2025-08-14 19:03:08
Enterpret—Transform customer feedback into product growth
Pragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications
Claude.ai—The AI for problem solvers and enterprise
Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things.
In this conversation, you’ll learn:
The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it)
Why following product “best practices” perfectly can actually accelerate your path to unemployment
The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant
How to push back on executives without saying “no” (the options, plus a recommendation framework)
The counterintuitive reason why the happiest PMs are also the most commercially minded
The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management
• Instagram: https://www.instagram.com/mttlmy
• LinkedIn: https://www.linkedin.com/in/mattlemay/
• Website: https://mattlemay.com/
(00:00) Introduction to Matt LeMay
(04:23) Matt’s background and transition to product management
(06:47) The goal of Matt's new book
(12:00) How to stress test your thinking as a PM
(15:32) Thinking like the CEO
(17:33) The role of a product manager
(23:36) The low-impact PM death spiral
(27:47) Case study: Mailchimp’s transition to a platform company
(32:53) Radical acceptance
(41:24) Embracing constraints in product management
(44:23) Steps to become an impact-first product team
(49:38) Setting effective goals
(01:02:15) Prioritization and impact estimation
(01:07:58) Navigating stakeholder management
(01:12:35) Summarizing the 3 steps
(01:16:36) Lightning round and final thoughts
• Pitchfork: https://pitchfork.com/
• Daniel Ek’s memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/
• How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy
• Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri
• Mailchimp: https://mailchimp.com/
• Intuit: https://www.intuit.com/
• Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/
• The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina
• Miro: https://miro.com/
• Prioritizing: https://www.lennysnewsletter.com/p/prioritizing
• Temptation Island on Netflix: https://www.netflix.com/title/81744518
• Mark L. Walberg’s website: https://markwalbergtv.com/about
• Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/
• Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp
• Matt’s review of Liz Phair’s self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/
• Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/
• RedMonk: https://redmonk.com/
• Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r
• Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ
• Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/
• Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006028
• The Wisdom of Insecurity: A Message for an Age of Anxiety: https://www.amazon.com/Wisdom-Insecurity-Message-Age-Anxiety/dp/0307741206/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
Lenny may be an investor in the companies discussed.
2025-08-12 20:45:21
👋 Welcome to a 🔒 paid edition 🔒 of my weekly newsletter. Each week, I tackle reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast | How I AI | Lennybot | Lenny’s Reads | Courses
P.S. Annual subscribers get a free year of 15+ premium products: Lovable, Replit, Bolt, n8n, Wispr Flow, Descript, Linear, Gamma, Superhuman, Granola, Warp, Perplexity, Raycast, Magic Patterns, Mobbin, and ChatPRD (while supplies last). Subscribe now.
Less than a month ago I published part 1 of this series, and it’s already my 9th most popular post of all time. This tells me there’s a growing need for curated, thoughtful content as an antidote to the endless slop filling our feeds and inboxes.
To continue building an essential reading library for product leaders, I’ve picked 10 more timeless reads that you probably haven’t read but should. This includes a handful that popped into my mind after I published part 1, suggestions you sent me, and a few honorary mentions for extra credit. The pieces below cover a wide spectrum of advice around growth, leadership, communication, entrepreneurship, and more.
I’m not including books here—that list is yet to come. If you have suggestions for essays I’m still sleeping on, please share them in the comments. 🙏
You can listen to this post in convenient podcast form here: Spotify / Apple / YouTube
“A product succeeds because it solves a problem for people. This sounds very basic, but it is the single most important thing to understand about building good products.
The first step in building something new is understanding what problem you want to solve, and for whom. This should be crystal clear before you start thinking about any solutions.
The second question you should ask yourself is ‘Why is this particular problem worth solving?’
If the audience you are building for is narrowly defined (and one that you are a part of), then you may be able to rely on your intuition to guide your product decision-making. If not, then you should rely on research and data to inform your decisions.
If you are a start-up founder, your path will be easier if you go after a problem for a narrowly defined audience, and then expand to broader audiences after you have some initial traction.
The problem you’re trying to solve should be easy to communicate in a sentence or two and resonate with someone from your target audience. If not, consider that a big red flag.”
“When I’m doing a poor job of communicating it can feel like I’m pushing with a rope. I have some clear vision in my head and people just aren’t doing what I expect. It can be a frustrating experience and it is tempting to blame the audience for not understanding. But make no mistake, when this happens, it is your fault. You have to sit down and ask questions from a place of humility to hear what they took away from what you said. Take full responsibility for any discrepancy from what you intended and make corrections with your entire audience.”
“The best executive communication starts with ‘Situation.’ The nickname for this is SCQA, or the Pyramid Principle.
The best executive communication starts with the state of affairs. It’s fact-based, unambiguous. It’s totally not controversial. No matter what side of an issue or a hard choice you’re on, you should be able to read the situation and go, ‘That pretty much sums it up.’ Whether you’re on one side or another of an issue, it doesn’t matter. You should read the situation and agree to it. Agree that’s fair.
