Lenny's Podcast: Product | Career | Growth

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship.

We discuss:
1. Why repair—not perfection—defines strong leadership
2. Why you need to connect before you correct to build cooperation and trust
3. The “most generous interpretation” framework for handling difficult behaviors
4. How to correctly set boundaries (vs. making requests)
5. The power of “I believe you, and I believe in you”
6. What it looks like to be a “sturdy” leader
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Brought to you by:
Merge—Fast, secure integrations for your products and agents: https://merge.dev/lenny
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Episode transcript: https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Dr. Becky Kennedy:
• X: https://x.com/GoodInside
• LinkedIn: https://www.linkedin.com/in/drbecky
• Instagram: https://www.instagram.com/drbeckyatgoodinside
• TikTok: https://www.tiktok.com/@drbeckyatgoodinside
• Website: https://www.goodinside.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Dr. Becky Kennedy
(05:14) Connecting parenting and leadership
(08:40) The power of repair
(11:05) Connecting before correcting
(17:45) Good Inside framework at work
(22:08) The most generous interpretation (MGI)
(25:46) Curiosity over judgment
(27:07) Understanding behavior change
(31:08) What potty training can teach us about workplace behavior
(34:40) Naming your intention
(35:41) Sturdy leadership
(40:52) How to set boundaries well
(46:33) The role of leadership and consensus
(50:50) The importance of being “locatable”
(52:40) A powerful story of betrayal and realization
(57:12) Building resilience over happiness
(01:00:34) The power of the phrase “I believe you, and I believe in you.”
(01:09:08) The Good Inside community and resources
(01:16:22) AI corner
(01:19:52) Good Inside’s mission
(01:22:26) Lightning round and final thoughts
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Referenced:
• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi
• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice
• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng
• Punch: https://en.wikipedia.org/wiki/Punch_(play)
• Figma: https://www.figma.com
• Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan
• Replit: https://replit.com
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• Lovable: https://lovable.dev
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• Claude: https://claude.ai
• ChatGPT: https://chatgpt.com
• Secrets We Keep on Netflix: https://www.netflix.com/title/81697668
• K Pop Demon Hunters on Netflix: https://www.netflix.com/title/81498621
• Liberty puzzles: https://libertypuzzles.com
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Recommended books:
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375
• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481
• Leave Me Alone!: A Good Inside Story About Deeply Feeling Kids: https://www.amazon.com/Leave-Me-Alone-Inside-Feeling/dp/1250413117
• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765/
• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072
• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Marc Andreessen is a founder, investor, and co-founder of Netscape, as well as co-founder of the venture capital firm Andreessen Horowitz (a16z). In this conversation, we dig into why we’re living through a unique and one of the most incredible times in history, and what comes next.

