How I built LennyRPG

Turning 300+ episode transcripts into a fun, playable game with AI

Mar 17 • Ben Shih

214

44

16

A guide to advanced B2B positioning

10 years, 300 companies, 4 non-obvious lessons on getting past the trickiest roadblocks

Mar 10 • April Dunford

336

15

18

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

A guide to solving team problems (without always blaming the people)

Mar 3 • Molly Graham

617

10

46

February 2026

How to use AI for your next job interview

Insights from 30+ tech professionals, and a free AI coach to put them into practice

Feb 24 • Noam Segal

550

22

31

How to do AI analysis you can actually trust

Four prompting techniques to prevent AI’s most common mistakes

Feb 17 • Caitlin Sullivan

365

5

35

Building AI product sense, part 2

A weekly ritual to help you understand and design trustworthy AI products for a messy world

Feb 10 • Marily Nika

230

4

21

How to build AI product sense

The secret is using Cursor for non-technical work (inside: 75 free days of Cursor Pro to try this out!)

Feb 3 • Tal Raviv and Aman Khan

533

38

45

January 2026

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

23 premium tools, over $25,000 in value. The most epic bundle in history just keeps getting better.

Jan 27 • Lenny Rachitsky

202

23

9

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

A step-by-step guide to jumping in and building your first ChatGPT app

Jan 20 • Colin Matthews

290

15

34

Best of Lenny’s Newsletter 2025

The 25 best posts from the past year, plus a few all-time classics

Jan 6 • Lenny Rachitsky

195

1

8

December 2025

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

What exactly AI is doing for people, which AI tools have product-market fit, where the biggest opportunities remain, and what it all means

Dec 23, 2025 • Noam Segal and Lenny Rachitsky

381

16

40

How to build your PM second brain with ChatGPT

Use AI to amplify your craft, not replace it

Dec 16, 2025 • Amir Klein

446

22

35