Lenny RachitskyModify

2026-07-21 20:45:10

👋 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

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This newsletter wouldn’t exist if I hadn’t taken a sabbatical.

Seven years into my stint at Airbnb, I took a three-month break. It was the first time I’d taken more than two weeks off in my more than 15-year career. I spent those months tinkering, reading, and traveling—and even snuck in a 10-day silent meditation retreat. At the end of it, I realized my heart wasn’t in the work anymore and that it was time for something new. So I left my job without much of a plan and spent the next six months exploring. Those six months turned into a year, that year turned into this newsletter, and the rest is history.

Looking back, I can say those were among the three most important months of my life, because they led me to what I do now—the most interesting, fulfilling, and impactful work I could have imagined.

Life makes it hard to get off the default path and back onto a road of your own design. Sometimes that looks like leaving your job, like I did. Other times, it means reconnecting to why you’re doing the work you’re already doing. Either way, in my experience and that of many friends, significant time away from your day-to-day is necessary for the mental, physical, or emotional shift that will reveal what’s next. What you need is what today’s guest author DJ DiDonna calls “Big Time Off.”

DJ is the founder of The Sabbatical Project and an early guest contributor to this newsletter, and today DJ’s book Big Time Off comes out! It’s a beautifully written, deeply researched book on the value of taking time off, with tangible advice, real-world case studies, and practical considerations for anyone who wants to shake things up. Below are some excerpts from his excellent book to help you start thinking about what a sabbatical might look like for you now or down the road.

I’d always wished there were a guide to help me think through that decision and make the most of this precious time off. We finally have one.

DJ will be in person in San Francisco at the Commonwealth Club on Thursday, July 23 (also streaming live online), interviewed by NPR podcast host Aarti Shahani. As a bonus, all Lenny’s readers are invited to the afterparty at Barebottle in Bernal Heights (8–10:30 p.m.)—your first drink is on DJ.

Also, for anyone who wants support on this journey, DJ has created a private WhatsApp community for Lenny’s readers. There he will host a live AMA on August 4 at 5 p.m. PT, as well as maintain an ongoing asynchronous forum for sabbatical questions, concerns, and ideas—click here to get your invitation.

Let’s get into it.

Almost 10 years ago, I stepped away from my dream job—a fintech company I’d co-founded—to spend a few months prioritizing the important over the urgent. I walked a long pilgrimage, cared for my mother during an illness, and knocked out some smaller items on my list, like writing a song and remodeling my kitchen.

Like Lenny, I came back changed. The time away made it clear that my old life no longer fit who I wanted to become.

So I left my company and set out to learn if my experience was unique or part of something bigger. I spent two years interviewing hundreds of sabbatical alums, which became a peer-reviewed paper and the foundation of my book, BIG TIME OFF: The Transformative Power of Sabbaticals and How to Take One.

Making sabbaticals accessible to everyone—not just the lucky few like me—takes rigorous evidence: evidence to convince business leaders (many of you included) to create supportive workplace policies, and policymakers to create supportive public policies. In this book, you’ll find plenty of evidence with which to make a business case.

But human stories of change are also necessary to convince the part of you that thinks taking time off would be irresponsible or impossible. That’s why personal journeys like Lenny’s matter, and that’s what’s at the core of the book: inspiration, permission, and a blueprint for the experience of a lifetime.

I’ve included excerpts from two practical chapters below to help you figure out how to approach your sabbatical, and how to avoid some common mistakes from the start. I hope it’s helpful.

The three archetypes of sabbatical takers

The type of sabbatical you choose depends on your life stage, job status, and a variety of other factors, such as personal responsibilities and desires. A 45-year-old father of three will not have the same considerations—or priorities—as a 30-something who just sold her company or a 26-year-old between jobs. That being said, a sabbatical doesn’t have to map perfectly with your age or the expectations of others. A gap year, for example, can make as much sense at 55 as it does at 18.

On top of what you’re able to pull off logistically, it’s important to consider your intentions for your time off in the context of who you are and what you really need. Which part of you is planning your sabbatical—is it your exhausted work self, your internal productivity monster, or the creative version of you from deep down? Understanding your tendencies doesn’t just give you a lens to help choose the most suitable sabbatical; it also provides a mirror to help you see the life that warrants reexamination. Ultimately, understanding the various types of sabbatical intentions will help you align your sabbatical to what you need and to return with greater self-understanding.

