Lenny's Reads

Lenny Rachitsky
  • 4.3 (6)
  • TECHNOLOGY
  • UPDATED WEEKLY

An audio edition of Lenny's Newsletter (powered by AI)

  1. How to do AI analysis you can actually trust

    5H AGO

    How to do AI analysis you can actually trust

    Ever run an AI analysis on customer data, only to discover the numbers were fabricated and the insights completely generic? In this episode, Caitlin Sullivan, a user-research veteran who's trained hundreds of product and research professionals, shares her four prompting techniques for getting trustworthy, actionable insights out of any LLM. After 2,000+ hours of testing customer discovery workflows with AI, she's identified the failure modes that break AI analysis and the reliable fixes for each one.In this episode, you'll learn: • How to catch the two types of AI quote hallucinations • Why AI defaults to useless generic themes and insights • Which LLM is best for analysis work (and which one fabricates the most) • How to turn vague signal into actual decision clarity • The final verification pass that stress-tests everything before it hits a deck Referenced: • Caitlin Sullivan: https://www.linkedin.com/in/caitlindsullivan/ • Claude Code for Customer Insights (Maven course): https://maven.com/caitlin/claude-code-insights • Claude: https://www.anthropic.com/claude • ChatGPT: https://chatgpt.com/ • Gemini: https://gemini.google.com/ • NotebookLM: https://notebooklm.google.com/ • Maze: https://maze.co/ • Whoop: https://www.whoop.com/ Read the newsletter: https://www.lennysnewsletter.com/p/how-to-do-ai-analysis-you-can-actually Subscribe to Lenny’s Newsletter: https://www.lennysnewsletter.com/subscribe Subscribe: • YouTube: https://www.youtube.com/@lennysreads • Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693 • Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj • Substack: https://lennysreads.com/ Follow Lenny • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ • Podcast: https://www.youtube.com/@lennyspodcast About Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com

    18 min
  2. Building AI product sense, part 2

    FEB 10

    Building AI product sense, part 2

    If you’re a premium subscriber, add the private feed to your podcast app at add.lennysreads.com Dr. Marily Nika, longtime AI PM at Google and Meta, shares a simple weekly ritual that rapidly builds AI product sense – the ability to translate probabilistic model behavior into products people can trust. In this episode, Marily walks through the framework for uncovering failure modes before users do. Listen now: YouTube | Apple | Spotify In this episode, you’ll learn • Why Meta added “Product Sense with AI” to its PM interview loop • The rituals that surface hidden failure modes • Why generative models confidently invent structure when confronted with mess • What minimum viable quality (MVQ) means and how to define three critical thresholds • Five strategic context factors that raise or lower your quality bar • Why you need to estimate your AI feature’s cost envelope early • How to design guardrails that protect users from model shortcomings • Four patterns that cover most real-world failure cases Referenced • AI PM Bootcamp & Certification • AI Product Sense & AI PM Interview prep • Dr. Marily Nika: https://www.linkedin.com/in/marilynika/ • How to build AI Product sense (Part 1) • Marily’s AI Product Academy Newsletter • Thriving as a senior IC PM in the AI era About Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com

    23 min

  3. JAN 27

    Product Pass drop: Canva, ElevenLabs, Manus, Factory, Amp, Railway, Framer—now free with your paid subscription

    If you’re a premium subscriber, add the private feed to your podcast app at add.lennysreads.com Your product builder's Product Pass just got even better. In this episode, we introduce the seven new premium partners joining the Product Pass, bringing the total value of a paid newsletter subscription to over $25,000. We cover all the new products, what they do, how people are using them, and the key details you need to know before subscribing. Listen now: YouTube | Apple | Spotify In this episode, you’ll learn: • Key features of each of the seven new products • Applicable, real-world examples of how people are using them • Which products are exclusive to Insider subscribers References: • Affinity • Amp • Canva Business • Duolingo • ElevenLabs • Every • Factory • Flourish • Framer • Harvey • Kernel • Leonardo.Ai • Lovable • Manus • Meta • Metabase • Mozart AI • n8n • Nvidia • Perplexity • Product Pass codes • Railway • Sentry This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

