2025-07-15 21:03:13
👋 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 | Swag
Annual subscribers now get a year free of Bolt, Perplexity Pro, Notion, Superhuman, Linear, Granola, and more. Subscribe now.
For something a little different, I’m going to share seven essays that have had the most impact on my product career—that you likely haven’t read.
There’s so much content flying at us these days, it’s hard to separate the “this sounds so smart!” from the “this is genuinely correct, helpful, and timeless.” The essays below are ones I find myself quoting from, sharing with people, and coming back to most often, even though most are decades old.
“The thing I’ve tried to do the last few years is ‘barbell’ my inputs. I basically read things that are either up to this minute or things that are timeless. I’m trying to not read anything that’s from yesterday through to like 10 years ago.” —Marc Andreessen
Note that this isn’t an exhaustive list. And I’m not including books—yet. This post is the beginning of an essential and timeless reading library meant specifically for product leaders.
I’d love your help building out this list. What’s missing? Let me know in the comments. Bonus points for sharing the impact it had on your career/life, and more bonus points for sharing stuff people may not have heard of. 👇
Bonus: You can also listen to this post in convenient podcast form: Spotify / Apple / YouTube.
“Let us imagine that a manager is walking down the hall and that he notices one of his subordinates, Jones, coming his way. When the two meet, Jones greets the manager with, ‘Good morning. By the way, we’ve got a problem. You see. . . .’ As Jones continues, the manager recognizes in this problem the two characteristics common to all the problems his subordinates gratuitously bring to his attention. Namely, the manager knows (a) enough to get involved, but (b) not enough to make the on-the-spot decision expected of him. Eventually, the manager says, ‘So glad you brought this up. I’m in a rush right now. Meanwhile, let me think about it, and I’ll let you know.’ Then he and Jones part company.
Let us analyze what just happened. Before the two of them met, on whose back was the ‘monkey’? The subordinate’s. After they parted, on whose back was it? The manager’s. Subordinate-imposed time begins the moment a monkey successfully leaps from the back of a subordinate to the back of his or her superior and does not end until the monkey is returned to its proper owner for care and feeding.
In accepting the monkey, the manager has voluntarily assumed a position subordinate to his subordinate. That is, he has allowed Jones to make him her subordinate by doing two things a subordinate is generally expected to do for a boss—the manager has accepted a responsibility from his subordinate, and the manager has promised her a progress report.
The subordinate, to make sure the manager does not miss this point, will later stick her head in the manager’s office and cheerily query, ‘How’s it coming?’ (This is called supervision.) Or let us imagine in concluding a conference with Johnson, another subordinate, the manager’s parting words are, ‘Fine. Send me a memo on that.’
Let us analyze this one. The monkey is now on the subordinate’s back because the next move is his, but it is poised for a leap. Watch that monkey. Johnson dutifully writes the requested memo and drops it in his out-basket. Shortly thereafter, the manager plucks it from his in-basket and reads it. Whose move is it now? The manager’s. If he does not make that move soon, he will get a follow-up memo from the subordinate. (This is another form of supervision.) The longer the manager delays, the more frustrated the subordinate will become (he’ll be spinning his wheels) and the more guilty the manager will feel (his backlog of subordinate-imposed time will be mounting).”
“Last year, when I talked about learning ‘how to handle being sentenced to freedom,’ a phrase I borrowed from Sartre, I meant roughly what people these days call ‘cultivating high agency.’ But I need to define my words, since some ways the phrase high agency is used feel foreign to me, and depressing.
Agency, as I see it, is an amalgamation of two skills, or mental dispositions: autonomy and efficacy.
Agency requires the capacity to formulate autonomous goals in life—the capacity to dig inside and figure out what wants to happen through you, no matter how strange or wrong it seems to others. In other words, it requires autonomy (which was what I was getting at when I said ‘authentically, and responsibly’).
Agency also requires the ability and willingness to pursue those goals. It requires the ‘will to know,’ the drive to see reality as it is, so you can manipulate it deftly and solve the problems you want to solve, instead of fooling yourself that certain problems are ‘unsolvable.’ In other words, efficacy (‘handle it effectively’).
Or phrased negatively, the opposite of agency can mean one of two things. Either (1) doing what you are ‘supposed to do,’ playing social games that do not align with what, on reflection, seems valuable to you and/or (2) being passive or ineffective in the face of problems (assuming your problems can’t be solved, that someone else should solve them, or working on things that do not in a meaningful way address the problem).
Agency is often framed as a hard-edged, type-A, aggressive approach. But over the last year, as I’ve been thinking about writing this essay, I’ve talked to a lot of highly agentic people, and I’ve read biographies about and interviews with people whose agency I admire and . . . hard-edged does not fit what I’ve seen. Often, agency is almost gentle—an attunement to the world and the self, a feeling out the details of reality, and a finding of the path of least resistance. There is sometimes considerable force involved, hard work, but it is like the force of a river being pulled toward the sea.”
(Technically this isn’t an essay, but who cares.)
“All of us who do creative work, we get into it because we have good taste. But it’s like there is this gap. For the first couple years that you’re making stuff, what you’re making isn’t so good. It’s not that great. It’s trying to be good, it has ambition to be good, but it’s not that good.
But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell that what you’re making is kind of a disappointment to you. A lot of people never get past that phase. They quit.
Everybody I know who does interesting, creative work went through years where they had really good taste and they could tell that what they were making wasn’t as good as they wanted it to be. They knew it fell short. Everybody goes through that.
And if you are just starting out or if you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you’re going to finish one story. It is only by going through a volume of work that you’re going to catch up and close that gap. And the work you’re making will be as good as your ambitions.
I took longer to figure out how to do this than anyone I’ve ever met. It takes a while. It’s gonna take you a while. It’s normal to take a while. You just have to fight your way through that.”
“Pretending to learn feels good. Actual learning often feels bad. A lot of people are just pretending to learn (memorizing passwords) when they think they’re learning. [. . .]
A lot of people read whole books just for the feeling of being the type of person who reads them, and retain no actual information about the world.
Avoiding playing pretend during your valuable learning time is important and psychologically difficult. A lot of people’s learning is limited by their insecurities and need for their social status to be reinforced. It often feels amazing to pretend to learn things, and unpleasant to actually learn. People are drawn to activities that make them feel high status, and repelled from activities that make them feel low status.”
“I believe this ‘more features = better’ mindset is at the root of the misjudgment, and is also the reason why so many otherwise smart people are bad at product design (e.g. most open source projects). If a MacBook with OSX and no keyboard were really the right product, then Microsoft would have already succeeded with their tablet computer years ago. Copying the mistakes of a failed product isn’t a great formula for success.
What’s the right approach to new products? Pick three key attributes or features, get those things very, very right, and then forget about everything else. Those three attributes define the fundamental essence and value of the product—the rest is noise. For example, the original iPod was: (1) small enough to fit in your pocket, (2) had enough storage to hold many hours of music and (3) easy to sync with your Mac (most hardware companies can’t make software, so I bet the others got this wrong). That’s it—no wireless, no ability to edit playlists on the device, no support for Ogg—nothing but the essentials, well executed.
We took a similar approach when launching Gmail. It was fast, stored all of your email (back when 4MB quotas were the norm), and had an innovative interface based on conversations and search. The secondary and tertiary features were minimal or absent. There was no ‘rich text’ composer. The original address book was implemented in two days and did almost nothing (the engineer doing the work originally wanted to spend five days on it, but I talked him down to two since I never use that feature anyway). Of course those other features can be added or improved later on (and Gmail has certainly improved a lot since launch), but if the basic product isn’t compelling, adding more features won’t save it.
By focusing on only a few core features in the first version, you are forced to find the true essence and value of the product. If your product needs ‘everything’ in order to be good, then it’s probably not very innovative (though it might be a nice upgrade to an existing product). Put another way, if your product is great, it doesn’t need to be good.”
