Lenny's Podcast: Product | Career | Growth

Tibo Sottiaux leads ChatGPT and Codex at OpenAI. Under his stewardship, OpenAI has shipped some of its most consequential consumer launches: Codex, ChatGPT Work, and most recently, the new Dots personal agent platform. He joined me at DevDay, hours after his team launched more than 20 new products, to talk about where things are heading.

We discuss:

1. Dots, OpenAI’s new personal AI assistant

2. Why most actions on the internet will soon be taken by agents

3. Why loops, graphs, and fine-tuning agent workflows are a passing phase

4. Which skills are trending up and down in the AI era

5. How Tibo’s Dot warned him about a production outage five minutes before the launch

6. OpenAI’s approach to AI safety

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Brought to you by:

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

DX—Engineering intelligence for the AI era

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Episode transcript: https://www.lennysnewsletter.com/p/openais-head-of-chatgpt-were-entering

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

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Where to find Tibo Sottiaux:

• X: https://x.com/thsottiaux

• LinkedIn: https://www.linkedin.com/in/thibault-sottiaux-27195366

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction to Tibo Sottiaux

(01:12) How Tibo uses AI in his daily work

(03:10) The vision for always-on AI agents

(06:15) How AI will continue to change work

(07:32) Bringing Codex, ChatGPT, and Dots together

(08:20) The sci-fi inspiration behind the technology

(09:02) Building AI with the community

(10:13) Understanding the Dots structure

(11:34) OpenAI’s open ecosystem and plugin revenue sharing

(13:39) How plugins get discovered and recommended

(14:39) The research behind Dots

(16:20) Where humans will remain valuable

(17:25) Agent fatigue, loneliness, and context switching

(18:55) The pressure to do more with AI

(20:09) An agent that spotted a production outage before a live demo

(21:42) Agent guardrails and connecting multiple devices

(23:25) The skills becoming more valuable in the AI era

(25:56) Advice for people early in their careers

(27:18) How teams build and ship inside OpenAI

(28:59) Autonomy, trust, and learning from mistakes

(30:45) Building for a future where agents dominate internet activity

(32:41) What Tibo has changed his mind about

(33:55) OpenAI’s approach to AI safety and alignment

(36:15) Moving beyond model pickers toward simpler AI

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Referenced:

• OpenAI Dots: https://chatgpt.com/features/dots

• Her on Netflix: https://www.netflix.com/title/70278933

• Star Trek: https://www.imdb.com/title/tt0060028

• Pi: https://pi.ai

• OpenCode: https://opencode.ai

• Notion: https://www.notion.com

• Figma: https://www.figma.com

• OpenClaw:

Molly Graham is back for round two, and this one is even more powerful. Molly has spent more than 20 years helping organizations and the humans inside them navigate growth and change. She’s held leadership roles at Google, Facebook, Quip, and the Chan Zuckerberg Initiative and is the host of TED’s WorkLife podcast (which she took over from Adam Grant). She also runs Glue Club, a leadership community for senior operators, and writes a popular newsletter called Lessons.

In our in-depth conversation, we discuss:

1. Why Molly’s famous “give away your Legos” career advice no longer holds true in an AI world

2. The grief, loneliness, and burnout sweeping through the tech industry right now

3. Why delegating to AI is fundamentally different from delegating to a human

4. The fear narrative around AI job displacement, and why it’s overblown

5. Which Legos you should never give to AI

6. What the best managers are doing right now

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Brought to you by:

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

DX—Engineering intelligence for the AI era

—

Episode transcript: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout

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

Highlights: https://lennyspodcast.com/mostreplayedmoments

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Where to find Molly Graham

• X: https://x.com/molly_g

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

• Substack: https://mollyg.substack.com

• Website: https://glueclub.com

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Molly Graham returns

(03:34) What is “Give away your Legos”?

(05:44) The origin story: Google, Facebook, and rapid scale

(11:27) What still holds true in an AI world

(18:13) Engineering’s identity shift: from rowing to steering

(22:09) Loneliness and the collapse of team structure

(24:06) The centaur and the reverse centaur

(25:36) The fear narrative: AI-branded layoffs and overblown doom

(29:20) Survey data: burnout is up to 55%, but half of people are thriving

(35:07) Cleaning up AI slop

(40:01) What’s actually different: delegating to AI vs. giving Legos to a human

(42:02) Why every worker is now a manager, whether they want to be or not

(49:07) Why giving things away creates space for new opportunities

(55:27) Advice for people in the age of AI

(59:38) What Legos you should never give away

(01:03:12) The human sandwich: vision at the top, AI in the middle, humans at the end

(01:05:00) Holding on to the things you love: grief, funerals, and what comes next

(01:09:39) Slow takeoff: why you’re not too late

(01:13:32) The most important skill to build right now

(01:18:58) A message for managers and leaders

(01:24:17) Key takeaways

(01:31:42) Final thoughts

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References: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout

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

Peter Sellis was the first product manager at Snapchat, where he spent seven years building one of the most beloved consumer products in history. He went on to serve as Head of Product at Discord, where he helped drive some of the fastest user growth the platform had seen. Having left his role at Discord, he gets to be especially real and unfiltered — nothing to promote, no PR, no comms team.

