Lenny's Podcast: Product | Career | Growth
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Inside the black box of AI: How AI models actually think | Emmanuel Ameisen (Anthropic)
18 oktober 2026 · 1 uur 12 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
DX—Engineering intelligence for the AI era
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Episode transcript: https://www.lennysnewsletter.com/p/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
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Highlights: https://lennyspodcast.com/mostreplayedmoments
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Where to find Emmanuel Ameisen:
• X: https://x.com/mlpowered
• LinkedIn: https://www.linkedin.com/in/ameisen
• Website: https://www.mlpowered.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to 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…
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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
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
DX—Engineering intelligence for the AI era
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Episode transcript: https://www.lennysnewsletter.com/p/why-every-company-now-needs-to-think
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Highlights: https://lennyspodcast.com/mostreplayedmoments
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Where to find Josh Woodward:
• X: https://x.com/joshwoodward
• LinkedIn: https://www.linkedin.com/in/joshwoodward
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(02:53) 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…
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OpenAI’s Head of ChatGPT: We’re entering a new era of AI (again) | Tibo Sottiaux
4 oktober 2026 · 37 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
DX—Engineering intelligence for the AI era
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Episode transcript: https://www.lennysnewsletter.com/p/openais-head-of-chatgpt-were-entering
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Tibo Sottiaux:
• X: https://x.com/thsottiaux
• LinkedIn: https://www.linkedin.com/in/thibault-sottiaux-27195366
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Tibo Sottiaux
(01:12) How Tibo uses AI in his daily work
(03:10) The vision for always-on AI agents
(06:15) How AI will continue to change work
(07:32) Bringing Codex, ChatGPT, and Dots together
(08:20) The sci-fi inspiration behind the technology
(09:02) Building AI with the community
(10:13) Understanding the Dots structure
(11:34) OpenAI’s open ecosystem and plugin revenue sharing
(13:39) How plugins get discovered and recommended
(14:39) The research behind Dots
(16:20) Where humans will remain valua…
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The grief, loneliness, and burnout sweeping through the tech industry right now | Molly Graham
27 september 2026 · 1 uur 34 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
DX—Engineering intelligence for the AI era
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Episode transcript: https://www.lennysnewsletter.com/p/the-grief-loneliness-and-burnout
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
Highlights: https://lennyspodcast.com/mostreplayedmoments
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Where to find Molly Graham
• X: https://x.com/molly_g
• LinkedIn: https://www.linkedin.com/in/mograham
• Substack: https://mollyg.substack.com
• Website: https://glueclub.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Molly Graham returns
(03:34) What is “Give away your Legos”?
(05:44) The origin story: Google, Facebook, and rapid scale
(11:27) What still holds true in an AI world
(18:13) Engineering’s identity shift: fro…
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90 minutes of unfiltered product advice from Snap and Discord’s product chief | Peter Sellis
20 september 2026 · 1 uur 37 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
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Episode transcript: https://www.lennysnewsletter.com/p/90-minutes-of-unfiltered-product
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Peter Sellis:
• X: https://x.com/petersellis
• LinkedIn: https://www.linkedin.com/in/disgruntled
• Website: https://pjs.lol
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(02:48) Why Peter avoided podcasts until now
(05:44) Designing teams like terrorist organizations
(10:35) Cult versus terrorist org: the key distinction
(11:19) Managing Nikita Bier
(12:56) Building orgs that handle spiky talent
(15:16) Why the median PM is probably bad
(18:28) Is the PM profession getting better?
(20:49) Snap’s three ads monetization challenges
(25:03) Snap’s underrated product track record
(27:57) Systems thinking
(32:19) Instag…
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How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)
8 september 2026 · 1 uur 23 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Episode transcript: https://www.lennysnewsletter.com/p/how-we-built-grok-bot-in-a-month
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Roman Ugarte:
• X: https://x.com/romanugarte_
• LinkedIn: https://www.linkedin.com/in/romanugarte
• Website: https://x.ai
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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 …
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Why companies are becoming a series of loops | Anish Acharya (a16z)
6 september 2026 · 1 uur 19 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Episode transcript: https://www.lennysnewsletter.com/p/why-companies-are-becoming-a-series
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Anish Acharya:
• Andreessen Horowitz: https://a16z.com/author/anish-acharya/
• LinkedIn: https://www.linkedin.com/in/anishacharya/
• X: https://x.com/illscience
• SoundCloud: https://soundcloud.com/illscience
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(02:25) The fear of AI creating a permanent underclass
(05:25) Why AI takeoff may be slower than expected
(08:02) …
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AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)
30 augustus 2026 · 1 uur 22 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Where to find Tara Seshan:
• X: https://x.com/tarstarr
• LinkedIn: https://www.linkedin.com/in/tarstarr
• Newsletter: https://substack.com/@taraseshan
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(02:18) What makes OpenAI’s culture so different
(06:42) Why AI product strategy is all about fast experimentation
(09:02) How the PM role is changing
(10:50) The shift from rowing to steering
(15:35) What changes when agents become coworkers
(20:05) Why ambition matters more than ever
(26:39) Building products for model…
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How to close $100K+ enterprise deals, step by step | Jen Abel
23 augustus 2026 · 1 uur 25 min
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Where to find Jen Abel:
• X: https://x.com/jjen_abel
• LinkedIn: https://www.linkedin.com/in/earlystagesales
• Website: https://www.jjellyfish.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(02:49) Why Jen is giving away her enterprise sales playbook
(05:54) Example: selling AI legal tech to SpaceX
(09:11) Step 1: Landing the meeting
(18:44) Step 2: Running the intro call
(30:00) Step 3: Running a follow-up call
(36:30) Step 4: Prepping the pitch/…
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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
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Where to find Ian Silber:
• X: https://x.com/iansilber
• LinkedIn: https://www.linkedin.com/in/iansilber
• Website: https://iansilber.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Ian Silber
(02:14) Why designers in general feel anxious about AI
(09:01) What makes specific designers thrive in the AI era
(13:41) Why Ian says it’s the best time in history to be a designer
(17:13) How product roles are converging
(22:24) Can AI design great products?
(23:54) Where human judgment still matters
(27:34) What Ian looks for when hiring designers
(30:20) Why systems thinking matters
(32:53) Balancing speed and craft
(38:05) Designing for vastly different audiences
(41:57) Solving the blank-box problem
(43:31) Ho…
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The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor
9 augustus 2026 · 1 uur 31 min
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. Lees meer
In our in-depth conversation, we discuss:
1. Inside today’s “tale of two cities” talent market
2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires
3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit
4. The worst question to ask when sourcing great talent
5. The rise of the forward deployed engineer—and how to become one
6. The biggest mistake founders make when hiring their first recruiter
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Where to find Adam Ward
• X: https://x.com/wardadamp
• LinkedIn: https://www.linkedin.com/in/adampward
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(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 importa…
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This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)
2 augustus 2026 · 1 uur 25 min
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). Lees meer
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Episode transcript: https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Tom Verrilli:
• X: https://x.com/tdrobbo
• LinkedIn: https://www.linkedin.com/in/tom-robertson-042
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(02:40) “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…
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Anthropic’s first technical PM on token maxing, the jagged edge, and living in the future | Dianne Penn
26 juli 2026 · 1 uur 34 min
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. Lees meer
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
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Episode transcript: https://www.lennysnewsletter.com/p/anthropics-first-technical-pm-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
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Where to find Dianne Penn:
• LinkedIn: linkedin.com/in/dianne-na-penn
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction
(02:31) 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
(49:5…
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Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO)
19 juli 2026 · 1 uur 12 min
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. Lees meer
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
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WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny
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Episode transcript: https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find 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/
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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…
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How tech workers actually feel about AI in 2026 | Annual AI sentiment survey (Noam Segal)
12 juli 2026 · 1 uur 36 min
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. Lees meer
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
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny
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Episode transcript: https://www.lennysnewsletter.com/p/how-tech-workers-actually-feel-about
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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
—
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: ht…
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Adam Mosseri: AI is a tailwind for authenticity
9 juli 2026 · 1 uur 8 min
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. Lees meer
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
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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
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Episode transcript: https://www.lennysnewsletter.com/p/adam-mosseri-ai-is-a-tailwind-for
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Adam Mosseri:
• X: https://x.com/mosseri
• LinkedIn: linkedin.com/in/mosseri
• Instagram: https://www.instagram.com/mosseri
…
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OpenAI Codex lead on the new shape of product work | Andrew Ambrosino
28 juni 2026 · 1 uur 10 min
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.” Lees meer
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.
