Eric Ries is the author of The Lean Startup, a book that reshaped how a generation of founders think about building companies. His new book, Incorruptible, explains how successful companies are destroyed by failing to protect what makes them valuable, and how to change it.

In our in-depth conversation, we discuss:

1. Why 80% of venture-backed founders are ousted within three years of going public

2. The governance structures that protect companies like Anthropic, Costco, and Novo Nordisk

3. The simple legal filing that takes two pages and could save your company

4. Financial gravity: why successful companies predictably get corrupted into mediocrity

5. Why mission-aligned companies like Anthropic reap major benefits from protecting their mission through governance

6. Why success won’t protect you—it instead makes you a bigger target

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny

Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Eric Ries:

• X: https://x.com/ericries

• LinkedIn: https://www.linkedin.com/in/eries

• Website: https://www.incorruptible.co

• Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://news.theleanstartup.com/

• Podcast:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ https://ericriesshow.com

• YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Eric Ries

(02:26) Introducing Incorruptible

(06:26) Protecting what you’ve built

(11:35) Why founders get ousted

(14:58) Too early, too late

(19:32) The blueprint: ethos plus integrity

(20:49) Novo Nordisk’s 100-year governance fortress

(26:41) The Vectura Group and Philip Morris

(33:16) The “harder is easier” principle

(37:22) Cloudflare’s mission emergence story

(42:43) Groupon’s email frequency death spiral

(45:37) How to define your purpose

(51:09) Mission-driven vs. mission-hopeful companies

(54:46) Integrity: structural and personal

(57:47) Shareholder primacy: the 40-year-old “natural law”

(01:00:04) Public benefit corporations: the easiest protection

(01:04:24) Downsides and objections

(01:06:08) The Anthropic example: fastest-growing company ever

(01:08:39) The torchbearers in every organization

(01:10:37) The culture bank: deposits and withdrawals

(01:12:28) OpenAI and Anthropic governance

(01:16:21) Mission guardians explained

(01:18:29) Spiritual holding companies

(01:21:53) The founder control trap

(01:25:25) Three things to do this week

(01:30:10) AI alignment and human alignment

(01:34:00) Conway’s law: org charts in architecture

(01:37:31) Book resources and farewell

—

References: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands

—

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.

Max Schoening is head of product at Notion, where he’s been especially effective at getting designers and PMs to ship code, prototype in the terminal, and launch extremely successful AI products. He was previously a PM at Google, ran design at Heroku, was VP of Design (and a part-time engineer) at GitHub, and is a two-time founder. He’s one of the most AI-forward product leaders out there and one of the deepest thinkers on how AI changes how we build and use software.

We discuss:

1. What’s most worked in getting designers and PMs to embrace AI

2. Why agency—not skills—is the thing that separates people who thrive from those who fall behind

3. How the first 10% of every project is now “free,” and what that means for product development

4. Max’s “tiny core” theory of great products: iPhone multitouch, the GitHub pull request, Notion blocks, Dropbox’s menu bar icon

5. Why the SaaSpocalypse is overstated

6. Why the amount of software has exploded but the quality hasn’t, and why that gap creates opportunity

—

Brought to you by:

WorkOS—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny

Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Max Schoening:

• X: https://x.com/mschoening

• LinkedIn: https://www.linkedin.com/in/max-schoening

• Website: https://max.dev

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Max Schoening

(01:55) The origin story of designers coding at Notion

(06:30) How much designers and PMs are shipping today

(08:24) The balance between shipping code and strategic work

(10:32) Why agency will help you thrive in the AI era

(11:49) Examples of high agency at Notion

(13:52) What we might lose as roles merge

(15:56) Advice for developing agency

(17:42) Malleable software explained

(20:43) The Dieter Rams video and design philosophy

(24:00) The SaaS apocalypse debate

(28:25) How product building has changed in the past two years

(30:27) What’s next in how we build products

(34:16) Token spend and ROI conversations

(37:39) Getting people to change how they work

(39:04) Max’s AI stack

(41:41) Which roles AI will transform next

(44:26) When companies will start caring about ROI

(48:38) Why Notion AI is so successful

(51:47) How to ship more quickly while maintaining quality

(56:40) Building taste through iterations

(1:00:09) What matters most in building successful products

(1:05:06) Using the jobs-to-be-done framework

(1:07:28) Hot take on universal basic income

(1:09:26) What Max would do with AGI

(1:10:53) Contrarian corner

(1:13:14) Failure corner

(1:16:20) Advice for young people in Silicon Valley

(1:19:20) Lightning round and final thoughts

—

Referenced: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more

—

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.