In our in-depth conversation, we discuss:

1. Why Peter designs teams like . . . terrorist organizations

2. What it was really like to manage Nikita Bier

3. Why the median PM is so bad

4. Why Snapchat’s ads business never reached its potential

5. Why growth almost always comes from the core product

6. Peter’s three “oxymorons” of great product management

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Brought to you by:

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

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/90-minutes-of-unfiltered-product

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

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Where to find Peter Sellis:

• X: https://x.com/petersellis

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

• Website: https://pjs.lol

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction

(02:48) Why Peter avoided podcasts until now

(05:44) Designing teams like terrorist organizations

(10:35) Cult versus terrorist org: the key distinction

(11:19) Managing Nikita Bier

(12:56) Building orgs that handle spiky talent

(15:16) Why the median PM is probably bad

(18:28) Is the PM profession getting better?

(20:49) Snap’s three ads monetization challenges

(25:03) Snap’s underrated product track record

(27:57) Systems thinking

(32:19) Instagram copying Snapchat’s worst features

(33:32) Software moats

(35:27) Taste, museum curators, and the art of saying no

(40:05) OpenAI, ads, and the trust auction mechanism

(46:25) Counterintuitive lesson: ride your best people hard

(50:13) Why collaboration is often overrated

(50:50) Growth lives in the core product

(57:50) When to bet on something genuinely new

(01:02:18) SpaceX and sunsetting the Falcon 9

(01:07:01) Ambition as a learnable muscle

(01:10:26) Long-term greedy: the ads philosophy

(01:13:36) The Core Product Value framework

(01:16:33) The three oxymorons of a great PM

(01:20:29) Contrarian corner

(01:26:00) Lightning round and final thoughts

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References: https://www.lennysnewsletter.com/p/90-minutes-of-unfiltered-product

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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.

Roman Ugarte helped incubate and build Grok Bot, the popular new knowledge-work agent from SpaceXAI. A small, isolated team took it from first line of code to a working internal product in four weeks, and to a hugely successful public launch just three weeks later. Before Grok Bot, Roman led Growth at Cursor, where he helped scale the company from 15 people to over 1,000 before its acquisition by SpaceX.

In our in-depth conversation, we discuss:

1. The origin story of Grok Bot

2. The key decision to build it from scratch instead of adding it to Cursor

3. Why the team personally onboarded nearly 300 of its first users

4. The two early product decisions that made Grok Bot so successful

5. Their “colleague-pilled” product philosophy

6. Roman’s advice on moats, and what has allowed Cursor to keep winning in the most competitive market in the world

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Brought to you by:

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

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month

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

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Where to find Roman Ugarte:

• X: https://x.com/romanugarte_

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

• Website: https://x.ai

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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

(02:09) The origin story: building from scratch in one month

(08:40) Why Grok Bot was built as a separate product

(11:20) Manually onboarding a couple hundred people

(14:29) Hiding internal mechanics from users

(18:41) Timeline from beta to public launch

(19:14) Unshipping features and simplifying

(23:50) Early use cases and feedback

(26:50) Product philosophy: “Grok Bot can now”

(30:02) Cloud-first architecture

(33:12) The fresh-start advantage

(35:54) The vision: a true team of AI colleagues

(39:20) The “colleague-pilled” framework

(42:36) Work versus personal: one product or two?

(47:14) Long-lived agents, persistent memory, and the computer abstraction

(51:04) Grok Bot as an always-on infovore and chief of staff

(53:35) How fast the team moves and what preserves the startup feeling

(58:20) SpaceXAI pillars

(1:00:44) The first 90% vs. the last 10%

(1:03:30) Moving fast at scale

(1:06:40) How Cursor kept winning in the most competitive market in the world

(1:10:04) Company values: “deleting the product” and “just do the thing”

(1:11:45) Moats: discovered, not planned

(1:15:11) Tips for new users and power users

(1:18:00) Lightning round and final thoughts

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References: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month

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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.

Anish Acharya is a General Partner at Andreessen Horowitz (a16z), where he has focused on consumer investing. Anish is one of the most insightful, thought-provoking, and in-the-weeds product investors I’ve met, and this conversation will get your mind buzzing. Before joining a16z, Anish was a serial founder and operator: he founded SocialDeck, which he sold to Google, then led multiple efforts inside Google before founding Snowball, which he sold to Credit Karma. At Credit Karma he rose to VP of Product and then GM of the consumer product and the broader credit card business.

In our in-depth conversation, we discuss:

1. Why you don’t have to worry about becoming part of the “permanent underclass”

2. Why company building will now involve creating a series of loops

3. What’s happening in consumer right now

4. Why the biggest opportunity in consumer is “/loop, make me happier”

5. Why moats are discovered, not designed

6. The rising importance of distribution as a moat

7. Being a model sommelier

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Brought to you by:

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

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series

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

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Where to find Anish Acharya:

• Andreessen Horowitz: https://a16z.com/author/anish-acharya/

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

• X: https://x.com/illscience

• SoundCloud: https://soundcloud.com/illscience

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction

(02:25) The fear of AI creating a permanent underclass

(05:25) Why AI takeoff may be slower than expected

(08:02) How companies are actually adopting AI

(11:25) Building AI products with loops

(15:25) Why human intuition still matters

(20:19) What the winners in AI are doing differently

(21:41) Generalists vs. specialists

(26:22) How to become a model sommelier

(32:03) /loop make me happier

(36:15) Why Anish is optimistic about the future of AI

(42:47) What happens when models become too dangerous

(46:29) How AI will change jobs and ambition

(51:34) The state of consumer AI

(54:30) How to build a durable moat in AI

(59:25) The power of distribution and word of mouth

(01:04:30) Making bigger bets and rethinking pricing

(01:09:17) Advice for product builders in the AI era

(01:11:48) Lightning round and final thoughts

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References: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series

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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.

