Episodes
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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
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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
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Where to find Peter Deng:
• X: https://x.com/pxd
• LinkedIn: https://www.linkedin.com/in/peterxdeng/
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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
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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 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
• Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/
• Airtable: https://www.airtable.com/
• George Lee on LinkedIn: https://www.linkedin.com/in/geolee/
• Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/
• Lauryn Motamedi on LinkedIn: https://www.linkedin.com/in/laurynmotamedi/
• Twilio: https://www.twilio.com/
• Nick Turley on LinkedIn: https://www.linkedin.com/in/nicholasturley/
• Ian Silber on LinkedIn: https://www.linkedin.com/in/iansilber/
• Thomas Dimson on LinkedIn: https://www.linkedin.com/in/thomasdimson/
• Joey Flynn on LinkedIn: https://www.linkedin.com/in/joey-flynn-8291586b/
• Ryan O’Rourke’s website: https://www.rourkery.com/
• Joanne Jang on LinkedIn: https://www.linkedin.com/in/jangjoanne/
• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff
• Jill Hazelbaker on LinkedIn: https://www.linkedin.com/in/jill-hazelbaker-3aa32422/
• Guy Kawasaki’s website: https://guykawasaki.com/
• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/
• Sachin Kansal on LinkedIn: https://www.linkedin.com/in/sachinkansal/
• IDEO design thinking: https://designthinking.ideo.com/
• The 7 Steps of the Design Thinking Process: https://www.ideou.com/blogs/inspiration/design-thinking-process
• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu
• Jeff Bezos’s quote: https://news.ycombinator.com/item?id=27778175
• Friendster: https://en.wikipedia.org/wiki/Friendster
• Myspace: https://en.wikipedia.org/wiki/Myspace
• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen
• “Smile” by Jay-Z: https://www.youtube.com/watch?v=SSumXG5_rs8&list=RDSSumXG5_rs8&start_radio=1
• The Wire on HBO: https://www.hbo.com/the-wire
• Felicis: https://www.felicis.com/
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Recommended books:
• Sapiens: A Brief History of Humankind: https://www.amazon.com/Sapiens-Humankind-Yuval-Noah-Harari/dp/0062316095
• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654
• The Silk Roads: A New History of the World: https://www.amazon.com/Silk-Roads-New-History-World/dp/1101912375
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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
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Brought to you by:
Eppo—Run reliable, impactful experiments
Stripe—Helping companies of all sizes grow revenue
Vanta—Automate compliance. Simplify security
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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
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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 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
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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): 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
• Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv
• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0
• State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo
• Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags
• Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=AfmBOor2jcxJQvWBZyFa030Qt0fIIov3hSiWvI9VFyjO-Qp478EPJIU7
• Is Role Prompting Effective?: https://learnprompting.org/blog/role_prompting?srsltid=AfmBOooiiyLD-0CsCYZ4m3SDhYOmtTyaTzeDo0FvK_i1x1gLM8MJS-Sn
• Introduction to Decomposition Prompting Techniques: https://learnprompting.org/docs/advanced/decomposition/introduction?srsltid=AfmBOoojJmTQgBlmSlGYQ8kl-JPpVUlLKkL4YcFGS5u54JyeumUwlcBI
• LLM Self-Evaluation: https://learnprompting.org/docs/reliability/lm_self_eval
• Philip Resnik on X: https://x.com/psresnik
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• Introduction to Ensembling Prompting: https://learnprompting.org/docs/advanced/ensembling/introduction?srsltid=AfmBOooGSyqsrjnEbXSYoKpG0ZlpT278NHQA6Fd8gMvNTJlWu7-qEYzh
• Random forest: https://en.wikipedia.org/wiki/Random_forest
• Chain-of-Thought Prompting: https://learnprompting.org/docs/intermediate/chain_of_thought?srsltid=AfmBOoqwE7SXlluy2sx_QY_VOKduyBplWtIWKEJaD6FkJW3TqeKPSJfx
• Prompt Injecting: https://learnprompting.org/docs/prompt_hacking/injection?srsltid=AfmBOoqGgqbfXStrD6vlw5jy8HhEaESgGo2e57jyWL8lkZKktt_P6Zvn
• Announcing HackAPrompt 2.0: The World’s Largest AI Red-Teaming Hackathon: https://learnprompting.org/blog/announce-hackaprompt-2?srsltid=AfmBOopXKsHxy4aUtsvPCUtEu7x74NCAEnlTIdNzo7nfMDVwZ9ilTlkp
• Infant with rare, incurable disease is first to successfully receive personalized gene therapy treatment: https://www.nih.gov/news-events/news-releases/infant-rare-incurable-disease-first-successfully-receive-personalized-gene-therapy-treatment
• 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
• Copilot: https://copilot.microsoft.com/chats/rcxhzvKgZvz8ajUrKdBtX
• GitHub Copilot: https://github.com/features/copilot
• Defensive Measures: https://learnprompting.org/docs/prompt_hacking/defensive_measures/introduction
• Sam Altman on X: https://x.com/sama
• Three Laws of Robotics: https://en.wikipedia.org/wiki/Three_Laws_of_Robotics
