How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook
These notes were generated by AI and may contain inaccuracies.
Be early. Don't order the most expensive thing on a video call menu. Have an appropriate background. Don't smell bad.
Etiquette is a skill for how to show up in a room with a low heart rate.
At Kleiner Perkins holiday party with all venture capitalists and CEOs at your first company, avoid high-stakes transactional mindset. Don't show up like an Energizer Bunny; project calm of abundance. This is part of the story, not the entire story.
Sam Lessin, partner at Slow Ventures, previous VP of Product at Facebook, two-time founder. Teaching classes worldwide, published book on etiquette. Covers introductions, small talk, meals, meetings.
Sponsor: Tene Webb (10web.io/lenny) AI website builder, VIP coding platform for WordPress, API service. Sponsor: DX (getdx.com/lenny) developer intelligence platform used by Dropbox, Booking.com, Adyen, Intercom.
Etiquette at intersection of hilarious and useful. Started with tweet, escalated to event, book. Double down in life.
In 2025/2026, software commoditizing, AI fear; etiquette matters for building trust, partnerships, mirroring expected behaviors when asking for trust with data/business.
Shallow truth: funny to teach Silicon Valley etiquette after narrative that none matters, just product.
Wearing t-shirt but knows rules.
Show up with low heart rate, self-confidence, calm of abundance, not scarcity. Give more than take, build relationships not collect cards.
No one teaches founders this; product matters but etiquette differentiates success from missing deals.
Mana from heaven product trumps etiquette rarely (99.9% startups), but work with great people for success.
Book divided into 10 social situations. V1 limited edition, ship early/ship often.
Introductions and Entering a Room
Be early, not half hour early (weird), but buffer for low heart rate. Arrive racing late raises heart rate. If late, apologize simply, move on; don't be flustered.
- Strong handshake: firm, don't crush; practice on friends.
- Repeat names back: "Hey Lenny, great to meet you" shows effort to remember, connect.
If someone else late, don't make them feel bad; opposite of own behavior.
VCs/founders often late on back-to-back Zooms; apologize but don't harp/indignant, unproductive, sets wrong dynamic.
Eye contact shows respect, presence; effort signals even if neurodivergent.
With partner: introduce them first. Trick if forget name: "Jessica, meet my wife" or flip "Lenny, please meet my wife Jessica" to elicit name. Let it hang for social grace.
Welcome people in, be inclusive, abundance mindset over scarcity/power dynamics (don't flock famous person).
Ask questions but balance give/get; not inquisition or self-centered spiel. Ping-pong exchange, not 10 questions in row/single player.
Match vocabulary to audience (professor vs. 12-year-old) to make relaxed/welcome.
Leave them wanting more: goal is "interesting person, want to hear/meet again" or them recommending you. Excuse gracefully; abundance, not one shot.
Uniquely American/Silicon Valley scarcity environment, especially young founders.
It reminds me of the Eminem song about one shot, one opportunity. Before a big presentation, listen to it to pump yourself up. In terms of putting people at ease, building relationships, and etiquette, even if this feels like your one shot, show up with self-confidence and calm of abundance. Act like this is not your only opportunity—it's an opportunity you're excited about. Stay engaged, remember it's okay not to know everything, focus on low heart rate and eye contact.
Don't be a sycophant or ridiculous. Ridiculous example: going up to Mark Zuckerberg, whom everyone recognizes, and saying, "Hi, I'm Sam, who are you?" Wrong: saying "You're the most important person I've ever met." Approach with grace, recognizing they're people. Play an iterative game—act like it's not your only chance to meet them. Ideally, leave them thinking, "That was a nice person, maybe I want to talk again." Don't demand email or phone number; let them offer it.
Use "great to see you" instead of "nice to meet you." It's difficult to put someone in an embarrassing situation by assuming you've met before. Example: speaker's wife story—before dating, he said "nice to see you" because he couldn't remember if they'd met (they had). Wife makes fun of speaker for not knowing if he's met people. "Great to see you" works whether first time or not. People aren't dumb—if you say "nice to meet you" to everyone, they suspect you might not remember them. Better than saying "nice to meet you" after meeting six times.
Subtle fragrance: don't smell bad or overpower with perfume/cologne. Scent should not be noticeable in any direction—no advantage to it being memorable. Applies equally to men and women. Upcoming "fem etiquette course" in January/February because women need additional advice.
Speaker's children (8-year-old, 6-year-old, 4-year-old) have terrible manners—they eat like animals, don't use fork/knife properly. Working on it; 6-year-old stands when wife comes to table (formal etiquette: stand when woman arrives). Modern tip: stand whenever anyone joins for a meal, man or woman. Ongoing debate at dinner table.
Taught class at Four Seasons for YC founders (Gary Tan got mad, so they did it). Gave certificates; irreverent elements like models showing dress codes, caviar/wine tasting. Focused on low heart rate, abundance mindset, eye contact, handshakes, respectful eating. Gary Tan mad possibly because founders seem like animals—young, coding-focused, unaware (e.g., leave coffee on table without asking where to put it). Valuable for awareness.
