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

—

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

—

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

(02:18) 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

—

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: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty

• Patrick Collison’s examples of fast projects: https://patrickcollison.com/fast

• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Andrew Ambrosino on X: https://x.com/ajambrosino

• Tyler Cowen’s website: https://tylercowen.com

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• “Chop wood, carry water” quote: https://buddhism.stackexchange.com/questions/15921/what-is-the-meaning-of-the-zen-quote-before-enlightenment-chop-wood-carry-wat

• 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live

• Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay

• Brie Wolfson on X: https://x.com/zebriez

• The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor: https://www.lennysnewsletter.com/p/the-playbook-for-building-high-talent

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

• Sutter Hill Ventures: https://shv.com

• Snowflake: https://www.snowflake.com

• Mike Speiser on LinkedIn: https://www.linkedin.com/in/mikespeiser

• Footnotes and Tangents: https://footnotesandtangents.substack.com

• The Power Broker Book Club: https://www.robertcaro.org/copy-of-six-books-six-ny-times-book

• The Odyssey: https://www.imdb.com/title/tt33764258

• Rashomon: https://www.imdb.com/title/tt0042876

• Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa

• Kevin Kwok on LinkedIn: https://www.linkedin.com/in/kevinakwok

• The Work You Do, the Person You Are: https://www.newyorker.com/magazine/2017/06/05/toni-morrison-the-work-you-do-the-person-you-are

• Ari Weinstein on X: https://x.com/AriX

• Sky: https://sky.app

• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

—

Recommended books:

• Barbarian Days: A Surfing Life: https://www.amazon.com/dp/0143109391

• Anna Karenina: https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421

• The Power Broker: https://www.amazon.com/dp/0394720245

• War and Peace: https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832

• Wolf Hall: https://www.amazon.com/dp/0312429983

—

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.

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

—

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

—

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

(02:49) 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

—

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): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

• Careers at State Affairs: https://stateaffairs.com/careers

—

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.

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

—

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

—

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 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: https://www.linkedin.com/in/joel-lewenstein

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

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

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater

• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna

• Maybe Happy Ending: https://www.maybehappyending.com

• The Invite: https://www.imdb.com/title/tt14173636

• Rivian: https://rivian.com

• Waymo: https://waymo.com

• Groupon: https://www.groupon.com

• How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital): https://www.lennysnewsletter.com/p/how-a-vc-and-a-tech-founder-used

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

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom

• Sam Altman on X: https://x.com/sama

—

Recommended book:

• The Design of Everyday Things: https://www.amazon.com/dp/0465050654

—

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.

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

—

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.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

• Granola: https://www.granola.ai

• Wispr Flow: https://wisprflow.ai

• 11 products I love, free for a year—the biggest Product Pass expansion in 2 years: https://www.lennysnewsletter.com/p/productpass-summer2026launch

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

• The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham

—

Recommended books:

• Emotional Intelligence: Why It Can Matter More Than IQ: https://www.amazon.com/dp/055338371X

• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100

• Scaling People: Tactics for Management and Company Building: https://press.stripe.com/scaling-people

—

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.

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: https://www.linkedin.com/in/mikekrieger

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus

• Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th

• Hex Threads: https://hex.tech/product/threads

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty

• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine

• Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head

• Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear

• Kara Swisher on X: https://x.com/karaswisher

• Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY

• Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1

• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

• Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app

• Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling

• E-fish.com: https://www.e-fish.com

—

Recommended books:

• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205

• The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063

• Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439

—

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

—

Lenny may be an investor in the companies discussed.

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-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Introducing Labs: https://www.anthropic.com/news/introducing-anthropic-labs

• Louis CK | about airplane Wi Fi: https://www.youtube.com/watch?v=me4BZBsHwZs

• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering

• The Anthropic Hive Mind: https://steve-yegge.medium.com/the-anthropic-hive-mind-d01f768f3d7b

• How to build a company that withstands any era | Eric Ries, Lean Startup author: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands

• Fallout on Prime Video: https://www.amazon.com/dp/B0CN4GGGQ2

• Fallout (video game): https://fallout.bethesda.net

• Claude Tag: https://www.anthropic.com/news/introducing-claude-tag

—

Recommended books:

• Crucial Conversations: Tools for Talking When Stakes Are High: https://www.amazon.com/dp/0071771328

• How to Raise an Adult: Break Free of the Overparenting Trap and Prepare Your Kid for Success: https://www.amazon.com/How-Raise-Adult-Overparenting-Prepare/dp/1627791779

• Incorruptible: Why Good Companies Go Bad... and How Great Companies Stay Great: https://www.amazon.com/dp/B0FWZZBPZB

—

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.

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

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/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): https://www.lennysnewsletter.com/p/the-design-process-is-dead

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

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

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

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

• InterPositive: https://weareinterpositive.com

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

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

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

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

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

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

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

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

—

Recommended books:

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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 burnout: https://www.lennysnewsletter.com/p/how-techs-most-resilient-workers

• Please stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater

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

• NPS Is The Worst: https://www.npsistheworst.com

• The Terminator: https://www.imdb.com/title/tt0088247

• Skynet: https://terminator.fandom.com/wiki/Skynet

• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu

• Devin: https://devin.ai

• An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union

• Redeploying Fable 5: https://www.anthropic.com/news/redeploying-fable-5

• Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble

• Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennysnewsletter.com/p/inside-linear-building-with-taste

• Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennysnewsletter.com/p/building-beautiful-products-with

• 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

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

• Elon Musk: ‘Chances are we’re all living in a simulation’: https://www.theguardian.com/technology/2016/jun/02/elon-musk-tesla-space-x-paypal-hyperloop-simulation

—

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.

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

—

Referenced:

• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering

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

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

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

• A rational conversation on where AI is actually going | Benedict Evans: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Mythos: https://www.anthropic.com/claude/mythos

• Fable: https://www.anthropic.com/claude/fable

• Pluralistic: The Reverse-Centaur’s Guide to Criticizing AI: https://pluralistic.net/2025/12/05/pop-that-bubble

• Plastic Dream Sequence on Instagram: https://www.instagram.com/plasticdreamsequence

• TikTok: https://www.tiktok.com

• Facebook–Cambridge Analytica data scandal: https://en.wikipedia.org/wiki/Facebook%E2%80%93Cambridge_Analytica_data_scandal

• Facebook Home: https://en.wikipedia.org/wiki/Facebook_Home

—

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.

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

• Words With Friends: https://wordswithfriends.com/

• Scrabble: https://playscrabble.com

• Reddit: https://www.reddit.com

• TED Radio Hour, MIT Media Lab founder, 1984 TED talk.: https://www.ted.com/talks/nicholas_negroponte_5_predictions_from_1984

• Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel

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

• Craig Newmark: https://en.wikipedia.org/wiki/Craig_Newmark

• How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor): https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier

• Angry Birds: https://www.angrybirds.com/

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

• Draw Something: https://en.wikipedia.org/wiki/Draw_Something

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

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

• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan

• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong

• Jason Citron on X: https://x.com/jasoncitron

• Stanislav Vishnevskiy on LinkedIn: https://www.linkedin.com/in/svishnevskiy

• Jeff Bezos on X: https://x.com/JeffBezos

• Andy Jassy on X: https://x.com/ajassy

• Niantic: https://nianticlabs.com

• Pokémon Go: https://pokemongo.com

• Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon

—

Recommended book:

• Life at the Speed of Play: Launch Products People Love!: https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=tmm_hrd_swatch_0

—

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.

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

(1:25:24) Lightning round

—

References: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper

—

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.

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: https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the

—

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.

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

In our in-depth conversation, we discuss:

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

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

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

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

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

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

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Eric Ries:

• X: https://x.com/ericries

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

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

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

• Podcast:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ https://ericriesshow.com

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Eric Ries

(02:26) Introducing Incorruptible

(06:26) Protecting what you’ve built

(11:35) Why founders get ousted

(14:58) Too early, too late

(19:32) The blueprint: ethos plus integrity

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

(26:41) The Vectura Group and Philip Morris

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

(37:22) Cloudflare’s mission emergence story

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

(45:37) How to define your purpose

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

(54:46) Integrity: structural and personal

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

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

(01:04:24) Downsides and objections

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

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

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

(01:12:28) OpenAI and Anthropic governance

(01:16:21) Mission guardians explained

(01:18:29) Spiritual holding companies

(01:21:53) The founder control trap

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

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

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

(01:37:31) Book resources and farewell

—

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

—

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

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

5. Why the SaaSpocalypse is overstated

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

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Max Schoening:

• X: https://x.com/mschoening

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

• Website: https://max.dev

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Max Schoening

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

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

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

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

(11:49) Examples of high agency at Notion

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

(15:56) Advice for developing agency

(17:42) Malleable software explained

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

(24:00) The SaaS apocalypse debate

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

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

(34:16) Token spend and ROI conversations

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

(39:04) Max’s AI stack

(41:41) Which roles AI will transform next

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

(48:38) Why Notion AI is so successful

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

(56:40) Building taste through iterations

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

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

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

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

(1:10:53) Contrarian corner

(1:13:14) Failure corner

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

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

—

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

—

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

—

Lenny may be an investor in the companies discussed.

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

In our in-depth conversation, we discuss:

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

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

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

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

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

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

7. This year’s crucible moment for Snap

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Evan Spiegel:

• X: https://x.com/evanspiegel

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

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

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Evan Spiegel

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

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

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

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

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

(16:00) Specs use cases

(17:56) The innovation process

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

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

(26:06) The origin story of Stories

(28:25) How screenshot detection saved early Snapchat

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

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

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

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

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

(41:57) How to develop young design talent

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

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

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

(51:30) Learning to communicate

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

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

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

(1:01:08) AI Corner

(1:04:02) Contrarian Corner

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

—

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

2. The emerging skills PMs need to develop right now

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

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

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

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

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

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Cat Wu:

• X: https://x.com/_catwu

• LinkedIn: linkedin.com/in/cat-wu

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Cat Wu

(01:29) Working with Boris Cherny

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

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

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

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

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

(12:53) Integrating with OpenClaw

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

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

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

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

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

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

(27:47) The /powerup command

(28:32) Why Anthropic has been so successful

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

(35:58) Tips for getting started with Cowork

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

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

(46:47) Which teams use the most tokens

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

(55:00) Why building evals is underappreciated

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

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

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

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

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

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

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

(1:15:19) Lightning round

—

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

—

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

—

Lenny may be an investor in the companies discussed.

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

In our in-depth conversation, we discuss:

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

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

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

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

5. The psychological barriers that prevent people from reinventing themselves

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

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

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Nikhyl Singhal:

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

• X: https://x.com/nikhyl

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

• Skip Community: https://skip.community

• Skip Coach: https://skip.coach

• Skip.help: https://skip.help

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Nikhyl Singhal

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

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

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

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

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

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

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

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

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

(30:14) The non-builder problem

(30:53) Should PMs code?

(34:15) Why experienced leaders still matter

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

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

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

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

(43:53) The “equal disappointment” algorithm

(46:39) You must cross the threshold

(48:37) This chaos will settle

(53:19) Finding your moment of joy

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

(1:00:53) The obsolescence mindset

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

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

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

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

(1:17:04) The surprising design plateau

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

(1:21:12) Lightning round

—

Referenced:

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

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

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

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

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

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

• Sam Altman on X: https://x.com/sama

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

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

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

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

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

• Codex: https://chatgpt.com/codex

• Lovable: https://lovable.dev

• Sonos: https://www.sonos.com

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

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

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

• Tesla: https://www.tesla.com

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

—

Recommended books:

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

In our in-depth conversation, Keith shares:

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

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

3. How to identify undiscovered talent

4. Why the PM role is dying

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

6. The specific interview question he asks every senior candidate

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

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Keith Rabois:

• X: https://x.com/rabois

• LinkedIn: linkedin.com/in/keith

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Keith Rabois

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

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

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

(10:05) Tactics for getting better at hiring

(15:31) The barrels vs. ammunition framework

(18:52) What makes someone a barrel

(22:36) How to attract the best talent

(26:18) Building companies on undiscovered talent

(27:53) Why better performance requires more pressure

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

(35:14) The future of the product triad

(41:03) Why design and code are merging

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

(51:22) Contrarian takes on customer feedback

(1:02:33) Identifying great AI opportunities

(1:05:13) Advice for evaluating statrups 

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

(1:15:05) Failure corner

(1:17:29) Lightning round

—

Referenced:

• Square: https://squareup.com

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

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

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

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

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

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

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

• Tony Xu on X: https://x.com/t_xu

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

• Faire: https://www.faire.com

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

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

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

• Lattice: https://lattice.com

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

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

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

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

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

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

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

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

• Opendoor: https://www.opendoor.com

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

• Lovable: https://lovable.dev

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

• Jon Chu on X: https://x.com/jonchu

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

• Rogo: https://rogo.ai

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

• Basis: https://www.getbasis.ai

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

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

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

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

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

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

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

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

—

Recommended books:

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

In our in-depth discussion, Amol shares:

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

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

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

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

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

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

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

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Amol Avasare:

• X: https://x.com/TheAmolAvasare

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

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

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

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

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

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

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

(18:05) Improving Mercury’s onboarding experience

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

(25:10) Anthropic’s org structure

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(1:46:49) Lightning round

—

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

—

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

—

Lenny may be an investor in the companies discussed.

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

In our in-depth conversation, Simon shares:

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

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

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

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

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

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

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

—

Brought to you by:

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

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

—

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

—

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

—

Where to find Simon Willison:

• X: https://x.com/simonw

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

• Website: https://simonwillison.net

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Simon Willison

(02:40) The November 2025 inflection point

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

(10:42) Vibe coding vs. agentic engineering

(13:57) The dark-factory pattern

(20:41) Where bottlenecks have shifted

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

(25:32) Defending of software engineers

(29:12) Why experienced engineers get better results

(30:48) Advice for avoiding the permanent underclass

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

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

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

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

(44:34) The impact of cheap code

(48:27) Simon’s AI stack

(54:08) Using AI for research

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

(59:01) The inherent ridiculousness of AI

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

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

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

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

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

(1:25:19) The normalization of deviance

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

(1:34:22) What’s next for Simon

(1:36:47) Zero-deliverable consulting

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

—

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

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

6. Browser limitations, memory issues, and practical workarounds

—

Brought to you by:

Mercury—Radically different banking

Omni—AI analytics your customers can trust

Orkes—The enterprise platform for reliable applications and agentic workflows

—

Where to find Claire Vo:

• X: https://x.com/clairevo

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

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

• Website: https://clairevo.com

• ChatPRD: https://www.chatprd.ai

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Claire and OpenClaw

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

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

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

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

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

(20:41) Security and privacy considerations

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

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

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

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

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

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

(49:58) Real examples and use cases

(56:41) Finn, Claire’s family agent

(1:00:05) Sage the Course Bot

(1:02:15) Common issues and workarounds

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

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

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

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

(1:16:24) What makes OpenClaw special

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

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

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

(1:29:32) Why this matters

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

—

Referenced:

• OpenClaw: https://openclaw.ai

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

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

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

• Telegram: https://telegram.org

• WhatsApp: https://www.whatsapp.com

• Fin: https://fin.ai

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

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

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

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

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

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

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

• Buffer: https://buffer.com

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

• Exa: https://exa.ai

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

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

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

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

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

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

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

• Oura Ring: https://ouraring.com/

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

• Hoopsalytics: https://hoopsalytics.com

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

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

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

—

Recommended books:

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

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

6. Why showing only one option is a mistake

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

—

Brought to you by:

Omni—AI analytics your customers can trust

Lovable—Build apps by simply chatting with AI

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

—

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

—

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

—

Where to find Jessica Fain:

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Jessica Fain

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

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

(06:00) How executives actually think

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

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

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

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

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

(19:08) How to present ideas

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

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

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

(32:10) Aligning product work with company strategy

(35:10) Quick summary

(37:31) Disarming the executive

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

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

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

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

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

(54:18) Clarifying information

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

(58:30) Shrinking big ideas into experiments

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

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

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

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

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

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

—

Referenced:

• Box: https://www.box.com

• Slack: https://slack.com

• Brightwheel: https://mybrightwheel.com

• Webflow: https://webflow.com

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

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

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

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

• Calendly: https://calendly.com

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

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

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

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

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

• Checkr: https://checkr.com

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

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

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

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

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

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

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

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

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

• Casa: https://getcasa.com

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

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

—

Recommended books:

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes.

We discuss:

1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump

2. Why Jacob sees 40% average movement when negotiations are run well

3. When negotiation actually starts (hint: it’s much earlier than you think)

4. Why information + timing create power

5. The biggest mistakes people make when negotiating

6. How to navigate the important “What’s your comp expectation?” question without anchoring too low

7. Why the best interviews feel more like discovery calls than interrogations

—

Brought to you by:

Orkes—The enterprise platform for reliable applications and agentic workflows

Mercury—Radically different banking

Omni—AI analytics your customers can trust

—

Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp

—

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

—

Where to find Jacob Warwick:

• Substack: https://www.execsandthecity.com

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

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

• Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course

—

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 Jacob Warwick

(04:12) How much comp people leave on the table

(07:52) Why you shouldn’t feel greedy asking for more

(09:45) What founders should know about negotiation

(13:03) How Jacob works behind the scenes

(15:35) The biggest mistakes people make when negotiating

(19:30) Home-field advantage and controlling the conversation

(23:02) The step-by-step approach to negotiating an offer

(30:17) Jacob’s passion and why these tips don’t work on kids

(32:04) Who should speak first about compensation

(35:36) Understanding power

(39:52) Breaking out of salary bands by focusing on pain points

(45:45) Brief summary

(47:20) Selling the vacation: How to visualize success

(50:07) Controlling the narrative and planting seeds

(59:01) Jacob’s role as hype man

(01:01:05) Positioning yourself like a product

(01:02:49) Making the process frictionless for hiring managers

(01:06:20) Flipping the interview to extract information

(01:12:17) Five tactical tips for negotiating comp

(01:21:45) What to do when negotiations fall apart

(01:25:05) Why negotiation is different for every individual

(01:28:55) Why outcomes aren’t predetermined

(01:32:52) Wild Hollywood negotiation stories

(01:37:35) The first step you should take after getting an offer

(01:40:30) Jacob’s personal mission

(01:44:42) Lightning round and final thoughts

—

Referenced:

• The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating

• Sam Altman on X: https://x.com/sama

• Tom Brady on X: https://x.com/TomBrady

• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8

• Salesforce: https://www.salesforce.com

• Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts

• Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon

• Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg

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

• Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that

• Chris Voss on X: https://x.com/fbinegotiator

• Werewolf: https://playwerewolf.co

• Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion

• How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy

• ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation

• Marvel: https://www.marvel.com

• Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030

• Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0

• Minuscule: https://www.youtube.com/user/Minuscule

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

• Macrofactor: https://macrofactor.com

• Whoop: https://www.whoop.com

• Gemini: https://gemini.google.com/app

• The Cody Dieruf Foundation: https://breathinisbelievin.org

• Cystic Fibrosis Foundation: https://www.cff.org

—

Recommended books:

• Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941

• Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X

• You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229

• Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034

—

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.

People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.

We discuss:

1. The collection of moments that led me to what I do now

2. When I added a paywall, and how I knew it was working

3. The hidden treadmill behind shipping a newsletter post and podcast episode every week

4. The most stressful moments I’ve had in business and in life

5. How I think about stress, consistency, and keeping the business small

—

Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184

—

Brought to you by:

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

Metaview—The AI platform for recruiting: https://metaview.ai/lenny

DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

—

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

—

Where to find Michelle Rial:

• X: https://x.com/TheRialMichelle

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

• Website: https://www.michellerial.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 and role reversal

(04:06) What would Lenny be doing without the newsletter?

(07:20) The moments that led to starting the newsletter

(09:58) Does Lenny still enjoy the work?

(12:42) Stress management and misophonia

(14:00) The psychedelic trip that changed everything

(15:45) Online happiness course and baseline optimization

(17:30) Thunder round: Lenny’s misophonia worst sounds

(20:20) What makes Michelle’s charts so shareable

(23:55) Where chart ideas come from (and why meditation helps)

(26:59) Where does “Lenny” come from?