    11 min
  4. ChatGPT apps are about to be the next big distribution channel: Here’s how to build one

    JAN 20

    ChatGPT apps are about to be the next big distribution channel: Here’s how to build one

    Colin Matthews, shares how ChatGPT apps are emerging as a powerful new distribution channel. In this episode, Colin shares how discovery will become contextual inside ChatGPT, what the architecture looks like, and why ChatGPT apps represent a rare distribution opportunity. He also covers two fast paths you can take to build and deploy your first ChatGPT app. In this episode, you'll learn: • Why chat-native apps could change the tech ecosystem • How users will discover apps contextually inside ChatGPT • The three UI modes for ChatGPT apps • The “one widget per message” constraint • How tools, widgets, and MCP fit together • Two build paths: Replit and Chippy References: • Adobe • AllTrails • Anthropic • Apple • Booking.com • Bolt • Canva • ChatPRD • Chippy • Colin Matthews • Coursera • Datavant • Descript • Devin • DoorDash • Expedia • Figma • Gamma • GitHub • Granola • Instacart • Linear • LinkedIn • Lovable • Magic Patterns • Maven • Mobbin • n8n • OpenAI • Perplexity • PostHog • Railway • Raycast • Replit • Shopify • Spotify • Stripe Atlas • Substack • Superhuman • Vercel • Warp • Wispr Flow • Zillow Read the newsletter https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the Subscribe to Lenny’s Newsletter https://www.lennysnewsletter.com/subscribe Subscribe • YouTube: https://www.youtube.com/@lennysreads • Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693 • Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj • Substack: https://lennysreads.com/ Follow Lenny • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ • Podcast: https://www.youtube.com/@lennyspodcast About Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com

    12 min
  5. AI tools are overdelivering: results from our large-scale AI productivity survey

    12/24/2025

    AI tools are overdelivering: results from our large-scale AI productivity survey

    Noam Segal, AI Insights Manager at Figma, shares the results from our comprehensive survey of 1,750 product managers, engineers, designers, and founders on how AI is reshaping their work. The findings are striking: more than half of respondents are saving at least half a day per week on their most important tasks. Since the quality of AI tools are improving at breakneck speed, Noam reveals we're watching the early innings of a compounding productivity revolution. In this episode, you'll learn: • Why 55% say AI has exceeded expectations and how it's improving work quality • Which roles are winning with AI (and which are struggling) • Where the biggest opportunities are • Which AI tools have product-market fit • Which AI tool dominates for most roles • Why engineers prefer specialized tools • Why 92% report significant downsides to AI tools • What AI agents need to take off References: • Airbnb: https://www.airbnb.com/ • Anthropic: https://www.anthropic.com/ • Build your personal AI copilot: https://www.lennysnewsletter.com/p/build-your-personal-ai-copilot • ChatGPT: https://chatgpt.com/ • Claude: https://claude.ai/ • Cursor: https://cursor.com/ • Figma: https://www.figma.com/ • Gemini: https://gemini.google.com/ • GitHub: https://github.com/ • Granola: https://www.granola.ai/ • How to build your second brain with ChatGPT: https://www.lennysnewsletter.com/p/how-to-build-your-pm-second-brain • Intercom: https://www.intercom.com/ • Lindy: https://www.lindy.ai/ • Lovable: https://lovable.dev/ • Manus: https://manus.im/ • Microsoft Copilot: https://copilot.microsoft.com/ • Midjourney: https://www.midjourney.com/home • Monday.com: https://www.monday.com • n8n: https://n8n.io/ • Noam Segal: https://www.linkedin.com/in/noamsegal/ • Notion: https://www.notion.com/ • Perplexity: https://www.perplexity.ai/ • Replit: https://replit.com/ • v0: https://v0.app/ • Zapier: https://zapier.com/ Read the newsletter https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results Subscribe to Lenny’s Newsletter https://www.lennysnewsletter.com/subscribe Subscribe • YouTube: https://www.youtube.com/@lennysreads • Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693 • Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj • Substack: https://lennysreads.com/ Follow Lenny • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ • Podcast: https://www.youtube.com/@lennyspodcast About Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com