2025-07-15 17:02:07
If you’re a premium subscriber
Add the private feed to your podcast app at add.lennysreads.com
I share seven timeless essays that have shaped how I think about product, startups, and career. These are the pieces I quote often, revisit regularly, and think about long after reading. You likely haven’t come across most of them—but they’re must-reads for any product leader.
In this episode, you’ll learn
How to stop inheriting other people’s monkeys
What real agency looks and feels like
Why good taste comes before good output
How to spot the difference between real and performative learning
How to find the essence or value of your product
What matters most in a startup: team, product, or market?
Why Musk’s “secret sauce” might be learnable
References
1,000 True Fans by Kevin Kelly
Aggregation Theory by Ben Thompson
Good Product Manager/Bad Product Manager by Ben Horowitz
How to Do Great Work by Paul Graham
If Your Product is Great, It Doesn’t Need to be Good **by Paul …
2025-07-14 19:03:12
CodeRabbit—Cut code review time and bugs in half. Instantly.
Lovable—Build apps by simply chatting with AI
Prerna Kaul is a product and platform leader who has spent over 14 years turning machine-learning research into consumer and B2B products at Amazon Alexa, AGI, Moderna, and now Panasonic Well. In today’s episode, she explains how she’s using AI to slash some of the most time-consuming, expensive tasks in life sciences—from generating 60,000-page FDA submissions to crafting communication frameworks that help product managers navigate complex stakeholder dynamics. Her innovations are saving millions of dollars and helping lifesaving treatments reach the market faster.
What you’ll learn:
How Prerna built an AI system that automates the creation of 60,000-page regulatory documents for the FDA—reducing a process that took 4 to 6 months and 20 specialists to just minutes
A step-by-step system for detecting and redacting PHI (protected health information) in clinical trial data using Claude
How to build user-friendly interfaces for non-technical colleagues using Streamlit to democratize AI tools
How to use Claude’s prompt generator to create powerful communication frameworks that help PMs navigate complex stakeholder situations
Why transparency about AI costs is crucial for gaining organizational buy-in and tracking ROI
A practical framework for approaching AI safety and ethics in highly regulated industries
LinkedIn: https://www.linkedin.com/in/prernakkaul/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
(00:00) Introduction to Prerna
(03:01) The FDA submission challenge: 60,000 pages, months of work, millions in costs
(05:20) Getting started in Claude: from prompt to production-ready prototype
(10:13) How Claude selected the right models for medical entity recognition
(12:04) Using Streamlit to create accessible UIs for non-technical users
(16:04) Detecting and redacting PHI in unstructured clinical notes
(18:44) Generating the Common Technical Document (CTD) for FDA submission
(21:54) Tracking and displaying AI operation costs for stakeholder buy-in
(24:38) Real-world impact on vaccine development timelines and costs
(26:12) Creating an AI communication coach for product managers
(30:22) Training Claude on classic literature and persuasion techniques
(31:53) Analyzing a complex stakeholder scenario with multiple competing priorities
(34:40) Getting personalized communication strategies inspired by tech leaders
(35:40) Summarizing strategic approaches
(38:26) Conclusion and final thoughts
• Claude: https://claude.ai/
• Streamlit: https://streamlit.io/
• Anthropic Console: https://console.anthropic.com/
• Claude Sonnet 4: https://www.anthropic.com/claude/sonnet
• Claude project chat (AI Product Management Stakeholder Challenges): https://claude.ai/share/caba4ab0-b28a-480c-8633-71920b12999e
• XML: https://www.w3.org/XML/
• Python: https://www.python.org/
• RegEx: https://regex101.com/
• Moderna: https://www.modernatx.com/
• FDA: https://www.fda.gov/
• Project Gutenberg: https://www.gutenberg.org/
• FDA Biologics License Application: https://www.fda.gov/vaccines-blood-biologics/development-approval-process-cber/biologics-license-applications-bla-process-cber
• Protected health information (PHI): https://www.hhs.gov/hipaa/for-professionals/privacy/laws-regulations/index.html
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2025-07-13 19:02:43
Brex—The banking solution for startups
Paragon—Ship every SaaS integration your customers want
Coda—The all-in-one collaborative workspace
Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days.