(28:54) Being recognized in public

(31:24) Early projects

(36:30) Michelle and Lenny’s yin and yang

(37:49) Missing office culture (but not really)

(39:37) Lenny’s face blindness

(40:47) The $100M fraud attack story

(42:50) Michelle’s childbirth emergency

(47:22) Michelle’s creative process

(51:58) Lenny’s favorite children’s books

(54:00) Product management lessons in parenting

(55:31) Defining product management in five words

(58:23) Why Michelle pivoted to children’s books

(01:01:30) The power of iteration and real experience

—

Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

—

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

Qasar Younis is the co-founder and CEO of Applied Intuition, a $15 billion AI company that adds intelligence to cars, tractors, planes, submarines, and other vehicles—essentially, Tesla or Waymo without the hardware. He was previously COO of Y Combinator, started his career as an engineer at GM and Bosch, and was born on a farm in Pakistan.

We discuss:

1. Why the biggest AI revolution will play out in mining, farming, construction, and trucking over the next 5 to 10 years, not in software

2. Why Qasar intentionally stayed under the radar for nearly a decade while building Applied Intuition, and why most founders shouldn’t do that

3. The truth about China’s AI capabilities and why comparisons to American companies are fundamentally flawed

4. The company values that drive Applied Intuition: speed above everything, laugh a lot, half the work is follow-up, never disappoint the customer

5. The biggest lessons from Qasar’s stint as YC’s COO, including that the most successful companies show traction very early

6. How reading old books is the best way to build taste

—

Brought to you by:

Omni—AI analytics your customers can trust

Vanta—Automate compliance. Simplify security.

Lovable—Build apps by simply chatting with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/the-most-successful-ai-company-youve-never-heard-of

—

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

—

Where to find Qasar Younis:

• X: https://x.com/qasar

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

• Website: https://qy.co

• Reading list: https://qy.co/books

—

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 Qasar and Applied Intuition

(04:01) The optimistic vision: How AI will create abundance

(08:49) Why anxiety about AI comes from misunderstanding—and how to fight fear with knowledge

(12:58) The market sell-off explained

(16:31) Self-driving cars: Why 30,000 annual deaths prove we need autonomy now

(20:22) The spectrum of physical AI

(28:00) How AI is coming just in time

(33:26) Why comparing Chinese AI companies to American AI companies is a category error

(39:12) Why Qasar finally joined Twitter after staying silent for a decade

(45:08) Why successful companies almost always show early signs of traction

(50:40) Applied Intuition’s core values

(56:00) Why the company cleans its own office—and never spent a dollar of raised capital

(58:50) Quasar’s reading philosophy

(01:06:14) How to operationalize listening to naysayers

(01:12:53) The importance of decisiveness

(01:14:55) Removing emotions from decisions

(01:19:02) Why most Silicon Valley CEOs don’t have great taste—and how to develop it

—

Referenced:

• Applied Intuition: https://www.appliedintuition.com

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

• Elad Gil’s website: https://eladgil.com

• Bosch: https://www.bosch.com

• Berkshire Hathaway: https://www.berkshirehathaway.com

• Naval Ravikant on X: https://x.com/naval

• Y Combinator: https://www.ycombinator.com

• Waymo: https://waymo.com/

• Tesla: https://www.tesla.com

• DeepSeek: https://www.deepseek.com

• Rivian: https://rivian.com

• Crate & Barrel: https://www.crateandbarrel.com

• OpenClaw: https://openclaw.ai

• Sam Altman on X: https://x.com/sama

• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig

• What Steve Jobs really meant when he said ‘Good artists copy; great artists steal’: https://www.cnet.com/tech/tech-industry/what-steve-jobs-really-meant-when-he-said-good-artists-copy-great-artists-steal

• 7 quotes on the power of reading from Charlie Munger: https://www.neil.blog/articles/7-quotes-power-reading-charlie-munger

• Andreessen Horowitz: https://a16z.com

• John Doerr on LinkedIn: https://www.linkedin.com/in/john-doerr-03248211

• Gandhi’s quote: https://www.azquotes.com/author/5308-Mahatma_Gandhi/tag/truth#google_vignette

• Steve Ballmer on X: https://x.com/Steven_Ballmer

• General Motors: https://www.gm.com

—

Recommended books:

• House of Huawei: The Secret History of China’s Most Powerful Company: https://www.amazon.com/House-Huawei-History-Powerful-Company/dp/0593544633

• Maintenance: Of Everything, Part One: https://press.stripe.com/maintenance-part-one

• The Autobiography of Malcolm X: As Told to Alex Haley: https://www.amazon.com/Autobiography-Malcolm-Told-Alex-Haley/dp/0345350685

• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

• The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916

• Made in America: https://www.amazon.com/Sam-Walton-Made-America/dp/0553562835

• My American Journey: https://www.amazon.com/American-Journey-Autobiography-Colin-Powell/dp/0679432965

• Guns, Germs, and Steel: The Fates of Human Societies: https://www.amazon.com/Guns-Germs-Steel-Fates-Societies/dp/0393317552

• Collapse: How Societies Choose to Fail or Succeed: https://www.amazon.com/Collapse-Societies-Choose-Succeed-Revised/dp/0143117009

• SPQR: A History of Ancient Rome: https://www.amazon.com/SPQR-History-Ancient-Mary-Beard/dp/0871404230

• A World Appears: A Journey into Consciousness: https://www.amazon.com/World-Appears-Journey-into-Consciousness/dp/198488199X

—

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.

Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify.

—

We discuss:

1. Why the classic discovery → mock → iterate design process is becoming obsolete

2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack

3. Whether AI will eventually surpass humans in taste and judgment

4. Why Jenny left a director role at Figma to return to IC work at Anthropic

5. The three archetypes Jenny is hiring for now

6. Why chatbot interfaces may be more durable than most people expect

—

Brought to you by:

Mercury—Radically different banking: https://mercury.com/?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q1_brand_campaign

Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/

Omni—AI analytics your customers can trust: https://omni.co/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/the-design-process-is-dead

—

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

—

Where to find Jenny Wen:

• X: https://x.com/jenny_wen

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

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

• Website: https://jennywen.ca

—

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 Jenny Wen

(04:23) Why the traditional design process is dead

(06:33) The two new types of design work

(10:00) How widespread this shift will be

(13:00) Day-to-day life as a designer at Anthropic

(18:45) Jenny’s AI stack

(20:03) Why Figma still matters for exploration

(22:25) Advice for working with engineers

(24:19) How to maintain craft, quality, and trust in the AI era

(27:35) Will AI ever have “taste”?

(31:38) The future of chatbot interfaces

(35:33) Moving from director back to IC

(41:00) The 10-day build of Claude Cowork

(46:06) Hiring: the three archetypes

(50:44) Advice for new and senior designers

(54:42) The value of “low leverage” tasks for managers

(57:52) Why the best teams roast each other

(01:01:45) The legibility framework

(01:07:22) Lightning round and final thoughts

—

Referenced:

• Figma: https://www.figma.com

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

• v0: https://v0.app

• Navigating a Design Career with Jenny Wen | Figma at Waterloo: https://www.youtube.com/watch?v=OHcBPMh2ivk

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

• Use Claude Code in VS Code: https://code.claude.com/docs/en/vs-code

• Claude Code in Slack: https://code.claude.com/docs/en/slack

• Lex Fridman’s website: https://lexfridman.com

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

• OpenClaw: https://openclaw.ai

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

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

• Socratica: https://www.socratica.info

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Evan Tana’s ‘legibility matrix’ on X: https://x.com/evantana/status/1927404374252269667

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

• Palantir: https://www.palantir.com

• Stripe: https://stripe.com

• Linear: https://linear.app

• Notion: https://www.notion.com

• Julie Zhuo’s website: https://www.juliezhuo.com

• Sentimental Value: https://www.imdb.com/title/tt27714581

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

• Noah Wyle: https://en.wikipedia.org/wiki/Noah_Wyle

• ER on Prime Video: https://www.amazon.com/gp/video/detail/B0FWZSDYRP

• Retro: https://retro.app

• Granola: https://www.granola.ai

—

Recommended books:

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394480767

• Insomniac City: New York, Oliver Sacks, and Me: https://www.amazon.com/Insomniac-City-New-York-Oliver/dp/162040494X

—

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.

Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li.

We discuss:

1. How Cisco went AI-first across 90,000 employees

2. His six-part framework for building great companies: timing, market, team, product, brand, distribution

3. Why he says he couldn’t have done this job without AI

4. His “right to win” strategic framework

5. His communication framework for preventing “packet loss” across an organization

6. Why he flips “praise in public, criticize in private” and does the exact opposite

7. The important communication lesson his mother taught him

—

Brought to you by:

Sentry—Code breaks, fix it faster: https://sentry.io/lenny

Framer—Build better websites faster: https://framer.com/lenny

Samsara—Saving lives with AI built for physical operations: https://samsara.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival

—

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

—

Where to find Jeetu Patel:

• X: https://x.com/jpatel41

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

• Website: https://blogs.cisco.com/author/jeetupatel

—

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 and welcome

(04:15) Insights from Cisco’s Al summit

(08:45) Transforming Cisco into an Al-first company

(15:33) What Cisco actually does in the Al infrastructure stack

(19:09) The future of Al

(24:36) Raising kids in the AI era

(29:46) “Permission to play” framework

(36:50) Lessons from great CEOs

(42:02) Leading at scale

(50:54) Why Jeetu inverts the ‘praise in public, criticize in private’ rule

(57:45) Surrounding yourself with good human beings

(58:35) Lessons from loss

(01:03:21) Career advice: platforms, hunger, and preparation

(01:10:21) The six-part framework for building great companies

(01:19:05) Lightning round and final thoughts

—

Resources and episode mentions: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival

—

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.

Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work.

