Lenny’s Podcast71 min
Julia Schottenstein · Jul 13, 2023
Key learnings- Evaluate early-stage companies on four dimensions: people, market, product, and distribution, and recognize that no company will…
- Look for signs of product spark, such as users who can't stop talking about the product and want to share it with teammates and…
- Build a strong standalone offense so you have a viable alternative in every M&A conversation rather than needing to sell.
Lenny’s Podcast115 min
Max Schoenig
Key learnings- Prototyping in code forces you to understand the medium, so designers and PMs gain better judgment about what the real product…
- Agency, the willingness to treat your company and role as malleable, matters more than any single skill as AI tools make…
- Start by making things; tinkering builds the belief that the world around you can be changed, which Max sees as the root of…
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 Podcast110 min
Anish Acharya · Sep 6, 2026
Key learnings- Treat each business function as an agent loop: map its inputs, outputs, and the points where it gets blocked, then supply…
- Expect loops to climb local maxima quickly, but plan for humans to supply out-of-distribution intuition that moves you to the…
- When an agent gets stuck, have a human coach it through the problem; the captured traces let the agent handle that case next time.
Lenny’s Podcast105 min
Tara Seshan · Aug 30, 2026
Key learnings- Be prolific and empirical rather than theoretical: get to something testable with users as fast as possible instead of writing…
- Sharpen the single most important hypothesis (the 'eigenquestion') and design fast tests to resolve it; that loop has always been…
- Build for where models will be in two to three months: building for current capabilities or for distant future capabilities are…
Lenny’s Podcast132 min
Gina Gotthilf · Oct 19, 2023
Key learnings- Anchor the company in a mission people can rally behind; it helps with organic growth, hiring, and resisting short-term…
- Keep growth lean and avoid paid acquisition early, since rising CAC and dependence on paid users can become an addiction that is…
- Focus relentlessly on retention by asking whether the product delivers real value; users who find real value stick around.
The Looking Glass podcastMar 11, 2026
Mar 11, 2026
Key learnings- Excellent growth teams look for opportunities that others in the organization tend to overlook, rather than only chasing the…
- Growth work at a marketplace like DoorDash requires balancing consumers, merchants, and dashers, so teams should consider the…
- Seven lessons framing suggests growth is treated as a repeatable discipline with distinct principles rather than a series of…
Lenny’s Podcast118 min
Dan Shipper · May 24, 2026
Key learnings- Keep using the newest models and agent tools for your real work, and experiment on your own time if your employer restricts…
- Expect most company AI to start as one shared agent that everyone can talk to, likely in Slack, rather than many personal agents…
- Design products so agents can be users too: make them easy to drive via CLI and browser-friendly, because the customer's own AI…
Lenny’s Podcast84 min
Adam Mosseri · Jul 9, 2026
Key learnings- Small pods of four to six generalist engineers plus a generalist 'product staff' role can move faster than large specialist…
- As building gets cheaper, spend more time deciding what to build; taste and judgment about strategy become the scarce skills, per…
- Keep investing in tomorrow's senior talent in each function, not just today's, or the organization will regret it in a few years.
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 Podcast68 min
Amjad Masad · Nov 21, 2024
Key learnings- Replit aims to remove the setup friction of building software by bundling the editor, runtime, packages, database, and deployment…
- Once AI removes the build bottleneck, the limiting factor shifts to how fast you can generate and articulate good ideas, so…
- Product managers can use an AI agent to build a v1 prototype, test it with real users, and then hand a validated concept to…
Lenny’s Podcast102 min
Roman Ugarte · Sep 8, 2026
Key learnings- Build a new product from scratch with a small, isolated team rather than retrofitting an existing surface, so each micro-decision…
- Onboard early users by hand and sit in on calls; fixing failures the same day compresses learning dramatically.
- Let users reveal patterns on their own before productizing them, then gently encourage the winning patterns without making them…
Lenny’s Podcast54 min
TiboSottiaux
Key learnings- Expect most actions on the internet to be taken by agents, so build products that can serve agent traffic at scale and handle the…
- Design for the capabilities you expect in roughly a year (about 10x better than today), not just what current models can do, to…
- Favor systems that learn from your goals and feedback over hand-tuned agent loops and workflows, which Tibo thinks will be…
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…
Substack podcastDec 27, 2025
Dec 27, 2025
Key learnings- Writing can sharpen thinking by forcing you to make vague ideas explicit and expose gaps in your reasoning.
- The claim 'writing is thinking' is useful but overextended; not all thinking happens through writing, and writing alone does not…
- Treat writing as one tool among several for thinking, alongside conversation, sketching, and deliberate reflection.
Lenny’s Podcast87 min
Benjamin Mann · Jul 20, 2025
Key learnings- Mann argues progress is accelerating, not plateauing: model releases now come every one to three months, and scaling laws…
- Define transformative AI by the Economic Turing Test: if an agent passes as a human hire for a role over a month or three, track…
- Use AI tools ambitiously and persistently; Mann says retrying a task from a fresh start succeeds far more often than repeatedly…
Lenny’s Podcast110 min
Jason Droege · Oct 9, 2025
Key learnings- Model improvement now relies heavily on experts (80% of Scale's expert network holds a bachelor's or higher) defining what good…
- Enterprise AI pilots that reach 60-70% accuracy feel close, but robust automation of important processes often takes 6-12 months…
- Validate a new business by checking whether it can sustain high gross margins and whether competitors can match the economics in…
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 Podcast91 min
Logan Kilpatrick · Feb 8, 2024
Key learnings- Products built on general-purpose AI should either be radically better than ChatGPT in specific ways or focus on a narrow…
- Give models rich context about who you are, your goals, and your audience; Logan argues context is the main lever for getting…
- Treat prompt engineering like briefing a capable human with no background: explain the situation, the audience, and what good…
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 Podcast117 min
Alexander Embiricos · Jan 12, 2026
Key learnings- Ship a product to a small group first, then learn empirically from usage rather than over-planning, especially in fast-moving AI…
- Onboard users into agentic tools by first working alongside them in the local IDE or terminal, then gradually configure…
- Give AI coding tools your hardest real tasks rather than trivial ones, and build trust by having the agent first understand the…