Tara Seshan leads product for Codex and ChatGPT Work at OpenAI (alongside previous podcast guest Andrew Ambrosino, who’s her engineering manager). Before OpenAI, Tara spent over six years at Stripe, where she joined as one of the first five product managers. She went on to lead product for Watershed, which Time magazine named one of the best inventions of 2022, and she is also a founder and Thiel Fellow. Most personally meaningful to me: Tara is one of the three inaugural Lenny’s Newsletter Fellows, a program I ran a couple of years ago to spotlight the most exciting up-and-coming product leaders.

In our in-depth conversation, we discuss:

1. The shift from “rowing” to “steering,” and why human judgment and ambition will become differentiators as AI takes on execution

2. How OpenAI thinks about building for model capabilities two to three months out

3. OpenAI’s best internal memes, such as “Is this maximally accelerated?” and “Are you mainlining it yet?”

4. Why ambition is the new bottleneck for companies, and why elevating others’ ambitions is now the key part of the PM job

5. Writing as thinking vs. writing as reporting

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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 Tara Seshan:

• X: https://x.com/tarstarr

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

• Newsletter: https://substack.com/@taraseshan

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction

(02:18) What makes OpenAI’s culture so different

(06:42) Why AI product strategy is all about fast experimentation

(09:02) How the PM role is changing

(10:50) The shift from rowing to steering

(15:35) What changes when agents become coworkers

(20:05) Why ambition matters more than ever

(26:39) Building products for models that do not exist yet

(29:21) How ChatGPT’s Chat and Work modes differ

(34:01) How OpenAI ships so quickly at scale

(39:14) The vibe shift happening inside Codex

(42:20) Why traditional roles are beginning to blur

(45:59) Where humans will continue to provide unique value

(48:20) How Tara uses AI in her own work

(51:38) The magic of the /visualize command

(52:39) Writing to think versus writing to report

(57:10) How to use AI without losing your ability to think

(01:00:15) Tara’s biggest lesson from Sutter Hill

(01:04:16) ChatGPT’s site output

(01:05:01) Why knowledge work is becoming more like coding

(01:07:55) Lightning round and final thoughts

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Referenced:

• Codex: https://chatgpt.com/codex

• ChatGPT Work: https://openai.com/chatgpt-work

• Stripe: https://stripe.com

• Watershed: https://watershed.com

• Thiel Fellowship: https://thielfellowship.org

• Meet your Lenny’s Newsletter Fellows: https://www.lennysnewsletter.com/p/meet-your-lennys-newsletter-fellows

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir

• The nature of product | Marty Cagan, Silicon Valley Product Group:

Jen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast. In our first conversation we went deep on founder-led sales; in our second we mapped the $1M–$10M playbook. This time we do something I’ve never seen on another podcast: walk step by step through the full enterprise sales cycle. Most people think it’s five steps. Jen shows it’s closer to 15.

In our in-depth conversation, we discuss:

1. Why the standard five-stage CRM pipeline is a forecasting tool, not a sales process, and what the real 15-step cycle looks like

2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously

3. How to craft a two-to-three-sentence message around giving them “alpha”

4. How to run an intro call that extracts maximum intelligence before you ever show a demo

5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away

6. Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum

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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 Jen Abel:

• X: https://x.com/jjen_abel

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

• Website: https://www.jjellyfish.com

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction

(02:49) Why Jen is giving away her enterprise sales playbook

(05:54) Example: selling AI legal tech to SpaceX

(09:11) Step 1: Landing the meeting

(18:44) Step 2: Running the intro call

(30:00) Step 3: Running a follow-up call

(36:30) Step 4: Prepping the pitch/frame for demo

(38:36) Step 5: Running the demo

(46:45) Step 6: Post-demo debrief

(48:59) Step 7 through 9: Preparing for and running the pilot

(01:03:44) Why the standard five-stage CRM pipeline doesn’t work

(01:04:49) Step 10: Post-pilot session

(01:07:48) What a healthy enterprise win rate looks like

(01:11:45) Steps 11 through 14: Navigating procurement and getting the signature

(01:18:01) How to think about expansion

(01:19:18) How buyers can say no without wasting everyone’s time

(01:21:53) Why enterprise sales is a lot like product management

(01:22:27) Closing thoughts

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Referenced:

• State Affairs: https://stateaffairs.com

• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel

• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr

• SpaceX: https://www.spacex.com

• Lemlist: https://www.lemlist.com

• Palantir: https://www.palantir.com

• Jason Lemkin on X: https://x.com/jasonlk

• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr):

Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of how we will interact with AI.

In our in-depth conversation, we discuss:

1. Why Ian believes this is the best time in history to be a product designer

2. Why engineers 10x’d with AI but design teams haven’t

3. What OpenAI looks for when hiring designers

4. “Just do less”: Ian’s counterintuitive advice to his designers

5. The future of ChatGPT as a super app

6. Where humans still win: user understanding, invention, and point of view

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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 Ian Silber:

• X: https://x.com/iansilber

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

• Website: https://iansilber.com

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Introduction to Ian Silber

(02:14) Why designers in general feel anxious about AI

(09:01) What makes specific designers thrive in the AI era

(13:41) Why Ian says it’s the best time in history to be a designer

(17:13) How product roles are converging

(22:24) Can AI design great products?