The next thing that comes out is the complication. A crisp, short statement about what has changed or what’s making things harder. What’s changed, what’s making things harder? The question, the ‘Q,’ falls automatically out of ‘S’ and ‘C’ and it’s almost always ‘What should we do?’ You can save yourself a lot of anxiety if you’re trying to practice this. If you get hung up on ‘Q,’ it’s almost always ‘What should we do?’
‘Answer,’ ‘A,’ answer first at the top of a pyramid. Pyramid-shape your evidence underneath it, and it has to resolve the complication 100%. […] Every conversation in [your] life is an opportunity to SCQA. Friends, loved ones, pets, conversations at the deli counter, everything.”
“When I ask new entrepreneurs what their distribution model will be, I often get answers like: ‘I don’t want to hire any of those Rolex-wearing, BMW-driving, overly aggressive enterprise sales slimeballs, so we are going to distribute our product like Dropbox did.’ In addition to taking stereotyping to a whole new level, this answer demonstrates a deep misunderstanding of how sales channels should be designed.
What is a sales channel? It’s a route to market for a product or set of products. It can range from your website to a sophisticated sales force. The sale itself must be supported with the right marketing, process, and optimization strategy. Selecting the right channel is critical for any business—and products often fail because the company chose the wrong route to market.”
“The market you choose to serve is one of the most important factors for an early-stage startup. And for most technologists, it’s a blind spot. To help, we wanted to share one way of thinking about market. […]
The simplest and most important way to think about market size is (a) how many potential customers are there and (b) what might each customer be worth to you. […]
Thinking about the number of customers and the revenue per customer is a tremendously clarifying way to think about a single company.”
“How do you grow? The ‘go-to’ answer for almost every question in startups is ‘build a great product’ or you need ‘product market fit.’ Every time I hear that answer, it feels completely [unsatisfying]. Building a great product is a piece of the puzzle, but it’s far from the full picture. There are terrible products that have reached $1B+ and amazing products that never make it anywhere. Why is that?”
2025-08-12 17:00:39
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In this episode, I share another 10 must-read essays that continue to shape how I think about product, startups, and career.
Whether you’re scaling a startup, leading a team, or sharpening your thinking, this episode will expand your perspective and give you practical tools you can use immediately.
In this episode, you’ll learn:
Why solving the right problem for the right audience is obvious - yet essential
Why leaders must take full responsibility for any communication discrepancies
How to use the SCQA (Situation, Complication, Question, Answer) framework for concise, persuasive messaging
Why sales, often overlooked, is critical to your product’s success
A tremendously clarifying way to think about your market
The four types of “fit” every startup needs
What we get wrong about our definition of a startup
How to start giving away your Legos
How reframing what you’re s…
2025-08-11 19:03:56
Why is this in your inbox? Because How I AI, hosted by Claire Vo, is part of the Lenny’s Podcast Network. Every Monday, we share a 30- to 45-minute episode with a new guest demoing a practical, impactful way they’ve learned to use AI in their work or life. No pontificating—just specific and actionable advice. Prefer to skip future episode drops? Unsubscribe from How I AI podcast notifications here.
CodeRabbit—Cut code review time and bugs in half. Instantly.
Vanta—Automate compliance and simplify security
Wade Chambers, Chief Engineering Officer at Amplitude, shares how his team built Moda—an internal AI tool that gives employees access to enterprise data across multiple systems, enabling faster product development and decision-making while fostering cross-functional collaboration.
What you’ll learn:
1. How Amplitude built a powerful internal AI tool in just 3 to 4 weeks of engineers’ spare time
2. A social engineering approach that made their AI tool go viral company-wide in just one week
3. How product managers use AI to analyze customer feedback across multiple data sources and identify key themes
4. A streamlined workflow that compresses research, PRD creation, and prototyping into a single meeting
5. Why role-swapping exercises with AI tools build empathy and cross-functional fluency across product, design, and engineering teams
6. How AI tools are helping engineering teams tackle persistent tech debt challenges more effectively
To celebrate 25,000 YouTube followers, we’re doing a giveaway. Win a free year of my favorite AI products, including v0, Replit, Lovable, Bolt, Cursor, and, of course, ChatPRD, by leaving a rating and review on your favorite podcast app and subscribing to the podcast on YouTube. To enter: https://www.howiaipod.com/giveaway.
LinkedIn: https://www.linkedin.com/in/wadechambers/
Amplitude: https://amplitude.com/blog/meet-the-team-wade-chambers
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
(00:00) Introduction to Wade Chambers
(02:53) The build vs. buy decision for internal AI tools
(04:55) What Moda is and how it works
(07:19) The social engineering approach to adoption
(09:17) Demo of Moda in Slack
(10:58) Data sources Moda has access to
(12:43) Analyzing customer feedback themes with Moda
(17:41) Behind the scenes: how Moda works technically
(23:24) Creating a PRD from a single customer insight
(27:30) How teams actually use AI-generated PRDs
(29:09) Impact on product development velocity
(32:37) Engineers, designers, and PMs swapping roles
(34:38) Recap of creating Moda
(36:00) Lightning round and final thoughts
• Glean: https://www.glean.com/
• ChatGPT: https://chat.openai.com/
• Cursor: https://cursor.com/
• Bolt: https://bolt.new/
• Figma: https://www.figma.com/
• Lovable: https://lovable.dev/
• v0: https://v0.dev/
• Amplitude: https://amplitude.com/
• Slack: https://slack.com/
• Confluence: https://www.atlassian.com/software/confluence
• Jira: https://www.atlassian.com/software/jira
• Salesforce: https://www.salesforce.com/
• Zendesk: https://www.zendesk.com/
• Google Drive: https://drive.google.com/
• Productboard: https://www.productboard.com/
• Zoom: https://zoom.us/
• Asana: https://asana.com/
• Dropbox: https://www.dropbox.com/
• GitHub: https://github.com/
• HubSpot: https://www.hubspot.com/
• Abnormal Security: https://abnormalsecurity.com/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2025-08-10 00:04:23
👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.
2025-08-09 19:02:45
Orkes—The enterprise platform for reliable applications and agentic workflows
Vanta—Automate compliance. Simplify security.
PostHog—How developers build successful products
Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched.
We discuss:
The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”)
How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied
The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity
Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more
The accidental decisions that changed history, including not having a waitlist
The impact ChatGPT will have on SEO and product growth
The counterintuitive reason why shipping unpolished AI features beats waiting for perfection
Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown
How TikTok comments became a primary user research channel early on
• X: https://x.com/nickaturley
• LinkedIn: https://www.linkedin.com/in/nicholasturley/
• Website: https://nickturley.com/
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
(00:00) Introduction to Nick Turley
(04:52) GPT-5 launch
(09:13) The vision for ChatGPT and AI assistants
(13:52) The early days of ChatGPT
(17:14) The success and impact of ChatGPT
(20:44) Product development and iteration
(23:11) Maximally accelerated: the OpenAI approach
(26:17) Retention and user engagement
(33:42) The future of chat interfaces
(36:31) The evolution of ChatGPT
(38:52) Subscription model and pricing strategies
(42:10) Enterprise adoption and challenges
(44:10) Balancing multiple product lines
(52:13) Emergent use cases and user feedback
(01:02:15) OpenAI’s unique product development approach
(01:05:07) The importance of team composition
(01:08:50) Balancing speed and quality in AI development
(01:14:23) The role of evals in product development
(01:16:13) The future of AI-driven content and GPTs
(01:21:51) Philosophy and product leadership
(01:23:47) Career journey and advice
(01:27:49) Lightning round and final thoughts
• GPT-5 and the new era of work: https://openai.com/index/gpt-5-new-era-of-work/
• Instacart: https://www.instacart.com/
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai
• Sam Altman on X: https://x.com/sama
• Figma: https://www.figma.com/
• Van Westendorp’s Price Sensitivity Meter: https://en.wikipedia.org/wiki/Van_Westendorp%27s_Price_Sensitivity_Meter
• Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/
• 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): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra
• Dropbox: http://dropbox.com/
• Airtable: https://www.airtable.com/
• Notion: https://www.notion.com/
• Instant Pot: https://instantpot.com/
• MS-DOS: https://en.wikipedia.org/wiki/MS-DOS
• Expanding on what we missed with sycophancy: https://openai.com/index/expanding-on-sycophancy/
• What we’re optimizing ChatGPT for: https://openai.com/index/how-we're-optimizing-chatgpt/
• Charlie Munger’s quote: https://www.goodreads.com/quotes/11903426-show-me-the-incentive-and-i-ll-show-you-the-outcome
• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next
• Beyond vibe checks: A PM’s complete guide to evals: https://www.lennysnewsletter.com/p/beyond-vibe-checks-a-pms-complete
• DALL-E: https://openai.com/index/dall-e-3/
• John Rawls: https://en.wikipedia.org/wiki/John_Rawls
• Robert Nozick: https://en.wikipedia.org/wiki/Robert_Nozick
• Her on Prime Video: https://www.amazon.com/Her-Joaquin-Phoenix/dp/B00IA3MX9A
• Westworld on Prime Video: https://www.amazon.com/Westworld-Season-1/dp/B01N05UD06
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx
• Nick’s Soundcloud: https://soundcloud.com/nickturley
• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884
• The Design of Everyday Things: https://www.amazon.com/dp/0465050654/
• A Fire upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
Lenny may be an investor in the companies discussed.