Lenny’s Newsletter♥ 263
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 Podcast71 min
Andy Raskin · May 28, 2023
Key learnings- Replace the 'arrogant doctor' pitch (problem, solution, why we're better) with a story that opens by naming a shift from an old…
- Name the old game in a few concise words, such as 'transactions' or 'opinions', since compact labels make the shift easy to…
- Show that winners are already playing the new game, and frame the stakes as a clear choice between a very negative and a very…
Lenny’s Podcast119 min
Matt LeMay · Aug 14, 2025
Key learnings- Ask whether you would fully fund your own team if you were the CEO; if you can't answer confidently, that signals a risk worth…
- Set team goals no more than one step away from company goals, so leadership immediately understands how your work contributes to…
- Keep impact first at every step, from OKRs and strategy to epics and daily backlog, rather than letting goals get cascaded into…
Lenny’s Newsletter · Free post♥ 495
Aug 8, 2023 · 40 min
Lenny Rachitsky opens a seven-part B2B startup playbook by examining how successful B2B companies found their original ideas. Drawing on dozens of founder interviews, he argues that a strong B2B idea combines an…
Lenny’s Newsletter · Free post♥ 137
Sep 29, 2020 · 19 min
Lenny Rachitsky asked founders of about two dozen well-known companies when they first knew they had product-market fit. Every company had a recognizable moment, but many only saw it after months or years of compounding…
Lenny’s Podcast99 min
Will Larson · Jan 7, 2024
Key learnings- Treat engineers as capable adults by giving them hard problems and accountability, which lets them grow into senior leadership…
- Build simple stock-and-flow models of processes like hiring pipelines, then compare them against historical data to find where…
- Write your engineering strategy down, even imperfectly; an unwritten strategy cannot be debugged or improved, and every function…
Lenny’s Podcast128 min
Chandra Janakiraman · Jan 26, 2025
Key learnings- Treat product strategy as the layer between mission/vision and the roadmap; it should name a few focus areas (strategic pillars)…
- Budget roughly 8 to 12 weeks for a small-S strategy, since it can be leveraged for about two years and the upfront investment is…
- Form a strategy working group of engineering, product design, and data (plus research or marketing if available) so the strategy…
Lenny’s Podcast101 min
Jag Duggal · May 16, 2024
Key learnings- Start from a deep, emotionally felt customer pain point rather than a feature idea; Nubank tied its origin to widely hated…
- Use the Sean Ellis survey as a gate before scaling: ask how disappointed users would be if the product disappeared, and raise the…
- Keep small, measure whether customers truly love it, and avoid scaling problems that aren't yet solved; scaling early creates big…
Lenny’s Podcast109 min
Benedict Evans · May 31, 2026
Key learnings- Treat AI as roughly as big as the internet or mobile, and recognize we are early, like 1997, with most applications not yet built…
- Expect adoption to be very uneven; survey data shows many people are not using AI at all, so don't assume the people in your…
- Ask whether a job is a task that can be automated or a deeper outcome; consultants and professionals are hired for judgment…
Lenny’s Podcast94 min
Bob Moesta · Aug 24, 2023
Key learnings- Customers hire products to make progress in a context; understanding the context and desired outcome matters more than simply…
- Start from the struggling moment that causes demand, since a product alone does not create demand; use those moments to guide…
- Model switching as forces: push and pull drive change, while anxiety of the new and habit of the present hold people back, and…
Substack · Shreyas Doshi♥ 86
Jun 19, 2026
Shreyas Doshi argues that founders and senior leaders in high-leverage roles benefit from clearly identifying what they are really selling, meaning the core value or outcome their product or leadership delivers beneath…
SVPG · Marty CaganFeb 18, 2020
Feb 18, 2020 · 7 min
Marty Cagan argues that organizations believe they are good at focus but usually chase 20-30 'critical' initiatives when only two or three truly matter. He contrasts this with Pandora's stakeholder-driven prioritization…
SVPG · Marty CaganSep 23, 2022
Sep 23, 2022 · 4 min
This essay, the third in a series on meaningful transformation, argues that companies must change how they choose which problems to solve, not just how they build or solve them. It moves beyond feature roadmaps toward…
Lenny’s Newsletter♥ 420
Mar 10, 2026 · 15 min
Subscriber post — summary onlyLenny's paid guest post by April Dunford, a positioning expert who has worked with 300+ B2B companies, covers four advanced roadblocks that derail positioning work. It argues that disagreement over competitors, product…
Lenny’s Newsletter · Free post♥ 314
Dec 27, 2022 · 7 min
“What a year. The newsletter crossed 300,000 subscribers (from 90K one year ago), the podcast became a top 10 technology podcast, and the subscriber Slack community continues to thrive. I never imagined reaching this scale, and none of this would be possible without you. From the bottom of my heart, thank you. Thank you for reading, for listening, and for subscribing. There’s so much more to come. To close out the year, like I did last…”
Lenny’s Newsletter · Free post♥ 119
Feb 9, 2021 · 11 min
Jackie Bavaro, drawing on research for her book Cracking the PM Career, argues that the hardest career step for many product managers is progressing from entry-level to senior PM, typically taking around three years…
SVPG · Marty CaganFeb 17, 2020
Feb 17, 2020 · 4 min
Marty Cagan argues that empowered product teams need hard problems to solve, and product strategy is the discipline of deciding which problems matter. He observes that many companies have plenty of features and projects…
SVPG · Marty CaganFeb 19, 2020
Feb 19, 2020 · 9 min
Marty Cagan argues that the insights forming the foundation of a product strategy are the hardest but most valuable part of product work, and they cannot be produced by a template or framework. He says strong insights…
Lenny’s Podcast91 min
Eoghan McCabe · Aug 21, 2025
Key learnings- When growth stalls in a late-stage SaaS business, cut costs hard and pick one clear strategic lane instead of trying to serve…
- Simplify and fairly price your product even at short-term revenue cost; McCabe gave away roughly $50M ARR to replace confusing…
- Price AI products on outcomes that align with customer value, like charging 99 cents per resolved ticket, rather than on the…
Product Talk · Teresa TorresJan 9, 2014
Jan 9, 2014 · 7 min
Teresa Torres argues that great products depend on a clear vision, which she treats as one of three pillars alongside sound decision making and building the right team. Product teams often assume alignment that doesn't…
SVPG · Marty CaganSep 11, 2026
Sep 11, 2026 · 10 min
Marty Cagan revisits the foundational product-management ideas he publicly argued for over the past two decades and identifies ten significant mistakes or blind spots. He concludes that his earlier emphasis on…
Lenny’s Newsletter♥ 560
Dec 19, 2023 · 21 min
Subscriber post — summary onlyLenny explains first-principles thinking as a beginner's-mind method: question assumptions, dig to the source, and rebuild problems from fundamental truths instead of copying analogies. He illustrates it with examples…
Lenny’s Podcast124 min
Drew Houston · Jan 9, 2025
Key learnings- Viral growth can be engineered: Houston credits a demo video, referral loops, and a beta waitlist that grew from 5,000 to 85,000…
- When a product is broadly useful, competitors can bundle it free into their platforms; Houston argues the real defense is…
- Borrow strategy from classic books: Houston credits Playing to Win and Only the Paranoid Survive for pushing him to narrow focus…
Product Talk · Teresa TorresApr 22, 2025
Apr 22, 2025
Teresa Torres and Petra Wille argue that many organizations do not have a clearly written product strategy, and that the strategy actually in play is often implicit and revealed by what teams build and learn. They…