Lenny’s Podcast129 min
Caitlin Kalinowski · May 17, 2026
Key learnings- Hardware can only be 'compiled' a handful of times, so teams must be more conservative, run reliability checks early, and solve…
- Define clear, written goals (cost, weight, resolution) before starting and resist changing them, since hardware is far less…
- Design the riskiest or hardest-to-physically-build parts first rather than starting with the components you already know how to…
Lenny’s Podcast136 min
Eric Ries, Lean Startup author · May 10, 2026
Key learnings- Protect your company's mission structurally from day one; waiting for success or later fundraises makes these protections…
- Check your own corporate charter and governance documents, since most founders never read them and may have signed away mission…
- Consider filing as a public benefit corporation with a specific purpose statement; it's a simple filing that defends against…
Lenny’s Newsletter♥ 370
May 5, 2026 · 8 min
Subscriber post — summary onlyLenny Rachitsky's guest author, a Google AI product leader, argues that the SaaS freemium playbook breaks down for AI products because each free request carries real compute cost. He proposes a modern AI paywall built…
Lenny’s Newsletter♥ 409
Apr 28, 2026 · 5 min
Subscriber post — summary onlyLenny Rachitsky, with Hilary Gridley, introduces Couch-to-5K for AI, a free program of under 10 minutes a day that builds AI skills progressively using Claude Code. The post argues that busyness is usually a disguise…
Lenny’s Podcast95 min
Evan Spiegel · Apr 26, 2026
Key learnings- Distribution is often underweighted compared with product-market fit; founders should plan how they will reach users, not just…
- Software features are easy to copy, so durable advantages come from ecosystems, creator/developer platforms, and…
- Connecting people to their closest relationships, rather than maximizing total friends, can be the more valuable network effect…
Lenny’s Podcast108 min
Cat Wu · Apr 23, 2026
Key learnings- Shorten the path from idea to user: AI-era timelines have shrunk from six months to days or a week, so PMs should focus on…
- Ship features as clearly labeled research previews to lower the commitment of launching and get fast user feedback that can be…
- Set a clear, specific goal for who the key user is and what success means, which rules out many approaches and speeds decisions.
Lenny’s Podcast115 min
Nikhyl Singhal · Apr 19, 2026
Key learnings- Expect the information-moving part of product work to be automated; judgment about what to build and whether changes are good…
- Build with AI tools to solve your own daily problems; you don't need to be an engineer, you need to know what good looks like.
- Aim to obsolete yourself: automate the parts of your job you dislike, as the best engineers do.
Lenny’s Newsletter♥ 458
Apr 14, 2026 · 15 min
Subscriber post — summary onlyThe post argues that 'AI agent' covers very different systems, so teams should first categorize each idea by architecture before prioritizing. It proposes three categories (deterministic automation, reasoning and acting…
Lenny’s Podcast105 min
Keith Rabois · Apr 12, 2026
Key learnings- Build the team first: Rabois argues the team you assemble determines the company you build, so hiring quality outranks market…
- Check hires 30 days after they join by asking whether you would make the same decision again; he says this short loop predicts…
- Run ruthless referencing with many references per senior hire, and frame questions around whether the person can be a world-class…
Lenny’s Newsletter · Free post♥ 509
Apr 7, 2026 · 9 min
“I’m so, so excited to share a guest post by Michelle Rial, my wife! Her first children’s book, Charts for Babies, comes out TODAY, and we thought: what better way to celebrate than collaborating on a post? Below, you get a glimpse into her brilliant mind. This visual guide is both inspiring and useful, and is for anyone trying to create something. Read it right now or bookmark it for the next time you get stuck. Are you feeling what…”
Lenny’s Podcast148 min
Amol Avasare · Apr 5, 2026
Key learnings- Expect most growth time to go to 'success disasters' once growth is rapid; firefighting breaking systems matters as much as new…
- In AI-first products, skew the growth portfolio toward larger swings, since future product value could be orders of magnitude…
- Treat activation as a top lever in AI products: identify user traits that predict which feature fits them, then guide them there.
Lenny’s Podcast142 min
Simon Willison · Apr 2, 2026
Key learnings- Coding agents crossed a reliability threshold around November 2025, so they now usually do what you ask, which changed how…
- Writing code is now cheap, so the bottlenecks move to ideation, prototyping, testing, and process; build several quick prototypes…
- Use test-driven development with agents: have them write tests, run them, and watch them fail first (Red/Green TDD) to keep…
Lenny’s Newsletter♥ 888
Mar 31, 2026 · 15 min
Subscriber post — summary onlyClaire Vo presents a step-by-step guide to installing, configuring, and using OpenClaw, an open-source personal AI agent that runs locally and takes instructions through everyday chat apps. The post covers hardware and…
Lenny’s Podcast134 min
Claire Vo · Mar 29, 2026
Key learnings- Run several purpose-built agents instead of one general agent; splitting tasks keeps each agent's context focused and reduces…
- Install OpenClaw on a separate clean machine such as an old laptop or Mac Mini, with its own local admin account, rather than…
- Onboard the agent like a new employee: give it its own email and calendar, share access selectively, and expand trust…
Lenny’s Newsletter♥ 439
Mar 24, 2026 · 7 min
Subscriber post — summary onlyLenny Rachitsky's biannual State of the Product Job Market update, based on TrueUp data, argues that early 2026 tech hiring is more optimistic than headlines suggest. It covers rising PM and engineering openings, the…
Lenny’s Podcast116 min
Jessica Fain · Mar 22, 2026
Key learnings- Treat stakeholder conversations as discovery interviews: go in to learn and strengthen your plan, not simply to get approval for…
- Remember executives have chaotic calendars and little context on your topic, so spend under 60 seconds at the start restating why…
- Ground your pitch in the executive's success metrics and board pressures, and show explicitly how your proposal moves those…
Lenny’s Newsletter♥ 328
Mar 17, 2026 · 23 min
Subscriber post — summary onlyDesigner Ben Shih describes building LennyRPG, a Pokémon-style pixel game where players meet and quiz Lenny's Podcast guests using transcripts from 300+ episodes. The post walks through his AI-assisted workflow…
Lenny’s Newsletter♥ 419
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♥ 818
Mar 3, 2026 · 14 min
Subscriber post — summary onlyMolly Graham introduces the Waterline Model, a diagnostic for underperforming teams that checks four levels in order: structure, dynamics, interpersonal, and individual. Her core argument is that many team problems are…
Lenny’s Podcast100 min
Jenny Wen · Mar 1, 2026
Key learnings- Classic linear design process (research, diverge, converge) is breaking down as engineers ship prototypes quickly; designers…
- Design work is splitting into two modes: supporting implementation and setting a vision, where the vision now often spans three…
- Designers can use coding tools to do last-mile polish and prototype in real code, rather than waiting on engineers for every…
Lenny’s Podcast109 min
Jeetu Patel · Feb 26, 2026
Key learnings- Distinguish a megatrend from a hype cycle: don't fight real megatrends like AI, and avoid vanity work chasing hype.
- Before investing, ask whether you have 'permission to play' and a route to mass distribution; otherwise dollars spent on product…
- Make bold bets clear and go all in once an experiment works, rather than hedging, while aligning individual success with the…
Lenny’s Newsletter♥ 739
Feb 24, 2026 · 22 min
Subscriber post — summary onlyLenny Rachitsky and researcher Noam Segal interviewed over 30 tech professionals about using AI in job hunts and found the strongest candidates built personal feedback loops with AI. The post packages those techniques…
Lenny’s Podcast131 min
Boris Cherny · Feb 19, 2026
Key learnings- Ship with minimal scaffolding and let the model choose tools and order of operations, rather than boxing it into rigid workflows…
- Watch how people hack your product for purposes it wasn't designed for; that latent demand, like data scientists using a terminal…
- Bet on the more general model over time instead of fine-tuning or tiny models, since scaffolding gains of 10-20% often vanish…
Lenny’s Newsletter♥ 421
Feb 17, 2026 · 26 min
Subscriber post — summary onlyCaitlin Sullivan, a user-research practitioner, explains four recurring ways AI-generated customer analysis goes wrong: invented or blended quotes, generic insights, signal that doesn't guide decisions, and missed…
Lenny’s Podcast98 min
Brian Halligan · Feb 15, 2026
Key learnings- Overrate less your gut feeling in interviews; rely on blind references and ask pointed questions like how likely you would be to…
- Prefer spiky candidates with visible weaknesses who will challenge you over polished candidates with the fewest weaknesses, and…
- Be cautious hiring executives straight from big companies; they often have mismatched expectations and high attrition in scaling…
Lenny’s Podcast105 min
Sherwin Wu V2 · Feb 12, 2026
Key learnings- Build for where models are going rather than where they are today, since products that are almost-working now can become…
- Treat fast-changing AI scaffolding skeptically: models often absorb tooling like vector stores and agent frameworks, so avoid…
- Don't blindly follow customer feature requests in AI; customers may anchor on local maxima while the underlying models are…
Lenny’s Newsletter♥ 252
Feb 10, 2026 · 18 min
Subscriber post — summary onlyMarily Nika, a former AI PM at Google and Meta, presents a weekly ritual for building AI product sense: probing a model with messy, ambiguous, and difficult inputs to map failure modes before users do. She argues PMs…
Lenny’s Podcast123 min
Lazar Jovanovic · Feb 8, 2026
Key learnings- Start a project with several parallel attempts (brain dump, typed prompt, design reference, code template) to find the strongest…
- Spend most of your time planning and chatting with the AI rather than executing, since clarity matters more than raw build speed.
- Write a set of source-of-truth docs (master plan, implementation plan, design guidelines, user journeys, tasks.md) so the agent…
Lenny’s Newsletter♥ 578
Feb 3, 2026 · 34 min
Subscriber post — summary onlyTal and Aman argue that the fastest way to build intuition for AI products is to use coding agents like Cursor for non-technical product work rather than consumer chat tools. The post walks readers through setup, model…
Lenny’s Podcast131 min
Dr. Becky Kennedy · Feb 1, 2026
Key learnings- Repair after a mistake, by owning your part and naming what you'll do differently, rebuilds trust; perfection is not the goal…
- Connect before correcting: join the other person's world first without an agenda, since connection builds the bridge that makes…
- Separate behavior from identity by assuming someone is good inside, which keeps conversations productive and makes defensiveness…