Evan Spiegel, the co-founder and CEO of Snap, is one of the very few people in the world who has successfully built and scaled a lasting consumer social product. Snapchat has nearly 1 billion MAUs, and Evan and his team invented some of the most important consumer products and features, including Stories, AR glasses, swipe-based navigation, the camera as the primary UX, and a lot more.

In our in-depth conversation, we discuss:

1. Why distribution is now the biggest challenge for creating a consumer technology business

2. How Snap innovates at scale with a 9-to-12-person design team: no titles, no hierarchy, hundreds of ideas reviewed weekly with the CEO

3. Why a pure software business is no longer a moat, and what actually creates durable competitive advantages today

4. How AI is changing the way designers work and why they’re now shipping code

5. Why every major Snap feature was copied and how that forced the company to work differently

6. Evan’s prediction that humanity’s comfort with AI will be a bigger bottleneck than the technology itself

7. This year’s crucible moment for Snap

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny

Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Evan Spiegel:

• X: https://x.com/evanspiegel

• Snapchat: https://www.snapchat.com/@evan

• LinkedIn: https://www.linkedin.com/in/evan-spiegel

• Website: https://www.spiegelfamilyfund.com

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Evan Spiegel

(02:28) Why consumer social products are so hard to build

(04:31) How Snapchat cracked distribution with close friends, not network size

(05:50) Why distribution is the new moat in the AI era

(08:39) Snapchat’s innovation track record (and why software isn’t a moat)

(11:39) Why Snap is betting on two of the hardest businesses: consumer social and hardware

(16:00) Specs use cases

(17:56) The innovation process

(21:34) The velocity of design work at Snapchat

(25:07) Why Evan says you must talk to customers

(26:06) The origin story of Stories

(28:25) How screenshot detection saved early Snapchat

(31:03) Why they waited to hire PMs—and what role they play now

(34:41) How AI is shifting the designer-PM-engineer triad

(36:10) Design as an intentional bottleneck for product cohesion

(37:24) Why staying close to customers matters for any leader

(39:39) What Evan looks for when hiring designers

(41:57) How to develop young design talent

(44:16) Designers shipping code with AI—and the guardrails needed at scale

(47:20) Using jobs-to-be-done to organize AI transformation

(48:50) How the CEO job has changed over 15 years

(51:30) Learning to communicate

(54:08) Why this year is Snapchat’s “crucible moment”

(56:22) Being the “middle child” in tech

(57:51) Screen-time philosophy with four kids (ages 2 to 15)

(1:01:08) AI Corner

(1:04:02) Contrarian Corner

(1:06:04) Lightning round and final thoughts

—

References: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is

—

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.

Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break into AI—and seeing firsthand what separates those who thrive from those who fall behind.

We discuss:

1. How Anthropic’s shipping cadence went from months to weeks to days

2. The emerging skills PMs need to develop right now

3. Why you need to build products that don’t yet fully work, so you’re ready when the next model closes the gap

4. Cat’s most underrated AI skill: asking the model to introspect on its own mistakes

5. Why Claude’s personality is core to its success

6. Why Anthropic’s mission alignment eliminates the friction that slows most large organizations

7. Why “just do things” is the most important principle for working at AI-native companies

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Vanta—Automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Cat Wu:

• X: https://x.com/_catwu

• LinkedIn: linkedin.com/in/cat-wu

• Newsletter: https://catwu.substack.com

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Cat Wu

(01:29) Working with Boris Cherny

(04:29) What Anthropic looks for when hiring PMs

(06:18) How to help your teams move fast

(08:58) How PRDs and roadmaps have evolved at Anthropic

(10:28) The Mythos model and Anthropic’s shipping velocity

(11:54) What happened with the Claude Code source code leak

(12:53) Integrating with OpenClaw

(14:19) How the PM team is structured at Anthropic

(15:42) How engineer and PM roles are merging

(17:54) Why product taste is the most valuable skill

(20:10) Where human brains will continue to be useful

(22:23) How to stay sane in constant chaos

(24:16) What gets sacrificed when you ship so fast

(27:47) The /powerup command

(28:32) Why Anthropic has been so successful

(32:28) When to use Claude Code vs. Desktop vs. Cowork

(35:58) Tips for getting started with Cowork

(38:44) Demo: Using Cowork to build slide decks overnight

(41:48) Cat’s PM tech stack and internal tools

(46:47) Which teams use the most tokens

(51:15) The emerging skills PMs need for AI companies

(55:00) Why building evals is underappreciated

(58:44) Why Claude’s character and personality matter so much

(1:00:44) How new models force product changes

(1:05:11) The vision for Claude Code and Cowork

(1:07:22) Advice for thriving in an AI-driven world

(1:09:18) Why 95% automation isn’t good enough

(1:11:58) Build apps you use every day, not prototypes

(1:13:41) The divide between AI skeptics and believers

(1:15:19) Lightning round

—

Referenced: https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves

—

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.

Nikhyl Singhal is the founder of The Skip, a community for senior product leaders; a former product exec at Meta, Google, and Credit Karma; and a many-time founder. He’s also one of the most honest, unfiltered voices on what’s actually happening in product management right now.

In our in-depth conversation, we discuss:

1. Why the next two years will be the most chaotic period in product management history

2. Why half of current product managers are at risk, and what separates those who’ll do well

3. Why you need to find your “moments of joy” with AI

4. The “smiling exhaustion” he’s seeing across the product community

5. The psychological barriers that prevent people from reinventing themselves

6. Why your resume’s fancy logos matter less than ever, and what matters now

7. His prediction that companies will shed 30,000 people and rehire 8,000—all AI-first

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Vanta—Automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Nikhyl Singhal:

• LinkedIn: https://www.linkedin.com/in/nikhyl

• X: https://x.com/nikhyl

• Podcast & Newsletter: https://skip.show

• Skip Community: https://skip.community

• Skip Coach: https://skip.coach

• Skip.help: https://skip.help

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Nikhyl Singhal

(02:25) The big picture: what’s changing for product managers

(10:00) Are product leaders doing better than 2-3 years ago?

(11:44) What will change in the next couple of years

(14:23) How companies are changing the way they build products

(15:51) What “judgment” really means for PMs

(17:46) Why there won’t be any more bad software

(20:25) The skills you need to be effective today

(23:31) Why there are more PM roles than ever

(24:27) The builder versus information-mover divide

(30:14) The non-builder problem

(30:53) Should PMs code?

(34:15) Why experienced leaders still matter

(35:44) The diversity setback nobody’s talking about

(37:21) Why your brand doesn’t matter as much anymore

(39:54) How valued skills are flipping upside down

(40:49) Why change is so hard for humans

(43:53) The “equal disappointment” algorithm

(46:39) You must cross the threshold

(48:37) This chaos will settle

(53:19) Finding your moment of joy

(58:50) Nikhyl’s AI stack and what he’s building

(1:00:53) The obsolescence mindset

(1:05:24) Specific advice for PMs right now

(1:08:58) The four jobs that will exist in the future

(1:11:59) Why alignment is changing (but not disappearing)

(1:15:40) How engineering is changing even more than PM

(1:17:04) The surprising design plateau

(1:18:49) Finding optimism in the chaos

(1:21:12) Lightning round

—

Referenced:

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career

• COBOL: https://en.wikipedia.org/wiki/COBOL

• United Airlines: https://www.united.com

• State of the product job market in early 2026: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9

• Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run

• Demis Hassabis on X: https://x.com/demishassabis

• Sam Altman on X: https://x.com/sama

• Dario Amodei on X: https://x.com/DarioAmodei

• Cross on Prime Video: https://www.amazon.com/Cross-Season-1/dp/B0D6X7ZZHC

• Jack Ryan on Prime Video: https://www.amazon.com/Tom-Clancys-Jack-Ryan/dp/B0CNDCMN8R

• 24 on Prime Video: https://www.amazon.com/24-Season-1/dp/B000HPF85A

• Claude Code: https://code.claude.com

• Codex: https://chatgpt.com/codex

• Lovable: https://lovable.dev

• Sonos: https://www.sonos.com

• “There are only four jobs” on X: https://x.com/yrechtman/status/2039012253341495462

• Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f

• Lioness on Paramount+: https://www.paramountplus.com/shows/lioness

• Tesla: https://www.tesla.com

• Albert Einstein’s quote: https://www.goodreads.com/quotes/115696-genius-is-1-talent-and-99-percent-hard-work

—

Recommended books:

• James: https://www.amazon.com/James-Novel-Percival-Everett/dp/0385550367

• The Adventures of Huckleberry Finn: https://www.amazon.com/Adventures-Huckleberry-Finn-Unabridged-Uncensored/dp/195483943X

—

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.

Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad).

In our in-depth conversation, Keith shares:

1. The barrels vs. ammunition hiring framework (and how to spot barrels)

2. Why talking to customers is actively harmful for consumer products

3. How to identify undiscovered talent

4. Why the PM role is dying

5. The three traits of the best-performing companies right now

6. The specific interview question he asks every senior candidate

7. Why CMOs (not engineers) are becoming the #1 consumer of tokens

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Vanta—automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Keith Rabois:

• X: https://x.com/rabois

• LinkedIn: linkedin.com/in/keith

• Website: https://www.khoslaventures.com

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Keith Rabois

(01:59) Why Keith hasn’t used a computer since 2010

(04:52) The team you build is the company you build

(07:40) How Keith learned to identify talent at PayPal

(10:05) Tactics for getting better at hiring

(15:31) The barrels vs. ammunition framework

(18:52) What makes someone a barrel

(22:36) How to attract the best talent

(26:18) Building companies on undiscovered talent

(27:53) Why better performance requires more pressure

(32:36) Career advice in the age of AI

(35:14) The future of the product triad

(41:03) Why design and code are merging

(49:35) What practicing law taught Keith about entrepreneurship

(51:22) Contrarian takes on customer feedback

(1:02:33) Identifying great AI opportunities

(1:05:13) Advice for evaluating statrups 

(1:12:36) Criticizing in public vs. private

(1:15:05) Failure corner

(1:17:29) Lightning round

—

Referenced:

• Square: https://squareup.com

• Jack Dorsey on X: https://x.com/jack

• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

• Simon Willison’s Weblog: https://simonwillison.net

• Vinod Khosla on X: https://x.com/vkhosla

• Peter Thiel on X: https://x.com/peterthiel

• Max Levchin on X: https://x.com/mlevchin

• David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks

• Tony Xu on X: https://x.com/t_xu

• David Sze on X: https://x.com/davidsze

• Faire: https://www.faire.com

• Max Rhodes on X: https://x.com/MaxRhodesOK

• Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson

• Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois

• Lattice: https://lattice.com

• Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights

• Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs)

• Eric Glyman on X: https://x.com/eglyman

• Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177

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

• Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html

• Opendoor: https://www.opendoor.com

• The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q

• Lovable: https://lovable.dev

• The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• Jeremy Stoppelman on X: https://x.com/jeremys

• 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

• Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol

• Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms

• Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway

• William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare

• Evan Moore on X: https://x.com/evancharles

• Andrew Mason on X: https://x.com/andrewmason

• Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941

• The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16

• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early

• David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden

• Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred

• Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000

• Jon Chu on X: https://x.com/jonchu

• Kanu Gulati on X: https://x.com/KanuGulati

• Rogo: https://rogo.ai

• Profound: https://www.tryprofound.com

• Basis: https://www.getbasis.ai

• Spellbook: https://www.spellbook.legal

• Roelof Botha on X: https://x.com/roelofbotha

• Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742

• Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp

• Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4

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

• “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224

—

Recommended books:

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012

• The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666

• The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934

—

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.

Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year.

In our in-depth discussion, Amol shares:

1. How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger

2. How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”)

3. Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive

4. Why activation is the single highest-leverage growth problem in AI

5. Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams)

6. How he uses Cowork to detect team misalignment in Slack

7. How the company’s focus on AI coding created a research flywheel that accelerated their models

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Vanta—Automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Amol Avasare:

• X: https://x.com/TheAmolAvasare

• LinkedIn: https://www.linkedin.com/in/amolavasare

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Amol and Anthropic’s growth

(03:15) The story of cold emailing Mike Krieger to get the job

(08:28) What it’s like leading growth at the fastest-growing company ever

(10:46) What the growth team actually does at Anthropic

(12:16) The concept of “success disasters”

(13:55) Why activation is the biggest challenge in AI products

(18:05) Improving Mercury’s onboarding experience

(20:57) The importance of adding the right kind of friction

(25:10) Anthropic’s org structure

(27:06) Why Anthropic focuses on big bets over micro-optimizations

(33:34) Automating growth experiments with Claude (CASH)

