Lenny’s Newsletter♥ 171
Sep 8, 2020 · 13 min
Subscriber post — summary onlyLenny walks through how his Airbnb team turned a problem of rejected booking requests into an 'Instant Book' strategy that grew instant bookings from about 5% to over 80%. He breaks strategy into three steps…
Lenny’s Newsletter♥ 198
Jan 26, 2021 · 18 min
Subscriber post — summary onlyApril Dunford gives a practical guide to product positioning, using a story about a mispositioned database product to show how context shapes customer assumptions. She argues positioning should be built by starting from…
Lenny’s Podcast85 min
Roger Martin · Jul 25, 2024
Key learnings- Strategy is an integrated set of choices that compels desired customer action, since customers are the one thing a company cannot…
- Work through the five cascade questions together: winning aspiration, where to play, how to win, required capabilities, and…
- Winning requires being either differentiated or lowest cost; without one of those, competitors can keep pushing you back step by…
Lenny’s Podcast122 min
Mihika Kapoor · Apr 21, 2024
Key learnings- Build a vision that ties together a user pain point, a proposed solution, and a proof point such as a testimonial or prototype…
- Pull research, design, and engineering feasibility into the vision early so it reflects what users feel and what the team can…
- Lean on prototypes and mocks before a project gets approved; seeing and feeling the future often persuades more than…
Lenny’s Newsletter♥ 569
Oct 18, 2022 · 7 min
Subscriber post — summary onlyLenny Rachitsky explains how mission, vision, strategy, goals, roadmap, and tasks connect, working from the top down and showing where to begin. He illustrates each layer with well-known company examples and uses a…
Lenny’s Podcast125 min
Ebi Atawodi · Dec 3, 2023
Key learnings- A vision should describe a picture of the future state, be lofty yet attainable, be free of today's technical limits, and be…
- Distinguish vision from mission: the vision is what the destination looks like, while the mission is the purpose and guiding…
- Write the vision as a 'once upon a time' story (current problem, a turning point, and the resulting changed world), or write the…
Lenny’s Podcast87 min
Anneka Gupta · Oct 17, 2024
Key learnings- Being strategic means pairing a compelling, simple 'why' behind decisions with the courage to champion hard, long-term changes…
- Reframe high-stress situations by asking what you can learn and by bringing humor into meetings, since your mood shapes how the…
- Summarize what others have said in meetings and end with a question inviting agreement or dissent; this builds trust and moves…
Lenny’s Podcast100 min
Richard Rumelt · Jan 21, 2024
Key learnings- Treat strategy as a response to one or two real challenges, not a list of ambitions, priorities, or aspirations; Rumelt suggests…
- A solid strategy has three parts: a diagnosis of the situation, a guiding policy for dealing with it, and coherent actions that…
- Test your strategy for bad signs: goals dressed up as strategy, fluffy jargon, missing diagnosis, and actions that contradict one…
Lenny’s Podcast116 min
Todd Jackson · Apr 11, 2024
Key learnings- Treat product-market fit as a progression across four levels rather than a binary, and expect it to take several years for most…
- At the nascent level, prioritize delivering insanely satisfying results to three to five customers; inefficiency such as manual…
- When stuck, change one or more of the four Ps (persona, problem, promise, product), and recognize that some companies keep one…
Lenny’s Newsletter · Free post♥ 193
Jan 28, 2020 · 8 min
““The only thing that matters is getting to product-market fit.” —Marc Andreessen I’ve noticed that most people (including myself) have only a vague grasp on what product-market fit actually is. And even fewer people are going after it in a systematic way. For my own benefit if nothing else, last year I began collecting the best descriptions of PMF that I could find across Twitter, podcasts, books, and blog posts. Below, I’ve put…”
Lenny’s Podcast131 min
Mike Maples Jr · Jul 7, 2024
Key learnings- Look for inflections: external turning points, whether technological, regulatory, or shifts in belief, that newly empower people…
- Stress-test any inflection by asking what specific new thing exists, how it empowers specific people, and under what conditions…
- A strong insight is non-obvious and non-consensus but also right; if everyone likes your idea, it is probably too similar to the…
Substack · Shreyas Doshi♥ 275
May 16, 2026
Shreyas Doshi describes a founder asking whether to go wide or deep, and argues that abstract framings like this feel productive but avoid the decision. The core advice is to push past comfortable generalities toward…
