
Lenny's Podcast: Product | Growth | Career
Entrepreneurship
Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.
Location:
United States
Description:
Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.
Language:
English
Episodes
Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann
7/20/2025
Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly.
In this conversation, we discuss:
1. The inside story of leaving OpenAI with the entire safety team to start Anthropic
2. How Meta’s $100M offers reveal the true market price of top AI talent
3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential
4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-2028
5. Why he believes 20% unemployment is inevitable
6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them
7. How focusing on AI safety created Claude’s beloved personality
8. What three skills he’s teaching his kids instead of traditional academics
—
Brought to you by:
Sauce—Turn customer pain into product revenue: https://sauce.app/lenny
LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny
Fin—The #1 AI agent for customer service: https://fin.ai/lenny
—
Transcript: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann
—
My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation
—
Where to find Ben Mann:
• X: https://x.com/8enmann
• LinkedIn: https://www.linkedin.com/in/benjamin-mann/
• Website: https://benjmann.net/
—
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 Benjamin
(04:43) The AI talent war
(06:28) AI progress and scaling laws
(10:50) Defining AGI and the economic Turing test
(12:26) The impact of AI on jobs
(17:45) Preparing for an AI future
(24:05) Founding Anthropic
(27:06) Balancing AI safety and progress
(29:10) Constitutional AI and model alignment
(34:21) The importance of AI safety
(43:40) The risks of autonomous agents
(45:40) Forecasting superintelligence
(48:36) How hard is it to align AI?
(53:19) Reinforcement learning from AI feedback (RLAIF)
(57:03) AI's biggest bottlenecks
(01:00:11) Personal reflections on responsibilities
(01:02:36) Anthropic’s growth and innovations
(01:07:48) Lightning round and final thoughts
—
Referenced:
• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/
• Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs
• Alexa+: https://www.amazon.com/dp/B0DCCNHWV5
• Azure: https://azure.microsoft.com/
• Sam Altman on X: https://x.com/sama
• Opus 3: https://www.anthropic.com/news/claude-3-family
• Claude’s Constitution: https://www.anthropic.com/news/claudes-constitution
• Greg Brockman on X: https://x.com/gdb
• Anthropic’s Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy
• Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff
• Unitree: https://www.unitree.com/
• Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke
• How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works
• RLHF:...
Duration:01:14:59
The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)
7/17/2025
Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work.
Learn:
1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S.
2. The most underrated AI tool for non-programmers
3. An inside look at Every’s AI-first workflow
4. Why every company needs an “AI operations lead”
5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths
6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools
7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools
—
Brought to you by:
CodeRabbit—Cut code review time and bugs in half. Instantly: https://www.coderabbit.ai/
DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny
PostHog—How developers build successful products: https://posthog.com/lenny
—
Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper
—
Where to find Dan Shipper:
• X: https://x.com/danshipper
• LinkedIn: https://www.linkedin.com/in/danshipper/
• Podcast: https://every.to/podcast
—
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) Welcome and introduction
(04:04) Hot takes on AI and job reshoring
(07:06) The power of Claude Code for non-coders
(14:35) The future of AI in business operations
(18:45) AI’s role in enhancing human skills
(22:26) The evolution of AI tools and their applications
(25:40) Building an AI-first company
(29:50) Innovative AI operations and team dynamics
(35:35) Dan's AI stack
(41:26) Compounding engineering
(48:29) The impact of AI on learning and development
(50:10) Accelerating career growth with AI
(51:36) Revolutionizing code review and workflow
(53:07) The importance of coding knowledge
(57:26) Building AI-driven products
(01:02:01) Innovative fundraising strategies
(01:08:45) Consulting and AI adoption in companies
(01:17:01) The allocation economy and future skills
(01:20:12) The value of generalists in the AI age
(01:24:07) Lightning round and final thoughts
—
Referenced:
• Claude Code: https://www.anthropic.com/claude-code
• Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/
• Microsoft Copilot: https://copilot.microsoft.com/
• Cursor: https://www.cursor.com/
• Base44: https://base44.com/
• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/
• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng
• Granola: https://www.granola.ai/
• Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify):...
Duration:01:34:57
Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital)
7/13/2025
Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days.
What you’ll learn:
1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately
2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team)
3. The three fundamental questions every founder should answer before writing a line of code
4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues
5. The seven “magic lenses” for choosing between multiple product ideas
6. The biggest mistake engineers make when building with AI tools
7. The paradox of speed: why “building nothing first” can get you to product-market fit faster
—
Brought to you by:
Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs
Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny
Coda—The all-in-one collaborative workspace: https://coda.io/lenny
—
Transcript: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky
—
Where to find Jake Knapp:
• X: https://twitter.com/jakek
• LinkedIn: https://www.linkedin.com/in/jake-knapp/
• Website: https://jakeknapp.com/
—
Where to find John Zeratsky:
• X: https://twitter.com/jazer
• LinkedIn: https://www.linkedin.com/in/johnzeratsky/
• Website: https://johnzeratsky.com/
—
In this episode, we cover:
(00:00) Introduction to Jake Knapp and John Zeratsky
(04:41) Origins of the Design Sprint
(11:06) The Foundation Sprint process
(14:40) Phase one: The basics
(16:57) Case study: Latchet
(28:50) Phase two: Differentiation
(36:24) The importance of differentiation
(40:15) Thoughts on price differentiation
(43:37) Case study: Mellow
(46:04) Custom differentiators
(49:30) The mini manifesto
(52:02) Phase three: Approach to the project
(54:50) Magic lenses activity
(01:02:39) Prototyping and testing
(01:10:00) Real-world examples and success stories
(01:15:15) Motivation behind The Foundation Sprint
(01:17:15) The outcome of the sprint: The founding hypothesis
(01:19:28) The Design Sprint
(01:28:19) The role of AI in prototyping
(01:36:50) Final thoughts and resources
—
Referenced:
• Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint
• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake
• Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/
• Character Capital: https://www.character.vc/
• Character Labs: https://www.character.vc/labs
• Etsy: https://www.etsy.com/
• Shopify: https://www.shopify.com/
• Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek
• Sonos: https://www.sonos.com/
• Vercel: https://vercel.com/
• Windsurf: https://windsurf.com/
• April Dunford on product positioning, segmentation, and optimizing your sales process:...
Duration:01:41:33
Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo
7/6/2025
Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a dollar of outside funding.