    14 min
  6. How to build your PM second brain with ChatGPT

    12/16/2025

    How to build your PM second brain with ChatGPT

    If you’re a premium subscriber, add the private feed to your podcast app at add.lennysreads.com In this episode, Amir Klein, from monday.com, shares a practical, battle-tested system for building a PM “second brain”. In this episode, Amir explains exactly how to set up a ChatGPT Project with a clear personality, feed it the messy context scattered across your tools, and then put it to work—drafting sign-up forms, spinning up prototypes, and tailoring comms for every audience. Listen now: YouTube | Apple | Spotify In this episode, you’ll learn: • Why context is the PM’s heaviest mental load • How to build a second brain that challenges you and mirrors your taste • The wealth of information your second brain can absorb • A simple loop to keep your second brain fresh • Three end-to-end use case examples References • Amir Klein • Build your personal AI copilot • ChatGPT • Claude • Figma • Gemini • Google Docs • Lovable • monday.com • Notion • Reddit • Slack Read the newsletter https://www.lennysnewsletter.com/p/how-to-build-your-pm-second-brain Subscribe to Lenny’s Newsletter https://www.lennysnewsletter.com/subscribe Subscribe • YouTube: https://www.youtube.com/@lennysreads • Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693 • Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj • Substack: https://lennysreads.com/ Follow Lenny • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ • Podcast: https://www.youtube.com/@lennyspodcast About Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com

    9 min
  7. How to spot a 1% startup early

    12/09/2025

    How to spot a 1% startup early

    If you’re a premium subscriber, add the private feed to your podcast app at add.lennysreads.comHow do certain early employees keep picking generational companies—again and again—before the rest of the world catches on? In this episode, we distill lessons from five such super-spotters whose resumes include Palantir, OpenAI, Facebook, Stripe, Linear, Figma, Notion, Slack, Box, Spotify, and Dropbox. You’ll learn the three rare traits they all look for, and how you can apply these signals to your own career and company-building.In this episode, you’ll learn:• How “ludicrous” ambition shows up• The underrated signs of founder greatness• How to evaluate an early product• What a “Jurassic Park” moment in startups means• How to think about risk as an early employee• Tactics to “optimize for serendipity” when breaking into rocket shipsReferences:• Alex Karp: https://x.com/PalantirTech• Bob McGrew: https://www.linkedin.com/in/bobmcgrew/• Box: https://www.box.com/• Christina Cordova: https://www.linkedin.com/in/cristinajcordova/• Daniel Ek: https://www.linkedin.com/in/daniel-ek-1b52093a/• Dylan Field: https://www.linkedin.com/in/dylanfield/• Dropbox: https://www.dropbox.com/• Facebook: https://www.facebook.com/• Figma: https://www.figma.com/• Hacker News: https://news.ycombinator.com/• Ivan Zhao: https://www.linkedin.com/in/ivanhzhao/• Linear: https://linear.app/• Meter: https://www.meter.com/• Notion: https://www.notion.so/• OpenAI: https://openai.com/• Palantir: https://www.palantir.com/• Patrick Collison: https://www.linkedin.com/in/patrickcollison/• PayPal: https://www.paypal.com/• Rasmus Andersson: https://www.linkedin.com/in/rasmusandersson/• Sean Rose: https://www.linkedin.com/in/sean-a-rose/• Slack: https://slack.com/• Soleio: https://www.linkedin.com/in/soleio/• Spotify: https://www.spotify.com/• Stewart Butterfield: https://www.linkedin.com/in/butterfield/• Stripe: https://stripe.com/• Terrence Rohan: https://www.linkedin.com/in/terrencerohan/Read the newsletter:• https://open.substack.com/pub/lenny/p/how-to-spot-a-top-1-startup-earlySubscribe to Lenny’s Newsletter:• https://www.lennysnewsletter.com/subscribeSubscribe:• YouTube: https://www.youtube.com/@lennysreads• Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693• Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj• Substack: https://lennysreads.com/Follow Lenny:• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/• Podcast: https://www.youtube.com/@lennyspodcastAbout:Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com