We discuss:

1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month

2. The counterintuitive product principles that drove Claude Code’s success

3. Why Boris believes coding is “solved”

4. The latent demand that shaped Claude Code and Cowork

5. Practical tips for getting the most out of Claude Code and Cowork

6. How underfunding teams and giving them unlimited tokens leads to better AI products

7. Why Boris briefly left Anthropic for Cursor, then returned after just two weeks

8. Three principles Boris shares with every new team member

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny

Sentry—Code breaks, fix it faster: https://sentry.io/lenny

Metaview—The AI platform for recruiting: https://metaview.ai/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

—

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

—

Where to find Boris Cherny:

• X: https://x.com/bcherny

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

• Website: https://borischerny.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 Boris and Claude Code

(03:45) Why Boris briefly left Anthropic for Cursor (and what brought him back)

(05:35) One year of Claude Code

(08:41) The origin story of Claude Code

(13:29) How fast AI is transforming software development

(15:01) The importance of experimentation in AI innovation

(16:17) Boris’s current coding workflow (100% AI-written)

(17:32) The next frontier

(22:24) The downside of rapid innovation 

(24:02) Principles for the Claude Code team

(26:48) Why you should give engineers unlimited tokens

(27:55) Will coding skills still matter in the future?

(32:15) The printing press analogy for AI’s impact

(36:01) Which roles will AI transform next?

(40:41) Tips for succeeding in the AI era

(44:37) Poll: Which roles are enjoying their jobs more with AI

(46:32) The principle of latent demand in product development

(51:53) How Cowork was built in just 10 days

(54:04) The three layers of AI safety at Anthropic

(59:35) Anxiety when AI agents aren’t working

(01:02:25) Boris’s Ukrainian roots

(01:03:21) Advice for building AI products

(01:08:38) Pro tips for using Claude Code effectively

(01:11:16) Thoughts on Codex

(01:12:13) Boris’s post-AGI plans

(01:14:02) Lightning round and final thoughts

—

References: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

—

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.

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach.

We discuss:

1. His LOCKS framework for evaluating founders

2. Why you should build your team like the 2004 Red Sox

3. Why hiring “spicy” candidates beats consensus picks

4. Why enterprise sales will be the last white-collar job AI replaces

5. Some of my favorite “Halliganisms”

—

Brought to you by:

Sentry—Code breaks, fix it faster: http://sentry.io/lenny

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

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

—

Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been

—

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

—

Where to find Brian Halligan

• X: https://x.com/bhalligan

• LinkedIn: linkedin.com/in/brianhalligan

• Delphi: https://www.delphi.ai/bhalligan

• Podcast: https://sequoiacap.com/series/long-strange-trip

—

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 Brian Halligan

(03:56) The perpetual state of constructive dissatisfaction

(05:25) Coaching CEOs

(07:49) The art of interviewing and hiring

(11:21) Getting the most out of reference calls

(13:10) Homegrown talent vs. big company hires

(16:31) Traits of successful CEOs

(19:40) Brian’s LOCKS framework for evaluating founders

(21:34) Are great CEO’s born or made?

(23:41) Giving effective feedback

(25:54) The future of go-to-market strategies

(31:56) Understanding forward deployed engineers

(34:17) How the CEO role has evolved over the last 20 years

(38:10) Halliganisms

(01:01:18) The CEO’s role in scaling a company

(01:02:41) Lightning round and final thoughts

—

Referenced:

• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria

• HubSpot: https://www.hubspot.com

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

• McKinsey & Company: https://www.mckinsey.com

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

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

• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg

• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca

• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel

• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392

• OpenClaw: https://openclaw.ai

• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat

• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159

• Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin

• Glassdoor: https://www.glassdoor.com

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a

• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia

• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir

• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh

• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan

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

• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution

• Delphi: https://www.delphi.ai

• Sonos: https://www.sonos.com

• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan

• The Boston Red Sox: https://www.mlb.com/redsox

—

Recommended book:

• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520

—

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.

Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents.

We discuss:

1. What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes

2. How AI is changing the role of managers

3. Why the productivity gap between AI power users and everyone else is widening

4. Why “models will eat your scaffolding for breakfast”

5. Why the next 12 to 24 months are a rare window where engineers can leap ahead before the role fully transforms

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers

Sentry—Code breaks, fix it faster

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform

—

Episode transcript: https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers

—

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

—

Where to find Sherwin Wu:

• X: https://x.com/sherwinwu

• LinkedIn: https://www.linkedin.com/in/sherwinwu1

—

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 Sherwin Wu

(03:10) AI’s role in coding at OpenAI

(06:53) The future of software engineering with AI

(12:26) The stress of managing agents

(15:07) Codex and code review automation

(19:29) The changing role of engineering managers

(24:14) The one-person billion-dollar startup

(31:40) Management lessons

(37:28) Challenges and best practices in AI deployment

(43:56) Hot takes on AI and customer feedback

(48:57) Building for future AI capabilities

(50:16) Where models are headed in the next 18 months

(53:35) Business process automation

(57:22) OpenAI’s ecosystem and platform strategy

(01:00:50) OpenAI’s mission and global impact

(01:05:21) Building on OpenAI’s API and tools

(01:08:16) Lightning round and final thoughts

—

Referenced:

• Codex: https://openai.com/codex

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• OpenClaw: https://openclaw.ai

• The creator of Clawd: “I ship code I don’t read”: https://newsletter.pragmaticengineer.com/p/the-creator-of-clawd-i-ship-code

• The Sorcerer’s Apprentice: https://en.wikipedia.org/wiki/The_Sorcerer%27s_Apprentice_(Dukas)

• Quora: https://www.quora.com

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

• Sarah Friar on LinkedIn: https://www.linkedin.com/in/sarah-friar

• Sam Altman on X: https://x.com/sama

• Nicolas Bustamante’s “LLMs Eat Scaffolding for Breakfast” post on X: https://x.com/nicbstme/status/2015795605524901957

• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html

• Overton window: https://en.wikipedia.org/wiki/Overton_window

• Developers can now submit apps to ChatGPT: https://openai.com/index/developers-can-now-submit-apps-to-chatgpt

• Responses: https://platform.openai.com/docs/api-reference/responses

• Agents SDK: https://platform.openai.com/docs/guides/agents-sdk

• AgentKit: https://openai.com/index/introducing-agentkit

• Ubiquiti: https://ui.com

• Jujutsu Kaisen on Crunchyroll: https://www.crunchyroll.com/series/GRDV0019R/jujutsu-kaisen?srsltid=AfmBOoqvfzKQ6SZOgzyJwNQ43eceaJTQA2nUxTQfjA1Ko4OxlpUoBNRB

• eero: https://eero.com

• Opendoor: https://www.opendoor.com

—

Recommended books:

• Structure and Interpretation of Computer Programs: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871

• The Mythical Man-Month: Essays on Software Engineering: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959

• There Is No Antimemetics Division: A Novel: https://www.amazon.com/There-No-Antimemetics-Division-Novel/dp/0593983750

• Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034

• Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373

—

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.

Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI.

We discuss:

1. Why having no coding background can be an advantage when building with AI

2. Why most of your time should go to planning and chat mode, not prompting

3. What to do when you get stuck: his 4x4 debugging workflow

4. The PRD and Markdown file system that keeps AI agents aligned across complex builds

5. Why kicking off four or five parallel prototypes is the best way to clarify your thinking

6. Why design skills and taste are going to be the most important skills in the future

7. His “genie and three wishes” mental model for making the most of AI’s limitations

8. How product, engineering, and design roles are converging—and what that means for your career

—

Brought to you by:

Strella—The AI-powered customer research platform: https://strella.io/lenny

Samsara—Saving lives with AI built for physical operations: https://samsara.com/lenny

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

—

Episode transcript: https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code

—

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

—

Where to find Lazar Jovanovic:

• X: https://x.com/lakikentaki

• LinkedIn: https://www.linkedin.com/in/lazar-jovanovic

• YouTube: https://www.youtube.com/@50in50challenge

• Starter Story course: https://build.starterstory.com/build/ai-build-accelerator?via=lazar (code LAZAR15 for 15% off)

—

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 Lazar and professional vibe coding

(04:53) What a professional vibe coder actually does day-to-day

(09:26) Why non-technical backgrounds can be an advantage

(12:24) The importance of self-awareness

(14:42) His “genie and three wishes” mental model

(17:43) Developing taste and judgment in the age of AI

(21:46) The parallel project approach for better outcomes

(29:30) Creating dynamic context windows with PRDs

(36:56) Why elite vibe coders focus on planning, not coding

(44:43) Creating MD files to guide AI development

(50:57) Why prototyping still matters

(56:50) Why “good enough” is no longer good enough

(01:00:53) The future of engineering in an AI world

(01:05:14) What to do when you get stuck: his 4x4 debugging workflow

(01:14:27) Helping agents learn from their mistakes

(01:15:35) Why watching agent output is more important than code

(01:19:08) The incredible pace of AI development

(01:22:55) Why emotional intelligence will become more valuable

(01:28:30) How to become a professional vibe coder

(01:30:10) Why building in public is the fastest path to opportunities

(01:37:03) Final thoughts on focusing on quality over tech stack

—

Referenced:

• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna

• Lovable: https://lovable.dev

• Lovable + Shopify: https://lovable.dev/shopify

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Mobbin: https://mobbin.com

• Dribbble: https://dribbble.com

• 21st.dev: https://21st.dev

• Lovable base prompt generator: https://building-advisor.lovable.app/

• Lovable PRD generator: https://chatgpt.com/g/g-67e1e85fbeac8191a69b95c6d5c42ef6-lovable-prd-generator

• Felix Haas’s newsletter: https://designplusai.com

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

• Glassmorphism: https://www.figma.com/community/plugin/1197106608665398190/glassmorphism

• UI style guide: http://uistyle.lovable.app

• Cloudflare: https://www.cloudflare.com

• Ben Tossell on X: https://x.com/bentossell

• 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

• Peter Thiel says AI will be ‘worse’ for math nerds than for writers: https://www.businessinsider.com/peter-thiel-ai-worse-for-math-professionals-than-writers-2024-4

• Andrej Karpathy on X: https://x.com/karpathy

• The 100-person AI lab that became Anthropic and Google’s secret weapon | Edwin Chen (Surge AI): https://www.lennysnewsletter.com/p/surge-ai-edwin-chen

• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody

• Slumdog Millionaire: https://www.imdb.com/title/tt1010048

—

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.

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship.