What you’ll learn:
1. The growth playbook that took Base44 from three friends to 400,000 users without spending any money on marketing
2. How he hasn’t written a single line of front-end code in three months—and how to structure your code repository to make it easier for AI to write your code
3. His AI productivity stack that allowed him to compete against heavily funded competitors
4. Why being a solo founder in AI might be the ultimate advantage (and the wedding story that almost killed the business)
5. The story of signing the $80M acquisition deal while war broke out with Iran
6. How to identify when to sell vs. stay independent (and why Maor chose acquisition despite being highly profitable)
7. The counterintuitive product decision that tripled activation by removing a “helpful” feature
8. How building in public on LinkedIn drove more growth than any paid channel
—
Brought to you by:
Sauce—Turn customer pain into product revenue
Dscout—The UX platform to capture insights at every stage: from ideation to production
Contentsquare—Create better digital experiences
—
Where to find Maor Shlomo:
• X: https://x.com/ms_base44
• LinkedIn: https://www.linkedin.com/in/maor-shlomo-1088b4144/
—
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 Maor and Base44
(08:16) The origin story: how Base44 came to be
(14:55) Bootstrapping and solo founding: challenges and insights
(22:52) Productivity hacks and tech stack for solo founders
(27:23) How to get started using Base44
(28:47) Thoughts on raising money
(34:05) Distribution in the age of AI
(36:09) Ambition and goals
(40:05) Growth strategies: from first users to thousands
(51:32) Building in public
(57:42) The solo founder journey
(01:00:23) Community support
(01:03:23) Hackathons and partnerships
(01:06:42) The importance of velocity in product development
(01:08:20) Technical stack and infrastructure insights
(01:15:24) Activation lessons
(01:18:19) The acquisition journey with Wix
(01:25:14) Final thoughts and advice for founders
—
Referenced:
• Base44: https://base44.com/
• Retool: https://retool.com/
• Tzofim: https://www.israelscouts.org/
• Y Combinator: https://www.ycombinator.com/
• RescueTime: https://www.rescuetime.com/
• Cursor: https://www.cursor.com/
• Wix: https://www.wix.com/
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Snowflake: https://www.snowflake.com
• Yoav Orlev on LinkedIn: https://www.linkedin.com/in/yoav-orlev-4a044b72
• WhatsApp: https://www.whatsapp.com/
• Amazon: https://www.amazon.com/
• Google:...
Duration:01:31:50
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
7/3/2025
Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital.
In this conversation, you’ll learn:
1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices
2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant)
3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”
4. Telltale signs you should shut down (or never start) that startup idea
5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication
6. His prediction that most knowledge work will be automated—and the skills to teach your kids now
—
Brought to you by:
Sauce—Turn customer pain into product revenue
Enterpret—Transform customer feedback into product growth
Miro—A collaborative visual platform where your best work comes to life
—
Where to find Andrew Wilkinson:
• X: https://x.com/awilkinson
• LinkedIn: https://www.linkedin.com/in/awilkinson/
—
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 Wilkinson
(04:07) Finding the right business idea
(07:18) Avoiding common business pitfalls
(11:58) Finding your unfair advantage
(17:08) Fish where the fish are
(20:08) Why boring is good
(25:30) Bootstrapping vs. venture capital
(31:20) Lessons from acquiring and managing businesses
(36:47) Avoiding people problems
(42:39) Leveraging AI in business and life
(49:30) The Limitless device
(53:13) Job displacement and AI’s future impact
(58:20) Advice for new grads
(01:02:50) Parenting in the age of AI
(01:05:26) The pursuit of happiness beyond wealth
(01:10:10) Mental health and medication
(01:16:45) Lightning round and final thoughts
—
Referenced:
• Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182
• Metalab: https://www.metalab.com/
• Letterboxd: https://letterboxd.com/
• AeroPress: https://aeropress.com/
• Brian Armstrong on X: https://x.com/brian_armstrong
• Warren Buffett’s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman
• Flow: https://www.getflow.com/
• Instacart: https://www.instacart.com/
• Things: https://culturedcode.com/things/
• Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/
• Salesforce: https://www.salesforce.com/
• Serato: https://serato.com/
• Chris Sparling on X: https://x.com/_sparling_
• Lindy: https://www.lindy.ai/
• Replit: https://replit.com/
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman)
• Malcolm Gladwell’s website: https://www.gladwellbooks.com/
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• Limitless: https://www.limitless.ai/
• Perplexity: https://www.perplexity.ai/
• Claude: https://claude.ai/
• ChatGPT: https://chatgpt.com/
• Gemini: https://gemini.google.com/app
• William Gibson’s quote:...
Duration:01:28:28
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding)
6/29/2025
David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft’s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel’s Pentium, Apple’s PowerBook, and Swiffer. Over 40 years, David’s team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation.
What you’ll learn:
1. The three-step process that generated names like Windsurf and Vercel
2. How a name can give you the edge that no marketing budget can buy
3. Why you won’t “know it when you see it”
4. Why Microsoft called Azure “a dumb name” before it became their billion-dollar cloud platform
5. Why polarizing opinions are the strongest signal that you’ve found the right name
6. How every letter of the alphabet creates a specific psychological vibration
7. The diamond framework: a 4-step process any founder can use to find their perfect name
8. Why domain names don’t matter anymore in the age of AI
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Stripe—Helping companies of all sizes grow revenue
OneSchema—Import CSV data 10x faster
—
Where to find David Placek:
• LinkedIn: https://www.linkedin.com/in/david-placek-05a82/
• Website: https://www.lexiconbranding.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 David and Lexicon Branding
(04:44) The story of Sonos
(09:27) The psychology of naming
(11:33) The initial resistance to Microsoft's Azure
(14:35) The importance of a great brand name
(18:11) The three steps of naming: create, invent, implement
(28:23) Qualities of great brand name creators
(31:24) How long the naming process takes
(32:12) The Windsurf case study
(36:10) Naming in the AI era
(39:37) When to change your name
(43:10) The role of linguists
(45:54) The power of letters in branding
(48:15) The Vercel case study
(50:12) The implementation phase
(52:52) Client management and market success
(55:16) The diamond exercise
(01:04:23) Suspending judgment
(01:07:31) Polarization and boldness
(01:11:01) Domain names
(01:12:48) Final thoughts and lightning round
—
Referenced:
• PowerBook: https://en.wikipedia.org/wiki/PowerBook
• Pentium: https://en.wikipedia.org/wiki/Pentium
• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry
• Swiffer: https://www.swiffer.com/
• Impossible Burger: https://impossiblefoods.com/
• Vercel: https://vercel.com/
• Windsurf: https://windsurf.com/
• CapCut: https://www.capcut.com/
• Azure: https://azure.microsoft.com/
• Sonos: https://www.sonos.com/
• John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/
• Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series)
• The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism
• Anduril: https://www.anduril.com/
• Anthropic: https://www.anthropic.com/
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and...
Duration:01:22:43
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng
6/22/2025
Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook’s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he’s investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech’s most iconic products and companies.
What you’ll learn:
1. Peter’s one‑sentence test for hiring superstars
2. Why your product (probably) doesn’t matter
3. Why you don’t need a tech breakthrough to build a huge business
4. The five PM archetypes, and how to build a team of Avengers
5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 100
6. The importance of data flywheels and workflows
—
Brought to you by:
Paragon—Ship every SaaS integration your customers want
Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications
Contentsquare—Create better digital experiences
—
Where to find Peter Deng:
• X: https://x.com/pxd
• LinkedIn: https://www.linkedin.com/in/peterxdeng/
—
In this episode, we cover:
(00:00) Introduction to Peter Deng
(05:41) AI and AGI insights
(11:35) The future of education with AI
(16:53) The power of language in leadership
(21:01) Building iconic products
(36:44) Scaling from zero to 100
(41:56) Balancing short- and long-term goals
(47:12) Creating a healthy tension in teams
(50:02) The five archetypes of product managers
(55:39) Primary and secondary archetypes
(58:47) Hiring for growth mindset and autonomy
(01:15:52) Effective management and communication strategies
(01:19:23) Presentation advice and self-advocacy
(01:25:50) Balancing craft and practicality in product management
(01:30:40) The importance of empathy in design thinking
(01:35:45) Career decisions and learning opportunities
(01:42:05) Lessons from product failures
(01:45:42) Lightning round and final thoughts
—
Referenced:
• OpenAI: https://openai.com/
• Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence
• Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire’s Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw
• Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What
• Herbert H. Clark: https://web.stanford.edu/~clark/
• Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/
• Ilya Sutskever (OpenAI Chief Scientist)—Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/
• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan
• Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• Granola: https://www.granola.ai/
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• OpenAI’s CPO on how AI...
Duration:01:55:28
AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)
6/19/2025
Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn’t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques.
In this episode, you’ll learn:
1. The 5 most effective prompt engineering techniques
2. Why “role prompting” and threatening the AI no longer works—and what to do instead
3. The two types of prompt engineering: conversational and product/system prompts
4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models
5. Why AI agents and robots will be the next major security threat
6. How to get started in AI red teaming and prompt engineering
7. Practical defense to put in place for your AI products
—
Brought to you by:
Eppo—Run reliable, impactful experiments
Stripe—Helping companies of all sizes grow revenue
Vanta—Automate compliance. Simplify security
—
Where to find Sander Schulhoff:
• X: https://x.com/sanderschulhoff
• LinkedIn: https://www.linkedin.com/in/sander-schulhoff/
• Website: https://sanderschulhoff.com/
• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC
• Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Sander Schulhoff
(04:29) The importance of prompt engineering
(06:30) Real-world applications and examples
(10:54) Basic prompt engineering techniques
(23:46) Advanced prompt engineering techniques
(29:00) The role of context and additional information
(39:24) Ensembling techniques and thought generation
(49:48) Conversational techniques for better results
(50:46) Introduction to prompt injection
(52:27) AI red teaming and competitions
(54:23) The growing importance of AI security
(01:02:45) Techniques to bypass AI safeguards
(01:05:21) Challenges in AI security and future outlook
(01:18:33) Misalignment and AI's potential risks
(01:25:03) Final thoughts and lightning round
—
Referenced:
• Reid Hoffman’s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822
• AI Engineer World’s Fair: https://www.ai.engineer/
• What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi
• Devin: https://devin.ai/
• Cursor: https://www.cursor.com/
• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• Granola: https://www.granola.ai/
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Behind the product: Replit | Amjad Masad (co-founder and CEO):...
Duration:01:37:46
How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)
6/15/2025
Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox.
In this episode, you’ll learn:
• How to teach your team to be able to “take a punch”
• Specific tactics to counter negative perceptions and reframe setbacks productively
• Powerful behavioral strategies to form positive habits
• Practical approaches for creating space in your workday to encourage creativity and deep thinking
• The underestimated potential of AI in accelerating your personal and professional growth
• Why you’re not the protagonist at your company (and why that’s liberating)
• How WHOOP uses reward loops to drive real behavior change
—
Brought to you by:
WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
Persona—A global leader in digital identity verification
Attio—The powerful, flexible CRM for fast-growing startups
—
Where to find Hilary Gridley:
• X: https://x.com/yourgirlhils
• LinkedIn: https://www.linkedin.com/in/hilarygridley/
• Newsletter: https://hils.substack.com/
• Maven course: https://maven.com/hilary-gridley/ai-powered-people-management
—
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) Hilary’s background
(04:31) Teaching teams to handle criticism and setbacks
(17:57) Behavioral activation and mental health in the workplace
(22:59) The importance of putting yourself out there
(27:51) Transparency and communication in leadership
(38:10) How to respectfully disagree with your manager
(41:49) How to use “magic questions” to decode how people think
(49:54) Why you’re not the protagonist at your company
(52:48) Aligning with the CEO's vision
(01:01:02) Building effective habits
(01:11:14) Promoting team well-being
(01:14:28) Creating space for creativity
(01:20:45) AI’s role in accelerating learning
(01:30:35) Pivotal career moments
(01:37:21) Lessons from failure
(01:39:49) Exciting new features of WHOOP 5.0
(01:44:19) Lightning round and final thoughts
—
Referenced:
• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with
• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager
• WHOOP: https://www.whoop.com/
• Big Health: https://www.bighealth.com/
• What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation
• Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/
• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/
• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/
• Coinbase: https://www.coinbase.com/
• Bridge: https://www.bridge.xyz/
• Stripe: https://stripe.com/
• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer
• Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf
• VO₂ max: https://en.wikipedia.org/wiki/VO2_max
• Peter Attia on X: https://x.com/PeterAttiaMD
• Hilary Gridley’s 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0
• The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown
• From chalkboards to chatbots: Transforming learning in Nigeria,...
Duration:01:54:39
35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley
6/12/2025
Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.
