Lenny's Podcast: Product | Career | Growth

Afleveringen

1. Inside the black box of AI: How AI models actually think | Emmanuel Ameisen (Anthropic)

   18 oktober 2026 · 1 uur 12 min

   Afspelen
   Emmanuel Ameisen is an interpretability researcher at Anthropic, where he looks inside LLMs like Claude to understand how they think. Before joining Anthropic, he spent years in applied ML at Stripe and Insight, and is the author of Building Machine Learning Powered Applications. His research has produced some of the most striking findings in the field: that models form general representations of concepts, plan many tokens ahead without stating those plans explicitly, and may exhibit something structurally similar to the distinction between conscious and unconscious processing in humans. Lees meer

   We discuss:

   1. Why the “next-token predictor” framing undersells how models actually plan and think

   2. Why anthropomorphizing AI can actually be the right approach

   3. Why models are “grown,” not built

   4. What the “J space” reveals about model self-awareness

   5. The smooth scaling curve behind what look like sudden capability jumps

   6. How interpretability connects to AI alignment and safety

   —

   Brought to you by:

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

   DX—Engineering intelligence for the AI era

   —

   Episode transcript: https://www.lennysnewsletter.com/p/a-mind-expanding-conversation-on

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

   —

   Highlights: https://lennyspodcast.com/mostreplayedmoments

   —

   Where to find Emmanuel Ameisen:

   • X: https://x.com/mlpowered

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

   • Website: https://www.mlpowered.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 Emmanuel Ameisen

   (01:30) Why AI models are grown, not built

   (05:57) Why next-token prediction is harder than it sounds

   (11:49) How models represent concepts and u…

2. Why every company now needs to think and operate like a lab team | Josh Woodward (Google Labs, Gemini, AI Studio)

   11 oktober 2026 · 1 uur 2 min

   Afspelen
   Josh Woodward is the head of Google Labs, the Gemini app, and AI Studio. He has spent over 17 years at Google and oversees its longest-running and largest labs team, whose products include NotebookLM (now Gemini Notebook), Project Genie, and Flow. His job is to find, experiment with, and scale new AI products, and he has built one of the most distinctive product cultures in the industry for generating ideas, running experiments, and, even more importantly, knowing when to quit. Lees meer

   In our in-depth conversation, we discuss:

   1. Why every company now needs to think and operate like a labs team

   2. Where the best ideas really come from

   3. The “almost possible” framework

   4. How to recognize genuine product-market fit early

   5. When to kill an idea

   6. What skills are rising in value in the AI era

   7. Why roles are not actually blurring into one universal builder role

   8. How to set up your internal labs team

   —

   Brought to you by:

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

   DX—Engineering intelligence for the AI era

   —

   Episode transcript: https://www.lennysnewsletter.com/p/why-every-company-now-needs-to-think

   —

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

   —

   Highlights: https://lennyspodcast.com/mostreplayedmoments

   —

   Where to find Josh Woodward:

   • X: https://x.com/joshwoodward

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

   —

   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

   (02:53) Why every company now needs to think like a labs team

   (05:43) Where great ideas come from

   (07:43) The “almost possible” framework

   (11:52) Finding product-market fit

   (16:09) Falling in love with the problem, not the solution

   (17:57) When to kill an idea

   (19:35…

3. OpenAI’s Head of ChatGPT: We’re entering a new era of AI (again) | Tibo Sottiaux

   4 oktober 2026 · 37 min

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

   We discuss:

   1. Dots, OpenAI’s new personal AI assistant

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

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

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

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

   6. OpenAI’s approach to AI safety

   —

   Brought to you by:

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

   DX—Engineering intelligence for the AI era

   —

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

   —

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

   —

   Where to find Tibo Sottiaux:

   • X: https://x.com/thsottiaux

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

   —

   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 Tibo Sottiaux

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

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

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

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

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

   (09:02) Building AI with the community

   (10:13) Understanding the Dots structure

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

   (13:39) How plugins get discovered and recommended

   (14:39) The research behind Dots

   (16:20) Where humans will remain valua…

4. The grief, loneliness, and burnout sweeping through the tech industry right now | Molly Graham

   27 september 2026 · 1 uur 34 min

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

   In our in-depth conversation, we discuss:

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

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

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

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

   5. Which Legos you should never give to AI

   6. What the best managers are doing right now

   —

   Brought to you by:

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

   DX—Engineering intelligence for the AI era

   —

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

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

   Highlights: https://lennyspodcast.com/mostreplayedmoments

   —

   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) Molly Graham returns

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

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

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

   (18:13) Engineering’s identity shift: fro…

5. 90 minutes of unfiltered product advice from Snap and Discord’s product chief | Peter Sellis

   20 september 2026 · 1 uur 37 min

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

   In our in-depth conversation, we discuss:

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

   2. What it was really like to manage Nikita Bier

   3. Why the median PM is so bad

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

   5. Why growth almost always comes from the core product

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

   —

   Brought to you by:

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

   Mercury—Radically different banking, now with Command

   —

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

   —

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

   —

   Where to find Peter Sellis:

   • X: https://x.com/petersellis

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

   • Website: https://pjs.lol

   —

   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

   (02:48) Why Peter avoided podcasts until now

   (05:44) Designing teams like terrorist organizations

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

   (11:19) Managing Nikita Bier

   (12:56) Building orgs that handle spiky talent

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

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

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

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

   (27:57) Systems thinking

   (32:19) Instag…

6. How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)

   8 september 2026 · 1 uur 23 min

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

   In our in-depth conversation, we discuss:

   1. The origin story of Grok Bot

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

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

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

   5. Their “colleague-pilled” product philosophy

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

   —

   Brought to you by:

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

   Mercury—Radically different banking, now with Command

   —

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

   —

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

   —

   Where to find Roman Ugarte:

   • X: https://x.com/romanugarte_

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

   • Website: https://x.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

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

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

   (11:20) Manually onboarding a couple hundred people

   (14:29) Hiding internal mechanics from users

   (18:41) Timeline from beta to public launch

   (19:14) Unshipping features and simplifying

   (23:50) Early use cases and feedback

   (26:50) Product …

7. Why companies are becoming a series of loops | Anish Acharya (a16z)

   6 september 2026 · 1 uur 19 min

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

   In our in-depth conversation, we discuss:

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

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

   3. What’s happening in consumer right now

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

   5. Why moats are discovered, not designed

   6. The rising importance of distribution as a moat

   7. Being a model sommelier

   —

   Brought to you by:

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

   Mercury—Radically different banking, now with Command

   —

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

   —

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

   —

   Where to find Anish Acharya:

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

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

   • X: https://x.com/illscience

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

   —

   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) The fear of AI creating a permanent underclass

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

   (08:02) …

8. AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)

   30 augustus 2026 · 1 uur 22 min

   Afspelen
   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. Lees meer

   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 model…

9. How to close $100K+ enterprise deals, step by step | Jen Abel

   23 augustus 2026 · 1 uur 25 min

   Afspelen
   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. Lees meer

   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/…

10. OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber

    16 augustus 2026 · 1 uur 12 min

    Afspelen
    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. Lees meer

    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) Ho…

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