Sitemap - 2025 - Lenny's Newsletter

How this former NYT columnist uses ChatGPT to brainstorm ideas, do research, and find the perfect metaphor | Farhad Manjoo

Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer)

🧠 Community Wisdom: How to encourage engineers to use AI more, best sales CRMs for early-stage startups, knowing your company's exit strategy, finding your first investors, and more

Announcing a brand-new podcast: “How I AI” with Claire Vo 🔥

Gumroad CEO’s playbook to 40x his team’s productivity with v0, Cursor, and Devin | Sahil Lavingia

Introducing How I AI

Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder & CEO)

🧠 Community Wisdom: Setting priorities across distributed teams, moving from manager to IC, upskilling your design capabilities as a PM, and more

A new perk for annual subscribers: A free year of the world's most beloved products (while supplies last)

Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js)

🧠 Community Wisdom: Learning to be more concise, reviewing design works, creating a strategy pre-PMF, moving from PM to design, building trust with customer support, and more

OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter)

Beyond vibe checks: A PM’s complete guide to evals

Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor)

🧠 Community Wisdom: Prototyping vs. writing PRDs, managing the emotional aspects of a career change, AI art, navigating feature requests, and more

The definitive guide to mastering product sense interviews

A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)

🧠 Community Wisdom: Implementing Shape Up, maximizing your product coaching experience, finding your lane with a hands-on leader, and more

How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions)

Lenny's Podcast guest policy

How to ship like a startup

Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO)

🧠 Community Wisdom: 225th issue + balancing child care and career transitions, pregnancy disclosure in new roles, measuring retention effectively, discount strategies, and more

Which companies produce the best product managers

The hidden power of introverts: How to thrive without changing who you are | Susan Cain (author of "Quiet")

🧠 Community Wisdom: Job search burnout, prioritizing features with many stakeholders, boosting product velocity, and more

Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz)

Why you’re so angry at work (and what to do about it)

Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder)

🧠 Community Wisdom: Designing great performance review templates, balancing oversight and autonomy with junior team members, when to rebuild vs. refactor, more

Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder)

1,000,000

The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic)

🧠 Community Wisdom: Finding your voice on established teams, focus tips for ADHD brains, how to best use Granola, and more

An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead)

Strategy Blocks: An operator’s guide to product strategy

How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of "Job Moves”)

🧠 Community Wisdom: Essential reading for early-stage founders, balancing unlimited SaaS plans with profitability, startup vs. big tech design careers, and more

How much product managers make in the U.S., Europe, and Canada

A founder’s guide to crisis management | Uri Levine (Waze co-founder, serial entrepreneur)

🧠 Community Wisdom: Streamlining leadership communication, scaling customer sales insights, memorable corporate swag ideas, consumer app retention metrics, public Speaking for PMs, and more

Pulling back the curtain on the magic of Y Combinator

OpenAI researcher on why soft skills are the future of work | Karina Nguyen (Research at OpenAI, ex-Anthropic)

🧠 Community Wisdom: Get a year free of Notion, Superhuman, Linear, Perplexity, Granola + Handling team negativity, AI-powered resume building, your first design hire, rethinking sprints, and more

Announcing the greatest product bundle ever: Get a year free of Granola, Notion, Superhuman, Linear, and Perplexity with an annual subscription

Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify)

🧠 Community Wisdom: Strengthening core PM skills, building an API-first culture, creating a PM offboarding ritual, product planning for small teams, cross-team support ticket management, and more

Linear’s secret to building beloved B2B products | Nan Yu (Head of Product)

Introducing the Foundation Sprint: From the creators of the Design Sprint

An operator’s guide to product strategy | Chandra Janakiraman (CPO at VRChat, ex-Meta, Headspace, Zynga)

🧠 Community Wisdom: Building a good foundation in product, workshop exercises for roadmap planning, structuring team syncs, career ladders for designers, and more

What’s in your stack: The state of tech tools in 2025

10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey)

🧠 Community Wisdom: Shifting from hands-on manager to strategic leader, staffing engineers on product analytics tools, hiring your second PM, design systems for marketing, and more

How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors)

Introducing Core 4: The best way to measure and improve your product velocity

How to build your product team from scratch, attract top product talent, go multi-product, and more | Rohini Pandhi (Mercury, Square)

🧠 Community Wisdom: Handling stakeholder pushback, user personas vs. JTBD, advice on take-home assignments, crowdsourcing the pricing of your SaaS, setting up a product consulting firm, and more

Behind the founder: Drew Houston (Dropbox)

A guide to AI prototyping for product managers

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

🧠 Community Wisdom: Proving your worth as a product leader, empowering junior PMs, when competitive research crosses the line, planning a department-wide onsite, and more

Inside Gong: How teams work with design partners, their pod structure, autonomy, trust, and more | Eilon Reshef (co-founder and CPO)