(23:54) Where human judgment still matters

(27:34) What Ian looks for when hiring designers

(30:20) Why systems thinking matters

(32:53) Balancing speed and craft

(38:05) Designing for vastly different audiences

(41:57) Solving the blank-box problem

(43:31) How ChatGPT is evolving beyond chat

(46:07) The vision for Codex

(49:07) What Ian wishes he knew on day one

(51:40) Why humility matters in AI

(53:41) Advice for designers who are feeling overwhelmed

(55:16) AI corner

(57:43) Failure corner

(01:00:45) Lightning round and final thoughts

(01:05:52) Lessons from Groupon

—

Referenced:

• OpenAI: https://openai.com

• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026

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

• 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template

• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape

• Notion: https://www.notion.com

• 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

• Joel Lewenstein on LinkedIn:

Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech.

In our in-depth conversation, we discuss:

1. Inside today’s “tale of two cities” talent market

2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires

3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit

4. The worst question to ask when sourcing great talent

5. The rise of the forward deployed engineer—and how to become one

6. The biggest mistake founders make when hiring their first recruiter

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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 Adam Ward

• X: https://x.com/wardadamp

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

—

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

(03:01) The state of the hiring market

(06:41) What roles are trending up and what roles are trending down

(11:25) The three-step hiring framework that changes everything

(21:58) Getting the right people to actually respond

(25:42) Keeping talent a top priority

(29:16) Inside Cursor’s recruiting operation

(32:19) How to relentlessly pursue top talent

(35:42) “Caring is free”

(38:33) The conversation most companies underestimate

(39:19) Rethinking the atomic unit of a search

(40:12) Other recruiting tactics

(45:04) What the on-site is really for

(49:35) The importance of work trials

(53:10) The offer stage

(57:53) Negotiations and comp

(01:01:50) The details that actually close the deal

(01:07:23) What it’s like working with an exec team who values recruiting

(01:09:42) Talent density

(01:11:18) The first recruiting hire most founders get wrong

(01:15:00) Building incredible teams

(01:18:12) The time between offer and acceptance

(01:19:48) What’s next for the recruiting function

(01:21:00) Lightning round

—

Referenced:

• Cursor: https://cursor.com

• Trilogy: https://trilogy.com

• Brie Wolfson on LinkedIn: https://www.linkedin.com/in/brie-wolfson-17758724

• Inside Cursor: https://colossus.com/article/inside-cursor

• SpaceX: https://www.spacex.com

• Joe Gebbia’s website: https://joegebbia.com

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• The Pitt on HBO Max: https://www.hbomax.com/shows/pitt-2024/e6e7bad9-d48d-4434-b334-7c651ffc4bdf

• The Bear on Hulu: https://www.hu…

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).

In our in-depth conversation, we discuss:

1. Why Whatnot’s product team was founded on the premise “we regret that product management exists”

2. How AI is reshaping the PM role

3. What Tom looks for when hiring PMs

4. The shift toward senior ICs doing the work

5. How AI has transformed data science at Whatnot

6. Tom’s “play the accordion” mental model

7. Why “hire great people and get out of their way” fails

8. His biggest lessons from his time at Twitter

—

Brought to you by:

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

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management

—

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

—

Where to find Tom Verrilli:

• X: https://x.com/tdrobbo

• LinkedIn: https://www.linkedin.com/in/tom-robertson-042

—

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

(02:40) “We regret that product management exists”: what it means and why

(08:30) When specialization makes sense, and when it doesn’t

(15:20) How Whatnot structures its PM org

(17:28) What 31,832 PM applications revealed about the function

(19:40) How to develop systems thinking

(22:10) The shift to senior ICs doing IC work

(32:26) Advice for PMs struggling in today’s market

(35:22) How AI has transformed work at Whatnot

(41:14) The data scientist problem

(42:48) Which roles are trending up and down

(44:48) What the product team of the future looks like

(46:29) Why core PM skills are the most durable in an AI world

(49:23) How to get the most out of the people you hire

(53:32) Navigating the CPO-founder relationship

(57:34) Advice for aspiring CPO’s

(59:16) How to know when to stand firm and when to step back

(01:01:38) Play the accordion: balancing strategic vision with fast iteration

(01:06:35) Agentic commerce vs. live commerce

(01:09:46) Lessons from Twitter

(01:13:07) Failure corner

(01:15:45) Lightning round and final thoughts

—

Referenced:

• 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:

Dianne Penn is Head of Product for Anthropic’s AI Research and Labs teams. She joined in 2023 as Anthropic’s first technical product manager, when the entire product team was five engineers, and has since helped ship every model from Claude 2 through Fable, and helped incubate Claude Code, MCP, Skills, computer use, tool use, and reasoning. Before Anthropic, she helped build Alexa’s AI at Amazon and, before that, traded high-yield bonds at JP Morgan Chase.

