together in those wild, shape-shifting clouds you see in videos—has no choreographer. Each bird follows three simple rules: stay close to your neighbors, don’t collide, and move in the same general direction. That’s it. From those three rules, something breathtaking appears. An outcome no single bird designed or planned.
Same with a beehive. No bee has the blueprint for the colony. Each bee just follows its local rules—tend the larvae, forage for pollen, respond to signals. But the colony as a whole can regulate its own temperature, navigate to food sources miles away, and survive for decades. A single ant isn’t intelligent in any impressive way. Yet an ant colony can find food, build bridges, regulate temperature, wage war, and adapt to changes in its environment. That capability doesn’t exist in any one of them; it only comes together in the colony as a whole.
That’s the strange magic of emergence: the whole becomes capable of things that are completely invisible at the level of the parts. Emergence is what happens when simple, consistent principles—applied locally, over time—produce something complex and beautiful that couldn’t have been predicted or designed in advance.
In an emergent career, you are both the individual bird and the whole murmuration—the one following the rules and the one becoming something those rules couldn’t have predicted. Every decision you make, every person you work with, every risk you take or don’t take—those are your local rules in action. You can’t see the pattern they’re creating from inside it. You can only see the next step. Yet over time, something emerges. A body of work, a reputation. Something that looks, in retrospect, like it was designed, even though no single decision along the way felt like a plan.
My whole career has been example after example of the power of emergence, but I’ll give you the best one, which is also the most recent. I stepped off the traditional career path four years ago with no plan. I simply started saying no to the jobs I was known for—COO roles at bigger and more impressive companies—because they no longer brought me joy. It was scary, and it felt necessary. I explored a bunch of different paths and worked hard to learn to listen to the parts of myself other than my ego. It was hard. I felt exhausted and confused a lot, particularly when someone offered me some new fancy job I knew I’d be great at. My ego really, really wanted to say yes. I kept saying no.
I built the leadership communities Glue Club and The Guild. I wrote on LinkedIn and Substack. Not because I had a vision for what any of this could become or because any of it made sense to anyone else, but because they made me happy every day. I was learning, working with people I loved, and having the kind of impact that mattered to me. All of it brought me energy, and I was committed to focusing on that compass. That said, more than any other time in my career, I felt like I was walking through a dark tunnel, with no sense of where I was going. Every magical moment in my career has been entangled with periods of confusion, discomfort, and darkness.
Then TED asked me to give a talk, and I said yes because I was excited about what I would learn and how I could connect with people through the talk. It felt a little random at the time but turned out to matter more than I expected. Someone on my team said, “I think this might be the beginning of something.” I said, “I just want the talk to be good.”
A year after my talk came out, TED came back and asked me to take over WorkLife, the podcast that TED and Adam Grant had spent seven years building. When they made that offer, it was like someone had turned the lights on in the tunnel. They saw me in a way that I could not see myself. That offer transformed my weird, disconnected pile of projects into a whole that felt like magic.
When I’ve talked to successful people about their own career path, almost all of them have a story that sounds like emergence.
As an example, I asked my friend Claire Hughes Johnson, the former COO of Stripe, about how she’s made career decisions and how she thinks about her life’s work. On paper, Claire’s path—politics, to senior operations and product leadership at Google, to COO of Stripe—looks very methodical and designed. But in conversation, she makes it clear that she never had a plan and was just focused on the right next step:
“Am I learning? Am I motivated? Am I in the right job? Is this the right impact? Is this what I want to be doing? . . . I think some people look [at my career] and they’re like, oh, you charted this course of success.
No, I was kind of unsatisfied, and just kept trying to find the thing . . . I don’t feel like I will figure out what my life’s work is. It will end up being the work that I did.”
It’s pretty weird to hear someone as successful as Claire say, even at this point in her career, that she doesn’t know what her life’s work is. But it honestly made me feel less crazy. As Claire explains it, she has two principles—she wants to learn and have a significant impact—and focuses on making the best next decision based on those.
To embrace emergence in your career, you have to do exactly what Claire does. You have to push past the traditional questions “How do I get where I want to go?” or “What is my life’s work?” and focus instead on asking, “What’s the right next step for someone with my principles, my energy, my values?”
That can be a harder question: Knowing your principles requires knowing yourself. Taking the next step in line with them often requires risk. You must tolerate uncertainty and real discomfort. You have to bet on yourself and have faith that the path will reveal itself.
After reflecting on my own experiences and hearing so many stories from brilliant successful people through WorkLife, I’ve come to believe that the two keys to an emergent career are defining (and redefining) your own local rules to help you make the next best decision, and following a few universal principles that increase the likelihood of career magic.
And then releasing control and having faith that those two frameworks will lead you to where you’re supposed to be.
Developing your local rules that guide how you make decisions requires listening to yourself and the data you collect over the days, months, and years of work. The ongoing challenge of an emergent career is honing and evolving those rules over time and experience.
I didn’t go looking to prove this theory. I stumbled on it by asking successful people how they made decisions. When they answered, they all offered up their own principles as guiding forces.
Mark Rober’s local rules are: focus on content that teaches, not just entertains; quality over quantity always; and sustainability over everything. He talked about how each of these have helped him decide when to grow his company and when to ignore the YouTube algorithm’s demand for daily posts.
Claire Hughes Johnson told me her compass has always been two words: learning and impact. If a decision gives her both, she moves toward it. If it doesn’t, she doesn’t.
One of my greatest mentors, Patty Stonesifer—an early executive at Microsoft, the first CEO of the Gates Foundation, and one of the first independent board members of Amazon—described four principles that she articulates in a mission statement: love and be loved, seek justice, learn, and laugh. She uses them to evaluate how she spends her time (she literally has a monthly worksheet she prints out to plan and evaluate her time against her principles).
Adam Grant, the organizational psychologist, has three. He talked about the principles that guide how he chooses which book to write next on WorkLife, but in a follow-up email, he crystallized his career decision principles down to: interest (“Will I wake up in the morning excited about it?”), importance (“Does it align with my values?”), and impact (“Can I make a unique contribution?”).
While writing this post, I asked Lenny what his are, and he said: follow my energy, keep the quality bar high, and be useful.
Mine, for the early part of my career, were three things: learning, people, and mission. I thought of it as a three-legged stool.
Learning, for me, didn’t mean a little learning—it meant a curve so steep I was terrified. I get energy from being in over my head. People meant I needed to be surrounded by people I was excited to learn from. And mission meant I needed to feel like the problem I was working on actually mattered and that I personally wanted to devote my time and energy to solving it. Not every important problem is the right one for me.
The point of these rules is to guide your personal decision-making. When presented with two choices, how do you decide what the right next step is? How do you explain why something that might feel so right to someone else feels wrong for you?
When Bret Taylor asked me to join him at Quip and help figure out the business, I ran it through my principles almost instinctively. Learning? Terrifying amounts of it—I’d never built a SaaS business, never done sales or marketing before. People? Bret is someone I was excited to keep learning from, and I knew he’d assemble an extraordinary team. Mission? Well, productivity software for teams didn’t feel especially meaningful to me—my stool had one wobbly leg—but I felt that the other two were so strong that it didn’t matter. I went in with my eyes open about why I was there and placed a bet based on my principles.
My local rules have changed over time—what I needed from work at 30 was different from what I needed at 40—and almost everyone’s do. Sometimes career decisions help you discover a rule (or a nuance of a rule) that you didn’t know was so important to you. That happened to Patty Stonesifer in the middle of her career. After leaving a senior executive role at Microsoft, she accepted a senior position at DreamWorks because it sounded cool. But about three months in, Bill and Melinda Gates approached her with the opportunity to help create and build the Gates Foundation, and she realized that at DreamWorks she was missing some pieces that were really important to her. That gut check led her to create her mission statement and articulate her “seek justice” pillar.
In that WorkLife conversation, she also shared that her enthusiasm for learning, one of her principles, can overpower everything and, like my wobbly stool legs, she’s had to think about ensuring that there is the right balance across the different principles to not let one of them guide all the decisions.
For me, the only principle that hasn’t changed at all is learning. I still need to be terrified or I’m bored. But I’ve gotten much more clear on the impact that matters to me, and the people leg of my principles has gotten more specific—I need people I look forward to working with every day, people who see me clearly, and people I can clearly unlock. I’ve added some new rules too, like “seek joy,” which wasn’t a priority for me earlier in my career. These days, loving my hours and days is one of the main ways I measure my overall career satisfaction.
The most powerful signal I’ve found for defining your own local rules is your energy. Not your ambitions, not what looks good on paper, not what your parents think—what work energizes you. The question to ask is “What actually lights me up today?” not “What should I want?”
There are a bunch of exercises out there that can help you do this. Here are two that have been really useful to me:
Spend a week scoring your energy after every part of your day. For many of us, this can be broken down into 30- or 60-minute segments like meetings or work blocks. At the end of the day, sit down and score each 30-minute block on a scale from 1 to 10. My coach, Maggie Hensle, had me do this when I was at a lost moment in one job, and it came back all 1s and 10s. My day was filled with an almost equal amount of work that lit me up and work that made me want to bash my head against the wall. But most importantly, when I really dissected the 10s, I realized that the best work for me was coaching, mentoring, sponsoring, and connecting with people. It was an important insight that indirectly led me to the community work that I do now.
Identify your peak moments. Whenever I am trying to understand the work that lights people up, I ask them a series of questions: “Looking back over the past three to five years, what are three key moments when you felt like you were at your best? What are the work moments you are proudest of over those years? When you think about activities where the time flew by or you felt like you could have kept going forever, what were they?” Questions like these help you describe the type of work that excites you and brings out the best in you. The ideal way to do this exercise is with a coach or a best friend—someone who is rooting for you and will hear the patterns when you describe your answers. That person can share back with you some of the words or themes that come up over and over again.
Whatever exercise you choose, you are looking for patterns. Those patterns are your local rules in disguise.
Knowing your local rules tells you how to decide on your best next step. But the truth is that there are also universal principles that increase the odds of magic. These behaviors and actions are not a plan. Instead, they’re creating the conditions for “good shit” to happen (to borrow Mark Rober’s words). And without them, you’re probably leaving a lot of magic on the table.
2026-08-03 23:02:21
Listen now on YouTube • Spotify • Apple Podcasts
Brought to you by:
Bolt.new—Turn your idea into a real product
Hyperagent—Deploy fleets of agents that handle real work
Nick Baumann from OpenAI joins Claire to demonstrate how he uses ChatGPT, Codex, and Voice to automate huge parts of his work and life. He walks through advanced workflows for managing tasks in parallel, monitoring email and expenses, booking travel, building and publishing websites, and even turning dozens of raw clips into finished videos.
ChatGPT Codex Voice doesn’t just answer questions. It can actually operate your computer while you keep talking. Nick Baumann demos the new interface live: he triggers it with a hotkey, the orb reads what’s on his screen through Appshots, and Codex spins up separate threads to book a flight, file an expense report, and check his calendar at the same time.
One of Codex’s most powerful features is also one of its least understood: thread-forking. When a task gets complicated, Codex can open a new thread, branch from an existing one, or pull context from previous conversations on its own. Users don’t have to manually organize everything first.
Heartbeats in ChatGPT Work offer a practical glimpse of always-on agents. Nick gets notified when a suspicious charge appears, a package is nearby, or an email needs his attention—and he set it all up without writing code.
ChatGPT Sites looks much closer to a real deployment platform than a lightweight demo. It includes a SQL database, file storage, environment variables, and email-based access controls. During the episode, Claire and Nick build and publish a live How I AI tips site, organized by tool and job function, in roughly the time it would normally take to set up a CMS template. For internal tools, small apps, and private resources, that starts to feel genuinely useful.
Nick’s video-editing workflow is one of the clearest examples of AI cutting real production work. He records 50 or 60 raw clips, uploads them, talks through the rough story he wants, and lets a custom plugin transcribe everything, scan the footage, choose the strongest takes, and assemble finished vertical videos overnight. What would normally eat up most of a content team’s day is largely handled while he sleeps.
Voice may be the best way to give AI context because it removes the pressure of figuring out exactly what to type. Claire calls this the “yapper’s API,” and the idea is simple: people often get more useful results when they talk freely than when they stare at an empty prompt box trying to be precise. Across two-person voice chat, mobile dictation, and Codex’s orb interface, the same pattern keeps showing up—people who talk to AI tend to give it more context, and more context usually leads to better work.
As AI gets more capable, latency is becoming a much bigger product decision. Nick often uses the highest-intelligence mode in Voice, but once a model has the tools it needs, speed can matter more than another small jump in reasoning quality. A lot of AI products are still designed around the assumption that waiting is unavoidable. As that changes, the tools that feel immediate will have a major advantage—especially for users who currently find AI too slow to bring into a live workflow.
Nick Baumann’s 3 Advanced ChatGPT Workflows: https://www.chatprd.ai/how-i-ai/nick-baumanns-3-advanced-chatgpt-workflows
↳ Use ChatGPT Voice as a Personal Assistant for Logistics and Travel: https://www.chatprd.ai/how-i-ai/workflows/use-chatgpt-voice-as-a-personal-assistant-for-logistics-and-travel
↳ Build and Deploy a Live Website with a Single ChatGPT Prompt: https://www.chatprd.ai/how-i-ai/workflows/build-and-deploy-a-live-website-with-a-single-chatgpt-prompt
↳ Automate UGC Video Editing From Raw Clips with ChatGPT: https://www.chatprd.ai/how-i-ai/workflows/automate-ugc-video-editing-from-raw-clips-with-chatgpt
If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.
Catch you next week,
Lenny
P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.
2026-08-03 20:04:26
Nick Baumann is on the Developer Experience team at OpenAI, where he spends his days building with, testing, and communicating the capabilities of ChatGPT Codex and ChatGPT Work. In this episode, Nick walks me through several features that have launched or evolved recently: the new voice interface with its screen-reading orb, the Heartbeats automation system in ChatGPT Work on mobile, the live ChatGPT Sites deployment feature, and his personal use case for AI-assisted UGC video editing.
Listen or watch on YouTube, Spotify, or Apple Podcasts
How two-person voice chat works
How Heartbeats work
How to build and deploy a live website with ChatGPT Sites
How to delegate a flight search, hotel booking, and expense report to Codex in a single voice conversation without opening a single app manually
Why ChatGPT Work on mobile is the most underutilized AI workflow for people already using the ChatGPT app
How to use a custom UGC Video plugin to feed 50 raw clips into ChatGPT, let it pull transcripts, pick the best takes, and assemble a finished vertical video overnight
Bolt.new—Turn your idea into a real product
Hyperagent—Deploy fleets of agents that handle real work
(00:00) Introduction to Nick Baumann
(02:56) What’s new in Codex
(05:40) ChatGPT Work and Heartbeats
(06:40) Live Codex voice demo
(13:25) Latency vs. intelligence
(14:36) Quick recap
(15:04) Voice on mobile and the ChatGPT Sites workflow
(21:24) Live UGC video demo
(32:30) How I AI website results
(34:04) Lightning round and final thoughts
• ChatGPT Codex: https://chatgpt.com/codex
• ChatGPT Sites: https://chatgpt.site
LinkedIn: linkedin.com/in/nick--baumann
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-08-02 20:32:02
Tom Verrilli is the chief product officer at Whatnot, a live shopping platform that’s become the fastest-growing U.S. marketplace business in history, with over $8 billion in GMV. Before joining Whatnot, Tom was CPO at Twitch and director of product growth at Twitter (during one of the most turbulent periods in the company’s history).
Listen on YouTube, Spotify, and Apple Podcasts
Why Whatnot’s product team was founded on the premise “we regret that product management exists”
How AI is reshaping the PM role
What Tom looks for when hiring PMs
The shift toward senior ICs doing the work
How AI has transformed data science at Whatnot
Tom’s “play the accordion” mental model
Why “hire great people and get out of their way” fails
His biggest lessons from his time at Twitter
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
• LinkedIn: https://www.linkedin.com/in/tom-robertson-042
• Whatnot: https://www.whatnot.com
• Building, and Whatnot: https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc
• Twitch: https://www.twitch.tv
• Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future
• Peter Bailis on LinkedIn: https://www.linkedin.com/in/pbailis
• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus
• Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th
• Hex Threads: https://hex.tech/product/threads
• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty
• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine
• Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head
• Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear
• Kara Swisher on X: https://x.com/karaswisher
• Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY
• Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1
• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7
• Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app
• Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling
• E-fish.com: https://www.e-fish.com
• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205
• The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063
• Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
Lenny may be an investor in the companies discussed.
2026-08-02 01:25:18
👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.
2026-07-28 23:54:24
👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Podcast | Lennybot | How I AI | Become an AI-Native Builder and other excellent AI/PM courses
If you thought this subscription couldn’t possibly get any better, you ain’t seen nothing yet.
Today, I’m adding 11 more incredible products to Lenny’s Product Pass: Runway, Higgsfield, Mercury Personal, Brain.fm, Customer.io, Resend, Pangram, Waking Up, Supercut, Readwise, and Jam.
This brings LennysProductPass.com to 34 products (!!!)—including one year free of Cursor, Wispr Flow, Replit, Lovable, Factory, Granola, Linear, and more. That’s over $40,000 in value for Insiders ($400/year), and over $36,000 for Annual subscribers ($200/year). Simply absurd.
Most of these companies have never offered a deal like this before, and supplies are limited. If you are already an Annual or Insider member, grab your codes here. If you are currently free or monthly, upgrade to unlock the Product Pass immediately.
I continue to invest in the Product Pass because I’ve been watching a gap widen between people who are having the most fun and success of their entire careers thanks to AI, and people who are feeling confused, stressed, and destabilized. For over seven years, I’ve been sharing practical advice, building community, and capturing insights from industry leaders, but for many people, access is often the trickiest part. These tools are expensive, and there are so many of them. It’s hard to know where to invest your time and money. That’s why the curation—only including products I genuinely love and recommend—and pushing every partner to offer a full free year are so important.
A typical free trial gives you only enough time to poke around and get at the surface level of a product. But with a full year of access, you and your team can build real things, form durable habits, and have enough time to figure out which tools deserve a lasting place in your stack.
This time around, because life is about more than work, I’m expanding the Product Pass to include a free year of my favorite personal tools, like Waking Up, Readwise, Brain.fm, and Mercury Personal.
Below, I share what’s new in the Product Pass today, why I love each of these products, and how to make the most of them in your work and life. Let’s get into it.
Disclaimer: You must be a new user of the product to redeem the free year, and some products are only available to Insider-tier subscribers. Please review the collection and terms and conditions before subscribing.
Offer: 1 year free of Runway Pro ($336 value)
What it is: An AI creative platform that generates video, images, audio, and avatars, all in one place. It runs Runway’s own frontier models (Gen-4.5, Aleph 2.0, Act-Two) alongside every other leading model (Seedance 2.5, Kling 3.0, Veo 3.1, GPT Image 2, Nano Banana 2, and more), so you always have the best model for the job, without juggling five subscriptions.
Why I love it: This is mind-blowing technology from a company I’ve been excited to partner with for a long time.