• Anthropic’s new AI model turns to blackmail when engineers try to take it offline: https://techcrunch.com/2025/05/22/anthropics-new-ai-model-turns-to-blackmail-when-engineers-try-to-take-it-offline/
• Palisade Research: https://palisaderesearch.org/
• When AI Thinks It Will Lose, It Sometimes Cheats, Study Finds: https://time.com/7259395/ai-chess-cheating-palisade-research/
• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html
• 1883 on Paramount+: https://www.paramountplus.com/shows/1883/
• Black Mirror on Netflix: https://www.netflix.com/title/70264888
• Daylight Computer: https://daylightcomputer.com/
• Theodore Roosevelt’s quote: https://www.goodreads.com/quotes/622252-i-wish-to-preach-not-the-doctrine-of-ignoble-ease
• HackAPrompt 2.0: https://www.hackaprompt.com/
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Recommended books:
• Ender’s Game: https://www.amazon.com/Enders-Ender-Quintet-Orson-Scott/dp/0812550706
• The River of Doubt: Theodore Roosevelt’s Darkest Journey: https://www.amazon.com/River-Doubt-Theodore-Roosevelts-Darkest/dp/0767913736
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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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
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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
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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
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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) 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
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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, one prompt at a time: https://blogs.worldbank.org/en/education/From-chalkboards-to-chatbots-Transforming-learning-in-Nigeria
• Product Management Logic Coach GPT: https://chatgpt.com/g/g-673290301700819084afa36bdbcdfa3b-product-management-logic-coach
• Dropbox: https://www.dropbox.com/
• WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/?srsltid=AfmBOor2pP5qC3n7I23Z0ZIrYE99CjAKT9xSHQxbuyxmz_wFUBGH3e-n
• Negative capability: https://en.wikipedia.org/wiki/Negative_capability
• John Keats: https://en.wikipedia.org/wiki/John_Keats
• The Rehearsal: https://www.hbo.com/the-rehearsal
• Zwift: https://www.zwift.com/
• Beavis and Butthead Do ‘Creep’: https://www.youtube.com/watch?v=zv_gSmH0Ieg
• “Sea Grapes” by Derek Walcott: https://www.poetryfoundation.org/poems/57111/sea-grapes
• Free month of WHOOP: https://join.whoop.com/us/en/hilary/
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Recommended books:
• 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/
• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599
• East of Eden: https://www.amazon.com/East-Eden-John-Steinbeck-Centennial/dp/0142004235
• The Sun Also Rises: https://www.amazon.com/Sun-Also-Rises-Hemingway-Library/dp/1501121960/
• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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
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This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.
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Where to find Bob Baxley:
• Instagram: https://www.instagram.com/baxley/
• LinkedIn: https://www.linkedin.com/in/bbaxley/
• Website: http://www.bobbaxley.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 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
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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 creatives are stronger together: https://thecreativelife.net/scenius/
• The Beatles website: https://www.thebeatles.com/
• Disneyland: https://disneyland.disney.go.com/destinations/disneyland/
• Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/
• Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more
• Larry Page: https://en.wikipedia.org/wiki/Larry_Page
• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin
• Design Principles: https://principles.design/
• Tableau: https://www.tableau.com/
• Figma: https://www.figma.com/
• Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements
• 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
• eBay: https://www.ebay.com/
• Williams Sonoma: https://www.williams-sonoma.com/
• Amazon: https://www.amazon.com/
• Monument to a Dead Child | Raw Data: https://podcasts.apple.com/ca/podcast/monument-to-a-dead-child/id1042137974
• Toast: https://pos.toasttab.com/
• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas
• The Plant: https://pixar.fandom.com/wiki/The_Plant
• 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
• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna
• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/
• John C. Houbolt: https://www.nasa.gov/centers-and-facilities/langley/john-c-houbolt/
• The Apollo program: https://www.nasa.gov/the-apollo-program/
• Archive clip: JFK at Rice University, Sept. 12, 1962—“We choose to go to the moon”: https://www.youtube.com/watch?v=QXqlziZV63k
• Alan Shepard: https://www.nasa.gov/former-astronaut-alan-shepard/\
• Blue Origin: https://www.blueorigin.com/
• Yuri Gagarin: https://en.wikipedia.org/wiki/Yuri_Gagarin
• Wernher von Braun: https://en.wikipedia.org/wiki/Wernher_von_Braun
• Yuri Kondratyuk: https://en.wikipedia.org/wiki/Yuri_Kondratyuk
• John Houbolt’s memo: https://space.stackexchange.com/questions/2823/text-of-john-houbolts-letter-proposing-lunar-orbit-rendezvous-for-apollo
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx
• Lawrence of Arabia on Prime Video: https://www.amazon.com/Lawrence-Arabia-Peter-OToole/dp/B0088OINTU
• Leica M6: https://leica-camera.com/en-US/photography/cameras/m/m6