What you’ll learn:
• Why design should report to engineering, not product
• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60
• How to create design tenets vs. principles (with real examples)
• The counterintuitive reason to delay drawing or prototyping as long as possible
• Why software is fundamentally a medium, like film or music (not just a tool)
• Why Bob “bounced off the culture” at Pinterest, and lessons from failure
• The lunar landing story that teaches us about championing radical ideas
• How to evaluate if a company truly values design before joining
• The moral obligation of software makers to build great products
—
This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.
—
Where to find Bob Baxley:
• Instagram: https://www.instagram.com/baxley/
• LinkedIn: https://www.linkedin.com/in/bbaxley/
• Website: http://www.bobbaxley.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 Bob Baxley
(03:52) Apple's lasting culture
(06:15) Navigating unique company cultures
(13:19) Finding a company that truly values your role
(15:46) What is design?
(17:17) How to help founders understand the value of design
(23:08) How to align product managers and designers
(26:31) Design reporting to engineering
(30:54) Integrating engineers early in the design process
(33:43) The maker mindset
(35:14) Challenging the assumption that design is time-intensive
(38:04) Design tenets vs. design principles
(45:25) The moral obligation of great design
(51:48) Understanding software as a medium
(01:01:20) Reducing ambiguity for product teams
(01:07:04) Giving designers space for creativity
(01:08:48) The "primal mark" concept
(01:12:05) AI prototyping tools: benefits and risks
(01:17:00) AI as a life coach
(01:21:22) Life lessons from the Apollo program
(01:28:24) Lightning round and final thoughts
—
Referenced:
• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs
• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney
• Pinterest: https://www.pinterest.com/
• X: https://x.com/
• Uber: https://www.uber.com/
• Airbnb: https://www.airbnb.com/
• Slack: https://slack.com/
• Ed Catmull on X: https://x.com/edcatmull
• John Lasseter on X: https://x.com/johnlasseter5
• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on
• Humane: https://en.wikipedia.org/wiki/Humane_Inc.
• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive
• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/
• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/
• Tim Cook on X: https://x.com/tim_cook
• ThoughtSpot: https://www.thoughtspot.com/
• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/
• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/
• Honeywell: https://www.honeywell.com
• IDEO: https://www.ideo.com/
• Nutanix: https://www.nutanix.com/
• Lego: https://www.lego.com/
• Leica: https://leica-camera.com/
• Porsche: https://www.porsche.com/
• Patagonia: https://www.patagonia.com
• Brian Eno’s website: https://www.brian-eno.net/
• Scenius: why...
Duration:01:41:59
How Mercado Libre built Latin America's most valuable company: 18k engineers, 30k deploys a day, and their own fleet of planes | Sebastian Barrios
6/8/2025
Sebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees. There, he led a team of more than 18,000 engineers across 18 countries and oversaw an astonishing 30,000 code deployments a day. Before Mercado Libre, he founded multiple startups, including a ridesharing company that competed directly with Uber in Latin America. And at just 17, he got a personal phone call from Steve Jobs asking him to take his app off the App Store. Today, Sebastian is the SVP of Engineering at Roblox.
What you’ll learn:
• Why Mercado Libre operates with 95% fewer PMs than typical tech companies (and how it actually works)
• How to maintain product quality with 30,000 daily deployments and distributed ownership
• The weekly email system Sebastian uses to maintain alignment with leadership
• How to build a culture of radical candor and direct feedback in a traditionally hierarchical region
• The counterintuitive approach to product reviews that keeps 18,000 engineers aligned
• How to evaluate hype cycles (crypto, AI) pragmatically while staying innovative
—
Brought to you by:
Merge—A single API to add hundreds of integrations into your app
Vanta—Automate compliance. Simplify security
LinkedIn Ads—Reach professionals and drive results for your business
—
Where to find Sebastian Barrios:
• LinkedIn: https://www.linkedin.com/in/zebas/
—
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 Sebastian Barrios and Mercado Libre
(05:03) Mercado Libre’s scale and unique ways of operating
(14:48) AI’s impact on operations
(19:19) Empowering teams and reducing fear of failure
(34:20) The importance of radical candor
(38:26) Weekly updates
(41:03) Avoiding hype cycles
(44:24) When Steve Jobs personally called 17-year-old Sebastian
(49:00) Building successful app businesses
(55:33) Unique personal habits
(01:04:00) Raising independent children
(01:07:15) Lightning round and final thoughts
—
Referenced:
• Mercado Libre: https://www.mercadolibre.com/
• Claude: https://claude.ai/
• Salesforce: https://www.salesforce.com/
• Nvidia: https://www.nvidia.com/
• TikTok: https://www.tiktok.com/
• Adobe: https://www.adobe.com/
• Uber: https://www.uber.com/
• OpenAI: https://openai.com/
• Marcos Galperin on LinkedIn: https://www.linkedin.com/in/marcosgalperin/
• Cursor: https://www.cursor.com/
• Windsurf: https://windsurf.com/
• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best
• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm
• How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers
• Intercom: https://www.intercom.com/
• Atlassian: https://www.atlassian.com/
• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice
• Managing up: https://www.lennysnewsletter.com/p/managing-up
• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook
• Everything Everywhere All at Once: https://www.imdb.com/title/tt6710474/
• Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7
• Bluey on Disney+: https://www.disneyplus.com/browse/entity-fa6973b9-e7cf-49fb-81a2-d4908e4bf694
•...
Duration:01:19:25
Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)
6/5/2025
Mike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024.
In this episode, you'll learn:
• How Anthropic uses AI to write 90-95% of code for some products and the surprising new bottlenecks this creates
• Why embedding product managers with AI researchers yields 10x the impact of traditional product development
• The three areas where product teams can still add massive value as AI gets smarter
• How Anthropic plans to compete with OpenAI long-term
• How to use Claude as your product strategy partner (with specific prompting techniques)
• Why Mike shut down Artifact despite loving the product, and what founders can learn from it
• Where AI startups should build to avoid getting killed by OpenAI, Anthropic, and Google
• Why MCP (Model Context Protocol) might reshape how all software works
• The counterintuitive product metrics that matter for AI
• How to evaluate whether your company is maximizing AI’s potential or just scratching the surface
—
Brought to you by:
Productboard—Make products that matter
Stripe—Helping companies of all sizes grow revenue
OneSchema—Import CSV data 10x faster
—
Where to find Mike Krieger:
• X: https://x.com/mikeyk
• LinkedIn: https://www.linkedin.com/in/mikekrieger/
—
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 Mike Krieger
(04:20) What Mike has changed his mind about regarding AI capabilities
(07:38) How to avoid scary AI scenarios
(08:55) Skills kids will need in an AI world
(11:53) How product development changes when 90% of code is written by AI
(17:07) Claude helping with product strategy
(21:16) A new way of working
(23:55) The future value of product teams in an AI world
(27:18) Prompting tricks to get more out of Claude
(29:52) The Rick Rubin collaboration on “vibe coding”
(32:42) How Mike was recruited to Anthropic
(35:55) Why Mike shut down Artifact
(42:41) Anthropic vs. OpenAI
(47:11) Where AI founders should play to avoid getting squashed
(51:58) How companies can best leverage Anthropic’s models and APIs
(54:29) The role of MCPs (Model Context Protocols)
(58:25) Claude’s questions for Mike
(01:03:15) Claude’s heartfelt message to Mike
—
Referenced:
• Anthropic: https://www.anthropic.com/
• Claude Opus 4: https://www.anthropic.com/claude/opus
• Dario Amodei on X: https://x.com/darioamodei
• AI 2027: https://ai-2027.com/
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook
• Claude Shannon: https://en.wikipedia.org/wiki/Claude_Shannon
• Information theory: https://en.wikipedia.org/wiki/Information_theory
• TypeScript: https://www.typescriptlang.org/
• Python: https://www.python.org/
• Rust: https://www.rust-lang.org/
• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor
• Announcing a brand-new podcast: “How I AI” with Claire Vo: https://www.lennysnewsletter.com/p/announcing-a-brand-new-podcast-how
• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k
• Jack Clark on LinkedIn: https://www.linkedin.com/in/jack-clark-5a320317/
• Artifact: https://en.wikipedia.org/wiki/Artifact_(app)
• Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein/
• Daniela Amodei on LinkedIn: https://www.linkedin.com/in/daniela-amodei-790bb22a/
• Boris Cherny on LinkedIn: https://www.linkedin.com/in/bcherny/
• Gunnar Gray on LinkedIn:...
Duration:01:06:18
Why Uber’s CPO delivers food on weekends | Sachin Kansal
6/1/2025
Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber’s global teams.
What you will learn:
1. Dogfooding at scale
2. “Ship, ship, ship” as a cultural mantra
3. Obsession with inputs over outputs
4. Uber’s hybrid marketplace vision for autonomy
5. How Uber changed its culture to focus on profitability
6. What to do when data says “no” but your gut says “yes”
7. Career advice: maximize cycles
8. AI as a research assistant, not an oracle
9. Uber rider etiquette tips
—
Brought to you by:
• Paragon—Ship every SaaS integration your customers want
• Stripe—Financial infrastructure to grow your revenue
• Coda—The all-in-one collaborative workspace
—
Where to find Sachin Kansal:
• LinkedIn: https://www.linkedin.com/in/sachinkansal/
—
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) Sachin’s background
(05:00) Dogfooding in practice
(11:24) Empathy and understanding drivers
(20:18) Balancing metrics and user experience
(22:04) Operationalizing dogfooding
(24:26) Challenges and solutions in dogfooding
(29:49) The motto: “ship, ship, ship”
(36:37) Product announcements and live demos
(40:49) Career advice for product managers
(43:51) The evolution of product management with AI
(46:55) Collaboration between engineers and product managers
(49:36) Uber’s vision for self-driving cars
(55:59) Uber’s path to profitability
(01:01:58) Balancing data and gut decisions
(01:07:21) AI tools in product management
(01:10:14) Failure corner
(01:13:48) Lightning round and final thoughts
—
Referenced:
• Uber: https://www.uber.com/
• Oracle: https://www.oracle.com/
• Snowflake: https://www.snowflake.com/en/
• Fivetran: https://go.fivetran.com/
• Uber for Business: https://www.uber.com/us/en/business
• McDonald’s: https://www.mcdonalds.com/
• Domino’s: https://www.dominos.com
• PalmPilot: https://en.wikipedia.org/wiki/PalmPilot
• Praveen Neppalli Naga on LinkedIn: https://www.linkedin.com/in/pneppalli/
• May Mobility: https://maymobility.com/
• Uber strikes deal with May Mobility to deploy ‘thousands’ of robotaxis: https://www.theverge.com/news/659563/uber-may-mobility-autonomous-ridehail-partnership
• Waymo: https://waymo.com/
• WeRide: https://www.weride.ai/
• Uber and Avride Announce Autonomous Delivery and Mobility Partnership: https://investor.uber.com/news-events/news/press-release-details/2024/Uber-and-Avride-Announce-Autonomous-Delivery-and-Mobility-Partnership/default.aspx
• Dara Khosrowshahi on X: https://x.com/dkhos
• Uber Elevate: https://www.uber.com/us/en/elevate/vision/
• Uber AV: https://www.uber.com/us/en/autonomous/
• Uber Reserve: https://www.uber.com/us/en/ride/how-it-works/reserve/
• Uber for teens: https://www.uber.com/us/en/ride/teens/
• Flywheel: https://www.flywheel.com/
• ChatGPT: https://chatgpt.com/
• Gemini: https://gemini.google.com/app
• NotebookLM: https://notebooklm.google/
• Behind the product: NotebookLM | Raiza Martin (Senior Product Manager, AI @ Google Labs): https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin
• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry
• Peaky Blinders on Netflix: https://www.netflix.com/title/80002479
• Deep research: https://openai.com/index/introducing-deep-research/
—
Recommended books:
• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies:...
Duration:01:21:57
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman
5/25/2025
Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing.
What you will learn:
1. Why do most marketing playbooks often fail, and what’s a better way?
2. Which marketing lever should I pull first?
3. Why is trying to be better than competitors usually a losing strategy?
4. How do I craft positioning that actually converts?
5. What makes messaging stick with developers, enterprises, and consumers?
6. What pricing experiments actually move revenue?
7. What is working at OpenAI really like?
8. Why does consistency and quality matter more than speed?
—
Brought to you by:
Eppo — Run reliable, impactful experiments
Airtable ProductCentral—Launch to new heights with a unified system for product development
LinkedIn Ads—Reach professionals and drive results for your business
—
Where to find Krithika Shankarraman:
• X: https://x.com/krithix
• LinkedIn: https://www.linkedin.com/in/krithix/
• Website: https://krithix.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 Krithika
(04:22) Early marketing lessons from OpenAI
(11:17) Diagnosing marketing needs
(15:06) The DATE framework and why being cheaper is a race to the bottom
(17:11) Marketing strategies at Retool
(22:29) Insights from marketing at Stripe
(32:33) The importance of consistent marketing communication
(39:55) Criteria for hiring a marketing expert
(41:43) “Capital M” vs. “lowercase m” marketing
(43:05) ChatGPT vs. Claude: market dominance
(45:31) The future of AI and its societal impact
(47:09) Work-life balance
(48:41) Transitioning to Thrive
(52:35) Career advice for marketers
(55:00) The importance of taste and creativity in the AI era
(01:00:04) AI product pricing
(01:03:21) AI tools in marketing
(01:05:17) Failure corner
(01:08:46) Lightning round and final thoughts
—
Referenced:
• OpenAI: https://openai.com/
• Stripe: https://stripe.com/
• Retool: https://retool.com/
• Dropbox: https://www.dropbox.com/
• Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew
• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan
• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy
• Netflix: https://www.netflix.com/
• Stripe Connect: https://stripe.com/connect
• John Collison on X: https://x.com/collision
• Patrick Collison on X: https://x.com/patrickc
• Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/
• Hackpad: https://en.wikipedia.org/wiki/Hackpad
• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg
• Wiz: https://www.wiz.io/
• Thrive Capital: https://thrivecap.com/
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Claude: https://claude.ai/new
• ChatGPT: https://chatgpt.com/
• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics
• Databricks: https://www.databricks.com/
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel,...
Duration:01:14:02
Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product)
5/22/2025
Mayur Kamat is the chief product officer at N26—a $9 billion neobank serving over 7 million customers in 25 countries—where he leads product, design, data, and research. Prior to N26, Mayur was Head of Product at Binance, growing the crypto exchange to a peak $400 billion valuation. Earlier in his career, he built and scaled products at Google (Gmail Mobile, Hangouts), Microsoft, and travel unicorn Agoda.
Learn:
1. How to find and focus on the highest-leverage problems
2. Why you shouldn’t optimize for compensation early in your career
3. Why you should optimize for strengths, not weaknesses
4. Why you need to decide if you truly want the C-suite path
5. Why working at a fintech company creates exceptional PMs
6. Strategy = hypothesis × experimentation velocity
7. Small, fast wins compound faster than big, slow bets
—
Brought to you by:
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Paragon—Ship every SaaS integration your customers want
• Vanta—Automate compliance. Simplify security.
—
Where to find Mayur Kamat:
• X: https://x.com/5degreez
• LinkedIn: https://www.linkedin.com/in/mayur/
—
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 Mayur’s background
(04:49) Working at Binance: An inside look
(18:18) Career advice for product managers
(27:00) PM career paths
(33:58) Understanding fintech customers
(36:00) Understanding your strengths
(44:46) Creating a culture of experimentation
(51:14) Hiring and developing top talent
(54:50) Building a diverse product portfolio
(57:08) Working in high talent density areas
(59:43) Personal and professional balance
(01:06:32) High-leverage opportunities and decision making
(01:14:28) AI tools in the workplace
(01:19:14) Failure corner
(01:25:11) Lightning round and final thoughts
—
Referenced:
• Binance: https://www.binance.us/
• Google: https://about.google/
• Microsoft: https://www.microsoft.com/
• Agoda: https://www.agoda.com
• N26: https://n26.com/
• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm
• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best
• Bezos Says Work-Life Balance is a “Debilitating” Phrase: https://www.investopedia.com/news/bezos-says-worklife-balance-debilitating-phrase/
• Maslow’s Hierarchy of Needs: https://www.simplypsychology.org/maslow.html
• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia
• Changpeng Zhao on LinkedIn: https://www.linkedin.com/in/cpzhao/
• Ray Dalio on LinkedIn: https://www.linkedin.com/in/raydalio/
• Porter’s five forces: https://en.wikipedia.org/wiki/Porter%27s_five_forces_analysis
• Jonathan Rosenberg on X: https://x.com/jjrosenberg
• Aura: https://buy.aura.com/
• Intercom: https://www.intercom.com/
• Palantir: https://www.palantir.com/
• Revolut: https://www.revolut.com/
• Chime: https://www.chime.com/
• Stripe: https://stripe.com/
• Dropbox: https://www.dropbox.com/
• Alex Algard on LinkedIn: https://www.linkedin.com/in/alexalgard
• Hiya: https://www.hiya.com/
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Gemini: https://gemini.google.com/app
• Writer: https://writer.com/
• Google Hangouts: https://en.wikipedia.org/wiki/Google_Hangouts
• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/
• Google Meet: https://meet.google.com/landing
• House on Hulu: https://www.hulu.com/series/ef39603f-eb90-4248-8237-f6168d7c1be1
• Big Bang Theory on Hulu: https://www.hulu.com/series/9bde5aeb-5297-4290-b173-19a4d59cc11d
• Adolescence on Netflix: https://www.netflix.com/title/81756069
• The White Lotus on HBO: https://www.hbo.com/the-white-lotus
• Robinhood:...
Duration:01:37:56
Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada
5/18/2025
Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One.
What you’ll learn:
1. How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product development
2. The three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat)
3. Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfaces
4. Why the PM role isn’t dying in the AI era—it’s evolving to emphasize tastemaking and editing
5. How living “one year in the future” can be operationalized with programs like Microsoft’s Frontier
6. How even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approaches
7. Insights on leadership differences between Microsoft’s Satya Nadella (known for multi-level thinking and early trendspotting) and Google’s Sundar Pichai (mastery of complex ecosystems)
8. The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could alone
9. A practical framework for evaluating zero-to-one product opportunities
—
Brought to you by:
Eppo—Run reliable, impactful experiments
Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications
Coda—The all-in-one collaborative workspace
—
Where to find Aparna Chennapragada:
• X: https://x.com/aparnacd
• LinkedIn: https://www.linkedin.com/in/aparnacd/
—
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 Aparna Chennapragada
(04:28) Aparna’s stand-up comedy journey
(07:29) Transition to Microsoft and enterprise insights
(10:00) The Frontier program and AI integration
(13:28) Understanding AI agents
(17:59) NLX is the new UX
(22:28) The future of product development
(31:16) Building a custom Chrome extension
(35:45) Leadership styles of Satya and Sundar
(37:47) Counterintuitive lessons in product building
(41:20) Inflection points for successful products
(45:16) GitHub Copilot and code generation
(48:34) Excel’s enduring success
(50:27) Pivotal career moments
(54:55) The future of human-agent collaboration
(56:25) Lightning round and final thoughts
—
Referenced:
• Google Lens: https://lens.google/
• Saturday Night Live: https://www.nbc.com/saturday-night-live
• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/
• Robinhood: https://robinhood.com/
• eBay: https://www.ebay.com/
• Capital One: https://www.capitalone.com/
• Microsoft: https://www.microsoft.com/
• Aparna’s LinkedIn post about enterprise vs. consumer: https://www.linkedin.com/posts/aparnacd_every-enterprise-user-feature-has-a-shadow-activity-7321176091610542080-8X-E/
• The Epic Split: https://en.wikipedia.org/wiki/The_Epic_Split
• AI Frontiers: https://www.microsoft.com/en-us/research/lab/ai-frontiers/
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai
• Deepseek: https://www.deepseek.com/
• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook
• Tobi Lütke’s post on X about reflexive AI: https://x.com/tobi/status/1909251946235437514
• GitHub Copilot:...