Over the course of my work, I have come across three archetypes among sabbatical takers: Achiever, Seeker, and Explorer. Recognizing yourself in these archetypes can help you make the best of your hard-earned break from routine. (You will likely identify with more than one of these archetypes, and that’s completely normal. In fact, many folks experience all three during their time off.)

Understanding what each archetype hopes to gain and into which traps they’re likely to fall will also allow you to take advantage of the experiences of many alumni who have gone before you. You’ll be better equipped to know when your work-obsessed self may be taking over. For example, sometimes you can redirect a competitive, work-obsessed mindset into a beneficial sabbatical activity, like volunteering your time for others or whipping yourself back into shape with gusto. Other times, you may realize that it’s this mindset itself, not your chosen activities, that you need some time away from.

The Achiever

The first and most common archetype is the achiever. Achievers view their sabbatical first and foremost as an opportunity to get things done.

Achievers are easy to recognize. They’re looking to make up for lost time by trying to squeeze years of life goals into a few months. They’re primed to view their sabbatical from the perspective of what they got done instead of how it made them feel. Don’t judge—most people initially conceive their sabbatical this way. Because we so rarely have freedom over large swaths of our life, it can be hard not to think about a sabbatical as a prime opportunity for productivity on the personal front.

What this archetype wants:

The achiever approaches their sabbatical with an accomplishment mindset. They often use external benchmarks—like fluency in a foreign language or completing a long hike—to determine whether they’re making progress. Or they attack private goals, like writing a book or organizing a community garden. This way, the achiever comes away from their sabbatical having accomplished something. Whether the product is applicable to their post-sabbatical life is beside the point. The achiever’s biggest fear is feeling like they wasted the opportunity to make some sort of tangible impact. They’ll use easily explainable milestones to guard themselves from looking or feeling unproductive.

An achiever can turn anything into an achievement. Type-A yogis are a textbook example. Instead of using their time off to simply do more yoga or attend a yoga retreat in a more exotic location, achievers devote their sabbaticals to becoming certified yoga instructors. It doesn’t matter that most of them don’t ever intend to teach yoga; the structure, magnitude, and mere fact of the accomplishment offer proof that they’ve “done something” on their time off. And that certified proof is irresistible.

What traps this archetype falls into:

Ironically, almost everyone I’ve spoken to who took this achievement-oriented approach to yoga regretted not taking the time to simply practice, learn, and play. What’s more, many of them found that the experience was almost anti-yoga. When you find yourself trying this hard to do something with your time off that’s supposed to be fun, the achiever mindset might be taking a little too much control over your sabbatical.

Tips for this archetype:

1. If you see yourself in this archetype, you’d be wise to force yourself to schedule a period of rest and healing at the start of your sabbatical. This is the time when many overachievers finally realize that their relationship to work has tangible negative effects on their bodies and minds. From ulcers to trigger fingers to insomnia and worse, stories of unexpectedly rapid healing from achievers who tend to themselves first when taking a sabbatical abound.

2. Consider how you think about your sabbatical wish list. Deconstruct the list of things you want to accomplish on sabbatical, paying attention to which goals have meaning for you personally versus ones that satisfy your accomplishment mindset. Does becoming a certified scuba instructor simply make a better post-sabbatical story than telling people your most treasured moments were playful days with your children? It’s almost inevitable that you will try to stuff your days and weeks on sabbatical with planned activities and aspirations, but for most, the real magic lies in serendipity and discovery, through play and experimentation.

The Seeker

The seeker also wants to accomplish something, but it’s less about reaching a destination than embarking on the journey. Seekers have questions, as much about themselves as the world outside them. The type of project a seeker pursues rarely feels urgent among the chaos and routine of normal life but remains important across large swaths of their life. Seekers are drawn to pilgrimages or road trips to reconnect with friends, family, people, and places from their past.

What this archetype wants:

Seekers are like personal archaeologists. They’re likely to engage in activities they used to love, trying to pick up on the scent of joy and engagement from the past. The external journey is a metaphor for the seeker’s ongoing internal search. They are deeply engaged in identity work, sensemaking on a path from uncertainty to certainty. A sabbatical beckons them to answer questions that have been bubbling up about the world and how they relate to it. Aspiring career switchers, or just folks looking to discern between garden-variety burnout and a strong signal to switch jobs, fit into this bucket.

I embarked on my sabbatical as a seeker. I had an overriding feeling that I’d ignored some core parts of myself for a long time. Primarily, that I’d neglected to make progress on deep questions within me about spirituality. I sensed that this project was important to me and required a lot more time and effort than I’d given it so far. I needed a more active approach if I wanted to make progress.

What traps this archetype falls into:

Seekers are prone to unrealistic expectations, which can put them at high risk of disappointment when they return from a sabbatical. The fact that they’ve finally made the time and space for something incredibly important and long overdue adds pressure to find the perfect next steps upon return. The kind of “good enough” steps that follow most sabbaticals—like staying at your old job for a bit longer or changing things up slightly before you make a big career move—are unlikely to satisfy seekers. In short, the quest for perfection becomes the enemy of success, spurring a more protracted sabbatical that becomes increasingly expensive and anxiety-inducing. Seekers should consider two strategies to avoid this vicious cycle.

Tips for this archetype:

1. Restrict the amount of time you allow yourself to seek. Seeking is a lifelong pursuit, not something you’re likely to knock out in several months. Instead of expecting to find your dream job (or state of being) by the end of your sabbatical, consider it a success to identify the next tangible step toward what your dream could be. You can control the process of the search, not the results. For example, have 20 coffee chats about career possibilities with people you admire. Your first sabbatical won’t be your last. To avoid burning out or spinning your wheels, it’s far better to end your sabbatical a bit closer to your ideal self than to flounder in the liminal state between the last thing and the next.

2. Prioritize others during your sabbatical. Seekers can easily lose track of time peering deep down into their personal rabbit hole. But sometimes the best way to learn about yourself is by setting your concerns aside entirely. Our research interviewees consistently recalled the time they spent with others as their most treasured moments. This finding emphasizes what the happiness literature has found over and over—that supporting other important people in your life and nurturing your relationships are instrumental to self-fulfillment.

The Explorer

Explorers have an appetite to see what’s out there in the world. They’re less concerned about how or if it will apply to their lives at the other end.

You don’t have to travel across the world to qualify as an explorer—I’ve met plenty of folks who, during their sabbaticals, spent time closer to home. They volunteered in their communities, experimented with new hobbies, and took shorter regional trips. All these detours took them out of their routine and cracked open their shells. Even going through a stack of books on your reading list can trigger awe. It can widen the aperture on what’s possible.

It’s rare to encounter a sabbatical that doesn’t incorporate a segment of pure exploration. Setting off on a journey is the most natural way to break free from routine life and to celebrate what’s next.

What this archetype wants:

For those who can afford to explore someplace far away, a sabbatical enables them to both get off the beaten path and to sufficiently sink in once they get there. As a burned-out marketing executive from our study put it, “I was having a very difficult time disengaging from my work for a couple of weeks after my sabbatical started, checking my personal email constantly and reflexively looking at my calendar. But as soon as my plane’s wheels left the runway en route to Bali—laptop behind—my work concerns evaporated completely.” Challenge yourself to get as far away from your routine experience of life as possible.

Exploration introduces uncertainty into our lives. In our world of limited vacation, we simply can’t afford to go off track and get lost. We can’t miss work, we can’t fly on weekdays, and we can’t risk traveling during shoulder seasons to save money. On sabbatical, you become time wealthy. Mistakes and inconveniences transform from vacation ruiners to serendipitous encounters. Exploring on our sabbaticals asks us instead to leave some important things to chance for a change. Living in the present and traveling flexibly leads to higher reported satisfaction among travelers and is correlated with greater psychological resilience.

What traps this archetype falls into:

While traveling far away may be the surest way to get out of your comfort zone, explorers who take an exotic, far-flung sabbatical often miss the beautiful things nearby, alienate themselves from their community, and set impossible standards for what quenches their sense of adventure. As a dyed-in-the-wool explorer, I know how difficult it is to go from a jet-setting expat to living a more sustainable life. But a well-balanced sabbatical (and life) requires also finding beauty in the mundane, closer to home.

Tip for this archetype:

1. Spend a significant portion of your sabbatical as a tourist in your own land. If you’re able to travel to far-flung places, do that first to completely disconnect and satisfy your more traditional sense of adventure. But then return to your routine surroundings and try to inhabit the energy that newcomers to a city have: Sign up for a special interest club, like a pottery or dance class. Volunteer locally or go to a city council meeting. It’s a totally normal mistake to treat your home turf as unworthy of the same attention and awe as some exotic locale. No matter how far afield your sabbatical takes you, the point isn’t to leave forever but to return home better off.

A field guide to your sabbatical

There’s a limit to how much you can prepare for a sabbatical.

There’s also a limit to how much you should prepare. You must make room for the unexpected opportunities that arise precisely from the lack of a plan, and the emotional discomfort that may accompany that. I get that this sounds like the worst-case scenario for the type As among us, but exploration enables growth, and growth requires discomfort. That’s the threshold you must cross on any journey of transformation, and the gooey insides of Sabbatical Land.

The advice you’ll appreciate the most from me won’t be a concrete recommendation for a beautiful beach or secluded retreat. Rather, it will be what helps you create the initial conditions for success: Your sabbatical should be long enough, it must contain the right components, and these pieces must be in the right order. These are the three guiding principles—setting, ingredients, and order.

This is a scaffolding to frame the journey in front of you, not be a “do this, don’t do that” checklist.

Three guiding principles

1. Setting: Duration and disconnection

Take big time off (more than you’re comfortable with)

In our time-scarce society, carving out enough uninterruptible time for your sabbatical is undoubtedly the most difficult step you’ll face. Is it any wonder that the most common question I receive is “How much time is sufficient for a sabbatical?”

I believe the sweet spot for sabbaticals is between six and 12 months1. It’s not easy to take such a big chunk of time off, which is why most people take an abbreviated break of a month or six weeks, kicking the can down the road for a longer break when things open up in the future. While you’ll still undoubtedly get some benefits from an extended vacation, which we’ll discuss further in chapter 11, don’t mistake a shorter break for a sabbatical. Not taking enough time off puts you at risk of ending up just short of the sought-after experience. It often takes six to eight weeks to begin to feel like you’re truly disconnected from routine life.

We’ve all experienced that moment toward the end of a vacation when we finally feel like we’re sinking in and enjoying ourselves, only to realize it’s time to head back to reality. It’s like that with sabbaticals. The most transformative aspects of sabbaticals often don’t start until at least two months in, after we’ve had a chance to heal and sufficiently leave our former life behind.

While there is ample evidence to suggest that anything under two months is too short, there’s less clarity on how long is too long. A small chunk of people I’ve interviewed felt as though being out of the workforce for more than a year felt right, and it worked for them. That said, I’ve witnessed significantly more folks who kept moving their return dates further and further into the future, getting caught in a cycle of self-doubt and guilt the longer they stayed outside of routine life. This makes sense: sabbatical takers feel enormous pressure to make their hard-won time off “worth it.” If their problems haven’t been resolved or their lives completely changed, can they really return to regular life satisfied?

Stressing yourself psychologically and financially while waiting for the perfect job is almost always worse than taking a modest next step toward your ultimate goals. So plan for sufficient time in Sabbatical Land, but consider setting a deadline for returning to work, even if—especially if—you haven’t yet landed on your dream job.

Set impenetrable boundaries to truly disconnect

Once you create the right container, you need to protect it by setting boundaries. This is more difficult than ever. Some 30 years ago, going abroad meant untethering. Your boss couldn’t reach you. Getting in touch with the folks at home meant an expensive long-distance call. As for the news, the New York Times didn’t go online until 1996, and you’d need to be in a cybercafe to read it. Now, a flick of the thumb could reveal a crisis at work, a salacious news story, or a pressing issue closer to home, and in the process spoil your serenity for the rest of the day.

I’m a purist when it comes to not working while on sabbatical, particularly when it comes in the form of consulting gigs related to your routine job. No matter how attractive the opportunity seems—no matter how little time it claims to take up—these projects tend to expand to fill the time available. A two-hour call once per week has a surprising amount of disruptive force, preventing spontaneity, requiring connectivity, and psychologically tying you to a past version of yourself. So set an away message and create a mail rule to auto-delete all inbound emails. Make sure your colleagues understand what constitutes a sufficient “break the glass” moment to interrupt your time off.

Money might be able to buy you incrementally more time off, but it can never replace the large swaths of uninterrupted time off it destroys. No matter how tempting it may seem, you will regret porous boundaries between your old life and your time off.

2. Ingredients: Embodiment and play

Get out of your head and into your body (and soul)

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2026-07-20 23:01:56

How the founder of Morning Brew built a Claude content machine that never runs out of ideas | Alex Lieberman (Tenex)

Brought to you by:

• Firecrawl—Power AI agents with clean web data

• Customer.io—Build customer engagement campaigns from a single prompt

Claire sits down with Alex Lieberman, Co-founder and Co-Managing Partner of Tenex, to dig into the AI content system he’s built inside Claude. Alex walks through how he finds ideas, gets interviewed by AI, codifies his voice, and runs drafts through a “Writer’s Council” before posting.

Biggest takeaways:

1. The blank page is the real enemy of consistent content, and an AI Oracle makes it disappear. Alex’s Oracle scans seven days of Slack, Notion, Gmail, and meeting notes, then surfaces 15 ranked content spikes each day—half from internal sources, half from the X and LinkedIn accounts he follows. Writing is actually the easy part; knowing what to say is where most people stall.

2. Map your current workflow before you touch any AI tool. Alex’s process started with drawing out every step of content creation as it already existed, then rebuilding it from scratch with no constraints. He found that most companies discover huge inefficiencies in this step that have nothing to do with AI at all. AI just forced them to look.

3. AI slop is mostly a people problem, not a model problem. Alex’s framing here is blunt: the only time the Content Machine produces slop is when the person being interviewed doesn’t share interesting enough ideas during the interview. The model is shaping clay, not inventing ideas. If the clay is bad, the sculpture will be bad.

4. Your voice lives in a Markdown file, and that file changes everything. Alex’s Content Machine pulls from a personal voice guide that captures his top-performing posts, hook formulas, content structures, and even specific language patterns like “self-deprecating confidence.” The system drafts against that file, which means it’s calibrated to how Alex actually writes rather than to some average of the internet.

5. A reinforcement loop is how your AI system gets better every time you use it. After every piece, Alex’s Content Machine compares the original draft to the published version, extracts generalizable lessons, and asks if they should be added to a permanent lessons file. Over time, the system stops making the same mistakes. This is the kind of feedback loop most people never build.

6. The interview panel is the step most people skip and the one that matters most. The system deploys six interviewer personas (Tim Ferriss, Joe Rogan, Larry King, Howard Stern, Barbara Walters, Michael Barrow) that ask follow-up questions until they’ve extracted enough specifics to write something real. Alex voice-to-texts his answers via Wispr Flow, so every sentence in the final draft traces back to something he actually said.

7. Your employees are your most underleveraged marketing channel, and most companies are actively suppressing them. Alex ran a version of employee content at Storyarb called “Own the Internet,” and it drove 40% of all inbound leads that quarter. At Tenex, he launched the Creator Cup with $5,000 in prizes to make posting feel like a team sport, not a chore. His argument to skeptical CEOs: the fastest way to lose a great employee is to make it impossible for them to build a personal brand.

8. A bootstrapped company can out-distribute a venture-backed one if it’s willing to show the work. Alex’s case is simple: Tenex can’t rely on TechCrunch coverage or top-tier investor mentions, so the team’s content is the visibility strategy. If the Creator Cup gets him one great engineer, the $5,000 prize pool pays back many times over compared with a recruiting agency fee. For bootstrapped companies, distribution isn’t optional, but the whole game.

9. The Writer’s Council won’t let a draft go out below a 9 out of 10. Six writer personas (including a character Alex calls “the AI slop allergist”) each score the draft and run a revision loop until the aggregate clears the threshold. That scoring mechanism is also what keeps Alex from having to manually police every post, so the system holds its standard even when he’s in a hurry.

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.

2026-07-20 20:04:47

Alex Lieberman co-founded Morning Brew in college and grew it into one of the most-read business newsletters in the world before selling it to Business Insider. Now he’s the co-founder and co-managing partner of Tenex. In this episode, Alex explains why distribution is becoming a durable moat, why founders and teams need to “climb Cringe Mountain,” and how he rebuilt his content process around AI without letting it produce generic slop. He walks us through every step of his Content Machine live: an Oracle that scans internal systems and the internet for content spikes, an interview panel that pulls out his real ideas, voice and style files that keep drafts sounding like him, an editorial council that scores and revises posts, and a lessons loop that learns from his feedback.

What you’ll learn:

1. Why the blank page is the biggest friction point in content creation, and how an AI Oracle eliminates it

2. How to map your current workflow before you add any AI

3. How Alex built a six-step Content Machine in Claude that goes from idea spike to publishable post

4. Why the interview step (not the drafting step) is where AI slop actually comes from

5. How to codify your voice in a Markdown file so an AI drafts in your register, not the internet’s average

6. Why your employees are your most underleveraged marketing channel right now

7. How the Tenex Creator Cup turned content creation into a team sport with a $5,000 prize pool

Brought to you by:

Firecrawl—Power AI agents with clean web data

Customer.io—Build customer engagement campaigns from a single prompt

In this episode, we cover:

(00:00) Introduction to Alex Lieberman

(02:35) Why Alex built a content machine

(06:56) Alex’s thoughts on AI slop

(09:00) Mapping the workflow from scratch

(13:24) The six-step Content Machine setup

(23:11) Live demo: Oracle, Interview Panel, and Writer’s Council in action

(30:38) Employee advocacy: the Tenex Creator Cup and $5K prize pool

(36:45) Lightning round: great engineers, AI use cases, slop fixes

Tools referenced:

• Claude / Claude Code (Anthropic): https://claude.ai

• Wispr Flow (voice-to-text transcription): https://wisprflow.ai

• Notion: https://notion.so

• Linear: https://linear.app

• Slack: https://slack.com

Other references:

• Morgan Housel: https://www.morganhousel.com

• David Perell: https://perell.com

• Shaan Puri / My First Million podcast: https://www.mfmpod.com

• Gary Vaynerchuk: https://garyvaynerchuk.com

Where to find Alex Lieberman:

X: https://x.com/businessbarista

LinkedIn: https://www.linkedin.com/in/alex-lieberman/

Tenex: https://www.tenex.co/

Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

2026-07-19 20:31:21

Elizabeth Stone is the Chief Product and Technology Officer (CPTO) at Netflix, where she oversees Engineering, Product, and Design. Since her first appearance on the podcast two years ago—which remained my second-most-popular episode for more than a year—she has expanded her role to lead product, in addition to engineering. Before Netflix, Elizabeth was VP of Science at Lyft, Chief Operating Officer at Nuna, an economist at Analysis Group, and a trader at Merrill Lynch.

In our in-depth conversation, we discuss:

1. Why “systems thinking” is now the most important skill she looks for

2. How to manage the flood of AI-generated output without losing quality or signal

3. How Netflix thinks about AI fluency as a universal expectation rather than a level-specific skill

4. What “excellence as an operating system” means

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

Where to find Elizabeth Stone:

• LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754

Referenced:

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• Claude Code: https://www.anthropic.com/product/claude-code

• Claude Cowork: https://www.anthropic.com/product/claude-cowork

• Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it

• Innovation for Filmmaking, By Filmmakers: Why InterPositive Is Joining Netflix: https://about.netflix.com/en/news/why-interpositive-is-joining-netflix

• InterPositive: https://weareinterpositive.com

• Netflix Prize: https://en.wikipedia.org/wiki/Netflix_Prize

• Quarterback on Netflix: https://www.netflix.com/title/81482895

• The Bill Simmons Podcast on Netflix: https://www.netflix.com/title/82186214

• Spencer Pratt on Instagram: https://www.instagram.com/spencerpratt

• Salman Rushdie’s Substack: https://salmanrushdie.substack.com

• Remarkably Bright Creatures on Netflix: https://www.netflix.com/title/81911351

• Eight Sleep: https://www.eightsleep.com

• Tour de France: https://www.letour.fr/en

Recommended books:

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• Into Thin Air: A Personal Account of the Mt. Everest Disaster: https://www.amazon.com/Into-Thin-Air-Personal-Disaster/dp/0385494785

• Liar’s Poker: https://www.amazon.com/Liars-Poker-Norton-Paperback-Michael/dp/039333869X

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.

My biggest takeaways from this conversation:

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2026-07-19 01:04:04

👋 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.

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2026-07-13 23:02:17

What a harness is and how to build one with Claude Agent SDK

Brought to you by:

Bolt.new—Turn your idea into a real product

Customer.io—Build customer engagement campaigns from a single prompt

Claire explains why harnesses matter and when they’re better than general-purpose tools like Claude Code or Codex, and walks through the custom Claude Agent SDK harness she built to automate Sentry bug triage at ChatPRD. You’ll see how she structured the workflow, encoded permissions, connected tools like Sentry and Linear, and turned a repeatable engineering task into something an agent can run more consistently every time.

Biggest takeaways:

1. A harness is just code around an AI agent—nothing more mysterious than that. The term has taken on an almost mythical quality in engineering circles, but I strip it down in this episode: a harness is code you write to make an AI agent more effective at a specific job. Cursor is a complex harness. Claude Code is a complex harness. Yours can be eight files and a terminal UI.

2. Build a harness when the same workflow needs the same setup and the same outcomes every time. The trigger is recognizing a job that is partly deterministic (defined steps, defined tools) and partly non-deterministic (the AI figures out root causes and writes the report). Sentry bug triage qualified because every investigation follows the same evidence-gathering process and ends with the same artifact bundle.

3. Opinionated tool adapters beat general MCP access for specialized workflows. Rather than giving the agent broad access to the Sentry MCP and letting it wander through traces, I built a custom Sentry adapter that pulls exactly what matters for a bug report and nothing else. That specificity makes the agent faster, cheaper, and less likely to go off-script.

4. Encoding permissions in the harness removes the need to prompt them every single time. In a general-purpose coding tool, you have to remember to say “investigate only, do not write code.” In my harness, that is a flag in the interface. I click “investigate,” paste the Sentry link, and the agent already knows its constraints without being told.

5. Structured artifacts are what separate a one-off investigation from a team-wide resource. Every time my harness runs, it outputs a task log, a Sentry issue brief, relevant logs, a worker report, and an HTML summary file. That artifact bundle means the engineering team gets a consistent, scannable record of every bug investigation without anyone having to write it up manually.

6. A harness lets you do multi-model routing in ways a single general-purpose tool never could. Claude Code is Claude. Codex is GPT. A custom harness using the Claude Agent SDK lets you pick the right model per step, enforce different tool policies per invocation, and swap models over time without changing how the interface works. That flexibility is one of the strongest arguments for owning the harness layer yourself.

7. The open chat field has been good enough, until it stopped being good enough. I acknowledge in this episode that just typing into Claude Code has produced real work. But this marks a shift in my thinking: general-purpose agents are now better used to orchestrate specialized harnesses than to do every job themselves. Giving a constrained agent a specific harness gets more consistent output than giving a powerful agent an open prompt.

This solo builder runs 24/7 local AI on his own hardware | Alex Finn

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Claire talks with Alex Finn about how he built a 24/7 local AI fleet using Mac Studios, a DGX Spark, an RTX 5090, and a custom dashboard to keep agents running around the clock. Alex breaks down what each machine is actually good for, how he routes work across local models like GLM, Qwen, and Ornith, and why “unlimited inference” changes the entire economics of AI workflows. They also get into his Claude Code build-and-review loop, his OpenClaw and Hermes setup, and the surprisingly practical playbook behind running your own always-on software factory.

Biggest takeaways:

1. The case for local AI isn’t ROI; it’s unlimited inference. The math on a $10,000 Mac Studio vs. a $20 ChatGPT subscription only looks crazy until you run an agent 24/7. At that scale, cloud APIs get expensive fast, and local models running around the clock open use cases that simply aren’t economically viable otherwise. Alex runs security scans, code reviews, and social signal monitoring on a continuous loop that would cost thousands a month in cloud credits.

2. Each hardware tier has a job. Mac Studio handles massive models slowly but at Opus-level intelligence (Alex runs GLM 5.2, which he calls Opus 4.8-equivalent, on a single Mac Studio). DGX Spark is the sweet spot: 128 GB of Nvidia unified memory plus CUDA speed, enough for models like Qwen 3.6 running fast. The RTX 5090 has only 32 GB of VRAM but is cloud-speed fast. Buy for the task, not the spec sheet.

3. Tailscale is the connective tissue for a multi-machine setup. Once all your machines are on the same Tailscale network, one agent (OpenClaw or Hermes) can hop across them, check the hardware, load the right model, and get it running without any manual configuration. Alex says there’s truly no technical knowledge required once Tailscale is installed, and he recommends it even if you only have one machine, because it also lets you test local apps from your phone.

4. Local models are the BDR; Claude Code is the closer. Alex’s security scanning loop is a good example of the hybrid model that actually works. A local model (GLM 5.2) scans code every 20 minutes and dumps findings into a Markdown file. Claude Code checks that report once a day and decides what’s real and worth fixing. The local model does the volume work cheaply; the frontier model does the judgment work precisely. Trying to run Claude Code every 20 minutes instead would cost thousands a month.

5. The software factory runs on two loops and a rocket emoji. Every morning, Alex does a planning session in Claude with a “morning build” prompt that produces a task list for his SaaS. The build loop picks those up and starts shipping. The review loop checks the work. When something passes review, Alex gets a Slack ping, and leaving a rocket emoji on it triggers an automated merge. He goes from morning brief to reviewing and merging code without touching the keyboard again until he does the approval round.

6. OpenClaw and Hermes fill different needs, and you probably want both. Alex prefers OpenClaw for the “big bang” wow moments and the emotional connection (his words). But Hermes has been more reliable under repeated updates. His solution is redundancy: three Hermes agents and two OpenClaw agents running simultaneously, so when three of the five are broken (which happens), the other two can fix them. The failover is deliberate, not accidental.

7. Task allocation by model intelligence is the skill that makes the fleet useful. GLM 5.2 is Opus-level smart but painfully slow, so it gets the deep, latency-tolerant work. Qwen 3.6 is quick and good enough to read Twitter for product signals. Ornith 1.0, a Qwen fine-tune with reinforcement learning baked in for coding, has beaten Qwen on every eval Alex has run and runs comfortably on a DGX Spark. The insight is that “smartest model everywhere” is wasteful; matching model intelligence to task complexity is what makes ambient AI economically coherent.

8. The vague posting about loops is partly a competitive moat. Alex’s theory: the companies building the best AI coding infrastructure (including OpenAI and Anthropic themselves) have internal loop systems that are their last real competitive advantage. If you can pump out high-quality code faster than anyone else because your build-review loop is better, you don’t go publishing a how-to. Claire’s counter-theory: most people vague-post because their loops are boring and vagueness gets more engagement than specifics. Both are probably true, depending on who’s doing the posting.

GPT-5.6 Sol vs. Claude Fable: Why OpenAI’s new model crushes my benchmark

Claire puts GPT-5.6 Sol head-to-head with Claude Fable, Sonnet 5, and the rest of the GPT-5.6 lineup using her own five-part benchmark for real product work. The result: Sol becomes her new daily driver. Claire breaks down exactly why and also shares where she’d still use Terra, Sonnet, or Fable instead.

Biggest takeaways:

1. GPT-5.6 Sol is the most practically effective model I’ve tested, even if Fable is theoretically smarter. I ran a five-category benchmark across PRDs, prototypes, wireframes, debugging, and agentic voice, and Sol had the highest taste score by a significant margin on the 70% Claire/30% machine split. That gap between “hyper-intelligent” and “actually ships” is real, and for product work Sol wins.

2. Full-fidelity prototypes from Sol are more functional and more opinionated than anything else I’ve tested. Across a doc scheduler, a dev tools incident triage site, and a consumer habit tracker app, Sol consistently produced designs with better visual hierarchy, semantic color use, and working interactivity. Fable’s outputs were fine; Sol’s were the ones I’d actually show a stakeholder.

3. Sol’s writing is just easier to work with. Fable writes like it has never met a human before, incredibly pedantic and almost inscrutable when you need to collaborate. Sol writes like a normal person, and that difference compounds fast when you’re iterating on PRDs or talking to an agent all day.

4. For PRD writing specifically, GPT-5.6 Terra might be the better pick. I asked Sol to greenfield-rebuild my approach to PRDs for 2026, and while Sol’s output was excellent, Terra’s clean, direct, no-frills business writing made me think it’s the right call when you want crisp, fast documentation without extra flair.

5. Fable gets too locked in its own frameworks; Sol is willing to reconsider. I had a hardened tool-calling loop in my prototyping product that only GPT-5.5 could run. Fable insisted it was a model problem and refused to budge. The moment I switched to Codex and told it to just fix it, Sol got Sonnet 5 working in one shot. That kind of practical flexibility is exactly what you need when building real products.

6. Sonnet 5 is still my favorite for agentic voice in Open Claw. Even after this whole benchmark, I gave Sonnet 5 a gold star for voice: aside from the dashes, it sounds the most human. I use Sonnet for my OpenClaw and I’m not changing that. Sol did a worse job on agentic voice overall, and I still can’t get GPT models to run well in my OpenClaw setup.

7. GPT-5.6’s video editing via Codex is one of my favorite new workflows. I dropped in a full recording from a talk I gave at Cursor’s event, asked for five hype-video clips, gave feedback on pacing and orientation, and had shareable social clips I could drop into CapCut in a fraction of the time. This use case alone justifies experimenting with GPT-5.6.

8. Browser use with Codex plus GPT-5.6 and @Chrome is the best agentic workflow I’ve found. I opened LinkedIn, told it to reply to high-value messages from executives and ChatPRD fans, and it burned through roughly 500 messages. I’ve also used it to test web apps and fill out forms. When I got rolled back to GPT-5.5 temporarily, my life was measurably worse. Learn @Chrome and just let it rip.

9. The “forest green” tell is real, so name it in your prompts. Sol has a strong aesthetic bias toward what feels like a woodland-themed palette hardcoded somewhere in its system. You will see a lot of green. I told the OpenAI team, I’m noting it here, and I’m already prompting against it when I want a different aesthetic direction.

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

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