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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 high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale

    The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale
    Jan 4 2026
    Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.We discuss:1. “Give away your Legos”: a framework for scaling yourself as a leader2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)4. Six rules for creating effective goals (and aligning everyone around them)5. Rules of thumb for leading through rapid scale and change6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor—Brought to you by:DX—The developer intelligence platform designed by leading researchersBrex—The banking solution for startupsGoFundMe Giving Funds—Make helping a habit—Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation—Where to find Molly Graham:• X: https://x.com/molly_g• LinkedIn: https://www.linkedin.com/in/mograham• Substack: https://mollyg.substack.com• Website: https://glueclub.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 Molly Graham(04:28) Molly’s background at Google, Facebook, Quip, and CZI(11:29) The “Give away your Legos” framework(16:44) Managing your inner monster(19:49) When not to give away your Legos(21:28) Embracing a long career(23:25) The J-curve vs. stairs approach to career growth(32:00) The gift of knowing yourself(34:28) Learning to be a professional idiot(38:30) The waterline model: snorkel before you scuba(47:16) Six rules for creating strong alignment around goals(57:15) Rules of thumb for leading through rapid scale(01:07:49) Investing in high performers vs. low performers(01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor(1:21:15) Pivoting from ambition to purpose(1:26:32) Finding stability in instability(01:29:44) Final thoughts—Referenced:• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage• Quip: https://quip.com• 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• Chan Zuckerberg Initiative: https://chanzuckerberg.com• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups• The Muppets: https://muppets.disney.com• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals• Founder mode: https://paulgraham.com/foundermode.html• Stripe: https://stripe.com• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison• John Collison on X: https://x.com/collision• Seth Godin’s best tactics for building remarkable products, strategies, ...
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    1 hr and 32 mins
  • We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)

    We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)
    Jan 1 2026
    Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.We discuss:1. How AI is fundamentally changing the sales function2. Why most SDRs and BDRs will be “extinct” within a year3. What Jason is observing across his portfolio about AI adoption in GTM4. How to become “hyper-employable” in the age of AI5. The specific AI tools and tactics he’s using that have been working best6. Practical frameworks for integrating AI into your sales motion without losing what works7. Jason’s 2026 predictions on where SaaS and GTM are heading next—Brought to you by:DX—The developer intelligence platform designed by leading researchersVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation—Where to find Jason Lemkin:• X: https://x.com/jasonlk• LinkedIn: https://www.linkedin.com/in/jasonmlemkin• Website: https://www.saastr.com• Substack: https://substack.com/@cloud—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 Jason Lemkin(04:36) What SaaStr does(07:13) AI’s impact on sales teams(10:11) How SaaStr's AI agents work and their performance(14:18) How go-to-market is changing in the AI era(19:19) The future of SDRs, BDRs, and AEs in sales(22:03) Why leadership roles are safe(23:43) How to be in the 20% who thrive in the AI sales future(28:40) Why you shouldn't build your own AI tools(30:10) Specific AI agents and their applications(36:40) Challenges and learnings in AI deployment(42:11) Making AI-generated emails good (not just acceptable)(47:31) When humans still beat AI in sales(52:39) An overview of SaaStr's org(53:50) The role of human oversight in AI operations(58:37) Advice for salespeople and founders in the AI era(01:05:40) Forward-deployed engineers(01:08:08) What's changing and what's staying the same in sales(01:16:21) Why AI is creating more work, not less(01:19:32) Why Jason says these are magical times(01:25:25) The "incognito mode test" for finding AI opportunities(01:27:19) The impact of AI on jobs(01:30:18) Lightning round and final thoughts—Referenced:• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• SaaStr Annual: https://www.saastrannual.com• Delphi: https://www.delphi.ai/saastr/talk• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/• Vercel: https://vercel.com• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently• 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• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• ElevenLabs: https://elevenlabs.io• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack• Bolt: https://bolt.new• Lovable: https://lovable.dev• Harvey: https://www.harvey.ai• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence• UiPath: https://www.uipath.com• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser• Agentforce: https://www.salesforce.com/form/agentforce• SaaStr’s AI Agent Playbook: https://saastr.ai/agents• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan• Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan• Sierra: https://sierra.ai• Fin: https://fin.ai• Deccan: https://www.deccan.ai• Artisan: https://www.artisan.co• Qualified: https://...
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    1 hr and 42 mins
  • 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)

    10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
    Dec 28 2025
    Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you’ve gone too far3. Matt’s transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.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 Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion’s success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling’s vision and success(01:17:48) AI’s impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman’s website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: ...
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    1 hr and 36 mins
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