We discuss:

1. Why repair—not perfection—defines strong leadership

2. Why you need to connect before you correct to build cooperation and trust

3. The “most generous interpretation” framework for handling difficult behaviors

4. How to correctly set boundaries (vs. making requests)

5. The power of “I believe you, and I believe in you”

6. What it looks like to be a “sturdy” leader

—

Brought to you by:

Merge—Fast, secure integrations for your products and agents: https://merge.dev/lenny

Metaview—The AI platform for recruiting: https://metaview.ai/lenny

Framer—Builder better websites faster: https://framer.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap

—

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

—

Where to find Dr. Becky Kennedy:

• X: https://x.com/GoodInside

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

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

• TikTok: https://www.tiktok.com/@drbeckyatgoodinside

• Website: https://www.goodinside.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 Dr. Becky Kennedy

(05:14) Connecting parenting and leadership

(08:40) The power of repair

(11:05) Connecting before correcting

(17:45) Good Inside framework at work

(22:08) The most generous interpretation (MGI)

(25:46) Curiosity over judgment

(27:07) Understanding behavior change

(31:08) What potty training can teach us about workplace behavior

(34:40) Naming your intention

(35:41) Sturdy leadership

(40:52) How to set boundaries well

(46:33) The role of leadership and consensus

(50:50) The importance of being “locatable”

(52:40) A powerful story of betrayal and realization

(57:12) Building resilience over happiness

(01:00:34) The power of the phrase “I believe you, and I believe in you.”

(01:09:08) The Good Inside community and resources

(01:16:22) AI corner

(01:19:52) Good Inside’s mission

(01:22:26) Lightning round and final thoughts

—

Referenced:

• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng

• Punch: https://en.wikipedia.org/wiki/Punch_(play)

• Figma: https://www.figma.com

• Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan

• Replit: https://replit.com

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Lovable: https://lovable.dev

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

• Claude: https://claude.ai

• ChatGPT: https://chatgpt.com

• Secrets We Keep on Netflix: https://www.netflix.com/title/81697668

• K Pop Demon Hunters on Netflix: https://www.netflix.com/title/81498621

• Liberty puzzles: https://libertypuzzles.com

—

Recommended books:

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481

• Leave Me Alone!: A Good Inside Story About Deeply Feeling Kids: https://www.amazon.com/Leave-Me-Alone-Inside-Feeling/dp/1250413117

• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765/

• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649

—

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.

Marc Andreessen is a founder, investor, and co-founder of Netscape, as well as co-founder of the venture capital firm Andreessen Horowitz (a16z). In this conversation, we dig into why we’re living through a unique and one of the most incredible times in history, and what comes next.

We discuss:

1. Why AI is arriving at the perfect moment to counter demographic collapse and declining productivity

2. How Marc has raised his 10-year-old kid to thrive in an AI-driven world

3. What’s actually going to happen with AI and jobs (spoiler: he thinks the panic is “totally off base”)

4. The “Mexican standoff” that’s happening between product managers, designers, and engineers

5. Why you should still learn to code (even with AI)

6. How to develop an “E-shaped” career that combines multiple skills, with AI as a force multiplier

7. The career advice he keeps coming back to (“Don’t be fungible”)

8. How AI can democratize one-on-one tutoring, potentially transforming education

9. His media diet: X and old books, nothing in between

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers

Brex—The banking solution for startups

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform

—

Episode transcript: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

—

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

—

Where to find Marc Andreessen:

• X: https://x.com/pmarca

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

• Andreessen Horowitz’s website: https://a16z.com

• Andreessen Horowitz’s YouTube channel: https://www.youtube.com/@a16z

—

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 Marc Andreessen

(04:27) The historic moment we’re living in

(06:52) The impact of AI on society

(11:14) AI’s role in education and parenting

(22:15) The future of jobs in an AI-driven world

(30:15) Marc's past predictions

(35:35) The Mexican standoff of tech roles

(39:28) Adapting to changing job tasks

(42:15) The shift to scripting languages

(44:50) The importance of understanding code

(51:37) The value of design in the AI era

(53:30) The T-shaped skill strategy

(01:02:05) AI’s impact on founders and companies

(01:05:58) The concept of one-person billion-dollar companies

(01:08:33) Debating AI moats and market dynamics

(01:14:39) The rapid evolution of AI models

(01:18:05) Indeterminate optimism in venture capital

(01:22:17) The concept of AGI and its implications

(01:30:00) Marc's media diet

(01:36:18) Favorite movies and AI voice technology

(01:39:24) Marc's product diet

(01:43:16) Closing thoughts and recommendations

—

Referenced:

• Linus Torvalds on LinkedIn: https://www.linkedin.com/in/linustorvalds

• The philosopher’s stone: https://en.wikipedia.org/wiki/Philosopher%27s_stone

• Alexander the Great: https://en.wikipedia.org/wiki/Alexander_the_Great

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

• Bloom’s 2 sigma problem: https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem

• Alpha School: https://alpha.school

• In Tech We Trust? A Debate with Peter Thiel and Marc Andreessen: https://a16z.com/in-tech-we-trust-a-debate-with-peter-thiel-and-marc-andreessen

• John Woo: https://en.wikipedia.org/wiki/John_Woo

• Assembly: https://en.wikipedia.org/wiki/Assembly_language

• C programming language: https://en.wikipedia.org/wiki/C_(programming_language)

• Python: https://www.python.org

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

• Perl: https://www.perl.org

• Scott Adams: https://en.wikipedia.org/wiki/Scott_Adams

• Larry Summers’s website: https://larrysummers.com

• Nano Banana: https://gemini.google/overview/image-generation

• Bitcoin: https://bitcoin.org

• Ethereum: https://ethereum.org

• Satoshi Nakamoto: https://en.wikipedia.org/wiki/Satoshi_Nakamoto

• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• Inside Google’s AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search): https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year

• DeepSeek: https://www.deepseek.com

• Cowork: https://support.claude.com/en/articles/13345190-getting-started-with-cowork

• Definite vs. indefinite thinking: Notes from Zero to One by Peter Thiel: https://boxkitemachine.net/posts/zero-to-one-peter-thiel-definite-vs-indefinite-thinking

• Henry Ford: https://www.thehenryford.org/explore/stories-of-innovation/visionaries/henry-ford

• Lex Fridman Podcast: https://lexfridman.com/podcast

• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz

• Eddington: https://www.imdb.com/title/tt31176520

• Joaquin Phoenix: https://en.wikipedia.org/wiki/Joaquin_Phoenix

• Pedro Pascal: https://en.wikipedia.org/wiki/Pedro_Pascal

• George Floyd: https://en.wikipedia.org/wiki/George_Floyd

• Replit: https://replit.com

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Grok Bad Rudi: https://grok.com/badrudi

• Wispr Flow: https://wisprflow.ai

• Star Trek: The Next Generation: https://www.imdb.com/title/tt0092455

• Star Trek: Starfleet Academy: https://www.imdb.com/title/tt8622160

• a16z: The Power Brokers: https://www.notboring.co/p/a16z-the-power-brokers

—

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.

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team.

We discuss:

1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market

2. A small tweak that’ll double response rates on your cancellation surveys

3. Why “it’s too expensive” is almost never the real reason customers cancel

4. The “elephant curve” of growth

5. How repositioning the same product can increase revenue 8x

6. When to reconsider if growth is even the right goal for your business

—

Brought to you by:

10Web—Vibe coding platform as an API

Strella—The AI-powered customer research platform

Brex—The banking solution for startups

—

Episode transcript: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing

—

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

—

Where to find Jason Cohen:

• Preorder Jason’s book: https://preorder.hiddenmultipliers.com/

• X: https://x.com/asmartbear

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

• Blog: https://longform.asmartbear.com

• Website: https://wpengine.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 Jason Cohen

(05:19) Jason’s writing journey

(08:25) Questions to ask when your product stops growing

(18:17) Getting real customer feedback

(20:27) Analyzing cancellation reasons

(26:54) Onboarding and activation

(29:35) Quick summary

(35:46) Revisiting pricing strategies

(41:46) Positioning strategies

(47:52) Why pricing is inseparable from your strategy

(52:06) The importance of net revenue retention (NRR)

(01:00:25) Asking whether or not this is good for the customer

(01:04:34) Leveraging existing customers

(01:06:42) Are your acquisition channels saturated? The “elephant curve”

(1:09:41) Why all marketing channels eventually decline

(01:12:04) Direct vs. indirect marketing channels

(1:13:36) Getting creative with new channels

(01:19:04) Do you actually need to grow?

(01:25:57) Deciding when to quit

(01:29:27) Book announcement

(01:33:21) AI corner

(01:34:35) Contrarian corner

(01:37:43) Lightning round and final thoughts

—

Referenced:

• Tyler Cowen’s website: https://tylercowen.com

• How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn

• Linear: https://linear.app

• Jira: https://www.atlassian.com/software/jira

• Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy

• M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing

• “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

• Buffer: https://buffer.com

• AG1: https://drinkag1.com

• How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng

• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth

• The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth

• HubSpot: https://www.hubspot.com

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/

• Ecosystem is the next big growth channel: https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth

• ChatGPT apps are about to be the next big distribution channel: Here’s how to build one: https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the

• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

• ER on Prime Video: https://www.amazon.com/ER-Season-1/dp/B0FWK5WJQ4

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

• Wispr Flow: https://wisprflow.ai

• Anker: https://www.anker.com

—

Recommended books:

• Will: https://www.amazon.com/Will-Smith/dp/1984877925

• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Hidden Multipliers: Small Things That Accelerate Growth: https://preorder.hiddenmultipliers.com

• On Writing Well: The Essential Guide to Mastering Nonfiction Writing and Effective Communication: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548

• Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

—

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.

Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor.