    9 min
  8. Ecosystem is the next big growth channel

    11/11/2025

    Ecosystem is the next big growth channel

    AI gave everyone speed - but that same speed flooded every distribution channel. Search traffic's down, inboxes are overrun, and even virality is harder when everyone's shipping quickly. In this episode, Emily Kramer reveals the strategy behind today's breakout companies: ecosystem. Instead of going direct, win through partners, creators, communities, and integrations that already have your audience's trust. If you're still relying on the old playbook in an AI-saturated world, this episode will help you rewire your strategy. In this episode, you’ll learn: • Why classic inbound, outbound, virality, events, and lifecycle are weakening in the AI era • What an ecosystem flywheel is and how it compounds credibility and distribution • The six most common ecosystem motions • How fast-growing teams such as Supabase, Clay, Lovable, and more are using an ecosystem strategy • How to pick partners using “coverage” and “composition” instead of vanity reach • What a win-win-win relationship looks like in an ecosystem • How to start an ecosystem strategy, prove it, then expand without diluting the signal References: • Aaron Cort: https://www.linkedin.com/in/aaroncort/ • AirOps: https://www.airops.com/ • Anthropic: https://www.anthropic.com/ • Arrows: https://www.arrows.to/ • Astro: https://www.astro.build/ • Baseten: https://www.baseten.co/ • Carta: https://carta.com/ • Clay: https://www.clay.com/ • Clio: https://www.clio.com/ • Craft Ventures: https://www.craftventures.com/ • Daniel Zarick: https://www.linkedin.com/in/danielzarick/ • Elena Verna: https://www.linkedin.com/in/elenaverna/ • ElevenLabs: https://elevenlabs.io/ • Emily Kramer: https://www.linkedin.com/in/emilykramer/ • Emily Kramer's newsletter: https://newsletter.mkt1.co/ • Ethan Smith: https://www.linkedin.com/in/ethanls/ • Gamma: https://gamma.app/ • GC AI: https://gc.ai/ • Graphite: https://graphite.dev/ • Grant Lee: https://www.linkedin.com/in/grantslee/ • HubSpot: https://www.hubspot.com/ • Lenny's Product Pass: https://lennysproductpass.com/ • Lovable: https://lovable.dev/ • Mercury: https://mercury.com/ • Midjourney: https://www.midjourney.com/ • Navattic: https://www.navattic.com/ • Supabase: https://supabase.com/ • “The ultimate guide to AEO” Lenny’s Podcast episode: https://www.youtube.com/watch?v=iT7kq-R3Gjc • Tom Orbach: https://www.linkedin.com/in/tomorbach/ • Tracksuit: https://www.tracksuit.com/ • Upstart: https://www.upstart.com/ • Vanta: https://www.vanta.com/ • Vercel: https://vercel.com/ • Wiz: https://www.wiz.io/ Read the newsletter https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth Subscribe to Lenny’s Newsletter https://www.lennysnewsletter.com/subscribe Subscribe • YouTube: https://www.youtube.com/@lennysreads • Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693 • Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj • Substack: https://lennysreads.com/ Follow Lenny • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ • Podcast: https://www.youtube.com/@lennyspodcast About Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com

    11 min
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Ratings & Reviews

4.3
out of 5
6 Ratings

About

An audio edition of Lenny's Newsletter (powered by AI)

Information

  • Creator
    Lenny Rachitsky
  • Years Active
    2025 - 2026
  • Episodes
    36
  • Rating
    Clean
  • Copyright
    © Lenny Rachitsky
  • Show Website
    Lenny's Reads

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