Don't be covered in schmutz. Show respect: anticipate room's dress code, don't overdress/underwear. Tuxedo at business casual stands out negatively; underdressing shows no respect.
Know rules to break them intentionally with cultural understanding. Story: first job at consulting firm, started Tuxedo Tuesdays as rebellion (business casual had minimum but no maximum)—associates wore tuxes, skipped client meetings. Simple rule: look put together, like you cared, made effort, but don't overdo.
- Dress one level up (easy win; not two or three). Can reduce formality (e.g., remove suit jacket).
- Fit over brand: well-fitting $20 shirt > misfitting $500 shirt. Most people intuitively see if suit fits. Expensive misfit signals lack of awareness, trying to impress with cost (not brand names like Rolex for startup founders—classless, shows trying too hard).
- If unsure dress level, ask—shows confidence, calm, humility. Fine for etiquette/dress expectations (e.g., NYC vs. SF differ). Not expected to know every cultural nuance.
Tip for dressing well: find someone who dresses well in your circle and ask for help. Basics: clean, well-fitting jeans.
- Tip well (don't be stingy; 20% minimum, up to 30%; not memorable).
- Split bills evenly; make easy for waiters.
- Don't order most expensive thing (signals insensitivity to cost, even if investor doesn't care).
- Order same wine.
- Don't order first—let others set tone (e.g., starters? meal length?). Go middle of pack to last.
Always offer to pay (within reason; turned down 99% time by VC). Don't if $10k dinner/expensive wine. For billionaire/normal meal, still offer—they'll decline. Gesture treats as equals. If paying with famous person, tip generously (e.g., 100% of bill) to match their level.
Don't want tip to be memorable negatively; focus on conversation/ideas, not stinginess.
Tipping confusing (restaurants, garbage, gardener, end-of-year, shade installer—no for latter if paid upfront). Idea: AI tipping app—photo of bill, geolocates, inputs situation, suggests amount.
If ordering nice wine, give sommelier a sip—be generous.
B for bread, D for drinks: Look at your hands to identify your bread plate (B on the left) and drinks (D on the right). People often wait for others to pick first but this mnemonic helps.
Forks and knives: Know placement; knife blade faces in when set down to avoid stabbing neighbor. Example: Gave feedback to entrepreneur—good job eating soup, but napkin in lap (not neck or side), knife pointed wrong way. Napkin on one leg vs. both: Avoid memorable napkin placement.
Etiquette gets you out of the way; it shouldn't be memorable. Like Kindle, don't think about the technology—let conversation flow.
Humor is great but conditional and subtle to audience. Avoid dirty jokes in wrong room. Humor shows mastery of social situation—telling joke up to the line or slightly off-color demonstrates comfort. Don't be remembered only as comedian; use sparingly, not knock-knock jokes with adults. Off-color sex joke requires confidence; failed joke is high risk.
Have file of jokes ranked from least to most offensive (e.g., in Bear app). Self-deprecating humor: Make fun of yourself, not others—safer, shows no risk of disparaging.
Have easy, crowd-pleasing stories (not 10 minutes). Social interactions like ping-pong: Carry conversation back and forth, put others at ease, show understanding and trustworthiness. Build on their stories.
Recognize when conversation ends and leave gracefully. Worst: Person stands there awkwardly. Use: "I'm going to grab a drink." Usually not invitation to join. Respect signs moment is passing.
Other way: Bring in third person—"Enjoyed this; have you met Steve? Let's go talk to Steve." Then exit (e.g., say hi to wife). Key: Subtlety, give plausible deniability, make people feel respected.
Hates Calendarly—drove their growth via viral rant calling it disrespectful. Provide real availability options. Default: Don't use Calendarly; especially if less senior/busy, ask their availability and make it work. If using link, ensure real slots; first three options should work.
Rescheduling: Give notice; be extra flexible for their schedule. Check time zones—avoid 4 AM slots. Respect reasonable times.
Respect EAs, PAs, gatekeepers: Number one classless move is disrespecting them. Show deep respect—thank for scheduling, follow up, eye contact, treat as equals. Story: When selling company to Airbnb, built relationship with EA/office manager—helps deals. Avoid overdoing (e.g., flowers feels transactional unless confident). Small things: Ask where to put coffee cup.
Embedding times in email ok, but prefers asking "when free?" Depends on who's asking—even 4 AM for Barack Obama. Calendar moves a lot; not flat hierarchy.
Calendarly risks: Someone booked cold pitch via found URL; similar names led to wrong meetings—but once committed, do it.
For founders: Offer their Calendly first; if not, provide yours—make it easy, do the work.
Proofread, get to point quickly, assume recipient busy. Email SLA: Acknowledge quickly (not 12-page essay), don't leave hanging. Imagine receiving: 10 paragraphs annoying, like monologue.
No emojis in business—step of familiarity, like jokes (use at risk). Match if they use; but prefer literate, clear text. Emojis ambiguous, cultural connotations, imply AI (e.g., 🙏). Custom emoji colors/packs or Genmoji: Big statement, signals time wasted vs. PMF/etiquette.
Email order: First recipient seems most important (CEO first, not assistant). CC valuable—means FYI, no immediate response. Subtlety in response order: Don't reply first if low on list. BCC: Never reply-all.
Mistakes: Never To: someone you're discussing to check name spelling—Gmail auto-adds. Proofread.
Etiquette is invisible stuff signaling wavelength, low heart rate, intuitive knowledge.
Arrive little early, not too early (e.g., hour early? Walk block). Don't sit in office long—feels like you've been waiting ages.
Arrive 10 to 15 minutes early for meetings to avoid leaving people hanging or appearing too eager by showing up much earlier. Start with small talk such as commenting on the weather or asking how someone's weekend was to cut the air and signal you are a normal person ready for business.
Small talk is like the TCP/IP handshake.
Small talk aligns wavelengths for effective communication, similar to an old modem connecting.
Always have your camera on for virtual meetings, dress appropriately, and ensure an appropriate background. Make your bed if visible, close closets, and avoid virtual backgrounds. These easy details matter significantly, especially for startup founders.
Clean up after yourself in real meetings. Offer to put your coffee cup or Diet Coke in the kitchen, even if staff will clean it. Acknowledge any mess. This is crucial when meeting LPs, as emphasized by partner Kevin Collard.
Stand when people leave the table to shake hands—don't sit. Follow up with short thank you notes expressing gratitude for their time. Don't take calls during meetings; if needed after time is up, say "I'm calling you right back" and walk away. Avoid making a production when exiting—just leave. In large groups, an Irish goodbye is ideal, perhaps thanking the host quietly.
The etiquette book will expand from 50-60 pages to a few hundred with community contributions, citing contributors. Classes planned next year in New York, Tel Aviv, and worldwide.
Goal of etiquette is building trust and projecting genuine confidence. Maintain an abundance mindset: you are worthy, have nothing to prove, it's okay to ask questions, and keep your heart rate low.
Built letter meme (lettermeme.com), a personal news aggregator that turns newsletters into daily cartoons for quick world overview. Pipe in trusted newsletters; receive email digest. Built initial version with vibe coding using Cursor, Digital Ocean, Cloudflare; engineers later upleveled it.
Seed venture capitalists investing in branded AI companies will lose massive amounts of money. Use AI as infrastructure like cloud in 2010 or internet in 2000, but AI companies (e.g., "AI blank") will go to zero due to capital intensity, dilution, commoditization, fragmented market, lack of lock-in. OpenAI at $500B market cap yields only ~25x for seed investors—a middling return. Avoid narrative-driven "religion"; disciplined seed investing doesn't work for capital-intensive businesses.
AI is a tool supercharging existing businesses, not a startup opportunity. Every generation seeks a new frontier (e.g., West, internet, mobile, crypto); AI narrative fits but isn't real terra nova.
Invest in businesses using AI or addressing AI implications (e.g., Sublime Security, Outtake for bot detection like Blade Runner Voight-Kampff test). Cultural shifts from AI create opportunities, not foundation models or "we win because AI."
Books
- The Ancient City (recommended by Marc Andreessen)
- Man's Search for Meaning
- Area 51: An Uncensored History of America's Top Secret Military Base
- Lessons of History by Will Durant (top recommendation: short, approachable, high intellectual return)
- The Fish That Ate the Whale (The Banana King)
- The Last Kings of Shanghai
Favorite Recent Movie/TV
Landman—fabulous. Tech folks now think they understand energy from watching it.
Favorite Recent Product
June Date dating app (junedate.com): Analyzes ChatGPT histories for accurate profiles and matching (Tinder 2.0). Distills who you are; simulates dates. Shockingly accurate self-description. Overhauls dating using AI implications without being an AI company.
Tried newsletter matchmaking: Too many qualified women, insufficient men wanting 25-year-old girlfriends.
Newsletter
No signup; email [email protected] or interact with LLM bot at wlesson.com (adds to list).
Life Motto
"Carthage must burn" from Facebook hackathon poster post-Plus launch—evokes intense, fun work periods.
Podcast: More or Less
With wife (runs The Information), Dave Morin, Brett Morin. Unfiltered friend chats posted raw. Enjoyable even if no audience; serves purposes better than expected.
Many friends and people cared about in the industry pick up pieces from the podcast and discuss them, making it a great conversation starter. Despite not being a huge podcast, it's big enough and surprisingly useful without growth strategies or payment. It's listened to and valuable by the people who matter, and remains fun despite being niche. Would happily do it with friends even if no one listened. Wild that people cared about find interesting pieces helpful. From a business perspective, discussing something leads entrepreneurs to offer better ideas.
This was such a fun chat. Very different from my regular podcast. I think people will find this extremely interesting and useful as I thought and also fun.
Venture firm: Slow Ventures, slow.co. Sam Lessin (@lessin everywhere: Twitter, Instagram, etc.). Email: [email protected] (reads it).
Come hang out in the pool house sometime.
Appreciates being on, fun to see each other, been too long.
Thank you for being here. Great to see you.
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