How people use Runway:
Building ads for leading brands like Coca-Cola
Making production-grade ads in one afternoon
Creating emotional ads for products that do (and don’t) exist
Producing jaw-dropping, award-winning films
Integrating image, video, audio, and real-time models in one platform
Offer: 1 year free of Brain.fm ($100 value)
What it is: Music designed to help you focus. Its patented technology is backed by peer-reviewed research showing it boosts brain waves and attention within minutes. There’s also a higher-intensity setting for ADHD brains, and modes specific to creativity, learning, and more.
Why I love it: Whenever I need to get deep work done, I first open Brain.fm and click play. I’ve recommended Brain.fm over half a dozen times in my newsletter, and I’m excited to be officially partnering with them to bring more focus to more people.
How people use Brain.fm:
Locking in to hours of flow
Pairing Brain.fm with a productivity tracker for deep work
Powering an ADHD-friendly day
Swapping out YouTube for real focus music
Building their daily focus stack
Offer: 1 year free of Higgsfield Pro plan ($348 value)
What it is: An AI video platform built for professional production, used by marketing teams, 390 of the Fortune 500 brands, and studios and filmmakers to create cinematic-quality content at scale. Describe a shot, upload a reference image, or start from a script, and Higgsfield takes care of the rest. It handles everything from single ads to full commercial campaigns to original long-form narrative series.
Why I love it: Higgsfield is especially great for ads, socials, and launch videos. I just created this delightful launch video promoting the Product Pass. In the past 15 months, they went from zero to $500M in ARR, one of the fastest growth ramps in history. NBD.
How people use Higgsfield:
Running a creative agency workflow through Claude
Building animated websites
Blending real footage with AI-generated VFX
Producing YouTube videos end-to-end with Claude Code
Offer: 1 year free of Waking Up ($129 value)
What it is: A mind-training app for anyone who wants to live with more intention. Founded by Sam Harris, it brings together meditation, neuroscience, philosophy, and practical wisdom from some of the world’s leading thinkers. Waking Up is less about “relaxation” and more about developing the mental skills underneath great work: greater self-awareness, better emotional regulation, and the ability to respond thoughtfully instead of react automatically.
Why I love it: I’ve been using the app since it came out, and it’s legitimately made me a happier person. The app has also moved far beyond meditation now.
How people use Waking Up:
Slowing down and recognizing what deserves attention
Transforming the relationship with the mind and its thoughts
Navigating chronic pain through a deeper mind-body connection
Discovering that meditation can happen anywhere, including while running
Finding clarity and perspective while raising children
Offer: 1 year free of Resend Transactional Pro ($240 value)
What it is: An email API built for developers. It’s predictable by design and has a simple, elegant interface, so you can start sending and receiving emails in minutes. With tools like a hosted MCP, Agent Skills, and a CLI, your agents can help you get email added to your app, so you never have to think about email again.
Why I love it: When I vibe coded LennysData.com with Claude Code and Codex, both platforms recommended I use Resend for email. Having now used it extensively, I couldn’t be happier. I even wrote a little something for them about my experience. It’s a special product (and team).
How people use Resend:
Replacing a legacy email provider and finding newfound confidence in email sending for Raycast
Powering entire features in Dub’s product with Resend Webhooks
Handling everything from small newsletters like Silly Software Club to complex use cases from enterprises like Gumroad, Warner Bros., eBay, Supabase, and more
Offer: 1 year free of Customer.io Essentials ($1,200 value)
What it is: An all-in-one AI-forward customer engagement platform for product-led teams. Build personalized campaigns across email, SMS, push, in-app, and webhooks, using your own first-party data to reach the right people with the right message at the right moment.
Why I love it: When I asked my reader community what product they use most for marketing emails, Customer.io came in #1 by a long shot.
How people use Customer.io:
Scaling marketing efforts to millions of users worldwide for Notion
Modernizing the marketing stack, increasing monthly send volume by more than 2,000%, and unlocking personalization at scale for the Georgia Aquarium
Upleveling messaging automation after a product launch for Attio
Offer: 1 year of Supercut Pro for 10 seats ($1,800 value)
What it is: A screen recorder for teams who’d rather record an update than sit in another meeting. Record your screen and yourself, share a link, and let people watch when it suits them. They can ask an AI assistant about anything said or shown in the video, and act on it. Supercut also has an MCP, so you can connect it to your agent and your AI stack to finish the workflow.