In our in-depth conversation, we discuss:

1. What Anthropic’s early days were like

2. The inflection points that turned Anthropic from an underdog into the fastest-growing company in history

3. How exactly Claude got so good at coding

4. The eval-driven development loop her team is pioneering

5. How to find joy in AI when everything is moving this fast

6. Why Claude’s willingness to push back is key to its success

7. Where human judgment remains irreplaceable

—

Brought to you by:

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

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/anthropics-first-technical-pm-on

—

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

—

Where to find Dianne Penn:

• LinkedIn: linkedin.com/in/dianne-na-penn

—

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

(02:31) Early Anthropic days

(08:55) Big milestones

(13:50) Inside the exponential

(20:02) Token maxing

(23:30) Anthropic Labs and the incubation model

(27:30) How the research role works

(31:35) How to become a top researcher

(35:18) Frontier model safeguards

(39:38) Hiring in the AI era

(44:16) Building an eval set

(47:48) Evals vs PRDs

(49:55) The importance of hands-on leadership

(52:46) Finding joy in AI

(58:10) How Dianne uses Claude

(01:01:05) Avoiding overreliance on AI

(01:03:50) The constitution that makes Claude better

(01:07:11) AI writing and verification

(01:11:40) Where human brains will continue to be valuable

(01:14:10) Navigating AI with kids

(01:16:26) Alignment, the future of the PM role, and burnout

(01:21:54) Lightning round and final thoughts

—

Referenced:

• Anthropic: https://www.anthropic.com

• Golden Gate Claude: https://www.anthropic.com/news/golden-gate-claude

• Dario Amodei’s website: https://darioamodei.com

• Scaling Laws and Interpretability of Learning from Repeated Data: https://www.anthropic.com/research/scaling-laws-and-interpretability-of-learning-from-repeated-data

• Tokenmaxxing: How Top Builders Use AI To Do The Work Of 400 Engineers: https://www.ycombinator.com/library/Pa-tokenmaxxing-how-top-builders-use-ai-to-do-the-work-of-400-engineers

• Garry Tan on X: https://x.com/garrytan

• Anthropic co-foun…

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: https://workos.com/lenny

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—

Episode transcript: https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future

—

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

—

Where to find Elizabeth Stone:

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

—

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

(02:25) AI and role confusion: the storming phase before the forming phase

(07:36) How roles have changed in the past two and a half years

(11:55) Will functions survive? The case for craft specialism

(13:26) What Netflix is hiring more of—and less of

(17:22) Why systems thinking is the rising skill across every function

(20:20) Is the design process dead?

(22:08) Skills trending down

(28:33) AI fluency and Netflix’s career ladder overlay

(31:00) AI use cases beyond coding

(35:12) Netflix’s AI history

(38:36) Excellence as an operating system

(41:11) The pillars of the excellence OS

(46:41) The keeper’s test—and why it’s mostly a positive conversation

(50:21) Attracting top talent in the age of frontier AI labs

(52:54) Junior talent, craft mastery, and the mentorship question

(56:25) Where engineering goes in 5 to 10 years

(59:45) The future of entertainment: beyond film and TV

(1:02:18) AI in Hollywood: Netflix’s creator-enablement position

(1:06:15) Lightning round and final thoughts

—

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):

Noam Segal is a longtime research leader across Airbnb, Meta, Twitter, Zapier, Intercom, and Figma, a certified coach, AI builder, and my community research lead. Together, we run the annual Tech Worker Sentiment Survey, now in its second year and one of the largest of its kind: a quantitative study of how people in tech actually feel about their jobs, AI, burnout, and the future of their careers. This year’s survey captured responses from thousands of workers across product, engineering, design, research, marketing, data, and sales, and the results are striking.

In our in-depth conversation, we discuss:

1. Why AI has split the tech workforce almost exactly in half—one half that’s thriving, another that’s shaken

2. The four emotional archetypes defining tech workers right now (the Energized, the Conflicted, the Disoriented, and the Resentful)

3. Why burnout has jumped an alarming 11 points in a single year

4. Why nobody in tech would recommend their job to someone entering the industry today

5. The #1 fear in tech right now (it’s not job loss to AI)

6. Why managers are the single biggest lever for employee well-being

7. Concrete advice for what employees and leaders can do right now

—

Brought to you by:

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

Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign

—

Episode transcript: https://www.lennysnewsletter.com/p/how-tech-workers-actually-feel-about

—

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

—

Where to find Noam Segal:

• X: https://x.com/noamseg

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

—

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 Noam Segal

(02:34) About the survey: methodology and scope

(06:04) The core finding: AI has split the tech workforce in half

(13:03) The AI identity stance

(14:40) The four archetypes: Energized, Conflicted, Disoriented, Resentful

(19:35) Burnout is surging (and why shipping faster is making it worse)

(22:53) A glimmer of hope

(24:55) Layoff worries

(29:15) The career recommendation NPS score

(36:45) The ladder metaphor: rungs disappearing beneath our feet

(45:14) AI is making us faster, not better

(52:53) The #1 fear: being squeezed to do more for the same pay

(55:55) The emotional landscape and “smiling exhaustion”

(01:01:02) Designers and researchers: the most negative group two years running

(01:06:27) Who’s happiest

(01:12:18) Managers: the single biggest lever on well-being

(01:18:47) The industry is “chaotic”

(01:24:53) What employees and leaders can do right now

(01:31:32) AI guilt and closing thoughts

—

Referenced:

• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026

• How tech’s most resilient workers handle…

Adam Mosseri is the Head of Instagram, where he oversees an app used by over 3 billion people. He also leads the team building Threads. Adam has run Instagram for longer than its founders did, after taking over from Kevin Systrom and Mike Krieger in 2018. A designer by training, he spent over 15 years at Meta, starting as a designer on Facebook’s mobile app, rising to lead Facebook’s News Feed, and eventually chosen to lead Instagram. During his tenure, Instagram’s user base has more than tripled.