We discuss:

1. The complete AI workflow that lets non-technical people build real products in Cursor

2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI)

3. Using slash commands to automate prompts

4. Zevi’s “peer review” technique, which uses different AI models to review each other’s code

5. Why this might be the best time to be a junior in tech, despite the challenging job market

6. How Zevi used AI to prepare for his Meta PM interviews

—

Brought to you by:

10Web—Vibe coding platform as an API

DX—The developer intelligence platform designed by leading researchers

Framer—Build better websites faster

—

Zevi's Slash Command Bank for Claude: ⁠https://zeviarnovitz.com/⁠

—

Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor

—

Archive of all Lenny's Podcast transcripts:

https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Zevi Arnovitz

• X: https://x.com/ArnovitzZevi

• LinkedIn: https://www.linkedin.com/in/zev-arnovitz

• Website: https://zeviarnovitz.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 Zevi Arnovitz

(04:48) Zevi’s background and journey into AI

(07:41) Overview of Zevi’s AI workflow

(14:41) Screenshare: Exploring Zevi’s workflow in detail

(17:18) Building a feature live: StudyMate app

(30:52) Executing the plan with Cursor

(38:32) Using multiple AI models for code review

(40:40) Personifying AI models

(43:37) Peer review process

(45:40) The importance of postmortems

(51:05) Integrating AI in large companies

(53:42) How AI has impacted the PM role

(57:02) How to improve AI outputs

(58:15) AI-assisted job interviews

(01:02:57) Failure corner

(01:06:20) Lightning round and final thoughts

—

Referenced:

• Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv

• Wix: https://www.wix.com

• Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w

• Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw

• Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg

• Bolt: https://bolt.new

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Lovable: https://lovable.dev

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

• StudyMate: https://studymate.live

• Dibur2text: https://dibur2text.app

• Claude: https://claude.ai

• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code

• Bun: https://bun.com

• Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction

• Cursor: https://cursor.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

• Wispr Flow: https://wisprflow.ai

• Linear: https://linear.app

• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

• Cursor Composer: https://cursor.com/blog/composer

• Replit: https://replit.com

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Base44: https://base44.com

• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo

• v0: https://v0.app

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Cursor Browser mode: https://cursor.com/docs/agent/browser

• Google Antigravity: https://antigravity.google

• Grok: https://grok.com

• Zapier: https://zapier.com

• Airtable: https://www.airtable.com

• Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system

• The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81

• AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08

• Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf

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

• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

• Loom: https://www.loom.com

• Cap: https://cap.so

• Supercut: https://supercut.ai

...References continued at: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor

—

Recommended books:

• The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153

• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910

• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

—

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.

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust.

We discuss:

1. Why etiquette matters

2. Sam’s framework for showing up confidently, with a low heart rate, in any room

3. How to navigate introductions, small talk, meetings, and meals like a pro

4. Simple hacks for remembering names and handling awkward social situations

5. 30+ specific etiquette tips

—

Brought to you by:

10Web—Vibe-coding platform as an API

DX—The developer intelligence platform designed by leading researchers

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

—

Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook

—

Archive of all Lenny's Podcast transcripts:

https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Sam Lessin:

• X: https://x.com/lessin

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

• Website: https://www.wlessin.com

• Podcast: https://moreorlesspod.com

• Lettermeme: https://lettermeme.com/lessin

—

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) Sam’s background

(04:18) The role of etiquette in business success

(09:30) Introductions and entering a room

(16:20) Engaging conversations and building relationships

(23:55) Hygiene and dress code essentials

(33:42) Dining etiquette

(37:15) Tipping etiquette

(41:36) The “B&D trick”

(43:05) Humor in social settings

(45:18) Self-deprecating humor

(47:42) Winding down conversations

(49:20) Scheduling etiquette

(55:23) Communication and email etiquette

(01:02:28) Meeting etiquette tips

(01:04:03) Virtual meeting best practices

(01:05:15) The importance of cleaning up after yourself

(01:05:58) Exiting and follow-up etiquette

(01:07:24) Final thoughts

(01:09:20) AI corner

(01:11:13) Contrarian corner

(01:16:25) Lightning round

—

Referenced:

• Y Combinator: https://www.ycombinator.com

• Kleiner Perkins: https://www.kleinerperkins.com

• “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq

• Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik

• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan

• Bain & Company: https://www.bain.com

• Evernote: https://evernote.com

• Calendly: https://calendly.com

• Morning Brew: https://www.morningbrew.com

• Cursor: https://cursor.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

• DigitalOcean: https://www.digitalocean.com

• Cloudflare: https://www.cloudflare.com

• SpaceX: https://www.spacex.com

• Marc Andreessen on X: https://x.com/pmarca

• Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD

• Dave Morin on X: https://x.com/davemorin

—

Recommended books:

• Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5

• Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A

• The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048

• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI

• Area 51: An Uncensored History of America’s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q

• The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X

• The Fish That Ate the Whale: The Life and Times of America’s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314

• The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439

—

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.

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering.

We discuss:

1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built

2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle

3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement

4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products

5. Why evals aren’t a cure-all, and the most common misconceptions people have about them

6. The skills that matter most for builders in the AI era

—

Brought to you by:

Merge—The fastest way to ship 220+ integrations: https://merge.dev/lenny

Strella—The AI-powered customer research platform: https://strella.io/lenny

Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs

—

Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced

—

Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp

—

Where to find Aishwarya Naresh Reganti:

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

• GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide

• X: https://x.com/aish_reganti

—

Where to find Kiriti Badam:

• LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam

• X: https://x.com/kiritibadam

—

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 Aishwarya and Kiriti

(05:03) Challenges in AI product development

(07:36) Key differences between AI and traditional software

(13:19) Building AI products: start small and scale

(15:23) The importance of human control in AI systems

(22:38) Avoiding prompt injection and jailbreaking

(25:18) Patterns for successful AI product development

(33:20) The debate on evals and production monitoring

(41:27) Codex team’s approach to evals and customer feedback

(45:41) Continuous calibration, continuous development (CC/CD) framework

(58:07) Emerging patterns and calibration

(01:01:24) Overhyped and under-hyped AI concepts

(01:05:17) The future of AI

(01:08:41) Skills and best practices for building AI products

(01:14:04) Lightning round and final thoughts

—

Referenced:

• LevelUp Labs: https://levelup-labs.ai/

• Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different

• Booking.com: https://www.booking.com

• Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123

• Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en

• The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis

• Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah

• Rackspace: https://www.rackspace.com

• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper

• Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html

• LMArena: https://lmarena.ai

• Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers

• Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck

• Airline held liable for its chatbot giving passenger bad advice—what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know

• Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis

• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

• Socrates’s quote: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living

• Noah Smith’s newsletter: https://www.noahpinion.blog

• Silicon Valley on HBO Max: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d

• Clair Obscur: Expedition 33: https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33/

• Wisprflow: https://wisprflow.ai

• Raycast: https://www.raycast.com

• Steve Jobs’s quote: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only

—

Recommended books:

•  When Breath Becomes Air: https://www.amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X

• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032

• A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285

—

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.

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.

We discuss:

1. “Give away your Legos”: a framework for scaling yourself as a leader

2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path

3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)

4. Six rules for creating effective goals (and aligning everyone around them)

5. Rules of thumb for leading through rapid scale and change

6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers

Brex—The banking solution for startups

GoFundMe Giving Funds—Make helping a habit

—

Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation

—

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

—

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 Molly Graham

(04:28) Molly’s background at Google, Facebook, Quip, and CZI

(11:29) The “Give away your Legos” framework

(16:44) Managing your inner monster

(19:49) When not to give away your Legos

(21:28) Embracing a long career

(23:25) The J-curve vs. stairs approach to career growth

(32:00) The gift of knowing yourself

(34:28) Learning to be a professional idiot

(38:30) The waterline model: snorkel before you scuba

(47:16) Six rules for creating strong alignment around goals

(57:15) Rules of thumb for leading through rapid scale

(01:07:49) Investing in high performers vs. low performers

(01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor

(1:21:15) Pivoting from ambition to purpose

(1:26:32) Finding stability in instability

(01:29:44) Final thoughts

—

Referenced:

• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652

• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage

• Quip: https://quip.com

• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

• Chan Zuckerberg Initiative: https://chanzuckerberg.com

• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups

• The Muppets: https://muppets.disney.com

• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell

• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve

• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks

• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath

• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921

• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you

• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz

• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model

• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc

• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about

• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals

• Founder mode: https://paulgraham.com/foundermode.html

• Stripe: https://stripe.com

• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison

• John Collison on X: https://x.com/collision

• Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow

—

Recommended books:

• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252

• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

—

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.

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.

We discuss:

1. How AI is fundamentally changing the sales function

2. Why most SDRs and BDRs will be “extinct” within a year

3. What Jason is observing across his portfolio about AI adoption in GTM

4. How to become “hyper-employable” in the age of AI

5. The specific AI tools and tactics he’s using that have been working best

6. Practical frameworks for integrating AI into your sales motion without losing what works

7. Jason’s 2026 predictions on where SaaS and GTM are heading next

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers

Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform

—

Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation

—

Where to find Jason Lemkin:

• X: https://x.com/jasonlk

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

• Website: https://www.saastr.com

• Substack: https://substack.com/@cloud

—

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 Jason Lemkin

(04:36) What SaaStr does

(07:13) AI’s impact on sales teams

(10:11) How SaaStr's AI agents work and their performance

(14:18) How go-to-market is changing in the AI era

(19:19) The future of SDRs, BDRs, and AEs in sales

(22:03) Why leadership roles are safe

(23:43) How to be in the 20% who thrive in the AI sales future

(28:40) Why you shouldn't build your own AI tools

(30:10) Specific AI agents and their applications

(36:40) Challenges and learnings in AI deployment

(42:11) Making AI-generated emails good (not just acceptable)

(47:31) When humans still beat AI in sales

(52:39) An overview of SaaStr's org

(53:50) The role of human oversight in AI operations

(58:37) Advice for salespeople and founders in the AI era

(01:05:40) Forward-deployed engineers

(01:08:08) What's changing and what's staying the same in sales

(01:16:21) Why AI is creating more work, not less

(01:19:32) Why Jason says these are magical times

(01:25:25) The "incognito mode test" for finding AI opportunities

(01:27:19) The impact of AI on jobs

(01:30:18) Lightning round and final thoughts

—

Referenced:

• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

• SaaStr Annual: https://www.saastrannual.com

• Delphi: https://www.delphi.ai/saastr/talk

• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/

• Vercel: https://vercel.com

• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Replit: https://replit.com

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• ElevenLabs: https://elevenlabs.io

• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack

• Bolt: https://bolt.new

• Lovable: https://lovable.dev

• Harvey: https://www.harvey.ai

• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence

• UiPath: https://www.uipath.com

• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser

• Agentforce: https://www.salesforce.com/form/agentforce

• SaaStr’s AI Agent Playbook: https://saastr.ai/agents

• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan

• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan

• Sierra: https://sierra.ai

• Fin: https://fin.ai

• Deccan: https://www.deccan.ai

• Artisan: https://www.artisan.co

• Qualified: https://www.qualified.com

• Claude: https://claude.ai

• HubSpot: https://www.hubspot.com

• Gamma: https://gamma.app

• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b

• Brex: https://www.brex.com

• Outreach: https://www.outreach.io

• Gong: https://www.gong.io

• Salesloft: https://www.salesloft.com

• Mixmax: https://www.mixmax.com

• “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

• Clay: https://www.clay.com

• Owner: https://www.owner.com

• Momentum: https://www.momentum.io

• Attention: https://www.attention.com

• Granola: https://www.granola.ai

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• Palantir: https://www.palantir.com

• Databricks: https://www.databricks.com

• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan

• Rippling: https://www.rippling.com

• Cursor: https://cursor.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 new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna

• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza

• Sora: https://openai.com/sora

• Reve: https://app.reve.com

• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/

• The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw

• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

—

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.

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

We discuss:

1. Why “extraordinary results demand extraordinary efforts”

2. Why you should deliberately understaff projects, and how to know when you’ve gone too far

3. Matt’s transition from COO to CPO and what surprised him about leading product

4. The “high alpha, low beta” framework for evaluating people, processes, and products

5. When founders should quit their startups (hint: much earlier than VCs want you to)

6. How to fight entropy in your organization through relentless energy and intensity

—

Brought to you by:

Google Gemini—Your everyday AI assistant: https://ai.dev/

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation

—

Where to find Matt MacInnis:

• X: https://x.com/stanine

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

• Email: [email protected]

—

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 Matt MacInnis and Rippling

(04:38) The importance of extraordinary efforts

(08:37) The challenges and rewards of relentless effort

(10:11) Your job as a leader is to preserve intensity

(12:39) You learn far more from success than failure

(16:34) Transitioning to chief product officer

(19:54) Fixing product management at Rippling

(25:27) The “high alpha, low beta” framework

(28:55) The PQL framework

(35:16) Hiring frameworks and team dynamics

(36:52) A helpful interview tactic

(40:00) Leading as a COO vs. a CPO

(42:34) The reality of product-market fit

(46:38) The problem with venture capital

(49:29) When founders should quit their startups

(41:48) The immutable market

(54:13) Lessons from Notion’s success

(57:43) Investment strategies and narrative violations

(01:00:42) The power of compounding, power law, and entropy

(01:07:02) Maintaining intensity and fighting entropy

(01:11:33) The importance of feedback and escalations

(01:14:31) Rippling’s vision and success

(01:17:48) AI’s impact on SaaS and business software

(01:23:42) AI corner

(01:26:23) Final thoughts and lightning round

—

Referenced:

• Rippling: https://www.rippling.com

• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman

• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill

• Carvana: https://www.carvana.com

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

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

• Inkling: https://www.inkling.com

• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari

• Notion: https://www.notion.com

• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law

• Seeking Alpha: https://seekingalpha.com

• Dennis Rodman’s website: https://dennisrodman.com

• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle

• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick

• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html

• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1

• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits

• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling

• Workday: https://www.workday.com

• Matic robots: https://maticrobots.com

• Wall-E: https://www.imdb.com/title/tt0910970

• Conviction: https://www.conviction.com

• Mike Vernal on X: https://x.com/mvernal

• Sarah Guo on X: https://x.com/saranormous

• No Priors: https://linktr.ee/nopriors

• Gemini: https://gemini.google.com

• ChatGPT: https://chatgpt.com

• Claude: https://claude.ai

• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier

• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c

• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker

—

Recommended books:

• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595

• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020

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

• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459

—

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.

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage.

We discuss:

1. The difference between jailbreaking and prompt injection attacks on AI systems

2. Why AI guardrails don’t work

3. Why we haven’t seen major AI security incidents yet (but soon will)

4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages

5. The practical steps organizations should take instead of buying ineffective security tools

6. Why solving this requires merging classical cybersecurity expertise with AI knowledge

—

Brought to you by:

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

Metronome—Monetization infrastructure for modern software companies: https://metronome.com/

GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation

—

Where to find Sander Schulhoff:

• X: https://x.com/sanderschulhoff

• LinkedIn: https://www.linkedin.com/in/sander-schulhoff

• Website: https://sanderschulhoff.com

• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC

—

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 Sander Schulhoff and AI security

(05:14) Understanding AI vulnerabilities

(11:42) Real-world examples of AI security breaches

(17:55) The impact of intelligent agents

(19:44) The rise of AI security solutions

(21:09) Red teaming and guardrails

(23:44) Adversarial robustness

(27:52) Why guardrails fail

(38:22) The lack of resources addressing this problem

(44:44) Practical advice for addressing AI security

(55:49) Why you shouldn’t spend your time on guardrails

(59:06) Prompt injection and agentic systems

(01:09:15) Education and awareness in AI security

(01:11:47) Challenges and future directions in AI security

(01:17:52) Companies that are doing this well

(01:21:57) Final thoughts and recommendations

—

Referenced:

• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff

• The AI Security Industry is Bullshit: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-bullshit

• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0

• OpenAI: https://openai.com

• Scale: https://scale.com

• Hugging Face: https://huggingface.co

• Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642

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

• ServiceNow: https://www.servicenow.com

• ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts: https://thehackernews.com/2025/11/servicenow-ai-agents-can-be-tricked.html

• Alex Komoroske on X: https://x.com/komorama

• Twitter pranksters derail GPT-3 bot with newly discovered “prompt injection” hack: https://arstechnica.com/information-technology/2022/09/twitter-pranksters-derail-gpt-3-bot-with-newly-discovered-prompt-injection-hack

• MathGPT: https://math-gpt.org

• 2025 Las Vegas Cybertruck explosion: https://en.wikipedia.org/wiki/2025_Las_Vegas_Cybertruck_explosion

• Disrupting the first reported AI-orchestrated cyber espionage campaign: https://www.anthropic.com/news/disrupting-AI-espionage

• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske

• Prompt Optimization and Evaluation for LLM Automated Red Teaming: https://arxiv.org/abs/2507.22133

• MATS Research: https://substack.com/@matsresearch

• CBRN: https://en.wikipedia.org/wiki/CBRN_defense

• CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel

• Trustible: https://trustible.ai

• Repello: https://repello.ai

• Do not write that jailbreak paper: https://javirando.com/blog/2024/jailbreaks

—

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.

Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy.

We discuss:

1. Why 60% to 70% of traditional growth tactics no longer apply in AI

2. Why you have to re-find product-market fit every 3 months

3. The specific growth tactics driving Lovable’s unprecedented growth

4. Why giving away product is a growth strategy that beats paid ads

5. “Minimum lovable product” as the new standard (not minimum viable product)

6. Why activation now belongs to product teams, not growth teams

7. Whether you should join an AI startup (honest tradeoffs)

—

Brought to you by:

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

Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web

Persona—A global leader in digital identity verification

—

Transcript: ⁠https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna⁠

—

My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation⁠

—

Where to find Elena Verna:

• X: https://x.com/elenaverna

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

• Newsletter: https://www.elenaverna.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 Elena Verna

(05:19) The scale and growth of Lovable

(08:55) Confidence in Lovable as a business

(12:17) Retention at Lovable

(15:02) Lovable’s unique growth levers

(28:13) The role of marketing in Lovable’s success

(38:09) Launching new features

(40:59) Hiring and team dynamics

(43:17) The value of vibe coding

(49:46) The importance of community

(51:47) Giving away your product for free

(56:26) Tripling their company size

(01:00:23) Product-market-fit challenges

(01:08:50) Advice for joining AI companies

(01:12:00) Work-life balance

(01:15:20) What it’s like to work at Lovable

(01:19:45) Women in tech

(01:25:29) Final thoughts and lightning round

—

Referenced:

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna

• Lovable: https://lovable.dev

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

• Stripe: https://stripe.com

• What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing

• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

• “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO): https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn

• Eric Ries on LinkedIn: https://www.linkedin.com/in/eries

• Elena’s post on LinkedIn about Lovable Missions: https://www.linkedin.com/posts/elenaverna_everythingispossible-lovableway-activity-7401627519646474242-hn6e

• SheBuilds: https://shebuilds.lovable.app

• Shopify + Lovable: https://lovable.dev/shopify

• The Product-Market Fit Treadmill: Why every AI company is sprinting just to stay in place: https://www.elenaverna.com/p/the-product-market-fit-treadmill

• Cursor: https://cursor.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

• Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

• The adjacent user: https://brianbalfour.com/quick-takes/the-adjacent-user

• Granola: https://www.granola.ai

• Wispr Flow: https://wisprflow.ai

• I’m worried about women in tech: https://www.elenaverna.com/p/im-worried-about-women-in-tech

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

—

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.

Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate—an AI agent designed to participate across the entire development lifecycle.

We discuss:

1. Why Codex has grown 20x since launch and what product decisions unlocked this growth

2. How OpenAI built the Sora Android app in just 18 days using Codex

3. Why the real bottleneck to AGI-level productivity isn’t model capability—it’s human typing speed

4. The vision of AI as a proactive teammate, not just a tool you prompt

5. The bottleneck shifting from building to reviewing AI-generated work

6. Why coding will be a core competency for every AI agent—because writing code is how agents use computers best

—

Brought to you by:

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

Fin—The #1 AI agent for customer service: https://fin.ai/lenny

Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc

—

Transcript: https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180365355/my-biggest-takeaways-from-this-conversation

—

Where to find Alexander Embiricos:

• X: https://x.com/embirico

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

—

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 Alexander Embiricos 

(05:13) The speed and ambition at OpenAI

(11:34) Codex: OpenAI’s coding agent

(15:43) Codex’s explosive growth

(24:59) The future of AI and coding agents

(33:11) The impact of AI on engineering

(44:08) How Codex has impacted the way PMs operate

(45:40) Throwaway code and ubiquitous coding

(47:10) Shipping the Sora Android app

(49:01) Building the Atlas browser

(53:34) Codex’s impact on productivity

(55:35) Measuring progress on Codex

(58:09) Why they are building a web browser

(01:01:58) Non-engineering use cases for Codex

(01:02:53) Codex’s capabilities

(01:04:49) Tips for getting started with Codex

(01:05:37) Skills to lean into in the AI age

(01:10:36) How far are we from a human version of AI?

(01:13:31) Hiring and team growth at Codex

(01:15:47) Lightning round and final thoughts

—

Referenced:

• OpenAI: https://openai.com

• Codex: https://openai.com/codex

• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Dropbox: http://dropbox.com

• Datadog: https://www.datadoghq.com

• Andrej Karpathy on X: https://x.com/karpathy

• 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

• Atlas: https://openai.com/index/introducing-chatgpt-atlas

• How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna: https://www.lennysnewsletter.com/p/how-block-is-becoming-the-most-ai-native

• Goose: https://block.xyz/inside/block-open-source-introduces-codename-goose

• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennysnewsletter.com/p/lessons-on-building-product-sense

• Sora Android app: https://play.google.com/store/apps/details?id=com.openai.sora&hl=en_US&pli=1

• The OpenAI Podcast—ChatGPT Atlas and the next era of web browsing: https://www.youtube.com/watch?v=WdbgNC80PMw&list=PLOXw6I10VTv9GAOCZjUAAkSVyW2cDXs4u&index=2

• How to measure AI developer productivity in 2025 | Nicole Forsgren: https://www.lennysnewsletter.com/p/how-to-measure-ai-developer-productivity

• Compiling: https://3d.xkcd.com/303

• Jujutsu Kaisen on Netflix: https://www.netflix.com/title/81278456

• Tesla: https://www.tesla.com

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Andreas Embirikos: https://en.wikipedia.org/wiki/Andreas_Embirikos

• George Embiricos: https://en.wikipedia.org/wiki/George_Embiricos: https://en.wikipedia.org/wiki/George_Embiricos

—

Recommended books:

• Culture series: https://www.amazon.com/dp/B07WLZZ9WV

• The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411

• A Fire Upon the Deep (Zones of Thought series Book 1): https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/1250237750

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

—

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.

Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what’s good vs. what’s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped—the fastest company in history to reach this milestone. Before founding Surge, Edwin was a research scientist at Google, Facebook, and Twitter and studied mathematics, computer science, and linguistics at MIT.

We discuss:

1. How Surge reached over $1 billion in revenue with fewer than 100 people by obsessing over quality

2. The story behind how Claude Code got so good at coding and writing

3. The problems with AI benchmarks and why they’re pushing AI in the wrong direction

4. How RL environments are the next frontier in AI training

5. Why Edwin believes we’re still a decade away from AGI

6. Why taste and human judgment shape which AI models become industry leaders

7. His contrarian approach to company building that rejects Silicon Valley’s “pivot and blitzscale” playbook

8. How AI models will become increasingly differentiated based on the values of the companies building them

—

Brought to you by:

Vanta—Automate compliance. Simplify security.

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

Coda—The all-in-one collaborative workspace

—

Transcript: https://www.lennysnewsletter.com/p/surge-ai-edwin-chen

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180055059/my-biggest-takeaways-from-this-conversation

—

Where to find Edwin Chen:

• X: https://x.com/echen

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

• Surge’s blog: https://surgehq.ai/blog

—

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 Edwin Chen

(04:48) AI’s role in business efficiency

(07:08) Building a contrarian company

(08:55) An explanation of what Surge AI does

(09:36) The importance of high-quality data

(13:31) How Claude Code has stayed ahead

(17:37) Edwin’s skepticism toward benchmarks

(21:54) AGI timelines and industry trends

(28:33) The Silicon Valley machine

(33:07) Reinforcement learning and future AI training

(39:37) Understanding model trajectories

(41:11) How models have advanced and will continue to advance

(42:55) Adapting to industry needs

(44:39) Surge’s research approach

(48:07) Predictions for the next few years in AI

(50:43) What’s underhyped and overhyped in AI

(52:55) The story of founding Surge AI

(01:02:18) Lightning round and final thoughts

—

Referenced:

• Surge: https://surgehq.ai

• Surge’s product page: https://surgehq.ai/products

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

• Gemini 3: https://aistudio.google.com/models/gemini-3

• Sora: https://openai.com/sora

• Terrence Rohan on LinkedIn: https://www.linkedin.com/in/terrencerohan

• Richard Sutton—Father of RL thinks LLMs are a dead end: https://www.dwarkesh.com/p/richard-sutton

• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html

• Reinforcement learning: https://en.wikipedia.org/wiki/Reinforcement_learning

• Grok: https://grok.com

• Warren Buffett on X: https://x.com/WarrenBuffett

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong

• Interstellar on Prime Video: https://www.amazon.com/Interstellar-Matthew-McConaughey/dp/B00TU9UFTS

• Arrival on Prime Video: https://www.amazon.com/Arrival-Amy-Adams/dp/B01M2C4NP8

• Travelers on Netflix: https://www.netflix.com/title/80105699

• Waymo: https://waymo.com

• Soda versus pop: https://flowingdata.com/2012/07/09/soda-versus-pop-on-twitter

—

Recommended books:

• Stories of Your Life and Others: https://www.amazon.com/Stories-Your-Life-Others-Chiang/dp/1101972122

• The Myth of Sisyphus: https://www.amazon.com/Myth-Sisyphus-Vintage-International/dp/0525564454

• Le Ton Beau de Marot: In Praise of the Music of Language: https://www.amazon.com/dp/0465086454

• Gödel, Escher, Bach: An Eternal Golden Braid: https://www.amazon.com/G%C3%B6del-Escher-Bach-Eternal-Golden/dp/0465026567

—

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.

Tomer Cohen is the longtime chief product officer at LinkedIn, where he’s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder program that teaches coding, design, and PM skills together. He’s also introduced a formal “Full Stack Builder” title and career ladder, enabling anyone from any function to take products from idea to launch. In this conversation, Tomer explains why product development has become too complex at most companies and how LinkedIn is building an AI-powered product team that can move faster, adapt more quickly, and do more with less.

We discuss:

1. How 70% of the skills needed for jobs will change by 2030

2. The broken traditional model: organizational bloat slows features to a six-month cycle

3. The Full Stack Builder model

4. Three pillars of making FSB work: platform, agents, and culture (culture matters most)

5. Building specialized agents that critique ideas and find vulnerabilities

6. Why off-the-shelf AI tools never work on enterprise code without customization

7. Top performers adopt AI tools fastest, contrary to expectations about leveling effects

8. Change management tactics: celebrating wins, making tools exclusive, updating performance reviews

—

Brought to you by:

Vanta—Automate compliance. Simplify security: https://vanta.com/lenny

Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/

Miro—The AI Innovation Workspace where teams discover, plan, and ship breakthrough products: https://miro.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/why-linkedin-is-replacing-pms

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180042347/my-takeaways-from-this-conversation

—

Where to find Tomer Cohen:

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

• Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498

—

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 Tomer Cohen

(04:42) The need for change in product development

(11:52) The full-stack builder model explained

(16:03) Implementing AI and automation in product development

(19:17) Building and customizing AI tools

(27:51) The timeline to launch

(31:46) Pilot program and early results

(37:04) Feedback from top talent

(39:48) Change management and adoption

(46:53) Encouraging people to play with AI tools

(41:21) Performance reviews and full-stack builders

(48:00) Challenges and specialization

(50:05) Finding talent

(52:46) Tips for implementing in your own company

(56:43) Lightning round and final thoughts

—

Referenced:

• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

• LinkedIn: https://www.linkedin.com

• Cursor: https://cursor.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

• Devin: https://devin.ai

• Figma: https://www.figma.com

• Microsoft Copilot: https://copilot.microsoft.com

• Windsurf: https://windsurf.com

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Lovable: https://lovable.dev

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

• APB program at LinkedIn: https://careers.linkedin.com/pathways-programs/entry-level/apb

• Naval Ravikant on X: https://x.com/naval

• One Song podcast: https://podcasts.apple.com/us/podcast/%D7%A9%D7%99%D7%A8-%D7%90%D7%97%D7%93-one-song/id1201883177

• Song Exploder podcast: https://songexploder.net

• Grok on Tesla: https://www.tesla.com/support/grok

• Reid Hoffman on X: https://x.com/reidhoffman

—

Recommended books:

• Why Nations Fail: The Origins of Power, Prosperity, and Poverty: https://www.amazon.com/Why-Nations-Fail-Origins-Prosperity/dp/0307719227

• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599

• The Beginning of Infinity: Explanations That Transform the World: https://www.amazon.com/Beginning-Infinity-Explanations-Transform-World/dp/0143121359

—

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.

Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy.

We discuss:

1. Why GTM is becoming more strategically important in the AI era

2. The rise of the GTM engineer

3. A primer on segmentation

4. How to build a sales org that engineers and product teams respect

5. The changing calculus of build vs. buy for go-to-market tools in the AI era

6. Why most customers buy to avoid pain rather than to gain upside

—

Brought to you by:

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

Lovable—Build apps by simply chatting with AI: https://lovable.dev/

Stripe—Helping companies of all sizes grow revenue: https://stripe.com/

—

Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation

—

Where to find Jeanne DeWitt Grosser:

• X: https://x.com/jdewitt29

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

—

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 Jeanne DeWitt Grosser

(05:26) Defining go-to-market

(08:43) The evolution of go-to-market roles

(11:23) The rise of the go-to-market engineer

(14:21) Implementing AI in sales processes

(15:28) Optimizing sales with AI agents

(23:47) Defining sales roles: SDRs and AEs

(26:04) When to hire a GTM engineer

(29:04) Hiring and scaling sales teams

(30:50) The ideal go-to-market engineer

(34:24) The go-to-market tool stack

(40:39) Advice on building a great sales bot

(44:34) Vercel’s unfair advantage

(46:37) Go-to-market as a product

(47:04) Innovative sales tactics at Stripe

(52:38) Effective go-to-market tactics

(01:00:37) Segmentation strategies

(01:09:31) Building a sales org that engineers love

(01:14:00) Thoughts on PLG and pricing

(01:16:44) Sales compensation and hiring

(01:19:24) Lightning round and final thoughts

—

Referenced:

• Vercel: https://vercel.com

• Stripe: https://stripe.com

• Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin

• Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman

• SDK: https://ai-sdk.dev/docs/introduction

• Gong: https://www.gong.io

• Lyft: https://www.lyft.com

• Instacart: https://www.instacart.com

• DoorDash: https://www.instacart.com

• “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

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

• Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle

• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

• Atlassian: atlassian.com

—

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.