Lenny’s Podcast111 min
Andrew Wilkinson · Jul 3, 2025
Key learnings- Choose a business in an area you're genuinely interested in, but look for the unglamorous niche where competition is low…
- Pick a first business that delivers a quick, simple win, since early success builds the confidence and narrative needed to keep…
- Look for a unique edge (skills, background, or access to audiences) and pivot toward the most profitable customer segment for…
Lenny’s Podcast110 min
Christopher Lochhead · Sep 17, 2023
Key learnings- Most businesses unknowingly choose to compete for a slice of an existing category; Lochhead argues category leaders capture about…
- Focus obsessively on the customer's problem, not just your solution, as Gojo did when it reframed hand washing without water to…
- Use new language (languaging) to change how people think about a problem, so they can perceive new value and be open to a new…
Lenny’s Newsletter · Free post♥ 612
Aug 4, 2020 · 5 min
This edition of Lenny Rachitsky's newsletter answers a reader question by curating his favorite product management templates and frameworks in one place. The collection spans 1-pagers and PRDs, business and team…
Lenny’s Newsletter · Free post♥ 131
Jun 14, 2019 · 13 min
Lenny Rachitsky reflects on seven years at Airbnb, from early engineer to PM, distilling lessons on building a company. He argues that strong culture and values create competitive advantage in hiring, speed, and…
Lenny’s Podcast113 min
Maggie Crowley · Nov 5, 2023
Key learnings- Great PMs simplify relentlessly: find the one thing to do and stick with it long enough to actually finish it.
- Read your documents out loud and cut anything complicated; if you can say it in conversation, write it that way.
- Follow up on results after launches by setting calendar reminders to check metrics weeks and months later, and share what you…
Lenny’s Podcast58 min
Seth Godin · Dec 8, 2024
Key learnings- Define quality as meeting spec, and relentlessly improve the spec in service of the people you serve rather than polishing…
- Treat good taste as anticipating what people want just before they do, and build it by working alongside people with high…
- Treat brand as a promise: decide what you stand for, what you don't do, and what you'd be missed for, then make a difficult…
Lenny’s Podcast107 min
Mark Pincus · Jun 14, 2026
Key learnings- Use Proven, Better, New: master what already works first, make it measurably better in ways 10 out of 10 existing users would…
- Assume your instincts are right but your specific ideas are often wrong; test many ideas in your innovation zone and fail for the…
- Start humbly and small; ambitious visions before product-market fit tend to cause failure, and early wins usually come from…
Lenny’s Podcast103 min
Dalton Caldwell · Apr 18, 2024
Key learnings- Keep the startup alive: the core mantra is 'don't die,' since much of startup success comes from persisting through near-death…
- Before quitting, ask whether you still enjoy the work, your co-founders, and your customers; if you love those, lean toward…
- A good pivot moves 'warmer,' toward domains you already know or have built experience in, and often grows out of what you learned…
Lenny’s Podcast68 min
Marty Cagan · Aug 21, 2022
Key learnings- Empowered product teams are handed problems to solve with measurable outcomes, not prioritized feature lists to ship; celebrate…
- Product managers are equally responsible for the 'how' - ensuring a solution is valuable, usable, feasible, and viable - not just…
- Limit problem validation time when the founder already understands the problem; spend most effort on solution discovery through…
Lenny’s Podcast65 min
Hamilton Helmer · May 5, 2024
Key learnings- Start thinking about strategy and power even before product-market fit, focusing on the underlying characteristics that might…
- A real power needs both a benefit (cost or price advantage) and a barrier that competitors cannot easily mimic; Helmer calls this…
- Early-stage startups should prioritize counter positioning, then consider network economies, scale economies, and switching costs…
Lenny’s Newsletter♥ 262
Jul 25, 2023 · 20 min
Subscriber post — summary onlyAn interview with Shopify's VP of Product, Glen Coates, on how the company plans around annual CEO themes, avoids OKR-style metrics ownership, reviews work through a staged system, and structures teams around merchant…
Lenny’s Newsletter · Free post♥ 244
Jun 2, 2023 · 15 min
Sho Kuwamoto, Figma's VP of Product, argues that Figma's success comes from putting customer needs first, a philosophy built into its culture from the early private beta. He describes how customer support became…