Lenny's Reads

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

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

  1. A guide to advanced B2B positioning

    2H AGO

    A guide to advanced B2B positioning

    It's never been easier to launch products, which means the biggest challenge product teams are facing is quickly becoming distribution. April Dunford, the world's leading expert on B2B positioning and author of Obviously Awesome, has spent 10 years working with more than 300 companies to help them stand out. In this episode, she goes beyond the basics to share tactics for overcoming four of the trickiest positioning roadblocks teams face. In this episode, you'll learn: • The four roadblocks every team faces when making positioning decisions • Why cross-functional teams almost always disagree on who they compete with • How to break the cycle of product pessimism • Why the "So what?" test is critical for defining your differentiated value • How to use your GTM strategy to drive positioning decisions — References: • April Dunford: https://www.linkedin.com/in/aprildunford/ • April Dunford's guest post on positioning: https://www.lennysnewsletter.com/p/positioning • April Dunford on Lenny's Podcast: https://www.youtube.com/watch?v=hdjlCLb9Hl8 • Salesforce: https://www.salesforce.com/ • Lenny's Product Pass: https://www.lennysproductpass.com/ — Read the full newsletter: https://www.lennysnewsletter.com/p/a-guide-to-advanced-b2b-positioning 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 — 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. How to debug a team that isn’t working: the Waterline Model

    6D AGO

    How to debug a team that isn’t working: the Waterline Model

    When their team underperforms, most managers jump straight to blaming people. Molly Graham—who's worked alongside Mark Zuckerberg, Sheryl Sandberg, and Chamath Palihapitiya—explains how that's one of the biggest leadership traps there is. In this episode, she shares the Waterline Model: a diagnostic model to help uncover the real source of team problems, before touching an org chart. In this episode, you'll learn: • Why blaming people for structural problems is one of the biggest leadership mistakes • The four layers of the Waterline Model, and why that order matters • Why you should always "snorkel before you scuba" • How self-preservation can be a rational response to a faulty environment • How to make clean, decisive calls when you finally reach the individual layer — References: • "Give Away Your Legos": https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/ • Glue Club: https://glueclub.com/ • Molly Graham: https://www.linkedin.com/in/mograham/ • Molly Graham on Lenny's podcast: https://www.youtube.com/watch?v=twzLDx9iers • Lenny's Product Pass: https://www.lennysproductpass.com/ — Read the full newsletter: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working 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 — 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

    13 min
  3. How to use AI for your next job interview

    FEB 24

    How to use AI for your next job interview

    What if you could get line-by-line feedback on every interview answer you gave, predict questions before you walk in, and surface stories you didn't know you had? Noam Segal, Lenny's Community Research Lead, interviewed over 30 tech professionals about how they use AI throughout the interview process, and used the findings to build a free Claude Code-based interview coach. His coach encodes every successful interview technique he uncovered (and then some), making it an invaluable tool you can plug into your job search today. In this episode, you'll learn: · Why interview prep is broken (and why there's no usable feedback loop) · How the most successful candidates built AI systems to close the gap · What the free AI Interview Coach does and how to set it up · How to stop sounding like every other candidate who prepped with AI · The action checklist for before, during, and after every interview References: · Claude: https://claude.ai/ · Granola: https://granola.ai/ · Claude Code Interview Coach (Github link): https://github.com/noamseg/interview-coach-skill · Lenny's Product Pass: https://lennysproductpass.com/ · Noam Segal: https://www.linkedin.com/in/noamsegal · PM Interview Copilot: https://www.benerez.com/copilot · Product sense guide: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering Read the newsletter https://www.lennysnewsletter.com/p/how-to-use-ai-in-your-next-job-interview 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
  4. How to do AI analysis you can actually trust

    FEB 17

    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
  5. 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

  6. 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
  7. 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
  8. 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
See All (39)

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
    39
  • Rating
    Clean
  • Copyright
    © Lenny Rachitsky
  • Show Website
    Lenny's Reads

You Might Also Like