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Lenny's Podcast: Product | Growth | Career

Lenny's Podcast: Product | Growth | Career

By: Lenny Rachitsky
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 Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.Lenny Rachitsky Economics Leadership Management & Leadership
Episodes
  • AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)

    AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)
    Jun 19 2025
    Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn’t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques.In this episode, you’ll learn:1. The 5 most effective prompt engineering 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=...
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    1 hr and 38 mins
  • 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)

    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)
    Jun 15 2025
    Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox.In this episode, you’ll learn:• How to teach your team to be able to “take a punch”• Specific tactics to counter negative perceptions and reframe setbacks productively• Powerful behavioral strategies to form positive habits• Practical approaches for creating space in your workday to encourage creativity and deep thinking• The underestimated potential of AI in accelerating your personal and professional growth• Why you’re not the protagonist at your company (and why that’s liberating)• How WHOOP uses reward loops to drive real behavior change—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million 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://...
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    1 hr and 55 mins
  • 35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley

    35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley
    Jun 12 2025
    Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.What you’ll learn:• Why design should report to engineering, not product• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60• How to create design tenets vs. principles (with real examples)• The counterintuitive reason to delay drawing or prototyping as long as possible• Why software is fundamentally a medium, like film or music (not just a tool)• Why Bob “bounced off the culture” at Pinterest, and lessons from failure• The lunar landing story that teaches us about championing radical ideas• How to evaluate if a company truly values design before joining• The moral obligation of software makers to build great products—This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.—Where to find Bob Baxley:• Instagram: https://www.instagram.com/baxley/• LinkedIn: https://www.linkedin.com/in/bbaxley/• Website: http://www.bobbaxley.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Bob Baxley(03:52) Apple's lasting culture(06:15) Navigating unique company cultures(13:19) Finding a company that truly values your role(15:46) What is design?(17:17) How to help founders understand the value of design(23:08) How to align product managers and designers(26:31) Design reporting to engineering(30:54) Integrating engineers early in the design process(33:43) The maker mindset(35:14) Challenging the assumption that design is time-intensive(38:04) Design tenets vs. design principles(45:25) The moral obligation of great design(51:48) Understanding software as a medium(01:01:20) Reducing ambiguity for product teams(01:07:04) Giving designers space for creativity(01:08:48) The "primal mark" concept(01:12:05) AI prototyping tools: benefits and risks(01:17:00) AI as a life coach(01:21:22) Life lessons from the Apollo program(01:28:24) Lightning round and final thoughts—Referenced:• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney• Pinterest: https://www.pinterest.com/• X: https://x.com/• Uber: https://www.uber.com/• Airbnb: https://www.airbnb.com/• Slack: https://slack.com/• Ed Catmull on X: https://x.com/edcatmull• John Lasseter on X: https://x.com/johnlasseter5• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on• Humane: https://en.wikipedia.org/wiki/Humane_Inc.• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/• Tim Cook on X: https://x.com/tim_cook• ThoughtSpot: https://www.thoughtspot.com/• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/• Honeywell: https://www.honeywell.com• IDEO: https://www.ideo.com/• Nutanix: https://www.nutanix.com/• Lego: https://www.lego.com/• Leica: https://leica-camera.com/• Porsche: https://www.porsche.com/• Patagonia: https://www.patagonia.com• Brian Eno’s website: https://www.brian-eno.net/• Scenius: why 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/...
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    1 hr and 42 mins

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