• Habitica: https://habitica.com/static/home
• Andor on Disney+: https://www.disneyplus.com/browse/entity-faba988a-a9f5-45f2-a074-0775a7d6f67a
• Edward Tufte quote: https://quotefancy.com/quote/1449650/Edward-Tufte-Good-design-is-clear-thinking-made-visible-bad-design-is-stupidity-made
• Ansel Adams quote: https://www.brainyquote.com/quotes/ansel_adams_106035
• It Takes a Village to Determine the Origins of an African Proverb: https://www.npr.org/sections/goatsandsoda/2016/07/30/487925796/it-takes-a-village-to-determine-the-origins-of-an-african-proverb
• Henry Modisett on LinkedIn: https://www.linkedin.com/in/henrymodisett/
• Perplexity: https://www.perplexity.ai/
• Golden State Warriors: https://www.nba.com/warriors/
• Steph Curry: https://www.espn.com/nba/player/_/id/3975/stephen-curry
—
Recommended books:
• From Counterculture to Cyberculture: Stewart Brand, the Whole Earth Network, and the Rise of Digital Utopianism: https://www.amazon.com/Counterculture-Cyberculture-Stewart-Network-Utopianism/dp/0226817423
• Hare Brain, Tortoise Mind: How Intelligence Increases When You Think Less: https://www.amazon.com/Hare-Brain-Tortoise-Mind-Intelligence/dp/0060955414
• The Elements of Typographic Style: https://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881791326
• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0060589469
• Time and the Art of Living: https://www.amazon.com/Time-Art-Living-Robert-Grudin/dp/0062503553/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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
• Mentava: https://www.mentava.com/
• Matt Bateman’s website: https://mattbateman.xyz/
• Beast Academy: https://beastacademy.com/
• David protein bars: https://davidprotein.com/
• Marc Andreessen on X: https://x.com/pmarca
• Tatami mats: https://en.wikipedia.org/wiki/Tatami
—
Recommended books:
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509
• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/
• The Odyssey: https://www.amazon.com/Odyssey-Homer/dp/0140268863
• The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119/
• Dune: https://www.amazon.com/Dune-Chronicles-Book-1/dp/0441013597/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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: https://www.linkedin.com/in/gunnargray/
• The Model Context Protocol: https://www.anthropic.com/news/model-context-protocol
• 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
• Jimmy Kimmel Live: https://www.youtube.com/user/JimmyKimmelLive
• ChatGPT: https://chatgpt.com/
• Gemini: https://gemini.google.com/app
• 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
• Windsurf: https://windsurf.com/
• Menlo Ventures: https://menlovc.com/
• Harvey: https://www.harvey.ai/
• Manus: https://manus.im/
• Bench: https://www.bench-ai.com/
• Strategy Letter V: https://www.joelonsoftware.com/2002/06/12/strategy-letter-v/
• Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/
—
Recommended books:
• The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951
• The Way of the Code: The Timeless Art of Vibe Coding: https://www.thewayofcode.com/
• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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: https://www.amazon.com/Blitzscaling-Lightning-Fast-Building-Massively-Companies/dp/1524761419
• Nobody Wants to Read Your Sh*t: Why That Is And What You Can Do About It: https://www.amazon.com/Nobody-Wants-Read-Your-Sh-ebook/dp/B01GZ1TJBI
• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648537
• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281
• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• 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
• 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
• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning
• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/
• Granola: https://www.granola.ai/
• Some people think AI writing has a tell—the em dash. Writers disagree: https://www.washingtonpost.com/technology/2025/04/09/ai-em-dash-writing-punctuation-chatgpt/
—
Recommended books:
• Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005
• Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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: https://robinhood.com/us/en/
• Nikita Bier’s post on X about Bible Chat: https://x.com/nikitabier/status/1915252215507210349
• Bible Chat: https://apps.apple.com/us/app/bible-chat-daily-devotional/id6448849666?mt=8
• Suno: https://suno.com/home
• Disfrutar: https://www.disfrutarbarcelona.com/
—
Recommended books:
• StrengthsFinder 2.0: https://www.amazon.com/StrengthsFinder-2-0-Tom-Rath/dp/159562015X
• The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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: https://github.com/features/copilot
• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/
• South Park “Underwear Gnomes” episode: https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17
• Google Home: https://home.google.com/welcome/
• Cursor: https://www.cursor.com/
• v0: https://v0.dev/
• Bolt: https://bolt.new/
• Lovable: https://lovable.dev/
• Replit: https://replit.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
• 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
• 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
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• Microsoft Excel World Championship: https://fmworldcup.com/microsoft-excel-world-championship/
• Google Now: https://en.wikipedia.org/wiki/Google_Now
• Hacks on Max: https://www.max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7
• Granola: https://www.granola.ai/