(38:20) How AI is starting to identify what experiments to run

(41:07) The future of PM, engineering, and design roles

(47:19) Why you might need more PMs as engineers get more productive

(51:13) How Amol uses AI to prototype ideas and skip PRDs

(58:10) Amol’s morning routine: AI analyzes 20 to 25 charts automatically

(1:03:31) Getting coaching from an AI version of your manager

(1:06:27) How Anthropic’s focus on coding and B2B drove their success

(1:12:10) Balancing growth with AI safety as a core mission

(1:18:09) Advice for thriving in an AI-first future

(1:22:53) Anthropic’s culture and the “notebook channels” on Slack

(1:35:12) Failure corner: Shutting down his startup after raising money

(1:38:25) The traumatic brain injury that changed everything

(1:46:49) Lightning round

—

References: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run

—

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.

Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net.

In our in-depth conversation, Simon shares:

1. Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works”

2. How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m.

3. Why mid-career engineers (not juniors) are most at risk right now

4. The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding)

5. The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA

6. Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster

7. Why the pelican riding a bicycle became the unofficial benchmark for AI model quality

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

Vanta—automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Simon Willison:

• X: https://x.com/simonw

• LinkedIn: https://www.linkedin.com/in/simonwillison

• Website: https://simonwillison.net

• Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Simon Willison

(02:40) The November 2025 inflection point

(08:01) What’s possible now with AI coding

(10:42) Vibe coding vs. agentic engineering

(13:57) The dark-factory pattern

(20:41) Where bottlenecks have shifted

(23:36) Where human brains will continue to be valuable

(25:32) Defending of software engineers

(29:12) Why experienced engineers get better results

(30:48) Advice for avoiding the permanent underclass

(33:52) Leaning into AI to amplify your skills

(35:12) Why Simon says he’s working harder than ever

(37:23) The market for pre-2022 human-written code

(40:01) Prediction: 50% of engineers writing 95% AI code by the end of 2026

(44:34) The impact of cheap code

(48:27) Simon’s AI stack

(54:08) Using AI for research

(55:12) The pelican-riding-a-bicycle benchmark

(59:01) The inherent ridiculousness of AI

(1:00:52) Hoarding things you know how to do

(1:08:21) Red/green TDD pattern for better AI code

(1:14:43) Starting projects with good templates

(1:16:31) The lethal trifecta and prompt injection

(1:21:53) Why 97% effectiveness is a failing grade

(1:25:19) The normalization of deviance

(1:28:32) OpenClaw: the security nightmare everyone is looking past

(1:34:22) What’s next for Simon

(1:36:47) Zero-deliverable consulting

(1:38:05) Good news about Kakapo parrots

—

References: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union

—

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.

Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life.

We discuss:

1. The exact step-by-step process to install and set up OpenClaw (it’s easier than you think)

2. How to avoid the biggest OpenClaw mistakes (don’t install it on your main computer)

3. Actual use cases that have changed Claire’s life (e.g. family scheduling, inbound sales, podcast prep, and course management)

4. Why multiple specialized agents beat one general-purpose agent

5. The security risks everyone worries about—and how to handle them

6. Browser limitations, memory issues, and practical workarounds

—

Brought to you by:

Mercury—Radically different banking

Omni—AI analytics your customers can trust

Orkes—The enterprise platform for reliable applications and agentic workflows

—

Where to find Claire Vo:

• X: https://x.com/clairevo

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

• Podcast: https://www.youtube.com/@howiaipodcast

• Website: https://clairevo.com

• ChatPRD: https://www.chatprd.ai

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Claire and OpenClaw

(08:00) The journey from OpenClaw skeptic to believer

(11:50) What OpenClaw actually does that’s useful

(13:35) OpenClaw vs. other AI agent products

(17:05) How to actually install OpenClaw: the basics

(18:49) Setting up like you’d onboard a real assistant

(20:41) Security and privacy considerations

(24:53) Live demo: Installing OpenClaw step-by-step

(28:47) Setting up Q: an agent for her kids’ homework

(34:08) Understanding “soul,” “identity,” and “memory”