In our in-depth conversation, we discuss:

1. How the canonical product team structure is changing in 2026, from baker’s-dozen specialist teams to lean pods of four to six generalists

2. The rise of the “product staff” role—a blending of PM, design, data science, and research into one generalist operator

3. Why Adam is bullish on designers even as functional boundaries dissolve, and which roles are most at risk

4. What the Instagram algorithm knows about you, and why it’s only now catching up to what people assumed it knew years ago

5. Why the rise of AI-generated content is a tailwind for Instagram, and how the company is thinking about creator identity in a synthetic-content world

6. The two biggest product failures of Adam’s career—Facebook Home and the first version of Reels

—

Brought to you by:

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

Mercury—Radically different banking, now with Command: https://mercury.com/command?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q3_brand_campaign

—

Episode transcript: https://www.lennysnewsletter.com/p/adam-mosseri-ai-is-a-tailwind-for

—

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

—

Where to find Adam Mosseri:

• X: https://x.com/mosseri

• LinkedIn: linkedin.com/in/mosseri

• Instagram: https://www.instagram.com/mosseri

• Threads: https://www.threads.com/@mosseri

—

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 Adam Mosseri

(02:09) How product teams are changing inside Meta

(05:48) Blurring roles and career anxiety

(14:01) Hiring traits that matter now

(16:48) How AI is resetting who succeeds at work

(19:38) How Meta thinks about token spend and AI costs

(23:23) Where human judgment still matters

(25:56) Why AI is not automatically great at strategy

(30:36) Why great product leaders are curators

(34:23) What Instagram’s algorithm actually knows about you

(38:08) Why chronological feeds often disappoint users

(40:56) Why AI content may be a tailwind for Instagram

(43:42) The future of AI and human content in the feed

(48:00) What Adam admires about other social platforms

(52:05) How he handles public criticism

(56:31) Lessons from the Instagram feed redesign backlash

(01:00:21) Adam’s biggest failure: Instagram on iPad

(01:03:03) His approach to kids, screens, and social media

(01:06:56) What Adam wants listeners to remember

—

Refere…

Andrew Ambrosino leads development of the Codex desktop app at OpenAI. Nearly 100% of OpenAI employees—not just engineers—now use Codex weekly. A lifelong builder with a background spanning engineering, design, product management, and founding companies, he is now responsible for turning the Codex desktop experience into what he calls “the best desktop app that has ever existed, full stop.”

In our in-depth conversation, we discuss:

1. Why AI has completely flipped the product development process

2. What “taste” really means as a professional skill, and why it is emerging as the most valuable capability in an AI-first workplace

3. Why Andrew believes the Codex app would have failed if they launched it last November (vs. in February)

4. The “zone defense” model for how product managers at OpenAI operate when everyone can build anything

5. How roles are collapsed on Andrew’s team, and why eliminating the concept of roles entirely is a big mistake

6. How Andrew uses Codex to run his own workflows

7. The vision for a home base that coordinates work across ChatGPT, Codex, and the tools people already use.

—

Brought to you by:

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

Mercury—Radically different banking, now with Command

—

Episode transcript: https://www.lennysnewsletter.com/p/openais-codex-lead-on-the-new-shape

—

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

—

Where to find Andrew Ambrosino:

• X: https://x.com/ajambrosino

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

• Website: https://ambrosino.io

—

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 Andrew Ambrosino

(02:30) How AI is changing the shape of product work

(06:32) When to use documents vs. prototypes

(10:25) What “taste” actually means

(12:06) Why AI is still bad at design

(16:18) Is the design process really dead?

(21:35) What the design process looks like on the Codex team

(23:41) Are product functions disappearing?

(27:22) Team structure

(30:12) IC vs. management

(31:37) Planning roadmaps

(35:16) Building features that don’t work yet

(38:13) The ambition problem: when you’re too AGI-pilled

(39:17) The latest frontier: loops and autonomous development

(52:05) How Andrew uses Codex to automate his entire job

(46:52) The power of computer use and browser automation

(49:10) Will we run all our SaaS apps inside Codex?

(52:05) The future vision for Codex

(57:20) The videographer who built a Premiere Pro extension with Codex

(59:30) Failure corner

(1:01:50) Lightning round

(1:07:03) BTS: How our producer uses Codex for editing

—

References: https://www.lennysnewsletter.com/p/openais-codex-lead-on-the-new-shape

—

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.

Fiona Fung leads the teams behind Claude Code and Cowork at Anthropic (overseeing Boris Cherny and the entire engineering and PM team). Before Anthropic, she spent 11 years at Microsoft building Visual Studio and TypeScript and then moved to Meta, where she started Facebook Marketplace (now generating over $100 billion in GMV annually), worked on Meta’s first smart glasses and AR glasses, and led infrastructure, growth, integrity, and safety teams at Instagram. She’s been an engineer for over 25 years and has a unique perspective on how the role of building software is changing.

In our in-depth conversation, we discuss:

1. What she’s learned about running a team that’s shipping 8x more code than before

2. Which roles AI will transform next

3. Specific ways her team uses AI

4. How Claude “routines” have changed how she operates as a manager

5. The context-switching problem no one has solved yet

6. The biggest unsolved problem in AI

7. What keeps her up at night

—

Brought to you by:

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

Mercury—Radically different banking, now with Command: https://mercury.com/

—

Where to find Fiona Fung:

• LinkedIn: linkedin.com/in/fionafung

—

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 Fiona Fung

(02:31) How the engineering role has transformed over 25 years

(09:28) What an AI-pilled software team looks like in 2026

(12:26) Using Claude to manage and review team output

(14:40) The evolution of code review and verification

(16:55) Who to hire: creative builders and deep systems experts

(18:18) The shift to ambitious thinking

(19:40) The growth mindset required to thrive in AI-native teams

(25:52) Helping small businesses adopt AI tools

(31:46) How Anthropic spots latent demand and builds for it

(35:08) The next frontier: asynchronous work with AI routines

(38:06) Agency and accountability in AI-native teams

(39:40) The vibe shift from token-maxing to ROI measurement

(44:24) The “bad vs. sad” quality framework

(49:34) Why all managers start as ICs at Anthropic

(55:24) Preventing skill atrophy

(58:43) Managing context switching with 20 AI agents running

(1:00:08) How PM and data science roles are transforming

(1:03:40) The importance of dogfooding and using your own product

(1:08:36) Outstanding questions

(1:12:48) The future of engineering jobs and education

(1:17:59) What keeps Fiona up at night: team culture at scale

(1:22:53) From six-month roadmaps to JIT (just-in-time) monthly planning

(1:27:03) Lightning round

—

References: https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering

—

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.