Duration:01:01:12
How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product)
5/15/2025
Dmitry Zlokazov is the head of product at Revolut, the $45 billion fintech giant operating in over 50 countries, serving more than 50 million customers, and producing some of the world’s top product leaders. Dmitry shares his hard-won lessons, contrarian org design principles, and day-to-day practices that power Revolut’s relentless shipping velocity, culture of ownership, and unparalleled “wow” product experience.
What you’ll learn:
1. Revolut’s unique organizational approach, where “product owners” manage cross-functional pods as “local CEOs,” with genuine end-to-end ownership and hiring/firing power
2. How a radical, ultra-flat structure enables more than 150 product owners to maintain founder-level quality and velocity across dozens of parallel launches
3. How Revolut maintains quality while shipping hundreds of features across over 50 countries
4. Why Revolut favors “raw intellect and hunger” over experience, and how internal transfers (including ex-engineers and ops managers) become the company’s most successful product leaders
5. How Revolut’s founders review every single UI shipped, and why this founder detail obsession scales rather than limits innovation
6. Their framework for launching new products—from ideation, validation, and first user cohort to rapid “algorithmization” and scaling across countries
7. The importance of treating products that are 99% done as closer to 0% done, vs. 100% done
—
This entire episode is brought to you by Stripe—Helping companies of all sizes grow revenue.
—
Where to find Dmitry Zlokazov:
• X: https://x.com/Dzlokazov
• LinkedIn: https://www.linkedin.com/in/zlokazov/
—
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 Dmitry and Revolut
(03:41) Revolut’s unique approach to product management
(06:58) The role and responsibilities of product owners
(09:28) Types of product owners at Revolut
(15:50) Building “wow” products
(25:00) Hiring practices
(31:33) Managing teams and projects
(41:07) Revolut’s diverse product offerings
(44:40) Scaling new products successfully
(52:10) Attracting top talent
(58:43) Failure corner
(01:02:49) Lightning round and final thoughts
—
Referenced:
• Revolut: https://www.revolut.com/
• Intercom: https://www.intercom.com/
• Palantir: https://www.palantir.com/
• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best
• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm
• Deliver WOW to our customers: https://www.revolut.com/blog/post/deliver-wow/
• Nik Storonsky on LinkedIn: https://www.linkedin.com/in/nstoronsky
• Vlad Yatsenko on LinkedIn: https://www.linkedin.com/in/yatsenko/
• How Palantir built the ultimate founder factory | Nabeel S. Qureshi (entrepreneur and writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi
• Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product
• Gokul Rajaram on X: https://x.com/gokulr
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Schlep blindness: https://www.paulgraham.com/schlep.html
• Revolut Launches RevPoints Loyalty Programme, Turning Daily Expenses into Exclusive Rewards: https://www.revolut.com/news/revolut_launches_revpoints_loyalty_programme_turning_daily_expenses_into_exclusive_rewards/
• Gemini: https://gemini.google.com/
• ChatGPT: https://chatgpt.com/
• Figma: https://www.figma.com/
• Oppenheimer: https://www.imdb.com/title/tt15398776/
• Manus: https://manus.im/
• Eisenhower...
Duration:01:10:02
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)
5/11/2025
Nabeel Qureshi is an entrepreneur, writer, researcher, and visiting scholar of AI policy at the Mercatus Center (alongside Tyler Cowen). Previously, he spent nearly eight years at Palantir, working as a forward-deployed engineer. His work at Palantir ranged from accelerating the Covid-19 response to applying AI to drug discovery to optimizing aircraft manufacturing at Airbus. Nabeel was also a founding employee and VP of business development at GoCardless, a leading European fintech unicorn.
What you’ll learn:
• Why almost a third of all Palantir’s PMs go on to start companies
• How the “forward-deployed engineer” model works and why it creates exceptional product leaders
• How Palantir transformed from a “sparkling Accenture” into a $200 billion data/software platform company with more than 80% margins
• The unconventional hiring approach that screens for independent-minded, intellectually curious, and highly competitive people
• Why the company intentionally avoids traditional titles and career ladders—and what they do instead
• Why they built an ontology-first data platform that LLMs love
• How Palantir’s controversial “bat signal” recruiting strategy filtered for specific talent types
• The moral case for working at a company like Palantir
—
Brought to you by:
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Attio—The powerful, flexible CRM for fast-growing startups
• OneSchema—Import CSV data 10x faster
—
Where to find Nabeel S. Qureshi:
• X: https://x.com/nabeelqu
• LinkedIn: https://www.linkedin.com/in/nabeelqu/
• Website: https://nabeelqu.co/
—
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 Nabeel S. Qureshi
(05:10) Palantir’s unique culture and hiring
(13:29) What Palantir looks for in people
(16:14) Why they don't have titles
(19:11) Forward-deployed engineers at Palantir
(25:23) Key principles of Palantir's success
(30:00) Gotham and Foundry
(36:58) The ontology concept
(38:02) Life as a forward-deployed engineer
(41:36) Balancing custom solutions and product vision
(46:36) Advice on how to implement forward-deployed engineers
(50:41) The current state of forward-deployed engineers at Palantir
(53:15) The power of ingesting, cleaning and analyzing data
(59:25) Hiring for mission-driven startups
(01:05:30) What makes Palantir PMs different
(01:10:00) The moral question of Palantir
(01:16:03) Advice for new startups
(01:21:12) AI corner
(01:24:00) Contrarian corner
(01:25:42) Lightning round and final thoughts
—
Referenced:
• Reflections on Palantir: https://nabeelqu.co/reflections-on-palantir
• Palantir: https://www.palantir.com/
• Intercom: https://www.intercom.com/
• Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best
• Gotham: https://www.palantir.com/platforms/gotham/
• Foundry: https://www.palantir.com/platforms/foundry/
• Peter Thiel on X: https://x.com/peterthiel
• Alex Karp: https://en.wikipedia.org/wiki/Alex_Karp
• Stephen Cohen: https://en.wikipedia.org/wiki/Stephen_Cohen_(entrepreneur)
• Joe Lonsdale on LinkedIn: https://www.linkedin.com/in/jtlonsdale/
• Tyler Cowen’s website: https://tylercowen.com/
• This Scandinavian City Just Won the Internet With Its Hilarious New Tourism Ad: https://www.afar.com/magazine/oslos-new-tourism-ad-becomes-viral-hit
• Safe Superintelligence: https://ssi.inc/
• Mira Murati on X: https://x.com/miramurati
• Stripe: https://stripe.com/
• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein
• Airbus: https://www.airbus.com/en
• NIH: https://www.nih.gov/
• Jupyter Notebooks: https://jupyter.org/
• Shyam Sankar on LinkedIn:...
Duration:01:37:29
How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)
5/8/2025
Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.
In our conversation, we cover:
1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”
2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience
3. Why teams most often fail (hint: it’s not lack of talent or strategy)
4. How busyness often masks deeper issues of self-worth
5. Why a “growth mindset” can be problematic
6. The importance of legacy and what it means to live a meaningful life
7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots
8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity
—
Brought to you by:
Eppo—Run reliable, impactful experiments
Contentsquare—Create better digital experiences
OneSchema—Import CSV data 10x faster
—
Where to find Jerry Colonna:
• X: https://x.com/jerrycolonna
• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/
• Website: https://reunion.reboot.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 Jerry Colonna
(04:12) Jerry’s key question
(06:55) The equation for great leadership
(09:37) The big lie of success and happiness
(12:12) The consciousness hack
(15:56) Getting over the fear of consequences
(20:23) The problem with bypassing our childhood baggage
(23:22) Radical self-inquiry: asking the tough questions
(27:05) Shared experiences: the power of community
(30:25) The trap of busyness and attachment
(40:45) Understanding our own intentions
(46:58) Legacy and purpose
(55:43) Writing for self-discovery
(57:12) The impact of AI on humanity
(01:05:00) Turning a growth mindset into a fixed mindset
(01:11:30) The role of radical self-inquiry in leadership
(01:19:24) Final thoughts and reflections
—
Referenced:
• Naropa University: https://www.naropa.edu/
• Fitler Club: https://fitlerclub.com
• Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/
• Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired’: https://www.today.com/popculture/news/will-smith-fame-rcna127830
• Seth Godin’s best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products
• The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism
• 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821
• Simon Sinek’s website: https://simonsinek.com/
• Mike Tyson Gives Morbid Response to Young Interviewer’s Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/
• Dan Shipper’s post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318
• Evernote: https://evernote.com/
• Claude: https://claude.ai
• Peter Senge on X: https://x.com/petersenge
• Carl Jung’s quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your
• Parker Palmer on LinkedIn:...
Duration:01:22:49
Inside Devin: The world’s first autonomous AI engineer that's set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition)
5/4/2025
Scott Wu is the co-founder and CEO of Cognition, the company behind Devin—the world’s first autonomous AI software engineer. Unlike other AI coding tools, Devin works like an autonomous engineer that you can interact with through Slack, Linear, and GitHub, just like with a remote engineer. With Scott’s background in competitive programming and a previous AI-powered startup, Lunchclub, teaching AI to code has become his ultimate passion.What you’ll learn:
1. How a team of “Devins” are already producing 25% of Cognition’s pull requests, and they are on track to hit 50% by year’s end
2. How each engineer on Cognition’s 15-person engineering team works with about five Devins each
3. How Devin has evolved from a “high school CS student” to a “junior engineer” over the past year
4. Why engineering will shift from “bricklayers” to “architects”
5. Why AI tools will lead to more engineering jobs rather than fewer
6. How Devin creates its own wiki to understand and document complex codebases
7. The eight pivots Cognition went through before landing on their current approach
8. The cultural shifts required to successfully adopt AI engineers
—
Brought to you by:
Enterpret—Transform customer feedback into product growth
Paragon—Ship every SaaS integration your customers want
Attio—The powerful, flexible CRM for fast-growing startups
—
Where to find Scott Wu:
• X: https://x.com/scottwu46
• LinkedIn: https://www.linkedin.com/in/scott-wu-8b94ab96/
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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 Scott Wu and Devin
(09:13) Scaling and future prospects
(10:23) Devin's origin story
(17:26) The idea of Devin as a person
(22:19) How a team of “Devins” are already producing 25% of Cognition’s pull requests
(25:17) Important skills in the AI era
(30:21) How Cognition’s engineering team works with Devin's
(34:37) Live demo
(42:20) Devin’s codebase integration
(44:50) Automation with Linear
(46:53) What Devin does best
(52:56) The future of AI in software engineering
(57:13) Moats and stickiness in AI
(01:01:57) The tech that enables Devin
(01:04:14) AI will be the biggest technology shift of our lives
(01:07:25) Adopting Devin in your company
(01:15:13) Startup wisdom and hiring practices
(01:22:32) Lightning round and final thoughts
—
Referenced:
• Devin: https://devin.ai/
• GitHub: https://github.com/
• Linear: https://linear.app/
• Waymo: https://waymo.com/
• GitHub Copilot: https://github.com/features/copilot
• Cursor: https://www.cursor.com/
• Anysphere: https://anysphere.inc/
• Bolt: https://bolt.new/
• StackBlitz: https://stackblitz.com/
• Cognition: https://cognition.ai/
• v0: https://v0.dev/
• Vercel: https://vercel.com/
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Assembly: https://en.wikipedia.org/wiki/Assembly_language
• Pascal: https://en.wikipedia.org/wiki/Pascal_(programming_language)
• Python: https://www.python.org/
• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox
• Datadog: https://www.datadoghq.com/
• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai
• Behind the product: Replit | Amjad Masad...
Duration:01:32:31