We discuss:
1. Why AI is arriving at the perfect moment to counter demographic collapse and declining productivity
2. How Marc has raised his 10-year-old kid to thrive in an AI-driven world
3. What’s actually going to happen with AI and jobs (spoiler: he thinks the panic is “totally off base”)
4. The “Mexican standoff” that’s happening between product managers, designers, and engineers
5. Why you should still learn to code (even with AI)
6. How to develop an “E-shaped” career that combines multiple skills, with AI as a force multiplier
7. The career advice he keeps coming back to (“Don’t be fungible”)
8. How AI can democratize one-on-one tutoring, potentially transforming education
9. His media diet: X and old books, nothing in between
—
Brought to you by:
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—
Episode transcript: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Marc Andreessen:
• X: https://x.com/pmarca
• Substack: https://pmarca.substack.com
• Andreessen Horowitz’s website: https://a16z.com
• Andreessen Horowitz’s YouTube channel: https://www.youtube.com/@a16z
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Marc Andreessen
(04:27) The historic moment we’re living in
(06:52) The impact of AI on society
(11:14) AI’s role in education and parenting
(22:15) The future of jobs in an AI-driven world
(30:15) Marc's past predictions
(35:35) The Mexican standoff of tech roles
(39:28) Adapting to changing job tasks
(42:15) The shift to scripting languages
(44:50) The importance of understanding code
(51:37) The value of design in the AI era
(53:30) The T-shaped skill strategy
(01:02:05) AI’s impact on founders and companies
(01:05:58) The concept of one-person billion-dollar companies
(01:08:33) Debating AI moats and market dynamics
(01:14:39) The rapid evolution of AI models
(01:18:05) Indeterminate optimism in venture capital
(01:22:17) The concept of AGI and its implications
(01:30:00) Marc's media diet
(01:36:18) Favorite movies and AI voice technology
(01:39:24) Marc's product diet
(01:43:16) Closing thoughts and recommendations
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Referenced:
• Linus Torvalds on LinkedIn: https://www.linkedin.com/in/linustorvalds
• The philosopher’s stone: https://en.wikipedia.org/wiki/Philosopher%27s_stone
• Alexander the Great: https://en.wikipedia.org/wiki/Alexander_the_Great
• Aristotle: https://en.wikipedia.org/wiki/Aristotle
• Bloom’s 2 sigma problem: https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem
• Alpha School: https://alpha.school
• In Tech We Trust? A Debate with Peter Thiel and Marc Andreessen: https://a16z.com/in-tech-we-trust-a-debate-with-peter-thiel-and-marc-andreessen
• John Woo: https://en.wikipedia.org/wiki/John_Woo
• Assembly: https://en.wikipedia.org/wiki/Assembly_language
• C programming language: https://en.wikipedia.org/wiki/C_(programming_language)
• Python: https://www.python.org
• Netscape: https://en.wikipedia.org/wiki/Netscape
• Perl: https://www.perl.org
• Scott Adams: https://en.wikipedia.org/wiki/Scott_Adams
• Larry Summers’s website: https://larrysummers.com
• Nano Banana: https://gemini.google/overview/image-generation
• Bitcoin: https://bitcoin.org
• Ethereum: https://ethereum.org
• Satoshi Nakamoto: https://en.wikipedia.org/wiki/Satoshi_Nakamoto
• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann
• Inside Google’s AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search): https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year
• DeepSeek: https://www.deepseek.com
• Cowork: https://support.claude.com/en/articles/13345190-getting-started-with-cowork
• Definite vs. indefinite thinking: Notes from Zero to One by Peter Thiel: https://boxkitemachine.net/posts/zero-to-one-peter-thiel-definite-vs-indefinite-thinking
• Henry Ford: https://www.thehenryford.org/explore/stories-of-innovation/visionaries/henry-ford
• Lex Fridman Podcast: https://lexfridman.com/podcast
• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz
• Eddington: https://www.imdb.com/title/tt31176520
• Joaquin Phoenix: https://en.wikipedia.org/wiki/Joaquin_Phoenix
• Pedro Pascal: https://en.wikipedia.org/wiki/Pedro_Pascal
• George Floyd: https://en.wikipedia.org/wiki/George_Floyd
• Replit: https://replit.com
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• Grok Bad Rudi: https://grok.com/badrudi
• Wispr Flow: https://wisprflow.ai
• Star Trek: The Next Generation: https://www.imdb.com/title/tt0092455
• Star Trek: Starfleet Academy: https://www.imdb.com/title/tt8622160
• a16z: The Power Brokers: https://www.notboring.co/p/a16z-the-power-brokers
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team.

We discuss:
1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market
2. A small tweak that’ll double response rates on your cancellation surveys
3. Why “it’s too expensive” is almost never the real reason customers cancel
4. The “elephant curve” of growth
5. How repositioning the same product can increase revenue 8x
6. When to reconsider if growth is even the right goal for your business
—
Brought to you by:
10Web—Vibe coding platform as an API
Strella—The AI-powered customer research platform
Brex—The banking solution for startups
—
Episode transcript: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Jason Cohen:
• Preorder Jason’s book: https://preorder.hiddenmultipliers.com/
• X: https://x.com/asmartbear
• LinkedIn: https://www.linkedin.com/in/jasoncohen
• Blog: https://longform.asmartbear.com
• Website: https://wpengine.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Jason Cohen
(05:19) Jason’s writing journey
(08:25) Questions to ask when your product stops growing
(18:17) Getting real customer feedback
(20:27) Analyzing cancellation reasons
(26:54) Onboarding and activation
(29:35) Quick summary
(35:46) Revisiting pricing strategies
(41:46) Positioning strategies
(47:52) Why pricing is inseparable from your strategy
(52:06) The importance of net revenue retention (NRR)
(01:00:25) Asking whether or not this is good for the customer
(01:04:34) Leveraging existing customers
(01:06:42) Are your acquisition channels saturated? The “elephant curve”
(1:09:41) Why all marketing channels eventually decline
(01:12:04) Direct vs. indirect marketing channels
(1:13:36) Getting creative with new channels
(01:19:04) Do you actually need to grow?
(01:25:57) Deciding when to quit
(01:29:27) Book announcement
(01:33:21) AI corner
(01:34:35) Contrarian corner
(01:37:43) Lightning round and final thoughts
—
Referenced:
• Tyler Cowen’s website: https://tylercowen.com
• How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn
• Linear: https://linear.app
• Jira: https://www.atlassian.com/software/jira
• Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942
• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan
• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam
• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy
• M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing
• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr
• Buffer: https://buffer.com
• AG1: https://drinkag1.com
• How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng
• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth
• The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth
• HubSpot: https://www.hubspot.com
• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building
• Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/
• Ecosystem is the next big growth channel: https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth
• ChatGPT apps are about to be the next big distribution channel: Here’s how to build one: https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the
• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths
• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams
• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead
• ER on Prime Video: https://www.amazon.com/ER-Season-1/dp/B0FWK5WJQ4
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD
• Wispr Flow: https://wisprflow.ai
• Anker: https://www.anker.com
—
Recommended books:
• Will: https://www.amazon.com/Will-Smith/dp/1984877925
• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867
• Hidden Multipliers: Small Things That Accelerate Growth: https://preorder.hiddenmultipliers.com
• On Writing Well: The Essential Guide to Mastering Nonfiction Writing and Effective Communication: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548
• Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor.

We discuss:
1. The complete AI workflow that lets non-technical people build real products in Cursor
2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI)
3. Using slash commands to automate prompts
4. Zevi’s “peer review” technique, which uses different AI models to review each other’s code
5. Why this might be the best time to be a junior in tech, despite the challenging job market
6. How Zevi used AI to prepare for his Meta PM interviews
—
Brought to you by:
10Web—Vibe coding platform as an API
DX—The developer intelligence platform designed by leading researchers
Framer—Build better websites faster
—
Zevi's Slash Command Bank for Claude: ⁠https://zeviarnovitz.com/⁠
—
Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor
—
Archive of all Lenny's Podcast transcripts:
https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Zevi Arnovitz
• X: https://x.com/ArnovitzZevi
• LinkedIn: https://www.linkedin.com/in/zev-arnovitz
• Website: https://zeviarnovitz.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to Zevi Arnovitz
(04:48) Zevi’s background and journey into AI
(07:41) Overview of Zevi’s AI workflow
(14:41) Screenshare: Exploring Zevi’s workflow in detail
(17:18) Building a feature live: StudyMate app
(30:52) Executing the plan with Cursor
(38:32) Using multiple AI models for code review
(40:40) Personifying AI models
(43:37) Peer review process
(45:40) The importance of postmortems
(51:05) Integrating AI in large companies
(53:42) How AI has impacted the PM role
(57:02) How to improve AI outputs
(58:15) AI-assisted job interviews
(01:02:57) Failure corner
(01:06:20) Lightning round and final thoughts
—
Referenced:
• Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv
• Wix: https://www.wix.com
• Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w
• Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw
• Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg
• Bolt: https://bolt.new
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Lovable: https://lovable.dev
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• StudyMate: https://studymate.live
• Dibur2text: https://dibur2text.app
• Claude: https://claude.ai
• Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code
• Bun: https://bun.com
• Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction
• Cursor: https://cursor.com
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• Wispr Flow: https://wisprflow.ai
• Linear: https://linear.app
• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu
• Cursor Composer: https://cursor.com/blog/composer
• Replit: https://replit.com
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• Base44: https://base44.com
• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo
• v0: https://v0.app
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• Cursor Browser mode: https://cursor.com/docs/agent/browser
• Google Antigravity: https://antigravity.google
• Grok: https://grok.com
• Zapier: https://zapier.com
• Airtable: https://www.airtable.com
• Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system
• The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81
• AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08
• Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx
• Loom: https://www.loom.com
• Cap: https://cap.so
• Supercut: https://supercut.ai
...References continued at: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor
—
Recommended books:
• The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153
• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910
• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust.

We discuss:
1. Why etiquette matters
2. Sam’s framework for showing up confidently, with a low heart rate, in any room
3. How to navigate introductions, small talk, meetings, and meals like a pro
4. Simple hacks for remembering names and handling awkward social situations
5. 30+ specific etiquette tips
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Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook
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Archive of all Lenny's Podcast transcripts:
https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Sam Lessin:
• X: https://x.com/lessin
• LinkedIn: https://www.linkedin.com/in/wlessin
• Website: https://www.wlessin.com
• Podcast: https://moreorlesspod.com
• Lettermeme: https://lettermeme.com/lessin
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Sam’s background
(04:18) The role of etiquette in business success
(09:30) Introductions and entering a room
(16:20) Engaging conversations and building relationships
(23:55) Hygiene and dress code essentials
(33:42) Dining etiquette
(37:15) Tipping etiquette
(41:36) The “B&D trick”
(43:05) Humor in social settings
(45:18) Self-deprecating humor
(47:42) Winding down conversations
(49:20) Scheduling etiquette
(55:23) Communication and email etiquette
(01:02:28) Meeting etiquette tips
(01:04:03) Virtual meeting best practices
(01:05:15) The importance of cleaning up after yourself
(01:05:58) Exiting and follow-up etiquette
(01:07:24) Final thoughts
(01:09:20) AI corner
(01:11:13) Contrarian corner
(01:16:25) Lightning round
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Referenced:
• Y Combinator: https://www.ycombinator.com
• Kleiner Perkins: https://www.kleinerperkins.com
• “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq
• Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan
• Bain & Company: https://www.bain.com
• Evernote: https://evernote.com
• Calendly: https://calendly.com
• Morning Brew: https://www.morningbrew.com
• Cursor: https://cursor.com
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• DigitalOcean: https://www.digitalocean.com
• Cloudflare: https://www.cloudflare.com
• SpaceX: https://www.spacex.com
• Marc Andreessen on X: https://x.com/pmarca
• Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD
• Dave Morin on X: https://x.com/davemorin
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Recommended books:
• Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5
• Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A
• The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048
• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI
• Area 51: An Uncensored History of America’s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q
• The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X
• The Fish That Ate the Whale: The Life and Times of America’s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314
• The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
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Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com