Mark Pincus founded Zynga—the company behind Words With Friends, FarmVille, and Zynga Poker—and has arguably created more hit consumer products than anyone in history. At Zynga, eight of 10 major game launches became massive hits, reaching over a billion players. Over the past five years, Mark has been synthesizing everything he’s learned about building successful consumer products and turning it into a book, Life at the Speed of Play, which comes out on June 23. This is the first interview he’s done about the book.

In our in-depth conversation, we discuss:

1. His “Proven, Better, New” framework: copy what’s proven, make it better so that 10 out of 10 people say “f*ck yes, I’ll use this”—then add something new

2. Why being less ambitious is the path to the most ambitious ideas

3. His rule of thumb that your instincts are right 95% of the time, but your ideas are wrong 75% of the time

4. “Kill hope before hope kills you”

5. How to raise kids in the age of AI

—

Brought to you by:

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

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

—

Episode transcript: https://www.lennysnewsletter.com/p/the-common-pattern-behind-successful

—

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

—

Where to find Mark Pincus:

• X: https://x.com/markpinc

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

• Website: https://www.lifeatthespeedofplay.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 Mark Pincus

(02:46) The Proven Better New framework overview

(07:29) Earning the right to innovate

(08:30) What “better” really means

(12:03) Quick summary of the framework

(12:40) Examples of the framework in action

(13:30) How to use proven correctly on your platform

(15:13) The moral arbitrage of copying

(23:55) Be less ambitious

(28:25) The Bolt.new story and staying humble

(33:15) Kill hope before hope kills you

(37:00) Using AI as a failure machine

(40:08) Why Zynga’s games succeeded (it wasn’t virality)

(48:36) The future of consumer social apps

(57:05) How to know if your product is a B+

(1:01:25) Distribution in the age of AI

(1:15:39) Make everyone a CEO

(1:18:18) Stay close to the metal

(1:21:35) Why Mark says micromanagement is beautiful

(1:23:35) The expert witness

(1:25:05) The number one job of a CEO is to be right

(1:26:35) What Mark is teaching his five kids

(1:35:14) Mark’s “why”

(1:37:08) Mark’s new book: Life at The Speed of Play

—

Referenced:

• Tribe.net: https://en.wikipedia.org/wiki/Tribe.net

• Zynga: https://www.zynga.com

• Sid Meier: https://en.wikipedia.org/wiki/Sid_Meier

• Electronic Arts: https://www.ea.com

• CityVille: https://en.wikipedia.org/wiki/CityVille<…

Tony Fadell created the iPod, co-created the iPhone, and founded Nest (which he sold to Google for $3.2 billion). He’s co-authored over 300 patents, was part of the legendary team at General Magic, and wrote one of the most important and inspiring books for builders, called Build.

In our in-depth conversation, we discuss:

1. The heated internal debates about whether the iPhone should have a physical keyboard

2. Why opinion-based decisions are essential for v1 products

3. Why marketing matters as much as the product itself, and how the iPod almost failed

4. Why voice will eventually become the primary interface with AI

5. Why cognitive surrender to AI is the biggest risk facing product builders today

—

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/father-of-the-ipod-and-iphone-on

—

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

—

Where to find Tony Fadell:

• X: https://x.com/tfadell

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

• Website: https://www.buildc.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 Tony Fadell

(02:23) The Blackberry vs. iPhone keyboard debate

(07:50) Micromanaging vs. kind lies: what great products actually need

(15:57) The Nest thermostat and smoke alarm story

(21:22) How to decide what’s worth building: pain plus new technology

(27:36) The three-generation rule: why nothing works the first time

(34:20) The full customer journey: why marketing defines your product

(40:53) The power of storytelling and the press-release-first approach

(48:37) The evolution of product management and the builder role

(50:27) Why AI-generated code creates brittle, unmaintainable products

(58:00) Storytelling techniques

(1:05:45) The next iPhone

(1:13:15) Hardware is back

(1:17:01) What Tony is most excited about

(1:21:38) Working with Tony

(1:25:36) Ethics, morals, and the responsibility of product builders

(1:32:40) How to connect with Tony and Build Collective

—

References: https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on

—

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.

Benedict Evans is an independent analyst and former partner at Andreessen Horowitz, where he spent years as their in-house “thinker” tracking the most important technology trends. For the past six years, he’s been publishing deeply researched presentations on where tech is heading, most recently focused on AI’s transformation of the economy. His work is read by founders, investors, and operators trying to make sense of a noisy field. His most controversial opinion: AI is as big a deal as the internet or mobile—and only as big.

In our in-depth conversation, we discuss:

1. Why we’re in “1997” for AI—early, exciting, and deeply uncertain about what comes next

2. Where value will actually accrue in the AI stack

3. The anti-AI backlash, and where it may lead

4. The surprising boom in consulting and professional services at AI companies

5. Why distribution is becoming the ultimate moat as software gets easier to build

6. Why the right question about your job isn’t “What percent can AI do?” but “Is this a task or a job?”

7. Why things will probably be okay—and what you need to do to prepare

—

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/a-rational-conversation-on-where

—

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

—

Where to find Benedict Evans:

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

• Newsletter: https://www.ben-evans.com/newsletter

• Website: https://www.ben-evans.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 Benedict Evans

(02:19) What people aren’t pricing in about AI’s impact

(06:24) Why we’re in the 1997 moment of AI

(09:44) The unexpected boom in professional services and consultants

(17:44) Why distribution is becoming the ultimate moat

(23:17) The coming job transformation: what’s real vs. panic

(27:33) Why AGI definitions keep shifting

(38:11) Where value will accrue: models vs. applications

(42:55) Distribution wars: Google, Meta, Apple, and OpenAI

(48:12) The anti-AI sentiment and backlash

(53:11) How to raise kids in an AI future

(58:27) What jobs to steer toward or away from

(59:20) The question nobody’s asking about AI

(1:06:25) How to be successful in this coming future

(1:08:43) AI corner

(1:11:43) Lightning round

—

Referenced: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where

—

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.

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models.

Dan’s predictions:

1. The future of work will happen inside Codex or Claude Code.

2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly.

3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”

4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.

5. PMs will thrive in the AI era.

6. Full-stack designers will become superheroes.

7. The AI job apocalypse is not happening.

8. Forward deployed engineer is the new most essential role.

9. CLIs are over.

10. Automation is a lie.

11. We will read way more AI-generated writing and we will like it.

12. We’ll be building software for humans and agents to use together.

—

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/the-ai-paradox-dan-shipper

—

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

—

Where to find Dan Shipper:

• X: https://x.com/danshipper

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

• Podcast: https://every.to/podcast

• Website: https://danshipper.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 Dan Shipper

(02:56) Dan’s unique position living in the AI future

(09:17) How the way we work will change in the coming year

(16:39) The case for general agents

(18:08) Codex and Claude Code as the new operating system for work

(25:39) How Cursor fits in

(27:42) How this changes what SaaS companies should build

(31:13) Why CLI is already over

(33:34) Two agents are better than one

(36:22) Why Dan is bullish on SaaS stocks

(39:01) Why automation doesn’t reduce human work

(47:00) The value of human-written code

(48:36) Quick recap

(50:15) How work is changing

(56:17) Why data scientists are drowning in bad analysis

(58:24) Which product/tech roles are least changed by AI

(1:02:17) We will read way more AI-generated writing and we will like it

(1:08:28) Why product managers will dominate the AI era

(1:11:05) Full-stack designers are the other big winners

(1:13:11) The AI job apocalypse won’t happen

(1:16:00) How to “ride the models” to stay relevant

(1:21:02) Final predictions and advice

(1:25:…

Caitlin Kalinowski was most recently at OpenAI helping build their robotics and hardware teams from scratch. Prior to that, she was head of AR glasses and VR hardware at Meta, where she led the teams building every generation of the Quest, Rift, and Orion, and was Meta’s first consumer electronics hire. Before this, she was technical lead on MacBook Air and Mac Pro at Apple, and helped engineer the original unibody MacBook Pro. She’s designed and engineered some of the hardest and most beloved consumer hardware products in history and is now focused on the next frontier: robotics.

In our in-depth conversation, we discuss:

1. VR—what happened?

2. The coming memory price shock and why she’s telling startups to pre-buy now

3. How the technologies built for VR became the foundation of modern warfare

4. Why humanoid robots are still just prototypes, and what’s actually gating mass deployment

5. Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman

6. Why she left OpenAI

—

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-were-at-the-beginning-of-the

—

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

—

Where to find Caitlin Kalinowski:

• X: https://x.com/kalinowski007

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

• Website: https://www.caitlinkalinowski.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 Caitlin Kalinowski

(02:32) Why VR didn’t take off despite incredible hardware

(04:55) The future of AR glasses and physical AI

(08:45) Why robotics and hardware are suddenly hot

(13:33) Why humanoid robots aren’t ready yet

(16:13) Supply chain bottlenecks threatening robotics

(17:31) Why magnets and actuators are critical dependencies

(20:51) The geopolitical implications of hardware supply chains

(24:48) AI safety concerns with physical robots

(26:50) Apple’s approach to hardware excellence

(30:10) Building a hardware program from scratch at Meta

(31:39) The Quest 2 cost reduction story

(33:07) Critical principles for hardware development

(39:58) The MacBook Air manila envelope moment

(41:01) The butterfly keyboard situation

(41:43) Lessons from Apple on customer feedback

(44:46) The memory price crisis coming for hardware

(49:31) How many components go into a robot

(52:53) When to use off-the-shelf vs. custom components

(55:02) How AI is changing hardware engineering

(1:00:27) Why humanoids aren’t the answer for most use cases

(1:03:05) When robots will build other robots

(1:06:23) What makes a robot feel human and connected

(1:09:15) Robots in the home

(1:12:00) What the next five years look like

(1:15:38) Why she left OpenAI

(1:18:09) How to hire exceptional hardware teams

(1:23:42) Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman

(1:27:27) Failure corner

(1:32:33) Lightning round

—

References:

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…

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

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 Co…

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…

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):

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/davi…

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 …

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…

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

• Wha…