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Lenny's Newsletter — Complete Archive

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Lenny's Newsletter — Complete Archive

By Lenny Rachitsky

Complete archive of 349 Lenny's Newsletter issues (2020-2025). Covers product management, growth, startups, leadership, hiring, strategy, and career advice from top PMs and operators.

  • 2117 pages
  • 467 chapters
  • Updated March 18, 2026

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A look inside · First page

How to build your PM second brain with ChatGPT (2025-12-16)

👋 Hey there, I’m Lenny. Each week, I tackle reader questions about building product, driving growth, and accelerating your career. For more: Lennybot | Lenny’s Podcast | How I AI | Lenny’s Reads | AI/PM courses | Public speaking course

Annual subscribers get 19 premium products for free for one year: Lovable, Replit, Gamma, n8n, Bolt, Devin, Wispr Flow, Descript, Linear, PostHog, Superhuman, Granola, Warp, Perplexity, Raycast, Magic Patterns, Mobbin, ChatPRD + Stripe Atlas (while supplies last). Subscribe now.

Someone smarter than me once said, “AI won’t replace you, but a person using AI better than you might.” I believe this is exactly right. Right now, we all need to be building the skills that help us become that person using AI better. Lucky for us, Amir Klein is already that person and has written a guide for the rest of us. Though it’s targeted at product managers, the advice and workflows can be implemented by anyone in any function. Thank you, Amir, for giving us a glimpse into the future and the concrete steps to get there.

For more, follow Amir on LinkedIn. You can also listen to this post in convenient podcast form on Spotify / Apple / YouTube.

The first month in my new role at monday.com, I was tasked with building our first AI agent. The goal was to create an AI co-pilot, something users could turn to for insights, explanations, or building complex workflows they wouldn’t know how to create on their own. To build that, I needed a ton of context—all the internal knowledge, decisions, assumptions, and scattered inputs that shape any product direction. And gathering all of that felt completely overwhelming.

I was drowning.

All that context lives everywhere: Slack channels, Notion pages, Monday boards, decks, Google Docs. Hundreds of tiny fragments I could never quite piece together. I kept running into mental blocks, forgetting what I knew from where, and getting stuck. Instead of trying to keep all of that context in my head like I always had, this time I wanted to try something new. I dumped everything I had into a ChatGPT Project, word-vomited all that was on my mind, and asked if it could help me get started. And boy, did it.

Finally, I felt like I could smell a roadmap on the horizon, a direction was forming, and things began to click. Even better, I felt somewhat in control without being stressed about storing everything in my head. I could store it in the AI instead—a second brain. Instead of all that information overloading my own brain and pulling my attention in a hundred different directions, I could finally focus on the product work I love and need to get right to be successful: understanding the problem, shaping the vision, and building something meaningful.

My good friend Tal taught us how to think with AI. I’m building on Tal’s post by showing what happens when AI becomes an extension of your mind—when it carries your context, grows alongside you, and ultimately amplifies what you’re capable of as a PM.

Add this book to your library to keep reading.

What’s inside

03A year free of PostHog ($16,500 value): The all-in-one analytics, experimentation, feature flag, surveys, session replay, error tracking, data warehouse, LLM analytics platform (2025-12-02)p. 13

06Part 2 of how to get the most out of your product pass—and welcome, Stripe Atlas, to the bundle! (2025-11-04)p. 32

21How to get the most out of your product pass, part 1 (2025-09-23)p. 74

32Taking the week off + a newsletter cadence update (2025-08-26)p. 92

43How tech’s most resilient workers handle burnout (2025-06-17)p. 154

46**Where to go from here**p. 167
47Taking the week off (2025-06-03)p. 168
48How tech workers really feel about work right now (2025-05-27)p. 168

65Announcing the greatest product bundle ever: Get a year free of Granola, Notion, Superhuman, Linear, and Perplexity with an annual subscription (2025-02-04)p. 272

72Taking the week off 🎄🕎🎁 (2024-12-31)p. 304

88Get Perplexity Pro free for 1 year (2024-09-23)p. 395

102Announcing the Lenny & Friends Summit 🙌 (2024-07-29)p. 479

104Taking the week off (2024-07-16)p. 483

107Meet your Lenny’s Newsletter Fellows ✨ (2024-07-01)p. 504

110How to use Perplexity in your PM work (2024-06-11)p. 519

113Taking the week off (2024-05-28)p. 528

117How Perplexity builds product (2024-04-30)p. 549

132How Gong builds product (2024-01-23)p. 655

137Taking the week off (and thank you!) (2023-12-26)p. 689

139The Best of Lenny’s Newsletter 2023 (2023-12-12)p. 698

149Skipping newsletter today (2023-10-10)p. 765

151How Linear builds product (2023-09-26)p. 781

163How Shopify builds product (2023-07-25)p. 893

166How Snowflake builds product (2023-07-11)p. 915

172How a traumatic brain injury made me a better PM—and person (2023-06-06)p. 957

175How Notion builds product (2023-05-30)p. 974

177How Ramp builds product (2023-05-23)p. 983

180How Miro builds product (2023-05-09)p. 999

184How to use ChatGPT in your PM work (2023-04-11)p. 1017

186Taking the week off (2023-04-04)p. 1019

188How Duolingo builds product (2023-03-21)p. 1027

194I built a Lenny chatbot using GPT-3. Here’s how to build your own. (2023-02-07)p. 1061

196How Coda builds product (2023-01-31)p. 1069

201The Best of Lenny’s Newsletter 2022 (2022-12-27)p. 1100

207How Figma builds product (2022-11-15)p. 1131

213Taking the week off (2022-10-04)p. 1158

249Taking the week off (2021-12-21)p. 1428

262Taking the week off (2021-10-19)p. 1488
26360 ideas to boost your growth (2021-10-12)p. 1489

267The 10 commandments of salary negotiation (2021-09-24)p. 1510

270How behavioral science can boost your conversion rates (2021-09-17)p. 1517

278Five habits of highly annoying product managers (2021-08-10)p. 1553

288Choosing Your North Star Metric (2021-06-16)p. 1587

299Why marketplaces fail (2021-04-13)p. 1639

303The PM 🤝 Design Partnership (2021-03-23)p. 1656

312Positioning (2021-01-26)p. 1700

315Increasing team velocity (2021-01-12)p. 1712

336Pricing your SaaS product (2020-10-27)p. 1780

343What it feels like when you've found product-market fit (2020-09-29)p. 1801

346When to hire your first product manager (2020-09-15)p. 1815

348Getting better at product strategy (2020-09-08)p. 1819

353**First, how does one measure retention?**p. 1837

356**First, how does one measure retention?**p. 1843

360My favorite product management templates (2020-08-04)p. 1853

369In summaryp. 1868

371Winning at SEO (2020-07-14)p. 1873

373How today's fastest growing B2B businesses found their first ten customers (2020-07-07)p. 1879

379**Inspiration for the week ahead 🧠**p. 1890
380Evaluating a (marketplace) business idea (2020-06-23)p. 1890

384Evaluating a (marketplace) business idea - Issue 31 (2020-06-23)p. 1896
385Q: I loved your series about [kickstarting and scaling a marketplace business](https://www.lennyrachitsky.com/p/how-to-kickstart-and-scale-a-marketplace). As an investor, I’m curious how you evaluate marketplace business ideas. What do you look for?p. 1896

387One team, one roadmap - Issue 30 (2020-06-16)p. 1898

389What is good retention? (2020-06-09)p. 1900

393In summaryp. 1905

398How the biggest consumer apps got their first 1,000 users (2020-05-12)p. 1913
399👉 [Updated version of this post here](https://www.lennysnewsletter.com/p/consumer-business-find-first-users) 👈p. 1914

402Setting goals - Issue 23 (2020-04-29)p. 1928

404Setting goals (2020-04-28)p. 1929

425How To Know If You're Supply or Demand Constrained 🤹‍♂️ - Phase 2 of Kickstarting and Scaling a Marketplace Business (2019-12-10)p. 2000

439The Secret to a Great Planning Process — Lessons from Airbnb and Eventbrite (2019-09-26)p. 2061

447**Step 2: Align on the problem with your team and stakeholders**p. 2093
448**Step 3: Keep coming back to the problem**p. 2094
449**A final note**p. 2095
450How to get into product management (2019-06-14)p. 2095

452Plan the How: The four most common paths into PMp. 2097

454What Buddhism Taught Me About Product Management (2019-06-14)p. 2106
4551. There is suffering 😨p. 2107
4562. All things are impermanent ❄️p. 2108
4573. There is no lasting self ⛄️p. 2109

460Create strong culture, values, and ritualsp. 2111
461**Nail the problem statement**p. 2111
462Set wildly ambitious goalsp. 2112
463Start with the ideal and work backwardp. 2113

465Maintain a high bar for everythingp. 2115

About this book

Complete archive of 349 Lenny's Newsletter issues (2020-2025). Covers product management, growth, startups, leadership, hiring, strategy, and career advice from top PMs and operators.