Lenny’s Podcast153 min
Marc Andreessen · Jan 29, 2026
Key learnings- Expect AI to make already-skilled people far more capable; the gains are largest for those who pair deep expertise with AI tools.
- Rather than fearing job loss, focus on task loss: jobs persist while the individual tasks composing them shift, which is how…
- Combine at least two or three domains deeply (e.g., coding, product, design); the combination of skills creates far more value…
Lenny’s Podcast145 min
Jason Cohen · Jan 25, 2026
Key learnings- Compute your growth ceiling: new customers added per month divided by monthly cancellation rate gives the maximum customer count…
- Ask 'what made you cancel?' rather than 'why did you cancel?' and use open-ended responses, since multiple-choice lists skew…
- Be skeptical of 'too expensive' as a cancellation reason; customers who already bought didn't find the price too high, so dig…
Lenny’s Newsletter♥ 297
Jan 20, 2026 · 20 min
Subscriber post — summary onlyColin Matthews explains that ChatGPT apps let third-party tools surface interactive widgets inside conversations, creating a potentially major distribution channel. The post covers how users discover apps contextually…
Lenny’s Podcast100 min
Zevi Arnovitz · Jan 18, 2026
Key learnings- Start slowly with a ChatGPT project acting as a skeptical 'CTO' before moving to coding tools, gradually easing into code to…
- Capture ideas quickly as Linear issues using reusable slash commands, so you can pick them up later with context already gathered.
- Separate the workflow into explore, plan, execute, review, and document phases, and have the AI ask clarifying questions before…
Lenny’s Podcast129 min
Sam Lessin · Jan 15, 2026
Key learnings- Aim to enter a room with a low heart rate and an abundance mindset rather than scarcity, since the conversation is a…
- Arrive a little early, roughly 10 to 15 minutes, and never make a late guest feel bad; a simple apology is enough.
- When you forget someone's name, introduce your partner first and let the moment hang so the other person picks up the name, or…
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…
Lenny’s Podcast110 min
Aishwarya Naresh Reganti + Kiriti Badam · Jan 11, 2026
Key learnings- AI products differ from traditional software mainly because user inputs and model outputs are both non-deterministic, so behavior…
- Each time you grant an AI system more decision-making autonomy, you give up some human control; autonomy should be earned through…
- Start with low-agency, high-human-control versions (e.g., suggestions to human agents) and log human corrections to build a…
Lenny’s Newsletter♥ 255
Jan 6, 2026 · 8 min
Subscriber post — summary onlyLenny Rachitsky's year-end roundup collects the most popular posts from his newsletter, grouped by theme such as AI, career, strategy, growth, and execution, plus a few all-time classics. He also reviews his 2025 goals…
Lenny’s Podcast120 min
Molly Graham · Jan 4, 2026
Key learnings- Keep handing off the work you've mastered so you can take on the next, bigger challenge; the job keeps growing, so you must keep…
- Name and externalize the emotional reactions to change, then give them about two weeks; anything lasting longer deserves a real…
- When a team struggles, snorkel before you scuba: check structure (goals, roles, expectations) and team dynamics before blaming…
Lenny’s Podcast175 min
Jason M Lemkin · Jan 1, 2026
Key learnings- Don't abandon a sales motion to chase pure product-led growth if customers need help to buy; many self-serve startups later need…
- Founders can close the first 10 customers themselves because they excel at the middle of conversations; focus on asking for next…
- Start hiring sales reps once founders spend about 20% of their time in sales and 20% recruiting; hire at least two reps so you…
Lenny’s Podcast123 min
Matt MacInnis · Dec 28, 2025
Key learnings- Extraordinary outcomes require extraordinary effort; if people feel comfortable at work, something has gone wrong, and leaders…
- Deliberately understaff projects, since overstaffing invites politics and pulls people onto low-priority work before it is clear…
- Withholding feedback is selfish because it optimizes for your own comfort; escalate issues in public and give direct feedback…
Lenny’s Newsletter♥ 451
Dec 23, 2025 · 24 min
Subscriber post — summary onlyLenny Rachitsky and Noam Segal report on a 1,750-respondent survey of tech workers about AI productivity. The core argument is that AI is overdelivering for most people, with the biggest gains in founders and PMs, while…
Lenny’s Podcast117 min
Elena Verna 4.0 · Dec 18, 2025
Key learnings- Expect most of your classic growth playbook to transfer poorly in fast-moving AI categories; Elena estimates only 30-40% of her…
- Build in public: pair regular product shipping with founder-led and employee social posts so the market sees constant change and…
- Give the product away generously, including credits for hackathons and events, since removing the barrier to trying an AI product…
Lenny’s Newsletter♥ 459
Dec 16, 2025 · 16 min
Subscriber post — summary onlyAmir Klein, writing via Lenny's newsletter, explains how he built an AI 'second brain' using ChatGPT Projects while launching monday.com's first AI agent. He covers giving the project a defined personality, feeding it…
Lenny’s Newsletter♥ 566
Dec 9, 2025 · 12 min
Subscriber post — summary onlyGuest author Terrence Rohan shares how five early employees who joined multiple iconic companies, including Palantir, OpenAI, Stripe, and Spotify, spotted breakout startups early. The post argues that three signals…
Lenny’s Podcast97 min
Edwin Chen · Dec 7, 2025
Key learnings- Define quality in rich, specific terms for each domain (e.g., what makes a poem Nobel-worthy, not just whether it has eight…
- Gather thousands of signals on each worker and task, from background and expertise to performance, and use them like an ML…
- Don't trust benchmarks at face value: many contain wrong answers, and optimizing for them can make models worse at messy…
Lenny’s Podcast88 min
Tomer Cohen · Dec 4, 2025
Key learnings- Prioritize clarity over being right: align the team on the problem and direction even if the bet might be wrong, since confusion…
- Test whether a disagreement is real or just a misunderstanding by asking people to restate your point in their own words before…
- Make sure stated priorities match resourcing; if your top initiative lacks your best engineers, the priority is not real.
Lenny’s Podcast100 min
Jeanne Grosser · Nov 30, 2025
Key learnings- Treat go-to-market as an integrated lifecycle spanning marketing, sales, customer success, and support, mapping the jobs to be…
- Expect the buyer experience of being sold to to become a differentiator, so design the sales journey as a distinctive, valuable…
- Frame value around avoiding pain and reducing risk, since many buyers purchase to avoid downside rather than chase upside…
Lenny’s Podcast133 min
Rachel Lockett · Nov 23, 2025
Key learnings- Coach instead of advising when the person has the context and skills to solve their own problem; advise only when urgency is high…
- Practice three levels of listening, especially level-three global listening that attends to emotions, body language, and context…
- Use the GROW model (goal, reality, options, way forward) as a flexible set of powerful questions to unlock someone's own solution.
Lenny’s Podcast109 min
Stewart Butterfield · Nov 20, 2025
Key learnings- Plot features on a utility curve to see whether extra investment is still on the steep part of the value gain or has reached…
- Judge a product by whether users understand what it does; in many places the real challenge is comprehension, not friction, so…
- Cultivate taste deliberately: taste can be trained, and leaning into craft can become a competitive advantage that less-attentive…
Lenny’s Podcast78 min
Dr. Fei Fei Li · Nov 16, 2025
Key learnings- Large labeled datasets were the missing ingredient that unlocked modern AI; big data, neural networks, and GPUs together formed…
- Pursue a north-star problem and commit to it for years, as ImageNet's object recognition focus did for her lab.
- Be willing to take intellectual and career risks, such as leaving tenure track or joining new ventures, when the mission and…
Lenny’s Podcast164 min
Grant Lee · Nov 13, 2025
Key learnings- Treat product-market fit as a real word-of-mouth engine: if over half of new signups come from organic sharing, the core growth…
- Make the first 30 seconds of the product magical, focusing on one clear 'egg' of value rather than many features, so new users…
- Practice founder-led marketing: write provocative but useful posts, share learnings regularly, and build credibility by giving…
Lenny’s Newsletter♥ 389
Nov 11, 2025 · 15 min
Subscriber post — summary onlyThe post argues that as AI makes building and reaching customers easier for everyone, traditional B2B channels like search, outbound, events and lifecycle email are getting noisier and less effective. It makes the case…
Lenny’s Podcast97 min
Jen Abel · Nov 9, 2025
Key learnings- Founder-led sales is a competitive advantage because founders are the visionary and can spot budding insights that salespeople…
- Write cold outreach that leads with relevance, a counterintuitive insight, and the problem rather than the solution, kept to…
- Before buying tools, manually find and write thoughtful notes to about 30 prospects; use the response pattern to refine messaging…
Lenny’s Newsletter♥ 271
Oct 28, 2025 · 26 min
Subscriber post — summary onlyLenny Rachitsky shares a product-and-brand guide compiled with builder-investor Justin Mares, covering health-focused choices for sleep, clothing, food, supplements, toxin mitigation, and everyday items. The core…
Lenny’s Podcast100 min
Dhanji R. Prasanna · Oct 26, 2025
Key learnings- Track AI impact with self-reported time savings plus validation metrics such as PR throughput and feature delivery, which Block…
- Expect the current AI value baseline to keep rising; adopt tools continuously and re-evaluate where they add value as…
- Non-technical staff building their own small internal tools with agents can compress weeks of waiting on engineering queues into…
Lenny’s Podcast102 min
Chip Huyen · Oct 23, 2025
Key learnings- Focus on what actually improves AI apps, such as talking to users, improving data, writing better prompts, and optimizing…
- Be cautious about committing to newly released technologies that have not been widely tested, since switching away from them…
- Fine-tuning and post-training can shape model behavior a lot, and many teams now focus effort there because base pre-training…
Lenny’s Podcast95 min
Nicole Forsgren · Oct 19, 2025
Key learnings- Before measuring anything, get crisp on the problem or goal, since teams often interpret vague mandates like 'improve developer…
- Shipping smaller changes more often tends to improve both speed and stability together, because small batches have smaller blast…
- DORA's four metrics (deployment frequency, lead time, time to restore, change fail rate) give a benchmark-style view of where you…
Lenny’s Newsletter♥ 839
Oct 14, 2025 · 20 min
Subscriber post — summary onlyLenny Rachitsky argues that non-technical people should use Claude Code, which he frames as a local-feeling AI agent that can act on files and tools on a computer. The post walks through installation steps, shows five…
Lenny’s Podcast118 min
Robby Stein · Oct 10, 2025
Key learnings- Search demand is expanding rather than dying: AI lets people ask more and harder questions, so growth comes from new query types…
- Build a product from a real user problem and stay dissatisfied with the status quo; keep making it better until it tips into…
- Use a J-curve retention analysis (day 7, 30, 90) to tell whether a product is flattening into real usage or steadily losing users.