Why I love it: As soon as I discovered Supercut, I switched off Loom and have never looked back. Design 🤌✨
How people use Supercut:
Turning videos explaining rough ideas into shipped features
Recording visual feedback and dumping it into Codex
Showcasing new features on social media
Keeping remote teams aligned without more meetings: explain new features or design challenges, or show a flow in motion
Replacing calls and emails with prospects and leads with personalized product demos
Offer: 1 year free of Jam Team plan for 10 seats ($1,920 value)
What it is: Jam makes it easy to report bugs with all the context an engineer or AI agent needs to fix them. Record your screen with the Jam browser extension and it will automatically capture console logs, network requests, device metadata, and user actions. It’s all bundled in one shareable link that can be pushed to Slack, an issue tracker, a coding agent, or any other location where bugs get fixed.
Why I love it: It’s simple, slick, powerful, and immediately useful.
How people use Jam:
Reporting bugs
Providing product feedback and instructions to your agent
Generating product documentation
Turning Jams into PRs
Fielding customer issues
Offer: 1 year free of Readwise and Reader ($120 value)
What it is: Readwise Reader is a powerful reading app for managing content overload. You save all your content—web articles, PDFs, email newsletters, ebooks, YouTube, podcasts, tweets, RSS, and Markdown—into one central repository. You can then read or listen to (using text-to-speech) those documents in a beautiful, distraction-free experience with first-class highlighting, annotating, and integrated AI tools.
Your AI agent can also tap into your library using the Readwise MCP server, allowing you to save any content and instantly have your agent know about it.
This is not to mention their Readwise highlights app (also part of the offer), which helps you easily retain and put to use what you’ve read.
Why I love it: I’ve been a Readwise user for over five years, and I love that they’ve expanded into being the new Pocket (RIP).
How people use Readwise:
Turning years of scattered highlights into a searchable second brain
Connecting a personal reading library directly to Claude
Processing everything you read
Powering a self-updating personal OS with the Readwise CLI
Creating the perfect second-brain stack with Readwise, Obsidian, and Claude
Offer: 1 year free of Pangram Professional ($540 value)
What it is: Not all AI-generated text uses the telltale “it’s not just x, it’s also y.” That’s why a second set of eyes can help. Pangram uses a fine-grain analysis that goes beyond surface-level tells, with a 1-in-10,000 false-positive rate verified by third-party benchmarks and researchers.
Why I love it: I use Pangram constantly. My favorite part is their Chrome (and Firefox) extension, which tells you which posts on LinkedIn, X, Substack, etc. are likely AI. 👀
How people use Pangram:
Verifying their own human writing
Testing never-digitized books in search of false positives
Citing their Pangram score as proof of human authorship
Offer: 2 years free of Mercury Personal ($480 value)
What it is: A banking1 product built by product people, not bankers. This is the personal account from Mercury, which is trusted by 300,000 entrepreneurs, including me!
Why I love it: You won’t find a better online banking experience than Mercury, business or personal. Everything is just easy.
How people use Mercury:
Using Command to manage bill migrations, categorize income, and overhaul their finances in one chat
Giving an AI agent a Mercury card and $250 to plan a date (spoiler: it booked a helicopter ride over the Bay and didn’t go rogue once)
Sending unlimited USD wires for free from their phone
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All of the products in the Product Pass are A+ awesome, and you don’t have to dive into all 34 at once. Consider the biggest issue in your life or work right now, and choose one or two products that might help. Pick a problem, pick a tool, and try it out. With your Lenny subscription, the rest will be waiting for you when you need them.
Have a fulfilling and productive week 🙏
If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts and gift options available.
Sincerely,
Lenny 👋
Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.