Sitemap - 2025 - Lenny's Newsletter

🧠 Community Wisdom: When leadership asks you to build an AI feature, giving feedback to people outside your team, transitioning from PM to BizOps, building an email verification flow, and more

$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder)

Building eval systems that improve your AI product

How Devin replaces your junior engineers with infinite AI interns that never sleep | Scott Wu (Cognition CEO)

How AI is reshaping the product role | Oji and Ezinne Udezue

🧠 Community Wisdom: Jira vs. Linear, balancing personal tasks and team priorities, becoming more resilient, revealing that you’re a new mom to recruiters, and more

How to find the perfect name

How to turn meeting notes into prototypes that your sales team can immediately demo to customers | Anjan Panneer Selvam (Acolyte Health)

How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO)

🧠 Community Wisdom: Optimal meeting cadence for small teams, summarizing notes from customer interviews, managing conflict in a community, tools to create a product video, and more

How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft)

Taking the week off + a newsletter cadence update

How to digest 36 weekly podcasts without spending 36 hours listening | Tomasz Tunguz (Theory Ventures)

Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO)

🧠 Community Wisdom: Sales 101 for engineers, standing out in the interview process, career transition after product management, how to push back on unrealistic role expansion, and more

How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO)

Why your AI product needs a different development lifecycle

Using Veo 3 to create AI-generated music videos, like a Tiny Desk Concert with Notorious B.I.G. and Kurt Cobain

Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge)

🧠 Community Wisdom: The changing product development process, trials vs. freemium, critiquing in a public setting, SEO in the AI era, defining scope when everyone’s a stakeholder, and more

The one question that saves product careers | Matt LeMay

Essential reading for product builders—part 2

How Amplitude built an internal AI tool that the whole company’s obsessed with (and how you can too) | Wade Chambers

🧠 Community Wisdom: Social-media-active CPOs, AI expectations in interviews, salary asks, resume gaps, analytics adoption vs. automation revenue, and more

Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI)

An exclusive inside look at GPT-5

25 proven tactics to accelerate AI adoption at your company

How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital)

Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA)

🧠 Community Wisdom: Claire Vo’s AMA + building executive presence as a PM, creating a referral program, product designers losing their edge, and more

He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more

Announcing 15+ free premium tools available exclusively to paid annual subscribers

How Block’s custom AI agent supercharges every team, from sales to data to engineering | Jackie Brosamer & Brad Axen

Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

🧠 Community Wisdom: Breaking into big tech as a junior PM, building onboarding flows with no-code tools, managing a cultural transition, internal vs. external hiring, and more

Build your personal AI copilot

Successfully coding with AI in large enterprises: Centralized rules, workflows for tech debt, and training your team | Zach Davis (Director of Engineering at LaunchDarkly)

Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann

🧠 Community Wisdom: Strategies for getting buy-in from leadership, design books we keep going back to, customer discovery when you have no customers, how much documentation you need, and more

The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every)

Essential reading for product builders—part 1

How this PM streamlines 60k-page FDA submissions and saves millions with Claude, Streamlit, and clever AI workflows | Prerna Kaul

Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital)

🧠 Community Wisdom: Best strategy and design books, building resilience as a PM, prioritizing roadmaps in B2B, optimizing websites for AI and language models, and more

The definitive guide to mastering product sense interviews

What people are vibe coding (and actually using)

Mastering ChatGPT: Advanced techniques for workplace communication and productivity | Hiten Shah

Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo

🧠 Community Wisdom: Using AI to accelerate a team’s velocity, interviewing backend engineers, tips for conducting willingness-to-pay interviews, when to pivot, and more

I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)

The definitive guide to mastering analytical thinking interviews

How to build prototypes that actually look like your product | Colin Matthews (product leader, AI prototyping instructor at Maven)

Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding)

🧠 Community Wisdom: Sticking to your committed timelines, keeping processes consistent across product teams, favorite AI prototyping tools, how to empower your PMs’ professional growth, and more

An AI glossary

An AI Glossary

How a 91-year-old vibe coded a complex event management system using Claude and Replit | John Blackman

From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng

🧠 Community Wisdom: Best cheap PM courses, the impact of AI on our cognitive capacity, recovering from a toxic manager and traumatic layoff, best practices for PM homework assignments, and more

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

How tech’s most resilient workers handle burnout

A designer's guide to Cursor: How to build interactive prototypes with sound, explore visual styles, and transform data visualizations | Elizabeth Lin

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)

🧠 Community Wisdom: Building context as a new PM, whether PMs should do financial modeling, managing mismatches between finance and product dashboards, what a “product” is, and more

35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley

How to get your entire team prototyping with AI

Gamma’s Head of Design on how his team uses AI to synthesize feedback, generate on-brand imagery, and maintain design quality while serving users in 60+ countries | Zach Leach

How Mercado Libre built Latin America's most valuable company: 18k engineers, 30k deploys a day, and their own fleet of planes | Sebastian Barrios

🧠 Community Wisdom: From take-homes to vibe-coding product interviews, most impactful tactics to validate a startup idea, whether growth PMs should be the highest-paid product people, and more

Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram)

Taking the week off

The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth)

Why Uber’s CPO delivers food on weekends | Sachin Kansal

🧠 Community Wisdom: Why effort-based estimation is broken, connecting Bolt/Lovable to existing apps, removing personal bias from product decisions, best analytics tools for under 1M events, more

How tech workers really feel about work right now

A 3-step AI coding workflow for solo founders | Ryan Carson (5x founder)

Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman

🧠 Community Wisdom: Building great working relationships with different functions, strategy at B2B vs. B2C companies, PC to Mac transition tips, hiring interns, and more

Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product)

Five principles for successfully managing managers

How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop)

Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada

🧠 Community Wisdom: When to hire a designer and have a design system, collecting feedback from support, how to make animated video with AI, feedback on StrengthsFinder, and more

How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product)

State of the product job market in 2025

A designer's guide to AI: Why designing in Cursor lets you prototype 10x faster, simplifies collaboration, and accelerates getting ideas out of your head | Joel Unger

How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

🧠 Community Wisdom: Pivoting to AI product management, how AI changed our product development cycles, books to teach kids about PM, dealing with misaligned co-founders, more

How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

The ultimate guide to negotiating your comp

Vibe coding a 3D multiplayer game in 15 minutes—with no game dev experience | Cody De Arkland (Senior Director of Developer Experience at Sentry)

Inside Devin: The world’s first autonomous AI engineer that's set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition)

🧠 Community Wisdom: Recommendations for feel-good content, measuring success of a PM, how to start your entrepreneurial journey, taking a day off to upskill, and more

The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO)

Make product management fun again with AI agents

How much product managers get paid in US, Europe, and Canada

The state of tech tools in 2025

Pulling back the curtain on the magic of Y Combinator

The operator’s guide to product strategy

Welcome to Lenny's Reads

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 some 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 and 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)