Lenny's Newsletter

How to build a company that withstands any era | Eric Ries, Lean Startup author

Lenny Rachitsky interviews Eric Ries, author of The Lean Startup, about his new book Incorruptible, which examines why successful companies get corrupted and how founders can protect their mission through governance structures. The conversation covers why 80% of venture-backed founders are ousted within three years of going public, and how companies like Anthropic, Costco, and Novo Nordisk use governance to protect their core values. Ries also discusses a simple two-page Delaware legal filing that can help founders maintain control and mission alignment.

Why SaaS freemium playbooks don’t work in AI, and what to do instead

Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)

Lenny's Newsletter features a podcast conversation with Max Schoening, Head of Product at Notion, covering how agency—not skills—is the key differentiator in the AI era. Schoening discusses why vibe coding produced more software but not better software, Notion's 'tiny core' theory of great products, and how Notion ships with a 'drive it like it's stolen' mentality. He also argues the SaaSpocalypse is overstated and that the gap between software quantity and quality creates opportunity.

The product skill you must now master: Reinvention

Your Couch-to-5K for AI

Hilary Gridley, a guest author on Lenny's Newsletter, introduces 'Couch-to-5K for AI,' a free progressive daily program designed to build an AI habit in under 10 minutes a day. Drawing on her behavior-change expertise from WHOOP, Dropbox, and Big Health, she argues that 'being too busy' is a proxy for procrastination and that breaking goals into the smallest possible first step is the key to building new skills. The program is an updated version of her 2024 '30 Days of GPT' initiative and now includes Claude Code to take users from chatting with AI to actually building with it.

Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel

Lenny Rachitsky interviews Snap co-founder and CEO Evan Spiegel on Lenny's Podcast, covering why distribution has become the most critical moat for consumer tech companies. Spiegel discusses how every major Snapchat feature was cloned by competitors, why pure software businesses no longer provide durable competitive advantages, and how hardware is now the only real moat. The episode also covers Snap's lean 9-to-12-person design team structure and how AI is changing product development workflows.

How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)

Not all AI agents are created equal

Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

Keith Rabois discusses his "barrels vs. ammunition" hiring framework and argues that talking to customers harms consumer products. He shares insights on how AI is collapsing the PM role and identifies traits of best-performing companies.

A visual guide to getting out of a creative slump

Michelle Rial, author of the new children's book Charts for Babies, shares a 12-point visual guide for overcoming creative slumps and maintaining human creativity in an AI-dominated world. The post emphasizes being comfortable with embarrassment, ignoring algorithms, using caffeine strategically, and managing overwhelm through breathwork.

Anthropic’s $1B to $19B growth run: how Claude became the fastest-growing AI product in history | Amol Avasare

Anthropic's Head of Growth Amol Avasare shares how Claude scaled from $1B to $19B ARR in 14 months through big bets, intentional onboarding friction, and an internal AI system called CASH for autonomous growth experiments. The conversation covers growth strategies, AI automation, and how the company's focus on coding created a research flywheel that accelerated their models.

An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines |…

Simon Willison, co-creator of Django and prominent AI voice, discusses how November 2025 marked an inflection point for AI coding agents and the future of software development. He shares insights on agentic engineering patterns, the risks to mid-career engineers, and emerging concepts like 'dark factories' where AI handles entire development cycles.

How to Navigate Org Drama

This newsletter episode discusses navigating organizational challenges like reorgs, bad managers, and blocked promotions in the modern workplace. It emphasizes that traditional approaches of being direct and escalating issues no longer work as effectively, requiring new strategies for dealing with workplace dysfunction.

OpenClaw: The complete guide to building, training, and living with your personal AI agent

From skeptic to true believer: How OpenClaw changed my life | Claire Vo

Claire Vo shares her transformation from OpenClaw skeptic to power user, now running nine specialized AI agents across family management, business operations, and content creation. The podcast episode provides a detailed guide on setting up and using OpenClaw effectively, including avoiding common mistakes and implementing real-world automation workflows.

State of the product job market in early 2026

Lenny Rachitsky's biannual State of the Product Job Market report for early 2026 shows PM openings at the highest levels in over three years (7,300+ globally), engineering roles surging past 67,000 globally, and AI-specific roles hockey-sticking. Design roles have plateaued since early 2023, while remote work opportunities continue to decline and the Bay Area is growing in importance.

The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

Lenny Rachitsky interviews Jessica Fain, product leader at Webflow and ex-Chief of Staff to the CPO at Slack, on the art of influencing executives. Fain shares tactical frameworks for getting buy-in, including aligning with executive incentives, presenting multiple options rather than one, and entering meetings to learn rather than convince. She argues that as AI automates more analytical work, human influence skills become increasingly valuable and irreplaceable.