(40:40) The unlock: multiple agents, not just one

(45:02) How to run multiple agents on one machine

(47:28) Jesse Genet’s homeschooling use case

(49:58) Real examples and use cases

(56:41) Finn, Claire’s family agent

(1:00:05) Sage the Course Bot

(1:02:15) Common issues and workarounds

(1:08:08) The Exa/Perplexity web search workaround

(1:09:29) Memory management and context overload

(1:12:09) Pro tip: Screen sharing to manage Mac Minis

(1:14:18) Using Google Workspace for agent collaboration

(1:16:24) What makes OpenClaw special

(1:20:15) The “yappers API” and ramble mode

(1:22:04) Using Claude Code as your OpenClaw brain surgeon

(1:25:16) Bringing management skills to AI agents

(1:29:32) Why this matters

(1:32:37) Lightning round and final thoughts

—

Referenced:

• OpenClaw: https://openclaw.ai

• Claude Cowork: https://claude.com/product/cowork

• Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics

• Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete

• Telegram: https://telegram.org

• WhatsApp: https://www.whatsapp.com

• Fin: https://fin.ai

• Why OpenClaw feels alive even though it’s not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175

• 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk

• Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org

• Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/

• ChatGPT Atlas: https://chatgpt.com/atlas

• Perplexity Comet: https://www.perplexity.ai/comet

• Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser

• Buffer: https://buffer.com

• Brave: https://brave.com/search/api/

• Exa: https://exa.ai

• Hilary Gridley on X: https://x.com/yourgirlhils

• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with

• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.youtube.com/watch?v=xDMkkOC-EhI

• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang

• How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

• Age of Attraction on Netflix: https://www.netflix.com/title/81779095

• Oura Ring: https://ouraring.com/

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

• Hoopsalytics: https://hoopsalytics.com

• DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp

• Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ref=sr_1_9

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

—

Recommended books:

• Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400

• Alice’s Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X

• Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184

—

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.

Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process.

We discuss:

1. Why great ideas often don’t get buy-in

2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much

3. Why executives are usually optimizing for a global maximum while you are often optimizing locally

4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”

5. Why you should go in to learn, not to convince

6. Why showing only one option is a mistake

7. Why AI will make influence more important, not less

—

Brought to you by:

Omni—AI analytics your customers can trust

Lovable—Build apps by simply chatting with AI

Vanta—Automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Jessica Fain:

• LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Jessica Fain

(03:53) Why influence is the highest-leverage skill in product

(04:47) Why great ideas fail without executive buy-in

(06:00) How executives actually think

(09:05) The fundamentals: context-setting, communication, and empathy

(10:22) Stop pitching for approval—start co-creating with execs

(12:59) Influence vs. politics (and why people get it wrong)

(15:44) How to disagree with execs without losing trust

(17:20) Going in to learn, not to convince

(19:08) How to present ideas

(26:05) The Minto-style approach and tailoring your communication to each exec

(28:22) Why Jessica doesn’t like the question “What’s top of mind for you?”

(30:24) Understanding incentives to unlock buy-in

(32:10) Aligning product work with company strategy

(35:10) Quick summary

(37:31) Disarming the executive

(40:49) Speed matters: why fast follow-up builds momentum

(43:32) How to run high-impact meetings (the 60-second rule)

(47:00) Why influencing execs is part of your job

(49:15) Asking for more resources and thinking in 10x bets

(52:23) What to do when your idea gets rejected

(54:18) Clarifying information

(56:50) How to build trust and make ideas stick

(58:30) Shrinking big ideas into experiments

(01:02:27) Common mistakes people make when influencing leaders

(01:06:00) How to grow into your next role

(01:09:32) How AI is changing influence and product work

(01:17:55) Using AI to simulate exec feedback and improve pitches

(01:21:15) Protecting our brains from overwhelm

(01:22:44) Lightning round and final thoughts

—

Referenced:

• Box: https://www.box.com

• Slack: https://slack.com

• Brightwheel: https://mybrightwheel.com

• Webflow: https://webflow.com

• April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood

• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua

• Atlassian: https://www.atlassian.com

• Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid

• Calendly: https://calendly.com

• Glassdoor: https://www.glassdoor.co.in/index.htm

• The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai

• Ethan Eismann on X: https://x.com/eeismann

• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield

• Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank

• Checkr: https://checkr.com

• Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl

• Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan

• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief

• Barbara Minto’s website: https://www.barbaraminto.com

• How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions

• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD

• Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2

• Casa: https://getcasa.com

• Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix

• Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles)

—

Recommended books:

• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927

• Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061

• A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243

• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

—

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.