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Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

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
  • The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins

    The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins
    Nov 2 2025
    Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls “column B” thinking: building toward a dream future rather than just using the bricks around you.We discuss:1. How “column B” thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints2. The power of setting “crazy big goals”3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch5. Canva’s “two-step plan”: build one of the world’s most valuable companies, then do the most good possible6. Melanie’s vision for 2050 and why she believes imagination is the first step toward a better world—Brought to you by:Vanta—Automate compliance. Simplify security. https://vanta.com/lennyStripe—Helping companies of all sizes grow revenue: https://stripe.com/Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com—Transcript: ⁠https://www.lennysnewsletter.com/p/the-making-of-canva⁠⁠—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation—Where to find Melanie Perkins:• X: https://x.com/melaniecanva• LinkedIn: https://www.linkedin.com/in/melanieperkins/—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 Melanie Perkins and Canva(04:44) Building a “column B” company(06:36) Operationalizing big visions(13:13) Crazy big goals and celebrations(22:00) Challenges and setbacks in Canva’s journey(26:30) Fundraising and investor rejections(29:36) Leadership and growth lessons(34:38) Canva’s goal-driven structure(35:46) Balancing work and personal life(38:02) Community-driven product development(40:37) The two-step plan for global impact(45:04) Canva’s biggest launch yet(48:10) How Canva approaches product expansion(52:37) AI integration in Canva(53:56) AI corner(55:22) Melanie’s vision for 2050 and beyond(01:00:07) Lightning round and final thoughts—Referenced:• Canva: https://www.canva.com/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa• UserTesting: https://www.usertesting.com/• Figma: https://www.figma.com/• Adobe: https://www.adobe.com/• Calm: https://www.calm.com/• Gandhi’s quote about happiness: https://www.brainyquote.com/quotes/mahatma_gandhi_105593• Help us improve Canva: https://www.canva.com/help/get-in-touch/general-feedback/—Recommended books:• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898/• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765• Designing the Obvious: A Common Sense Approach to Web and Mobile Application Design: https://www.amazon.com/Designing-Obvious-Common-Approach-Application/dp/0321749855—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. To hear more, visit www.lennysnewsletter.com
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    1 hr and 6 mins
  • How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna

    How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna
    Oct 26 2025
    Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO).We discuss:1. How Block’s internal open-source agent, called Goose, is saving employees 8 to 10 hours weekly2. How the company measures AI productivity gains across technical and non-technical teams3. Which teams are benefiting most from AI (it’s not engineering)4. The boring organizational change that boosted productivity even more than AI tools5. Why code quality has almost nothing to do with product success6. How to drive AI adoption throughout an organization (hint: leadership needs to use the tools daily)7. Lessons from building Google Wave, Google+, and other failed products—Brought to you by:Sinch—Build messaging, email, and calling into your product: https://sinch.com/lennyFigma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/Persona—A global leader in digital identity verification: https://withpersona.com/lenny—Where to find Dhanji R. Prasanna:• LinkedIn: https://www.linkedin.com/in/dhanji/—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 Dhanji(05:26) The AI manifesto: convincing Jack Dorsey(07:33) Transforming into a more AI-native company(12:05) How engineering teams work differently today(15:24) Goose: Block’s open-source AI agent(20:18) Measuring AI productivity gains across teams(21:38) What Goose is and how it works(32:15) The future of AI in engineering and productivity(37:42) The importance of human taste(40:10) Building vs. buying software(44:08) How AI is changing hiring and team structure(53:45) The importance of using AI tools yourself before deploying them(55:13) How Goose helped solve a personal problem with receipts(58:01) What makes Goose unique(59:57) What Dhanji wishes he knew before becoming CTO(01:01:49) Counterintuitive lessons in product development(01:04:56) Why controlled chaos can be good for engineering teams(01:08:07) Core leadership lessons(01:13:36) Failure corner(01:15:50) Lightning round and final thoughts—Referenced:• Jack Dorsey on X: https://x.com/jack• Block: https://block.xyz/• Square: https://squareup.com/• Cash App: https://cash.app/• What is Conway’s Law?: https://www.microsoft.com/en-us/microsoft-365-life-hacks/organization/what-is-conways-law#• Goose: https://github.com/block/goose• Gosling: https://github.com/block/goose-mobile• Salesforce: https://www.salesforce.com/• Snowflake: https://www.snowflake.com/• Claude: https://claude.ai/• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann• OpenAI: https://openai.com/• 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• Llama: https://www.llama.com/• Cursor: https://cursor.com/• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• Top Gun: https://www.imdb.com/title/tt0092099/• Lenny’s vibe-coded Lovable app: https://gdoc-images-grab.lovable.app/• Afterpay: https://github.com/afterpay• Bitkey: https://bitkey.world/• Proto: https://github.com/proto-at-block• Brad Axen on LinkedIn: https://www.linkedin.com/in/bradleyaxen/• Databricks: https://www.databricks.com/• Carl Sagan’s quote: https://www.goodreads.com/quotes/32952-if-you-wish-to-make-an-apple-pie-from-scratch• Google Wave: https://en.wikipedia.org/wiki/Google_Wave• Google Video: https://en.wikipedia.org/wiki/Google_Video• Secret: https://en.wikipedia.org/wiki/Secret_(app)• Alien Earth on FX: https://www.fxnetworks.com/shows/alien-earth• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o• Fargo TV series on Prime Video: https://www.amazon.com/Fargo-Season-1/dp/B09QGRGH6M• Steam Deck OLED display: https://www.steamdeck.com/en/oled• Doc Brown: https://backtothefuture.fandom.com/wiki/Emmett_Brown—Recommended books:• The Master and Margarita: https://www.amazon.com/Master-Margarita-Mikhail-Bulgakov/dp/0802130119• Tennyson Poems: https://www.amazon.com/Tennyson-Poems-Everymans-Library-Pocket/dp/1400041872/—Production and marketing by https://penname.co/. For inquiries about sponsoring the ...
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    1 hr and 27 mins
  • Al Engineering 101 with Chip Huyen (Nvidia, Stanford, Netflix)

    Al Engineering 101 with Chip Huyen (Nvidia, Stanford, Netflix)
    Oct 23 2025
    Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has built multiple successful AI products and platforms and works directly with enterprises on their AI strategies, giving her unique visibility into what’s actually happening inside companies building AI products.We discuss:1. What people think makes AI apps better vs. what actually makes AI apps better2. What pre-training vs. post-training is, and why fine-tuning should be your last resort3. How RLHF (reinforcement learning from human feedback) actually works4. Why data quality matters more than which vector database you choose5. Why high performers are seeing the most gains from AI coding tools6. Why most AI problems are actually UX issues—Brought to you by:Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.comPersona—A global leader in digital identity verification: https://withpersona.com/lenny—Where to find Chip Huyen:• X: https://x.com/chipro• LinkedIn: https://www.linkedin.com/in/chiphuyen/• Website: https://huyenchip.com/• Substack: https://substack.com/@chiphuyen—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 Chip Huyen(04:28) Chip’s viral LinkedIn post(07:05) Understanding AI training: pre-training vs. post-training(08:50) Language modeling explained(13:55) The importance of post-training(15:20) Reinforcement learning and human feedback(22:23) The importance of evals in AI development(31:55) Retrieval augmented generation (RAG) explained(38:50) Challenges in AI tool adoption(43:19) Challenges in measuring productivity(45:20) The three-bucket test(49:10) The future of engineering roles(55:31) ML Engineers vs. AI engineers(57:12) Looking forward: the impact of AI(01:05:48) Model capabilities vs. perceived performance(01:08:23) Lightning round and final thoughts—Referenced:• Chip’s LinkedIn post on what actually improves AI apps: https://www.linkedin.com/posts/chiphuyen_aiapplications-aiengineering-activity-7358971409227792384-y0mf/• Prediction and Entropy of Printed English: https://www.princeton.edu/~wbialek/rome/refs/shannon_51.pdf• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody•Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO): https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord• First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course): https://www.lennysnewsletter.com/p/why-ai-evals-are-the-hottest-new-skill• 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• Stanford webinar—How AI Is Changing Coding and Education, Andrew Ng & Mehran Sahami: https://www.youtube.com/watch?v=J91_npj0Nfw• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann• Lenny’s vibe-coded app made on Lovable: https://gdoc-images-grab.lovable.app/• Story of Yanxi Palace: https://www.imdb.com/title/tt8865016/• Steve Jobs’s quote: https://www.goodreads.com/quotes/427317-remembering-that-i-ll-be-dead-soon-is-the-most-important—Recommended books:• The Complete Sherlock Holmes: https://www.amazon.com/Complete-Sherlock-Holmes-Volumes/dp/0553328255• AI Engineering: Building Applications with Foundation Models: https://www.amazon.com/AI-Engineering-Building-Applications-Foundation/dp/1098166302• The Selfish Gene: https://www.amazon.com/...
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    1 hr and 23 mins
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