Lenny's Newsletter

🧠 Community Wisdom: What great product leaders do differently, Claude vs. ChatGPT, receiving hard feedback two weeks into the job, tips for joining a pre-PMF startup, and more

Kyle Harrison

Revisiting The Outcome Distortion Complex

Saastr

If You Are at Scale, You Now Have 2 Full-Time Jobs: Keep Your Installed Base Happy. And Winning the AI Agent War in Your Space.

Stage 2

How to Build an AI Account Qualifier That Thinks Like Your Best Rep

Ed Sim

What’s 🔥 in Enterprise IT/VC #495

Saastr

A Terrible, Terrible Week in Software Stocks. But Not Necessarily a Terrible 12 Months.

Sammy Abdullah

SaaS founders: we built a VC discovery site for you

A16Z Crypto

Stablecoins are going local

A Wealth of Common Sense | Ben Carlson

Don’t Fight the Stock Market

Joe Lonsdale

Ep 151: The Myth of Michael Milken with Richard Sandler

Glenn Borok

Ten Bets or Two Hundred: Two Theories of the Power Law

Craft Ventures

Investing in Comfy: The Operating System for Generative Media

Saanya Ojha

OpenAI Gets Back to Work

Net Interest | Marc Rubinstein

Apple Turnover

99% Derisible | Yoni Rechtman

Context is the fifth primitive

Aspiring for Intelligence | Vivek Ramaswami & Sabrina Wu

From Scarcity To Abundance

Sammy Abdullah

UnlockedVC is the Matchmaking Platform SaaS Founders and Investors Deserve Right Now

Saastr

Medallia Is Just the Opening Act. Here’s the List of PE SaaS Deals Most at Risk.

Turner Novak

🎧🍌 The $5B Venture Growth Buyout Playbook | Alex Israel, CEO of Metropolis

A16Z

Charts of the Week: Software Ate the World

Newcomer | Eric Newcomer

Stakes Keep Getting Higher for the SpaceX IPO

Clouded Judgement | Jamin Ball

Clouded Judgement 4.24.26 - The AI-Driven Employment Explosion

Not Boring | Packy McCormick

Weekly Dose of Optimism #190

Saastr

Top 10 Learnings from Sapphire Ventures’ 2026 Software x AI Report: 80+ $100m ARR AI Startups, The Ultra Round is The New Normal, and Enterprise is 50%+ of VC Now

Earnest Sweat

Prep Time