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
—
Episode transcript: https://www.lennysnewsletter.com/p/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) W…
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What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams)
21 juni 2026 · 1 uur 39 min
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. Lees meer
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
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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
(…
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The hidden pattern behind successful products | Mark Pincus (founder of Zynga)
14 juni 2026 · 1 uur 39 min
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. Lees meer
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
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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
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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
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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 fra…
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Father of the iPod and iPhone on building taste, judgment, and creativity in the AI era | Tony Fadell
7 juni 2026 · 1 uur 35 min
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. Lees meer
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
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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
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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
—
Where to find Tony Fadell:
• X: https://x.com/tfadell
• LinkedIn: https://www.linkedin.com/in/tonyfadell
• Website: https://www.buildc.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to 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 …
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A rational conversation on where AI is actually going | Benedict Evans
31 mei 2026 · 1 uur 20 min
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. Lees meer
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
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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
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Benedict Evans:
• LinkedIn: https://www.linkedin.com/in/benedictevans
• Newsletter: https://www.ben-evans.com/newsletter
• Website: https://www.ben-evans.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Benedict …
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The AI paradox: More automation, more humans, more work | Dan Shipper
24 mei 2026 · 1 uur 34 min
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. Lees meer
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.
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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
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Where to find Dan Shipper:
…
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Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)
17 mei 2026 · 1 uur 39 min
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. Lees meer
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
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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) W…
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How to build a company that withstands any era | Eric Ries, Lean Startup author
10 mei 2026 · 1 uur 39 min
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. Lees meer
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) Introductio…
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Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)
3 mei 2026 · 1 uur 27 min
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. Lees meer
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 tod…
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Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel
26 april 2026 · 1 uur 10 min
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. Lees meer
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…
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How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)
23 april 2026 · 1 uur 26 min
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. Lees meer
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 shippi…
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Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)
19 april 2026 · 1 uur 35 min
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. Lees meer
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
(14:2…
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Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
12 april 2026 · 1 uur 23 min
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). Lees meer
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 undisco…
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Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare
5 april 2026 · 1 uur 53 min
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. Lees meer
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 M…
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An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison
2 april 2026 · 1 uur 40 min
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. Lees meer
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
• Li…
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From skeptic to true believer: How OpenClaw changed my life | Claire Vo
29 maart 2026 · 1 uur 47 min
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. Lees meer
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: Installin…
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The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
22 maart 2026 · 1 uur 34 min
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. Lees meer
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
…
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The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
15 maart 2026 · 1 uur 55 min
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. Lees meer
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…
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How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky
12 maart 2026 · 1 uur 7 min
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. Lees meer
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) In…
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The most successful AI company you’ve never heard of | Qasar Younis
8 maart 2026 · 1 uur 24 min
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. Lees meer
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 ab…
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The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude)
1 maart 2026 · 1 uur 17 min
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. Lees meer
—
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) …
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AI is critical for humanity’s survival: Cisco president on the AI revolution | Jeetu Patel
26 februari 2026 · 1 uur 27 min
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. Lees meer
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…
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Head of Claude Code: What happens after coding is solved | Boris Cherny
19 februari 2026 · 1 uur 28 min
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. Lees meer
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 experimenta…
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Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)
15 februari 2026 · 1 uur 15 min
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. Lees meer
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
(3…
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“Engineers are becoming sorcerers” | The future of software development with OpenAI’s Sherwin Wu
12 februari 2026 · 1 uur 20 min
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. Lees meer
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 …
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The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder)
8 februari 2026 · 1 uur 42 min
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. Lees meer
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/…
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A child psychologist’s guide to working with difficult adults | Dr. Becky Kennedy
1 februari 2026 · 1 uur 32 min
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. Lees meer
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 an…
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Marc Andreessen: The real AI boom hasn’t even started yet
29 januari 2026 · 1 uur 45 min
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. Lees meer
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) T…
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5 questions to ask when your product stops growing | Jason Cohen (2x unicorn founder)
25 januari 2026 · 1 uur 46 min
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. Lees meer
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 p…
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The non-technical PM’s guide to building with Cursor | Zevi Arnovitz (Meta)
18 januari 2026 · 1 uur 15 min
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. Lees meer
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)…
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How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin
15 januari 2026 · 1 uur 27 min
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. Lees meer
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…
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Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon
11 januari 2026 · 1 uur 26 min
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. Lees meer
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
—
Wher…
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The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale
4 januari 2026 · 1 uur 32 min
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. Lees meer
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
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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation
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Where to find Molly Graham:
• X: https://x.com/molly_g
• LinkedIn: https://www.linkedin.com/in/mograham
• Substack: https://mollyg.substack.com
• Website: https://glueclub.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) 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-c…
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We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)
1 januari 2026 · 1 uur 42 min
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. Lees meer
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
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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
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Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents
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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation
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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
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn…