Lenny’s Newsletter

A weekly column offering insights on product development, enhancing growth, and fast-tracking your career.

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AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt)

1 week ago | lennysnewsletter.com | Lenny Rachitsky

Listen now:YouTube // Apple // SpotifyBrought to you by:Eppo—Run reliable, impactful experimentsStripe—Helping companies of all sizes grow revenueVanta—Automate compliance. Simplify securitySander Schulhoff is the OG prompt engineer.
How tech’s most resilient workers handle burnout

1 week ago | lennysnewsletter.com | Lenny Rachitsky

If you’re a premium subscriberAdd the private feed to your podcast app at add.lennysreads.comThree weeks ago, Noam Segal and I shared data showing that 84% of tech workers feel burned out. That left one big question: Who are the 16% who aren’t? This episode is their playbook. We analyzed 175 follow-up surveys and spoke with 15 “burnout conquerors” to understand how they’ve cracked the code.
How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

1 week ago | lennysnewsletter.com | Lenny Rachitsky

Listen now:YouTube // Apple // SpotifyBrought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsPersona—A global leader in digital identity verificationAttio—The powerful, flexible CRM for fast-growing startupsHilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices.
35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley

2 weeks ago | lennysnewsletter.com | Lenny Rachitsky

The “Beatles principle” for team size—you get genius with 4 people, not 8 or 24. The original Mac team was just 20 people; the iPhone team was 24. Small teams create coherent, magical products. Design should report to engineering, not product—it’s most successful when considered “phase zero” of the engineering process rather than a separate function.
How to get your entire team prototyping with AI

2 weeks ago | lennysnewsletter.com | Colin Matthews

👋 Welcome to a 🔒 subscriber-only edition 🔒 of my weekly newsletter. Each week I tackle reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast |How I AI| Lennybot | Lenny’s Reads | Courses | SwagAnnual subscribers now get a free year of Bolt, Perplexity Pro, Notion, Superhuman, Linear, Granola, and more. Subscribe now. Colin Matthews holds the distinct honor of having not one but two posts in my top 10 most popular posts of all time.
How to get your entire team prototyping with AI

2 weeks ago | lennysnewsletter.com | Lenny Rachitsky |Colin Matthews

Current time: 0:00 / Total time: -13:38Audio playback is not supported on your browser. Please upgrade. If you’re a premium subscriberAdd the private feed to your podcast app at add.lennysreads.comColin Matthews was a longtime PM and is the creator of my favorite AI prototyping course, AI Prototyping for Product Managers. He already has two posts in my all-time top 10 — and I wouldn’t be surprised if this becomes his third.
How Mercado Libre built Latin America's most valuable company: 18k engineers, 30k deploys a day, and their own fleet of planes | Sebastian Barrios

2 weeks ago | lennysnewsletter.com | Lenny Rachitsky

Listen now:YouTube // Apple // SpotifyBrought to you by:Merge—A single API to add hundreds of integrations into your appVanta—Automate compliance. Simplify securityLinkedIn Ads—Reach professionals and drive results for your businessSebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees.
Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram)

3 weeks ago | lennysnewsletter.com | Lenny Rachitsky

Listen now:YouTube // Apple // SpotifyBrought to you by:Productboard—Make products that matterStripe—Helping companies of all sizes grow revenueOneSchema—Import CSV data 10x fasterMike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024.
Taking the week off

3 weeks ago | lennysnewsletter.com | Lenny Rachitsky

I’m taking this week off to recharge (per my PTO policy). If you’re looking to learn something in the meantime, I encourage you to play around with Lennybot. It’s trained on every single one of my newsletter posts and podcast interviews. It’s good. And totally free. Some questions to ask it to get you going:How do I find an idea for a new product? How do I write a strategy doc? What can I do to get promoted faster? How do I know if I should be a founder?
Why Uber’s CPO delivers food on weekends | Sachin Kansal

3 weeks ago | lennysnewsletter.com | Lenny Rachitsky

Listen now:YouTube // Apple // SpotifyBrought to you by:Paragon—Ship every SaaS integration your customers wantStripe—Financial infrastructure to grow your revenueCoda—The all-in-one collaborative workspaceSachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber).