Lenny's Podcast: Product | Growth | Career

• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)

  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 techniques2. Why “role prompting” and threatening the AI no longer works—and what to do instead3. The two types of prompt engineering: conversational and product/system prompts4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models5. Why AI agents and robots will be the next major security threat6. How to get started in AI red teaming and prompt engineering7. Practical defense to put in place for your AI products—Brought to you by:Eppo—Run reliable, impactful experimentsStripe—Helping companies of all sizes grow revenueVanta—Automate compliance. Simplify security—Where to find Sander Schulhoff:• X: https://x.com/sanderschulhoff• LinkedIn: https://www.linkedin.com/in/sander-schulhoff/• Website: https://sanderschulhoff.com/• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC• Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Sander Schulhoff(04:29) The importance of prompt engineering(06:30) Real-world applications and examples(10:54) Basic prompt engineering techniques(23:46) Advanced prompt engineering techniques(29:00) The role of context and additional information(39:24) Ensembling techniques and thought generation(49:48) Conversational techniques for better results(50:46) Introduction to prompt injection(52:27) AI red teaming and competitions(54:23) The growing importance of AI security(01:02:45) Techniques to bypass AI safeguards(01:05:21) Challenges in AI security and future outlook(01:18:33) Misalignment and AI's potential risks(01:25:03) Final thoughts and lightning round—Referenced:• Reid Hoffman’s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822• AI Engineer World’s Fair: https://www.ai.engineer/• What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi• Devin: https://devin.ai/• Cursor: https://www.cursor.com/• Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Granola: https://www.granola.ai/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons• Behind the product: Replit | Amjad Masad (co-founder and CEO): 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/—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—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—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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  1:37:46
• How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

  Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox.In this episode, you’ll learn:• How to teach your team to be able to “take a punch”• Specific tactics to counter negative perceptions and reframe setbacks productively• Powerful behavioral strategies to form positive habits• Practical approaches for creating space in your workday to encourage creativity and deep thinking• The underestimated potential of AI in accelerating your personal and professional growth• Why you’re not the protagonist at your company (and why that’s liberating)• How WHOOP uses reward loops to drive real behavior change—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsPersona—A global leader in digital identity verificationAttio—The powerful, flexible CRM for fast-growing startups—Where to find Hilary Gridley:• X: https://x.com/yourgirlhils• LinkedIn: https://www.linkedin.com/in/hilarygridley/• Newsletter: https://hils.substack.com/• Maven course: https://maven.com/hilary-gridley/ai-powered-people-management—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Hilary’s background(04:31) Teaching teams to handle criticism and setbacks(17:57) Behavioral activation and mental health in the workplace(22:59) The importance of putting yourself out there(27:51) Transparency and communication in leadership(38:10) How to respectfully disagree with your manager(41:49) How to use “magic questions” to decode how people think(49:54) Why you’re not the protagonist at your company(52:48) Aligning with the CEO's vision(01:01:02) Building effective habits(01:11:14) Promoting team well-being(01:14:28) Creating space for creativity(01:20:45) AI’s role in accelerating learning(01:30:35) Pivotal career moments(01:37:21) Lessons from failure(01:39:49) Exciting new features of WHOOP 5.0(01:44:19) Lightning round and final thoughts—Referenced:• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager• WHOOP: https://www.whoop.com/• Big Health: https://www.bighealth.com/• What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation• Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/• Coinbase: https://www.coinbase.com/• Bridge: https://www.bridge.xyz/• Stripe: https://stripe.com/• The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer• Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf• VO₂ max: https://en.wikipedia.org/wiki/VO2_max• Peter Attia on X: https://x.com/PeterAttiaMD• Hilary Gridley’s 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0• The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown• From chalkboards to chatbots: Transforming learning in Nigeria, 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/—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—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—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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  1:54:39
• 35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley

  Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.What you’ll learn:• Why design should report to engineering, not product• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60• How to create design tenets vs. principles (with real examples)• The counterintuitive reason to delay drawing or prototyping as long as possible• Why software is fundamentally a medium, like film or music (not just a tool)• Why Bob “bounced off the culture” at Pinterest, and lessons from failure• The lunar landing story that teaches us about championing radical ideas• How to evaluate if a company truly values design before joining• The moral obligation of software makers to build great products—This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.—Where to find Bob Baxley:• Instagram: https://www.instagram.com/baxley/• LinkedIn: https://www.linkedin.com/in/bbaxley/• Website: http://www.bobbaxley.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Bob Baxley(03:52) Apple's lasting culture(06:15) Navigating unique company cultures(13:19) Finding a company that truly values your role(15:46) What is design?(17:17) How to help founders understand the value of design(23:08) How to align product managers and designers(26:31) Design reporting to engineering(30:54) Integrating engineers early in the design process(33:43) The maker mindset(35:14) Challenging the assumption that design is time-intensive(38:04) Design tenets vs. design principles(45:25) The moral obligation of great design(51:48) Understanding software as a medium(01:01:20) Reducing ambiguity for product teams(01:07:04) Giving designers space for creativity(01:08:48) The "primal mark" concept(01:12:05) AI prototyping tools: benefits and risks(01:17:00) AI as a life coach(01:21:22) Life lessons from the Apollo program(01:28:24) Lightning round and final thoughts—Referenced:• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney• Pinterest: https://www.pinterest.com/• X: https://x.com/• Uber: https://www.uber.com/• Airbnb: https://www.airbnb.com/• Slack: https://slack.com/• Ed Catmull on X: https://x.com/edcatmull• John Lasseter on X: https://x.com/johnlasseter5• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on• Humane: https://en.wikipedia.org/wiki/Humane_Inc.• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/• Tim Cook on X: https://x.com/tim_cook• ThoughtSpot: https://www.thoughtspot.com/• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/• Honeywell: https://www.honeywell.com• IDEO: https://www.ideo.com/• Nutanix: https://www.nutanix.com/• Lego: https://www.lego.com/• Leica: https://leica-camera.com/• Porsche: https://www.porsche.com/• Patagonia: https://www.patagonia.com• Brian Eno’s website: https://www.brian-eno.net/• Scenius: why 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 podcast@lennyrachitsky.com.—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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  1:41:59
• How Mercado Libre built Latin America's most valuable company: 18k engineers, 30k deploys a day, and their own fleet of planes | Sebastian Barrios

  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 appVanta—Automate compliance. Simplify securityLinkedIn 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 podcast@lennyrachitsky.com.—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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  1:19:25
• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

  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 matterStripe—Helping companies of all sizes grow revenueOneSchema—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 podcast@lennyrachitsky.com.—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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  1:06:18

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