How to show up in any room with a low heart rate: Sam Lessin's etiquette playbook for founders

Executive overview

Most founders underinvest in social skills, assuming the product speaks for itself. In a world where trust and human connection are increasingly differentiating, that's a costly mistake.

Sam Lessin's core reframe: etiquette is not about rules — it's about showing up with a low heart rate. Calm, confidence, and an abundance mindset signal trustworthiness more than any pitch.

• Etiquette removes friction; it should be invisible, not memorable
• The goal in any room is to leave people wanting more, not exhausted
• These skills compound across introductions, meals, meetings, and emails

Introductions and entering a room

• Arrive a few minutes early — it keeps your heart rate low and signals respect
• If late, give a brief apology and move on; don't dwell or make it a scene
• If someone else is late, never make them feel bad about it
• Repeat a person's name back when introduced: it signals focus and effort
• Use "great to see you" (not "nice to meet you") when unsure if you've met before — it works either way
• Firm handshake; don't crush; don't sit when shaking hands
• Introduce your partner or companion first; use the "let it hang" technique to recover a forgotten name — turn to your companion, prompt the introduction, and let the other person fill the gap

Conversations

• Think of conversation as ping-pong: hit the ball back, don't serve ten in a row
• Ask questions, but avoid making it feel like an interrogation — give to get
• Match vocabulary and register to the person you're talking to
• Leave them wanting more; don't deliver your entire life story in one interaction
• Come in with an abundance mindset — this is not your one shot, act accordingly
• With famous people: neither sycophantic nor pretending not to know who they are; treat them as equals
• Know how to exit gracefully: look for the winding-down signals; offer a handoff ("have you met Steve?") to close a conversation smoothly

Hygiene and dress

• Scent should be unnoticeable in either direction — no strong fragrance, no bad smell
• Dress one level up from expected; you can always remove a jacket
• Fit matters far more than brand or price — a well-fitting cheap shirt beats a misfitting expensive one
• Don't show up to a startup context with a Rolex or obvious status markers — it signals insensitivity, not success
• If unsure about dress code, ask — it signals confidence and cultural awareness, not ignorance

Dining

• Don't order first; let the host or senior person set the tone, then match it
• Don't order the most expensive thing on the menu or the priciest wine — even if they don't care, they notice
• Always offer to pay, even with someone wealthy — you'll almost certainly be declined, but the gesture counts; if you do pay, tip accordingly
• Tip generously; 20% is the floor in most situations; the tip should not be memorable in either direction
• B for bread, D for drinks — make a B and D with your hands to remember which plate and glass are yours
• Knife blade faces inward when resting
• Napkin in your lap, not tucked into your collar
• Tip sommeliers and give them a taste if you've ordered something interesting
• Ask where to put your cup or glass when done — it signals awareness and respect for the space

Small talk and humor

• Small talk is the TCP/IP handshake — it establishes wavelength before real communication begins
• Humor is the ultimate signal of comfort in a room; used well, it builds trust fast
• Don't be remembered as only the comedian; use humor sparingly and read the room
• Dirty jokes or edgy humor carry high risk — only deploy when you're very confident in the room
• Self-deprecating humor is always safe; making fun of others is high risk
• Keep a running list of go-to stories and jokes ranked from least to most edgy
• Have a few punchy, crowd-pleasing stories in your arsenal for back-and-forth moments

Scheduling

• Default: let the more senior or busier person name times, then make it work on your end
• If you must share availability, give real, meaningful options — not just a Calendly link as a reflex
• If rescheduling, give maximum notice and be more flexible, not less, about the new time
• Check time zones explicitly — getting it wrong is an easy, avoidable mistake
• Treat EAs and PAs with genuine respect — they are gatekeepers and their impression matters; small gestures go a long way

Email and communication

• Keep emails short; imagine receiving the email you just wrote — if it feels heavy, it is
• Acknowledge emails promptly; you don't owe a long reply, but you do owe a signal you've seen it
• Avoid emojis in business contexts; they carry cultural ambiguity and can imply AI-generated text
• Order recipients by importance: the primary recipient goes first; CC means "FYI, not expecting a reply"
• Never reply-all to a CC'd email unless directly addressed
• Proofread — and never add someone to the To field just to check the spelling of their name

Meetings

• Arrive 10–15 minutes early; walking around the block is better than arriving an hour ahead
• Camera on for video calls; have an appropriate background; close your closet
• Avoid virtual backgrounds if you can — a tidy real environment is better
• Start with brief small talk to establish rapport before getting to business
• Clean up after yourself — offer to take your cup to the kitchen; it's a small signal of awareness that people notice and remember

Exiting

• Stand when someone leaves the table; stand to shake hands — never shake from a seated position
• Send a follow-up thank you note; brief is fine, but the gesture is always appreciated
• Don't answer your phone mid-exit — hit "call you right back" and then leave properly
• Don't make a production of leaving; in large group settings, an Irish goodbye (say a quiet farewell to the host and slip away) is often the best option

The contrarian investor take on AI

• Using AI in your startup is table stakes — like not using the cloud in 2010
• The distinction that matters: a great business that uses AI versus a company whose pitch is "we are an AI company"
• Foundation models and pure-play AI startups are highly capital-intensive; even OpenAI has been a mediocre seed investment on the numbers
• Seed investing does not work in capital-intensive businesses — dilution destroys the math even if the company succeeds
• What Lessin does look for: businesses shaped by the cultural and social implications of AI — identity verification, trust infrastructure, human-AI interface problems