• Alan Kay quote: https://www.brainyquote.com/quotes/alan_kay_100831
• Sindhu Vee’s website: https://sindhuvee.com/
• Nate Bargatze’s website: https://natebargatze.com/
—
Recommended book:
• A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains: https://www.amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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 quote: https://quoteinvestigator.com/2017/11/18/planning/
• Wealth protection: https://help.revolut.com/help/security-logging-in/wealth-protection/what-is-wealth-protection/
—
Recommended books:
• The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205
• Build: An Unorthodox Guide to Making Things Worth Making―Personal Journey from Product Designer to Mentor: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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: https://www.linkedin.com/in/shyamsankar/
• Palantir Gotham for Defense Decision Making: https://www.youtube.com/watch?v=rxKghrZU5w8
• Foundry 2022 Operating System Demo: https://www.youtube.com/watch?v=uF-GSj-Exms
• SQL: https://en.wikipedia.org/wiki/SQL
• Airbus A350: https://en.wikipedia.org/wiki/Airbus_A350
• SAP: https://www.sap.com/index.html
• Barry McCardel on LinkedIn: https://www.linkedin.com/in/barrymccardel/
• Understanding ‘Forward Deployed Engineering’ and Why Your Company Probably Shouldn’t Do It: https://www.barry.ooo/posts/fde-culture
• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/
• Retool’s Path to Product-Market Fit—Lessons for Getting to 100 Happy Customers, Faster: https://review.firstround.com/retools-path-to-product-market-fit-lessons-for-getting-to-100-happy-customers-faster/
• How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe): https://www.lennysnewsletter.com/p/how-to-foster-innovation-and-big
• Looker: https://cloud.google.com/looker
• Sorry, that isn’t an FDE: https://tedmabrey.substack.com/p/sorry-that-isnt-an-fde
• Glean: https://www.glean.com/
• Limited Engagement: Is Tech Becoming More Diverse?: https://www.bkmag.com/2017/01/31/limited-engagement-creating-diversity-in-the-tech-industry/
• Operation Warp Speed: https://en.wikipedia.org/wiki/Operation_Warp_Speed
• Mark Zuckerberg testifies: https://www.businessinsider.com/facebook-ceo-mark-zuckerberg-testifies-congress-libra-cryptocurrency-2019-10
• Anduril: https://www.anduril.com/
• SpaceX: https://www.spacex.com/
• Principles: https://nabeelqu.co/principles
• Wispr Flow: https://wisprflow.ai/
• Claude code: https://docs.anthropic.com/en/docs/agents-and-tools/claude-code/overview
• Gemini Pro 2.5: https://deepmind.google/technologies/gemini/pro/
• DeepMind: https://deepmind.google/
• Latent Space newsletter: https://www.latent.space/
• Swyx on x: https://x.com/swyx
• Neural networks in chess programs: https://www.chessprogramming.org/Neural_Networks
• AlphaZero: https://en.wikipedia.org/wiki/AlphaZero
• The top chess players in the world: https://www.chess.com/players
• Decision to Leave: https://www.imdb.com/title/tt12477480/
• Oldboy: https://www.imdb.com/title/tt0364569/
• Christopher Alexander: https://en.wikipedia.org/wiki/Christopher_Alexander
—
Recommended books:
• The Technological Republic: Hard Power, Soft Belief, and the Future of the West: https://www.amazon.com/Technological-Republic-Power-Belief-Future/dp/0593798694
• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296
• Impro: Improvisation and the Theatre: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178/
• William Shakespeare: Histories: https://www.amazon.com/Histories-Everymans-Library-William-Shakespeare/dp/0679433120/
• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884
• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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:
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—
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: https://www.linkedin.com/in/parker-j-palmer-5a92b110/
• The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living
—
Recommended books:
• Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536
• Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139
• Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511
• 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431
• Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586
• The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
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/
—
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 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 (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• Windsurf: https://windsurf.com/
• COBOL: https://en.wikipedia.org/wiki/COBOL
• Fortran: https://en.wikipedia.org/wiki/Fortran
• Magic the Gathering: https://magic.wizards.com/en
• Aura frames: https://auraframes.com/
• AirPods: https://www.apple.com/airpods/
• Steven Hao on LinkedIn: https://www.linkedin.com/in/steven-hao-160b9638/
• Walden Yan on LinkedIn: https://www.linkedin.com/in/waldenyan/
—
Recommended books:
• How to Win Friends & Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034
• The Power Law: Venture Capital and the Making of the New Future: https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999X
• The Great Gatsby: https://www.amazon.com/Great-Gatsby-F-Scott-Fitzgerald/dp/0743273567
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
Michael Truell is the co-founder and CEO of Anysphere, the company behind Cursor—the fastest-growing AI code editor in the world, reaching $300 million in annual recurring revenue just two years after its launch. In this conversation, Michael shares his vision for the future, lessons learned, and advice for preparing for the fast-approaching AI future.
What you’ll learn:
• Cursor's early pivot from automating CAD to automating code
• Michael’s vision for “what comes after code” and how programming will evolve
• Why Cursor built their own custom AI models despite not starting there
• Key lessons from Cursor’s rapid growth
• Why “taste” and logic design will become more valuable engineering skills than technical coding ability
• Why the market for AI coding tools is much larger than people realize—and why there will likely be one dominant winner
• Michael’s advice for engineers and product teams preparing for the AI future
—
Brought to you by:
Eppo—Run reliable, impactful experiments
Vanta—Automate compliance. Simplify security
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—
Where to find Michael Truell:
• X: https://x.com/mntruell
• LinkedIn: https://www.linkedin.com/in/michael-t-5b1bbb122/
• Website: https://mntruell.com/
—
In this episode, we cover:
(00:00) Introduction to Michael Truell and Cursor
(04:20) What comes after code
(08:32) The importance of taste
(12:39) Cursor’s origin story
(18:31) Why they chose to build an IDE
(22:39) Will everyone become engineering managers?
(24:31) How they decided it was time to ship
(26:45) Reflecting on Cursor's success
(32:03) Counterintuitive lessons on building AI products
(34:02) Inside Cursor's stack
(38:42) Defensibility and market dynamics in AI
(46:13) Tips for using Cursor
(51:25) Hiring and building a strong team
(59:10) Staying focused amid rapid AI advancements
(01:02:31) Final thoughts and advice for aspiring AI innovators
—
Referenced:
• Cursor: https://www.cursor.com/
• Microsoft Copilot: https://copilot.microsoft.com/
• Scaling laws for neural language models: https://openai.com/index/scaling-laws-for-neural-language-models/
• MIT: https://www.mit.edu/
• Telegram: https://telegram.org/
• Signal: https://signal.org/
• WhatsApp: https://www.whatsapp.com/
• Devin: https://devin.ai/
• Visual Studio Code: https://code.visualstudio.com/
• Chromium: https://chromium.googlesource.com/chromium/src/base/
• Exploring ChatGPT (GPT) Wrappers—What They Are and How They Work: https://learnprompting.org/blog/gpt_wrappers
• 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 founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff
• DALL-E 3: https://openai.com/index/dall-e-3/
• Stable Diffusion 3: https://stability.ai/news/stable-diffusion-3
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.
What you’ll learn:
1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team
2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment
3. How focusing on impact, rather than just shipping features, has transformed the company’s culture
4. The story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioning
5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster
6. Daniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective
—
Brought to you by:
• Enterpret—Transform customer feedback into product growth
• Airtable ProductCentral—Launch to new heights with a unified system for product development
• Vanta—Automate compliance. Simplify security
—
Where to find Daniel Lereya:
• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/
—
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 Daniel and monday.com
(04:20) The pivotal moment: competitors shipping faster
(08:50) Setting ambitious goals
(17:44) Focusing on impact rather than features
(27:07) Transforming your product quarterly
(32:07) Scaling monday.com: challenges and strategies
(39:14) How monday.com maintains transparency as a public company
(45:40) The importance of taking risks
(51:02) Counterintuitive lessons in product development
(54:33) The value of timeboxing and deadlines
(57:28) Embracing user feedback
(59:54) Adapting leadership styles
(01:04:43) Personal reflections on leadership
(01:10:41) Handling crises and strategic planning
(01:17:28) The role of AI in work and personal life
(01:22:13) Final thoughts and lightning round
—
Referenced:
• Monday.com: https://monday.com/
• The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board
• Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/
• Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/
• Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/
• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile
• A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks
• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of
• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox
• SpaceX: https://www.spacex.com/
• Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/
• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra
• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome
• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/
• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/
• ChatGPT: https://chatgpt.com/
• Cursor: https://www.cursor.com/
• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin
• FIFA 22: https://store.playstation.com/en-us/concept/10002538/
• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890
• Google Photos: https://photos.google.com/
—
Recommended books:
• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup
• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595
• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860
• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
AI is rapidly changing how we live and work. It’s exciting, but also overwhelming. If you’re struggling to keep up, and wondering how to actually use these magical new tools to improve the quality and efficiency of your work, I’m thrilled to introduce How I AI with Claire Vo—the first ever new podcast under the Lenny’s Podcast network. Claire is an engineer, three-time CPO, and AI builder. In each episode, her guest shows you a specific, practical, and impactful way they’ve learned to use AI. Forget theoretical debates—this podcast is about real, valuable use cases. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether you’re building products, leading teams, or just looking to level up your AI skills, How I AI is for you.
—
SUBSCRIBE TO THE SHOW
→ YouTube: https://www.youtube.com/channel/UCRYY7IEbkHLH_ScJCu9eWDQ
→ Spotify: https://open.spotify.com/show/4aRP2XSavdtrLG5FZoonOK
→ Apple: https://podcasts.apple.com/us/podcast/how-i-ai/id1809663079
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
Varun Mohan is the co-founder and CEO of Windsurf (formerly Codeium), an AI-powered development environment (IDE) that has been used by over 1 million developers in just four months and has quickly emerged as a leader in transforming how developers build software. Prior to finding success with Windsurf, the company pivoted twice—first from GPU virtualization infrastructure to an IDE plugin, and then to their own standalone IDE.
In this conversation, you'll learn:
1. Why Windsurf walked away from a profitable GPU infrastructure business and bet the company on helping engineers code
2. The surprising UI discovery that tripled adoption rates overnight.
3. The secret behind Windsurf's B2B enterprise plan, and why they invested early in an 80-person sales team despite conventional startup wisdom.
4. How non-technical staff at Windsurf built their own custom tools instead of purchasing SaaS products, saving them over $500k in software costs
5. Why Varun believes 90% of code will be AI-generated, but engineering jobs will actually increase
6. How training on millions of incomplete code samples gives Windsurf an edge, and creates a moat long-term
7. Why agency is the most undervalued and important skill in the AI era
—
Brought to you by:
• Brex—The banking solution for startups
• Productboard—Make products that matter
• Coda—The all-in-one collaborative workspace
—
Where to find Varun Mohan:
• X: https://x.com/_mohansolo
• LinkedIn: https://www.linkedin.com/in/varunkmohan/
—
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) Varun’s background
(03:57) Building and scaling Windsurf
(12:58) Windsurf: The new purpose-built IDE to harness magic
(17:11) The future of engineering and AI
(21:30) Skills worth investing in
(23:07) Hiring philosophy and company culture
(35:22) Sales strategy and market position
(39:37) JetBrains vs. VS Code: extensibility and enterprise adoption
(41:20) Live demo: building an Airbnb for dogs with Windsurf
(42:46) Tips for using Windsurf effectively
(46:38) AI’s role in code modification and review
(48:56) Empowering non-developers to build custom software
(54:03) Training Windsurf
(01:00:43) Windsurf’s unique team structure and product strategy
(01:06:40) The importance of continuous innovation
(01:08:57) Final thoughts and advice for aspiring developers
—
Referenced:
• Windsurf: https://windsurf.com/
• VS Code: https://code.visualstudio.com/
• JetBrains: https://www.jetbrains.com/
• Eclipse: https://eclipseide.org/
• Visual Studio: https://visualstudio.microsoft.com/
• Vim: https://www.vim.org/
• Emacs: https://www.gnu.org/software/emacs/
• Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze): https://www.lennysnewsletter.com/p/lessons-from-uri-levine
• IntelliJ: https://www.jetbrains.com/idea/
• Julia: https://julialang.org/
• Parallel computing: https://en.wikipedia.org/wiki/Parallel_computing
• Douglas Chen on LinkedIn: https://www.linkedin.com/in/douglaspchen/
• Carlos Delatorre on LinkedIn: https://www.linkedin.com/in/cadelatorre/
• MongoDB: https://www.mongodb.com/
• Cursor: https://www.cursor.com/
• GitHub Copilot: https://github.com/features/copilot
• Llama: https://www.llama.com/
• Mistral: https://mistral.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): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• React: https://react.dev/
• Sonnet: https://www.anthropic.com/claude/sonnet
• OpenAI: https://openai.com/
• FedRamp: https://www.fedramp.gov/
• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/
• Amdahl’s law: https://en.wikipedia.org/wiki/Amdahl%27s_law
• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra
—
Recommended book:
• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
Guillermo Rauch is the founder and CEO of Vercel, creators of v0 (one of the most popular AI app building tools), and the mind behind foundational JavaScript frameworks like Next.js and Socket.io. An open source pioneer and legendary engineer, Guillermo has built tools that power some of the internet’s most innovative products, including Midjourney, Grok, and Notion. His mission is to democratize product creation, expanding the pool of potential builders from 5 million developers to over 100 million people worldwide.
In this episode, you’ll learn:
1. How AI will radically speed up product development—and the three critical skills PMs and engineers should master now to stay ahead
2. Why the future of building apps is shifting toward prompts instead of code, and how that affects traditional product teams
3. Specific ways to improve your design “taste,” plus practical tips to consistently create beautiful, user-loved products
4. How Guillermo built a powerful app in under two hours for $20 (while flying and using plane Wi-Fi) that would normally take weeks and thousands of dollars in engineering time
5. The exact strategies Vercel uses internally to leverage AI tools like v0 and Cursor, enabling their team of 600 to ship faster and better than ever before
6. Guillermo’s actionable advice on increasing your product quality through rapid iteration, real-world user feedback, and creating intentional “exposure hours” for your team
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Brought to you by:
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Vanta — Automate compliance. Simplify security
• LinkedIn Ads—Reach professionals and drive results for your business
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Where to find Guillermo Rauch:
• X: https://x.com/rauchg
• LinkedIn: https://www.linkedin.com/in/rauchg/
• Website: https://rauchg.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 Guillermo Rauch
(04:43) v0's mission
(07:03) The impact and growth of v0
(15:54) The future of product development with AI
(19:05) Empowering engineers and product builders
(24:01) Skills for the future: coding, math, and eloquence
(35:05) v0 in action: real-world applications
(36:40) Tips for using v0 effectively
(45:46) Core skills for building AI apps
(49:44) Live demo
(59:45) Understanding how AI thinks
(01:04:35) AI integration and future prospects
(01:07:22) Building taste
(01:13:43) Limitations of v0
(01:16:54) Improving the design of your product
(01:20:09) The secret to product quality
(01:22:35) Vercel’s AI-driven development
(01:25:43) Guillermo's vision for the future
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Referenced:
• v0: https://v0.dev/
• Vercel: https://vercel.com/
• GitHub: https://github.com/
• Cursor: https://www.cursor.com/
• Next.js Framework: https://nextjs.org/
• Claude: https://claude.ai/new
• Grok: https://x.ai/
• Midjourney: https://www.midjourney.com
• SocketIO: https://socket.io/
• Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao
• Notion: https://www.notion.com/
• Automattic: https://automattic.com/
• 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
• v0 Community: https://v0.dev/chat/community
• Figma: https://www.figma.com/
• Git Commit: https://www.atlassian.com/git/tutorials/saving-changes/git-commit
• What are Artifacts and how do I use them?: https://support.anthropic.com/en/articles/9487310-what-are-artifacts-and-how-do-i-use-them
• Design Engineering at Vercel: https://vercel.com/blog/design-engineering-at-vercel
• CSS: https://en.wikipedia.org/wiki/CSS
• Tailwind: https://tailwindcss.com/
• Wordcel / Shape Rotator / Mathcel: https://knowyourmeme.com/memes/wordcel-shape-rotator-mathcel
• Steve Jobs’s Ultimate Lesson for Companies: https://hbr.org/2011/08/steve-jobss-ultimate-lesson-fo
• Bloom Hackathon: https://bloom.build/
• Expenses Should Do Themselves | Saquon Barkley x Ramp (Super Bowl Ad): https://www.youtube.com/watch?v=p1Tgsy7D0Jg
• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp
• JavaScript: https://www.javascript.com/
• React: https://react.dev/
• Mapbox: https://www.mapbox.com/
• Leaflet: https://leafletjs.com/
• Escape hatches: https://react.dev/learn/escape-hatches
• Supreme: https://supreme.com/
• Shadcn: https://ui.shadcn.com/
• Charles Schwab: https://www.schwab.com/
• Fortune: https://fortune.com/
• Semafor: https://www.semafor.com/
• AI SDK: https://sdk.vercel.ai/
• DeepSeek: https://www.deepseek.com/
• Stripe: https://stripe.com/
• Vercel templates: https://vercel.com/templates
• GC AI: https://getgc.ai/
• OpenEvidence: https://www.openevidence.com/
• Paris Fashion Week: https://www.fhcm.paris/en/paris-fashion-week
• Guillermo’s post on X about making great products: https://x.com/rauchg/status/1887314115066274254
• Everybody Can Cook billboard: https://www.linkedin.com/posts/evilrabbit_activity-7242975574242037760-uRW9/
• Ratatouille: https://www.imdb.com/title/tt0382932/
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
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Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe -
Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook.
In this episode, you’ll learn:
1. How OpenAI structures its product teams and maintains agility while developing cutting-edge AI
2. The power of model ensembles—using multiple specialized models together like a company of humans with different skills
3. Why writing effective evals (AI evaluation tests) is becoming a critical skill for product managers
4. The surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescence
5. How “vibe coding” is changing how companies operate
6. What OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity)
7. “Model maximalism” and why today’s AI is the worst you’ll ever use again
8. Practical prompting techniques that improve AI interactions, including example-based prompting
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Brought to you by:
• Eppo—Run reliable, impactful experiments
• Persona—A global leader in digital identity verification
• OneSchema—Import CSV data 10x faster
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Where to find Kevin Weil:
• X: https://x.com/kevinweil
• LinkedIn: https://www.linkedin.com/in/kevinweil/
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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) Kevin’s background
(04:06) OpenAI’s new image model
(06:52) The role of chief product officer at OpenAI
(10:18) His recruitment story and joining OpenAI
(17:20) The importance of evals in AI
(24:59) Shipping quickly and consistently
(28:34) Product reviews and iterative deployment
(39:35) Chat as an interface for AI
(43:59) Collaboration between researchers and product teams
(46:41) Hiring product managers at OpenAI
(48:45) Embracing ambiguity in product management
(51:41) The role of AI in product teams
(53:21) Vibe coding and AI prototyping
(55:55) The future of product teams and fine-tuned models
(01:04:36) AI in education
(01:06:42) Optimism and concerns about AI’s future
(01:16:37) Reflections on the Libra project
(01:20:37) Lightning round and final thoughts
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Referenced:
• OpenAI: https://openai.com/
• The AI-Generated Studio Ghibli Trend, Explained: https://www.forbes.com/sites/danidiplacido/2025/03/27/the-ai-generated-studio-ghibli-trend-explained/
• Introducing 4o Image Generation: https://openai.com/index/introducing-4o-image-generation/
• Waymo: https://waymo.com/
• X: https://x.com
• Facebook: https://www.facebook.com/
• Instagram: https://www.instagram.com/
• Planet: https://www.planet.com/
• Sam Altman on X: https://x.com/sama
• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k
• OpenAI evals: https://github.com/openai/evals
• Deep Research: https://openai.com/index/introducing-deep-research/
• Ev Williams on X: https://x.com/ev
• OpenAI API: https://platform.openai.com/docs/overview
• Dwight Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720
• 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
• StackBlitz: https://stackblitz.com/
• Claude 3.5 Sonnet: https://www.anthropic.com/news/claude-3-5-sonnet
• Anthropic: https://www.anthropic.com/
• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile
• Chad: https://chatgpt.com/g/g-3F100ZiIe-chad-open-a-i
• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/
• Figma: https://www.figma.com/
• Julia Villagra on LinkedIn: https://www.linkedin.com/in/juliavillagra/
• Andrej Karpathy on X: https://x.com/karpathy
• Silicon Valley CEO says ‘vibe coding’ lets 10 engineers do the work of 100—here’s how to use it: https://fortune.com/2025/03/26/silicon-valley-ceo-says-vibe-coding-lets-10-engineers-do-the-work-of-100-heres-how-to-use-it/
• Cursor: https://www.cursor.com/
• Windsurf: https://codeium.com/windsurf
• GitHub Copilot: https://github.com/features/copilot
• Patrick Srail on X: https://x.com/patricksrail
• Khan Academy: https://www.khanacademy.org/
• CK-12 Education: https://www.ck12.org/
• Sora: https://openai.com/sora/
• Sam Altman’s post on X about creative writing: https://x.com/sama/status/1899535387435086115
• Diem (formerly known as Libra): https://en.wikipedia.org/wiki/Diem_(digital_currency)
• Novi: https://about.fb.com/news/2020/05/welcome-to-novi/
• David Marcus on LinkedIn: https://www.linkedin.com/in/dmarcus/
• Peter Zeihan on X: https://x.com/PeterZeihan
• The Wheel of Time on Prime Video: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R
• Top Gun: Maverick on Prime Video: https://www.amazon.com/Top-Gun-Maverick-Joseph-Kosinski/dp/B0DM2LYL8G
• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske
• MySQL: https://www.mysql.com/
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Recommended books:
• Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X
• The Accidental Superpower: Ten Years On: https://www.amazon.com/Accidental-Superpower-Ten-Years/dp/1538767341
• Cable Cowboy: https://www.amazon.com/Cable-Cowboy-Malone-Modern-Business/dp/047170637X
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe - Show more
