Lenny's Podcast: Product | Growth | Career

• A founder’s guide to crisis management | Uri Levine (Waze co-founder, serial entrepreneur)

  Uri Levine is a co-founder of Waze (which was acquired by Google for $1.3 billion in 2013), along with nine other companies (including another company he sold for over $1 billion). He’s also been on 20 boards and has been an advisor to over 50 startups. He recently released a new chapter of his best-selling book Fall in Love with the Problem, Not the Solution, which provides a guide to surviving crises at your company. In this episode, we cover:• The two types of startup crisis and how to handle them• Why speed of action is the most important thing• How to keep your team motivated when things look dire• A framework for deciding whether or not to pivot• What to do when product-market fit disappears• How to approach raising money during a crisis• More—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Rippling—Automate HR, IT, and finance so you can scale faster• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/a-founders-guide-to-crisis-management-uri-levine—Where to find Uri Levine:• X: https://twitter.com/urilevine1• LinkedIn: https://www.linkedin.com/in/uri-levine• Website: https://urilevine.com• Book: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637746601/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=&sr=—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Welcome back, Uri!(05:10) The new chapter: navigating crises(08:15) Types of crises founders face(29:10) Navigating cash crises(38:31) The importance of never giving up(46:26) How to keep people engaged through a crises(47:59) Transparency in crisis management(56:58) Navigating product-market-fit challenges(59:27) Deciding when to pivot or shut down(01:13:34) Real-life startup survival stories(01:17:06) Avoiding and preparing for crises(01:21:21) Final thoughts and book promotion—Referenced:• Waze: https://www.waze.com/• Moovit: https://en.wikipedia.org/wiki/Moovit• Order Chat: https://www.crunchbase.com/organization/order-chat• Fibo: https://finder.startupnationcentral.org/company_page/fibo• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox• TomTom: https://www.tomtom.com/• Khosla Ventures: https://www.khoslaventures.com/• WeSki: https://www.weski.com/• Larry Silverstein: https://en.wikipedia.org/wiki/Larry_Silverstein• Oversee: https://oversee.biz/• Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups• 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• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/• Zip: https://zip.co/us• Qualcomm: https://www.qualcomm.com/• Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_148788—Recommended book:• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs (updated 2025 version): https://urilevine.com/book/#Pre-order—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:23:45
• OpenAI researcher on why soft skills are the future of work | Karina Nguyen (Research at OpenAI, ex-Anthropic)

  Karina Nguyen leads research at OpenAI, where she’s been pivotal in developing groundbreaking products like Canvas, Tasks, and the o1 language model. Before OpenAI, Karina was at Anthropic, where she led post-training and evaluation work for Claude 3 models, created a document upload feature with 100,000 context windows, and contributed to numerous other innovations. With experience as an engineer at the New York Times and as a designer at Dropbox and Square, Karina has a rare firsthand perspective on the cutting edge of AI and large language models. In our conversation, we discuss:• How OpenAI builds product• What people misunderstand about AI model training• Differences between how OpenAI and Anthropic operate• The role of synthetic data in model development• How to build trust between users and AI models• Why she moved from engineering to research• Much more—Brought to you by:• Enterpret—Transform customer feedback into product growth• Vanta—Automate compliance. Simplify security• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen—Where to find Karina Nguyen:• X: https://x.com/karinanguyen_• LinkedIn: https://www.linkedin.com/in/karinanguyen28• Website: https://karinanguyen.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 Karina Nguyen(04:42) Challenges in model training(08:21) Synthetic data and its importance(12:38) Creating Canvas(18:33) Day-to-day operations at OpenAI(20:28) Writing evaluations(23:22) Prototyping and product development(26:57) Building Canvas and Tasks(33:34) Understanding the job of a researcher(35:36) The future of AI and its impact on work and education(42:15) Soft skills in the age of AI(47:50) AI’s role in creativity and strategy development(53:34) Comparing Anthropic and OpenAI(57:11) Innovations and future visions(01:07:13) The potential of AI agents(01:11:36) Final thoughts and career advice—Referenced:• What’s in your stack: The state of tech tools in 2025: https://www.lennysnewsletter.com/p/whats-in-your-stack-the-state-of• Anthropic: https://www.anthropic.com/• OpenAI: https://openai.com/• What is synthetic data—and how can it help you competitively?: https://mitsloan.mit.edu/ideas-made-to-matter/what-synthetic-data-and-how-can-it-help-you-competitively• GPQA: https://datatunnel.io/glossary/gpqa/• Canvas: https://openai.com/index/introducing-canvas/• Barret Zoph on LinkedIn: https://www.linkedin.com/in/barret-zoph-65990543/• Mira Murati on LinkedIn: https://www.linkedin.com/in/mira-murati-4b39a066/• JSON Schema: https://json-schema.org/• Anthropic—100K Context Windows: https://www.anthropic.com/news/100k-context-windows• Claude 3 Haiku: https://www.anthropic.com/news/claude-3-haiku• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html• Cursor: https://www.cursor.com/• How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management• Lee Byron on LinkedIn: https://www.linkedin.com/in/lee-byron/• GraphQL: https://graphql.org/• Claude in Slack: https://www.anthropic.com/claude-in-slack• Sam Altman on X: https://x.com/sama• Jakub Pachocki on LinkedIn: https://www.linkedin.com/in/jakub-pachocki/• Lennybot: https://www.lennybot.com/• ElevenLabs: https://elevenlabs.io/• Westworld on Prime Video: https://www.amazon.com/Westworld-Season-1/dp/B01N05UD06• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k• Tuple: https://tuple.app/• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:14:33
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify)

  Tobi Lütke is the founder and CEO of Shopify, a $130 billion business that powers over 10% of all U.S. e-commerce. Starting as a snowboard shop in 2004, Shopify has become the leading commerce platform by consistently approaching problems differently. Tobi remains deeply technical, frequently coding alongside his team, and is known for his unique approach to leadership, product development, and company building. In our conversation, we discuss:• Why complexity kills entrepreneurship• How to develop and leverage your unique talent stack• How specifically Tobi approaches thinking from first principles• The importance of focusing on unquantifiable qualities like joy and delight• Why Tobi works backward from a 100-year vision• Why metrics should support decisions, not make them• The power of following your curiosity• What Tobi believes it takes to be a great product leader• Much more—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Liveblocks—Ready-made collaborative features to drop into your product• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook—Where to find Tobi Lütke:• X: https://x.com/tobi• LinkedIn: https://www.linkedin.com/in/tobiaslutke/• Website: https://tobi.lutke.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) Welcome and introduction(04:17) The Tobi tornado(07:10) Maximizing human potential(11:05) Education and personal growth(16:47) Operating without KPIs(25:00) First-principles thinking(40:04) Remote work(45:59) Why Tobi never stopped coding(54:46) Embracing disagreement(01:01:27) The 100-year vision(01:09:29) Balancing tactics and positioning(01:17:15) Encouraging entrepreneurship(01:19:34) The power of good UX(01:28:42) The talent stack and unique opportunities(01:34:30) The role of passion in product development(01:36:39) Final thoughts and farewell—Referenced:• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams• The ultimate guide to performance marketing | Timothy Davis (Shopify): https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis• Brandon Chu on building product at Shopify, how writing changed the trajectory of his career, the habits that make you a great PM, pros and cons of being a platform PM, how Shopify got through Covid: https://www.lennysnewsletter.com/p/brandon-chu-on-what-its-like-to-build• IRC: https://en.wikipedia.org/wiki/IRC• Goodhart’s law: https://en.wikipedia.org/wiki/Goodhart%27s_law• Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates/• How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product• The Last Dance on Netflix: https://www.netflix.com/title/80203144• Autoregressive Models for Natural Language Processing: https://medium.com/@zaiinn440/autoregressive-models-for-natural-language-processing-b95e5f933e1f• Archimedean property: https://en.wikipedia.org/wiki/Archimedean_property• Tabula rasa: https://en.wikipedia.org/wiki/Tabula_rasa• Daniel Weinand on LinkedIn: https://www.linkedin.com/in/danielweinand/• World of Warcraft: https://worldofwarcraft.blizzard.com• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/• Monorepo: https://en.wikipedia.org/wiki/Monorepo• The Sarbanes Oxley Act: https://sarbanes-oxley-act.com/• Shopify builds Shopify Balance with Stripe to give small businesses an easier way to manage money: https://stripe.com/customers/shopify• Stanford marshmallow experiment: https://en.wikipedia.org/wiki/Stanford_marshmallow_experiment• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong/• We are the Web: https://link.wired.com/public/32945405—Recommended books:• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713• The Infinite Game: https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:41:42
• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product)

  Nan Yu is the head of product at Linear, one of the most beloved and fastest-growing B2B SaaS products out there today, and the gold standard for high-performing tech teams. In our conversation, we discuss:• Why speed and quality aren’t actually at odds• Linear’s unique approach to product development• Nan’s systematic approach to creativity• Linear’s philosophy on deadlines• The “double triangle” framework for product management• Nan’s approach to landing his dream product roles• Much more—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Paragon—Ship every SaaS integration your customers want• Wix Studio—The web creation platform built for agencies—Find the transcript at: https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu—Where to find Nan Yu:• X: https://x.com/thenanyu• LinkedIn: https://www.linkedin.com/in/thenanyu/—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 Nan Yu and Linear(04:54) Survey insights: Linear vs. Jira(07:51) The speed vs. quality myth(09:24) Building and iterating quickly(15:31) Avoiding bloat in enterprise software(23:57) Understanding user needs deeply(30:09) How to approach customer calls(34:10) Creating strong emotional hooks(40:31) Managing the product backlog(44:46) Systemizing creativity(48:16) Demo: Saving drafts in Linear(51:38) Breaking constraints and building at extremes(54:15) Adopting new tools(58:22) The “double triangle” framework for product management(01:04:23) Effective job-hunting strategies for PMs(01:09:15) Thoughts on deadlines(01:14:15) Lightning round—Referenced:• Jira: https://www.atlassian.com/software/jira• Linear: https://linear.app/• Patrick Collison’s post on X: https://x.com/patrickc/status/1869422495985750459• Magnus Carlsen on X: https://x.com/magnuscarlsen• Hikaru Nakamura on X: https://x.com/gmhikaru• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead• Customer Request feature on Linear: https://linear.app/customer-requests• Everlane: https://www.everlane.com/• Schlep Blindness: https://paulgraham.com/schlep.html• Linear’s triage tool: https://linear.app/docs/triage• Patrick Collison’s post about mental models on X: https://x.com/patrickc/status/1443215022029619200• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of• Mode: https://mode.com/• The Diplomat on Netflix: https://www.netflix.com/title/81288983• Sakura Micron pens: https://www.amazon.com/SAKURA-PIGMA-MICRON-ESSENTIAL-COLORS/dp/B07VJFXT3C/—Recommended books:• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:21:08
• An operator’s guide to product strategy | Chandra Janakiraman (CPO at VRChat, ex-Meta, Headspace, Zynga)

  Chandra Janakiraman is the chief product officer, executive vice president, and a board member at VRChat. Previously, he was a product leader at Meta, where he led Facebook’s social experience interfaces and Reality Labs’ growth; served as CPO at Headspace, where he helped relaunch the platform, driving a 4x subscriber boost; and was a GM at Zynga, delivering massive hit games that reached hundreds of millions. In our conversation, Chandra shares:• His playbook for developing a product strategy• The difference between “small s” and “big S” strategy• How to run strategy sprints• Who should be involved in strategy work• Common pitfalls in strategy development• The role of AI in future strategy development• More—Brought to you by:• Eppo—Run reliable, impactful experiments• Airtable ProductCentral—Launch to new heights with a unified system for product development• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/an-operators-guide-to-product-strategy-chandra-janakiraman—Where to find Chandra Janakiraman:• LinkedIn: https://www.linkedin.com/in/chandramohanj/—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) Chandra’s background(04:47) The importance of strategy(12:40) Defining product strategy(15:42) Developing a winning strategy: an overview(18:51) The preparation phase(30:46) The strategy sprint process(45:51) The design sprint (51:19) Document writing(57:39) Rolling out your strategy(01:01:28) Resourcing and roadmapping(01:04:42) Strategy lessons from Zynga(01:11:34) Strategy lessons from Meta(01:15:55) Big S strategy(01:26:58) AI in strategy formulation(01:38:12) Final thoughts and lightning round—Referenced:• Headspace: https://www.headspace.com/• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin• VRChat: https://hello.vrchat.com/• Andrew Chen on LinkedIn: https://www.linkedin.com/in/pmandrewchen/• Template: Working Backwards PR FAQ: https://www.workingbackwards.com/resources/working-backwards-pr-faq• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake• Identify your bullseye customer in one day | Michael Margolis (UX Research Partner at Google Ventures): https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis• Chandra’s flow chart: https://docs.google.com/document/d/1SLmQ0oRFadzJnNM3MJetnLUvB18U4W4GXU4KtJ2ujEQ/edit?tab=t.0• Chandra’s strategy template: https://docs.google.com/document/d/1iNeYUaMnpicvkpVZO-gj9cCxLeHfWN0xtGm_QoxgemE/edit?tab=t.0#heading=h.5d3jz6v86yrs• Zynga: https://www.zynga.com/• David Foster Wallace’s quote about water: https://www.goodreads.com/quotes/97082-there-are-these-two-young-fish-swimming-along-and-they• Oculus: https://en.wikipedia.org/wiki/Oculus• Elon Musk’s quote: https://www.youtube.com/shorts/wf8TadbGYok• Concept car: https://en.wikipedia.org/wiki/Concept_car• Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview• Armand Ruiz on LinkedIn: https://www.linkedin.com/in/armand-ruiz/• What is a multi-armed bandit? Full explanation: https://amplitude.com/explore/experiment/multi-armed-bandit• IF on Prime Video: https://www.amazon.com/IF-John-Krasinski/dp/B0CW19SCVW• Dune: Part 2 on AppleTV+: https://tv.apple.com/us/movie/dune-part-two/umc.cmc.363aycnv6vy9qgekvew6fveb9• Dune Prophecy on Max: https://www.max.com/shows/dune-prophecy-2024/57660b16-a32a-476f-89da-3302ac379e91• Capybara Go on the App Store: https://apps.apple.com/ph/app/capybara-go/id6596787726• Bluesky: https://bsky.app/• Steve Jobs: The Lost Interview on Prime Video: https://www.amazon.com/Steve-Jobs-Lost-Interview/dp/B01IJD1BES—Recommended books:• The Art of War: https://www.amazon.com/Art-War-Sun-Tzu/dp/1599869772• Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487/• Good Strategy Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239/• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422• Sprint: https://www.amazon.com/SPRINT-Jake-Zeratsky-Knapp/dp/0593076117• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473• 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 Ten Faces of Innovation: Strategies for Heightening Creativity: https://www.amazon.com/dp/0385512074—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:47:22

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