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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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

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

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

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:...