What you’ll learn:
1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately
2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team)
3. The three fundamental questions every founder should answer before writing a line of code
4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues
5. The seven “magic lenses” for choosing between multiple product ideas
6. The biggest mistake engineers make when building with AI tools
7. The paradox of speed: why “building nothing first” can get you to product-market fit faster
• X: https://twitter.com/jakek
• LinkedIn: https://www.linkedin.com/in/jake-knapp/
• Website: https://jakeknapp.com/
• X: https://twitter.com/jazer
• LinkedIn: https://www.linkedin.com/in/johnzeratsky/
• Website: https://johnzeratsky.com/
(00:00) Introduction to Jake Knapp and John Zeratsky
(04:41) Origins of the Design Sprint
(11:06) The Foundation Sprint process
(14:40) Phase one: The basics
(16:57) Case study: Latchet
(28:50) Phase two: Differentiation
(36:24) The importance of differentiation
(40:15) Thoughts on price differentiation
(43:37) Case study: Mellow
(46:04) Custom differentiators
(49:30) The mini manifesto
(52:02) Phase three: Approach to the project
(54:50) Magic lenses activity
(01:02:39) Prototyping and testing
(01:10:00) Real-world examples and success stories
(01:15:15) Motivation behind The Foundation Sprint
(01:17:15) The outcome of the sprint: The founding hypothesis
(01:19:28) The Design Sprint
(01:28:19) The role of AI in prototyping
(01:36:50) Final thoughts and resources
• Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint
• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake
• Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/
• Character Capital: https://www.character.vc/
• Character Labs: https://www.character.vc/labs
• Etsy: https://www.etsy.com/
• Shopify: https://www.shopify.com/
• Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek
• Sonos: https://www.sonos.com/
• Vercel: https://vercel.com/
• Windsurf: https://windsurf.com/
• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning
• Positioning: https://www.lennysnewsletter.com/p/positioning
• 10 things we know to be true: https://about.google/company-info/philosophy/
• Gandalf: https://en.wikipedia.org/wiki/Gandalf
• Frodo: https://en.wikipedia.org/wiki/Frodo_Baggins
• Mordor: https://en.wikipedia.org/wiki/Mordor
• 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley: https://www.lennysnewsletter.com/p/35-years-of-product-design-wisdom-bob-baxley
• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas
• Base44: https://base44.com/
• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo
• Google Meet: https://meet.google.com/
• Blue Bottle Coffee: https://bluebottlecoffee.com
• Reclaim: https://reclaim.ai/
• The official Foundation Sprint + Design Sprint template: https://www.character.vc/miro-template
• Rippling: https://www.rippling.com/
• Latchet: https://latchet.com/
• Mellow: http://getmellow.com/
• AxionOrbital: https://axionorbital.space/
• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY
• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422
• Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114
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.
2025-07-13 01:00:52
👋 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.
2025-07-12 01:09:33
If you’re a premium subscriber
Add the private feed to your podcast app at add.lennysreads.com
Ben Erez is a former PM at Meta, the first PM at three different startups, and now a full-time interview coach and educator. In this episode, Ben shares the five-part framework he developed after studying dozens of mock interviews, interviewing 50+ candidates at Facebook, and coaching hundreds of PMs through their job searches. It’s designed to help you master one of the most misunderstood stages of the PM interview loop: the product sense interview.
In this episode, you’ll learn
Ben’s five-part framework for acing product sense interviews
How to set assumptions and lead with structure
How to define a clear mission that guides every decision
A process for segmenting users and developing strong personas
How to map user journeys and surface high-impact problems
A method for brainstorming, prioritizing, and scoping solutions
Lessons from mock-examples (Claude, Meta, and Netflix)
Common pitfalls to avoid, and how to practice effectively
References
AI Practice Copilot for Product Sense & Analytical Thinking Interviews
The Definitive Guide to Mastering Analytical Thinking Interviews
Follow Lenny: Twitter/X | LinkedIn | Podcast
Follow Ben: Twitter/X | LinkedIn | Newsletter
About
Welcome to Lenny’s Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot.