Lenny’s Newsletter♥ 284
Mar 25, 2025 · 13 min
Subscriber post — summary onlyMihika Kapoor, who helped build FigJam and launched Figma Slides, shares seven lessons for keeping a startup mindset inside a large company. The core argument is that speed, prototypes, open progress-sharing, strong…
Lenny’s Podcast102 min
Rahul Vohra · Mar 23, 2025
Key learnings- Virality rarely comes from viral mechanics; a viral factor above one is essentially unsustainable, so word of mouth driven by…
- Track your time with a simple running log of task switches instead of your calendar, then review it weekly to see where your…
- When leadership is stretched thin, hire a president to take over operations and executive team management so the CEO can spend…
Lenny’s Newsletter♥ 200
Mar 18, 2025 · 8 min
Subscriber post — summary onlyLenny Rachitsky follows up his earlier analysis by ranking companies whose former product managers most often start companies, raise Series A rounds, accelerate their careers, or become product leaders. Using alumni…
Lenny’s Podcast115 min
Eric Simons · Mar 13, 2025
Key learnings- Eric Simons says deep technology bets can take years to find their market; his team stayed alive by bootstrapping and keeping…
- Simons advises treating spending as a default no until you see real customer pull, and buying software with the goal of cutting…
- Simons notes that when a launch unexpectedly takes off, pricing and infrastructure often break first; Bolt rolled out upgrade…
Lenny’s Newsletter♥ 372
Mar 11, 2025 · 19 min
Subscriber post — summary onlyExecutive coach Natalie Rothfels observes widespread workplace anger among clients and offers a four-step process for turning it into useful insight. Drawing on Buddhist, Internal Family Systems, and somatic ideas, she…
Lenny’s Podcast79 min
Anton Osika · Mar 9, 2025
Key learnings- Be precise and explicit when prompting an AI builder: say exactly what you expect and which parts are not working, rather than…
- Use the agent's chat mode to ask how something works or why it isn't doing what you want; this builds understanding while you…
- Expect to spend a full week taking one real problem from idea to a working product that people use; Anton suggests that alone…
Lenny’s Podcast83 min
Ivan Zhao · Mar 6, 2025
Key learnings- Hide a grand vision inside a product people already want: Notion's 'sugar-coated broccoli' approach meant shipping familiar…
- Test whether your early adoption comes from real users, not just from your own taste: Ivan warns that building too much for…
- Don't be afraid to reset the codebase when the foundation is wrong, and favor better abstractions, since a small core can…
Lenny’s Newsletter · Free post♥ 333
Mar 4, 2025 · 14 min
“This newsletter just hit a big milestone: one million subscribers. This is both exciting and absurd. No part of me imagined it would reach these heights. What started as an “experiment” just over five years ago is now the world’s largest product newsletter, podcast, and community. I’m feeling very proud. Milestones like these are a great opportunity to pause and reflect, so I put out a call on X and LinkedIn and asked y’all what…”
Lenny’s Podcast121 min
Matt Mullenweg · Mar 2, 2025
Key learnings- Build a movement, not just a product: give community members a philosophy and shared identity, plus many ways to contribute…
- A platform only becomes durable when its ecosystem of plugins and themes is a moat competitors can't easily replicate.
- Open source licensing like the GPL guarantees users and builders keep their freedoms even if the steward changes course…
Lenny’s Podcast133 min
Keith Coleman & Jay Baxter · Feb 27, 2025
Key learnings- Surface notes only when raters who normally disagree both find them helpful; seeking cross-polarized agreement is what keeps…
- Open participation to everyone with basic verification and random selection, rather than curating contributors, so the system…
- Set the quality bar conservatively: showing a bad note damages trust far more than withholding a good one, so the team accepts…
Lenny’s Newsletter♥ 350
Feb 25, 2025 · 21 min
Subscriber post — summary onlyChandra Janakiraman, shared with Lenny Rachitsky, presents Strategy Blocks, a step-by-step product strategy framework. It has a 2-year 'small s' strategy built from preparation, sprints, design work, writing, and…
Lenny’s Newsletter♥ 242
Feb 18, 2025 · 7 min
Subscriber post — summary onlyLenny Rachitsky shares compensation benchmarks for product managers across the U.S., Europe, the U.K., and Canada, using Pave data drawn from over 23,000 PMs. The post breaks down base salary, equity, and total comp by…
Lenny’s Newsletter♥ 274
Feb 11, 2025 · 15 min
Subscriber post — summary onlyA data-driven deep dive into Y Combinator's roughly 4,900 companies, examining survival, exits, unicorn rates, funding, geography, and founder traits. The core argument is that YC's edge lies in picking strong founders…
Lenny’s Podcast81 min
Karina Nguyen · Feb 9, 2025
Key learnings- Build rigorous evals first: define deterministic pass/fail behaviors (e.g., correct time handling) and human win-rate comparisons…
- Use prompting as a fast prototyping method to test product ideas before engineering investment, as Karina did with file uploads…
- Synthetic data scales cheaply for teaching core product behaviors, but human expert data is still needed for specialized…
Lenny’s Podcast108 min
Tobi Lutke · Feb 2, 2025
Key learnings- Start new product decisions from first principles by re-deriving them from today's building blocks instead of copying what…
- Be suspicious of pitches to build a better version of what everyone already does; doing the same thing cannot yield something…
- Stay close to the details of the work, including the underlying technology, so decisions rest on real understanding rather than…
Lenny’s Podcast112 min
Nan Yu · Jan 30, 2025
Key learnings- Speed and quality aren't a trade-off; true craftspeople move fast because they are competent, so aim to get a workable version…
- Treat the first version as a best guess to test key assumptions, not a polished deliverable, and release it to internal users…
- Refuse feature requests that add customization for middle-manager reporting at the expense of individual contributors' workflows…
Lenny’s Newsletter♥ 302
Jan 28, 2025 · 19 min
Subscriber post — summary onlyLenny Rachitsky previews Jake Knapp and John Zeratsky's upcoming book Click and their new two-day Foundation Sprint for launching big projects. The post traces the origin of the approach to the Google Meet story and…
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 Newsletter · Free post♥ 360
Jan 21, 2025 · 22 min
Lenny Rachitsky and survey partner Noam Segal report results from a survey of 6,500+ tech professionals on the tools they use, love, and want to replace. The clearest shift since 2020 and 2022 is AI assistants, led by…
Lenny’s Podcast86 min
Graham Weaver · Jan 16, 2025
Key learnings- Ask yourself what you would pursue if you knew you wouldn't fail, then work backward from that goal to find a path toward it.
- Write down your limiting beliefs and fears on paper; once externalized they lose power and become concrete to-do items you can…
- Build accountability through an executive coach, a like-minded friend, or a weekly written form tracking goals and next steps.
Lenny’s Newsletter♥ 247
Jan 14, 2025 · 17 min
Subscriber post — summary onlyLenny Rachitsky introduces Core 4, a unified developer productivity framework built with DX and the authors of DORA, SPACE, and DevEx. The post explains how to baseline team velocity with an anonymous survey, calculate…
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…
Lenny’s Newsletter♥ 763
Jan 7, 2025 · 19 min
Subscriber post — summary onlyA practical guide to AI prototyping for product managers, covering the main categories of tools (chatbots, cloud development environments, local developer assistants) and when to use each. It walks through turning Figma…
Lenny’s Podcast115 min
Alisa Cohn · Jan 5, 2025
Key learnings- Before a hard conversation, identify what you're making it mean (e.g., fear of upsetting someone) and check your intent: the aim…
- Frame performance feedback around observable facts and expectations, citing what you've heard from multiple people, and keep your…
- Build the relationship with positive, specific feedback regularly so people hear criticism as coming from someone who wants to…
Lenny’s Podcast110 min
Shaun Clowes · Dec 29, 2024
Key learnings- Start every document from the customer, market, and competitor perspective rather than internal execution, since…
- Right-size qualitative research: interview roughly 7 to 14 people, because fewer gives too little signal and more stops yielding…
- Use LLMs to hunt for where your strategy doesn't fit customer feedback, not to confirm what you already believe, and to infer…
Lenny’s Newsletter♥ 182
Dec 24, 2024 · 11 min
Subscriber post — summary onlyLenny Rachitsky, working with Crunchbase data, ranks the most active and most successful U.S. angel investors across several time windows. The post is a directional guide to who early-stage founders might approach, and…
Lenny’s Podcast73 min
Marc Benioff · Dec 22, 2024
Key learnings- Test many tactics at once when launching, then double down on whichever one proves to be the winning strategy.
- Cultivate a beginner's mind so you keep seeing possibilities instead of assuming you already know what will work.
- Treat your company as a startup even at scale; the journey, not the stock price, should be the reward.
Lenny’s Podcast150 min
Farhan Thawar · Dec 19, 2024
Key learnings- Choose the harder path when options are close: even if it fails, you gain skills and work with stronger people, whereas the easy…
- Write down a personal framework of what you care about in a job, and use it to filter opportunities and decide when to leave a…
- Build intensity by producing more output per minute rather than adding hours; a focused hour with strong people can outpace a…
Lenny’s Newsletter · Free post♥ 356
Dec 17, 2024 · 9 min
This is Lenny Rachitsky's year-end roundup of his newsletter and podcast, organized as a curated guide to his best content by the problem a reader wants solved. Rather than a single argument, it is a directory: it…
Lenny’s Podcast118 min
Jackson Shuttleworth · Dec 15, 2024
Key learnings- Streaks are an engagement amplifier, not a substitute: first make sure the core product is something users want to return to…
- Choose a unit of use that matches real engagement; simplifying the streak to one lesson kept users, but dumbing it down to one…
- Focus effort on the first seven days, since loss aversion appears to kick in once a streak reaches about seven days and retention…