Lenny's Podcast: Product | Career | Growth cover art

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 art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

    The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
    Mar 22 2026
    Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process.We discuss:1. Why great ideas often don’t get buy-in2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much3. Why executives are usually optimizing for a global maximum while you are often optimizing locally4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”5. Why you should go in to learn, not to convince6. Why showing only one option is a mistake7. Why AI will make influence more important, not less—Brought to you by:Omni—AI analytics your customers can trustLovable—Build apps by simply chatting with AIVanta—Automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jessica Fain:• LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989—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 Jessica Fain(03:53) Why influence is the highest-leverage skill in product(04:47) Why great ideas fail without executive buy-in(06:00) How executives actually think(09:05) The fundamentals: context-setting, communication, and empathy(10:22) Stop pitching for approval—start co-creating with execs(12:59) Influence vs. politics (and why people get it wrong)(15:44) How to disagree with execs without losing trust(17:20) Going in to learn, not to convince(19:08) How to present ideas(26:05) The Minto-style approach and tailoring your communication to each exec(28:22) Why Jessica doesn’t like the question “What’s top of mind for you?”(30:24) Understanding incentives to unlock buy-in(32:10) Aligning product work with company strategy(35:10) Quick summary(37:31) Disarming the executive(40:49) Speed matters: why fast follow-up builds momentum(43:32) How to run high-impact meetings (the 60-second rule)(47:00) Why influencing execs is part of your job(49:15) Asking for more resources and thinking in 10x bets(52:23) What to do when your idea gets rejected(54:18) Clarifying information(56:50) How to build trust and make ideas stick(58:30) Shrinking big ideas into experiments(01:02:27) Common mistakes people make when influencing leaders(01:06:00) How to grow into your next role(01:09:32) How AI is changing influence and product work(01:17:55) Using AI to simulate exec feedback and improve pitches(01:21:15) Protecting our brains from overwhelm(01:22:44) Lightning round and final thoughts—Referenced:• Box: https://www.box.com• Slack: https://slack.com• Brightwheel: https://mybrightwheel.com• Webflow: https://webflow.com• April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua• Atlassian: https://www.atlassian.com• Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid• Calendly: https://calendly.com• Glassdoor: https://www.glassdoor.co.in/index.htm• The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai• Ethan Eismann on X: https://x.com/eeismann• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield• Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank• Checkr: https://checkr.com• Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl• Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief• Barbara Minto’s website: https://www.barbaraminto.com• How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff• Building product at Stripe: craft, metrics...
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    1 hr and 34 mins
  • The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)

    The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)
    Mar 15 2026
    Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes.We discuss:1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump2. Why Jacob sees 40% average movement when negotiations are run well3. When negotiation actually starts (hint: it’s much earlier than you think)4. Why information + timing create power5. The biggest mistakes people make when negotiating6. How to navigate the important “What’s your comp expectation?” question without anchoring too low7. Why the best interviews feel more like discovery calls than interrogations—Brought to you by:Orkes—The enterprise platform for reliable applications and agentic workflowsMercury—Radically different bankingOmni—AI analytics your customers can trust—Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Jacob Warwick:• Substack: https://www.execsandthecity.com• YouTube: https://www.youtube.com/@ExecsandtheCity• Website: https://www.thinkwarwick.com• Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course—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 Jacob Warwick(04:12) How much comp people leave on the table(07:52) Why you shouldn’t feel greedy asking for more(09:45) What founders should know about negotiation(13:03) How Jacob works behind the scenes(15:35) The biggest mistakes people make when negotiating(19:30) Home-field advantage and controlling the conversation(23:02) The step-by-step approach to negotiating an offer(30:17) Jacob’s passion and why these tips don’t work on kids(32:04) Who should speak first about compensation(35:36) Understanding power(39:52) Breaking out of salary bands by focusing on pain points(45:45) Brief summary(47:20) Selling the vacation: How to visualize success(50:07) Controlling the narrative and planting seeds(59:01) Jacob’s role as hype man(01:01:05) Positioning yourself like a product(01:02:49) Making the process frictionless for hiring managers(01:06:20) Flipping the interview to extract information(01:12:17) Five tactical tips for negotiating comp(01:21:45) What to do when negotiations fall apart(01:25:05) Why negotiation is different for every individual(01:28:55) Why outcomes aren’t predetermined(01:32:52) Wild Hollywood negotiation stories(01:37:35) The first step you should take after getting an offer(01:40:30) Jacob’s personal mission(01:44:42) Lightning round and final thoughts—Referenced:• The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating• Sam Altman on X: https://x.com/sama• Tom Brady on X: https://x.com/TomBrady• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8• Salesforce: https://www.salesforce.com• Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts• Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon• Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom• Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that• Chris Voss on X: https://x.com/fbinegotiator• Werewolf: https://playwerewolf.co• Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion• How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy• ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation• Marvel: https://www.marvel.com• Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030• Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0• Minuscule: https://www.youtube.com/user/Minuscule• Claude Cowork: https://claude.com/product/cowork• Macrofactor: https://macrofactor.com• Whoop: https://www.whoop.com• Gemini: https://gemini.google.com/app• The Cody Dieruf Foundation: https://breathinisbelievin.org• Cystic Fibrosis Foundation: https://...
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    1 hr and 55 mins
  • How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky

    How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky
    Mar 12 2026
    People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.We discuss:1. The collection of moments that led me to what I do now2. When I added a paywall, and how I knew it was working3. The hidden treadmill behind shipping a newsletter post and podcast episode every week4. The most stressful moments I’ve had in business and in life5. How I think about stress, consistency, and keeping the business small—Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyMetaview—The AI platform for recruiting: https://metaview.ai/lennyDX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Michelle Rial:• X: https://x.com/TheRialMichelle• LinkedIn: https://www.linkedin.com/in/michellerial• Website: https://www.michellerial.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 and role reversal(04:06) What would Lenny be doing without the newsletter?(07:20) The moments that led to starting the newsletter(09:58) Does Lenny still enjoy the work?(12:42) Stress management and misophonia(14:00) The psychedelic trip that changed everything(15:45) Online happiness course and baseline optimization(17:30) Thunder round: Lenny’s misophonia worst sounds(20:20) What makes Michelle’s charts so shareable(23:55) Where chart ideas come from (and why meditation helps)(26:59) Where does “Lenny” come from?(28:54) Being recognized in public(31:24) Early projects(36:30) Michelle and Lenny’s yin and yang(37:49) Missing office culture (but not really)(39:37) Lenny’s face blindness(40:47) The $100M fraud attack story(42:50) Michelle’s childbirth emergency(47:22) Michelle’s creative process(51:58) Lenny’s favorite children’s books(54:00) Product management lessons in parenting(55:31) Defining product management in five words(58:23) Why Michelle pivoted to children’s books(01:01:30) The power of iteration and real experience—Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. To hear more, visit www.lennysnewsletter.com
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    1 hr and 7 mins
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