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.

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

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

Tomasz Tunguz | Tomasz Tunguz

Competitive Strategy in the Age of AI

Sierra Ventures

Our Seed Investment in Band, Building the Backbone for Enterprise AI