The Low-Heart-Rate Playbook: Sam Lessin on Etiquette Rules Silicon Valley Founders Skip

Sam Lessin, a partner at Slow Ventures, former Facebook VP of product and two-time founder, says he likes things at the intersection of hilarious and useful. His etiquette work began with a tweet that escalated into an event, then a book and more. Humor helps cut through noise, he says, but only if there is a deeper truth underneath.

The serious case, he argues, is that software is getting commoditized and technology is no longer a cute sideshow. People are anxious about AI and their jobs, and founders ask customers to trust them with data and business. In that environment, meeting people where they are, building trust and mirroring expected behaviors are real tools; the shallow truth is simply that it is funny to teach Silicon Valley etiquette after years of "just focus on your product."

His central image is etiquette as a skill for showing up in a room with a low heart rate. A young founder at a big holiday party may feel it is a one-shot chance and turn transactional, and "if you show up like a little Energizer Bunny" they project the wrong vibe. Lessin recommends taking a beat, bringing abundance rather than scarcity, giving more than you take, and building relationships rather than collecting business cards.

He concedes that a company with truly world-changing technology can get away with almost anything, but says that is not the experience of 99.9 percent of startups. Skipping these rules, he says, just creates an unnecessary uphill battle.

On entering a room, Lessin's first rule is to be early, though not half an hour early. A buffer lets you take a beat in the waiting room instead of arriving with a racing heart. If you are late, he says, apologize simply and move on rather than turning it into a five-alarm fire, and if the other person is late, don't make them feel bad.

He recommends a firm but not crushing handshake and repeating the person's name back when you meet, as in "Hey, Lenny, it's great to meet you." It makes the name easier to remember and shows you are making an effort to connect. Eye contact matters too: people are taking their time to meet you, and even if neurodivergence makes it hard, he says the visible effort goes a long way.

For forgotten names, he shares a trick from the book. Introduce your partner to the other person in a way that leaves a gap, such as "Jessica, I want to introduce you," and let the other person fill in their name. He notes it gives plausible deniability and uses the social situation to your advantage, and both he and Rachitsky admit they are bad with names.

Lessin says to welcome people into conversations, especially when a famous VC or founder walks in and a group flocks to them. Inclusiveness fits the abundance mindset. He also warns against both extremes with questions: delivering a four-minute startup spiel is self-centered, but firing six questions in a row feels like an inquisition, so the aim is a back-and-forth game of ping-pong where each person plays, not a single-player exchange.

He suggests loosely matching vocabulary to the person in front of you, whether a professor or a twelve-year-old, without mirroring them or speaking in jargon. The goal of an interaction, he says, is to leave people thinking you were interesting and they would like to talk again, or even to recommend you to someone across the room. That means leaving them wanting more and knowing when to excuse yourself.

On famous people, Lessin advises not being sycophantic but also not being ridiculous: introducing yourself to Mark Zuckerberg as if you don't know who he is, or declaring him the most important person you've met, are both wrong. Treat them as people, remember it is an iterative game, and let them offer their email rather than demanding it.

Another small tip is to say "great to see you" rather than "nice to meet you." It works whether or not you have met, whereas telling someone you are glad to meet them after five prior meetings is embarrassing. Lessin shares that he did exactly this with his future wife before they started dating.

On fragrance, Lessin says you shouldn't overpower the room or smell bad; your scent should not be noticeable in either direction. He says the book's advice applies broadly to men and women, though a separate course on women's etiquette is planned. He also tells a funny story about teaching his own children, including a six-year-old who now stands when his mother comes to the table.

He describes the class he first ran for YC founders at the Four Seasons, which mixed irreverent elements like fashion experts and caviar and wine tastings with serious basics: a low heart rate, an abundance mindset, eye contact, handshakes and how to eat respectfully. He explains that young founders have been holed up coding, and leaving a coffee on the table without asking where to put it is a subtle sign of low awareness of their environment.

For dress, he says to anticipate how the room will dress and neither massively overdress nor underdress. Dressing one level up is an easy win, and fit beats brand: a well-fitting $20 shirt is better than a misfitting $500 one. He adds that a startup founder should not wear a Rolex, because it reads as trying too hard.

When unsure what the dress code or expectations are, just ask, he says. Asking shows confidence, calm and humility, and expectations differ between places like New York and San Francisco. He suggests finding someone you think dresses well and asking for help.

On dining, Lessin says to split bills evenly, make things easy for waiters, and avoid ordering the most expensive thing on the menu, because an investor may not care but will notice you are insensitive to cost. He suggests not ordering first, letting the host set the tone and matching it, and ordering somewhere in the middle of the pack.

Within reason, he says you should always offer to pay, and expect to be turned down. He would offer even to a billionaire at a normal meal, treating the dinner as a conversation between equals, but not if they ordered a $10,000 bottle of wine. If you do pay for someone well known, he says to tip generously, because the gesture only works if the tip matches how they would tip.

On tipping generally, his advice is "tip a lot," with 20 percent as the minimum and the standard that nobody you are paying for would bat an eye at your tip. Still, he says you don't want the tip to be memorable either, since dinner partners should recall the conversation. He and Rachitsky joke about building an AI tipping calculator that takes a photo of the bill.

A few table tips round it out: offer the sommelier a taste if you order something nice, remember "BD" (bread plate on the left, drinks on the right) by looking at your hands, point the knife blade inward, and keep your napkin in your lap. The point of etiquette, Lessin says, is that it gets out of the way so the conversation can flow.

Lessin loves humor but says it is conditional on the audience and can be overdone. Telling a joke that is right up to the line shows mastery of a social situation, but a joke that no one laughs at is a huge risk, and you shouldn't be remembered only as the comedian. He keeps a loosely ranked list of jokes from least to most offensive.

He recommends self-deprecating humor: you can make fun of yourself as much as you want, whereas making fun of others signals familiarity and is high risk the moment it feels disparaging. He also suggests having a few easy, short stories ready, so conversations stay a back-and-forth rather than your monologue or theirs.

When it is time to end a conversation, he says to recognize the signs and respect them: if someone says they are going to grab a drink, that is not an invitation to join. You can also bring someone else into the conversation and hand them off. The key, he says, is to give both sides plausible deniability so that everyone feels respected.

Lessin says he is famous for hating Calendly, and recalls a rant about it that got millions of engagements. His view is that if you are the less senior or less busy person, you should ask when the other person is free and make it work, rather than defaulting to a scheduling link. If you do send availability or use a scheduling agent, the options must be real, and one of the first three should work.

When rescheduling, give as much notice as possible and be more accommodating of what the other person can do. Double-check time zones and avoid proposing times that land at 4 a.m. for them. He is also against a flat hierarchy where all meetings are the same, noting that his own calendar moves more than most people's and he would make time for someone like a head of state.

He calls respecting EAs and PAs the number one rule: not respecting people who help the other person is the quickest way to look classless. Thank them, follow up, and ask where to put your coffee cup, but don't overdo it with something like flowers for the EA, which becomes too transactional. He tells a story of a banker on the sale of his company to Airbnb who built a good relationship with the EA and office manager.

If you are asking for a meeting with a founder, he says it is fine to ask for their scheduling link and add yours in parentheses, since the key is making it easy for the person you want to do business with. In his words, "you're asking for something, you do the work."

Lessin's email rules are to proofread, get to the point quickly, assume the reader is busy, and avoid emojis in a business context. He personally believes email carries a kind of SLA: he doesn't owe a 12-page essay but does owe a quick acknowledgment. Before sending, imagine receiving it: ten paragraphs is like announcing a ten-minute monologue.

On emojis, he says they are a step of familiarity and feel like jokes, to be used at your own risk, and that they can be hard to read across cultures and even imply AI-generated text. He adds that heavily customized emojis make a statement about how much you have invested in them, and that you should aim to come across as a literate, clear person.

He also says there is a language to who you put in the To line and the CC line, and in what order. If the assistant is first and the CEO is fourth, you have probably done it wrong, and if you are the fifth CC you are not expected to respond first. He shares a cautionary story: never put someone you are discussing in the To line just to check the spelling of their name.

Lessin ties this to the broader point that etiquette is invisible stuff you shouldn't spend 80 percent of your brain on. If you do it intuitively, he says, you signal that you share a well of knowledge and cultural connection, which is what makes you trustworthy.

For in-person meetings, Lessin says to arrive ten to fifteen minutes early, and if you are an hour early, walk around the block rather than sitting in someone's office. Start with small talk, which he describes as a "modem crash" or TCP/IP handshake that gets you ready to communicate. It feels transparent, he says, but it signals that you are a normal person who is here for business.

For virtual meetings, he says to keep your camera on, dress appropriately and have a tidy background, with the bed made and the closet closed. He is not a fan of virtual backgrounds. He adds that cleaning up after yourself, such as offering to take your coffee cup to the kitchen, is the easiest way to avoid looking bad, and he says his partner Kevin is maniacal about this with limited partners.

When leaving, stand to shake hands and rise when people leave the table, then follow up with a short thank-you note. If a call interrupts as a meeting ends, tell the caller you will call back rather than picking up and waving. In large groups an "Irish goodbye" can be the best goodbye, with a thank-you to the host.

Lessin says the book is only 50 to 60 pages now and will grow, with classes planned in places like Tel Aviv and New York, and he invites listeners to send in tips. He closes with his TL;DR: etiquette is about building trust and projecting genuine confidence, keeping an abundance mindset, remembering you have nothing to prove, and asking questions with a low heart rate.

In the AI corner, Lessin says he is skeptical of most AI applications, but has enjoyed Lettermeme, a personal news aggregator he built that turns the newsletters he doesn't have time to read into daily cartoons. He vibe-coded the first version himself with tools like Cursor, DigitalOcean and Cloudflare, then handed it to engineer friends because vibe coding doesn't really scale.

His contrarian view is that seed investors in companies branded as AI companies will lose an impossibly large amount of money in the coming years. He says not using AI in a startup would be like not using the cloud in 2010, but there is a difference between a great business supercharged by AI and a so-called AI business. He argues even OpenAI is a middling seed investment, with seed investors making something like 25 times their money, because these companies are so capital-consumptive.

He lists reasons: seed investing does not work in highly capital-intensive businesses, the products are commoditizing, and the lock-in is unclear. He compares the AI story to the human desire for a "terra nova" like the American West or the internet, and says AI is powerful for existing businesses but not a great startup opportunity.

What he does invest in are businesses that use AI or address its cultural implications, such as companies working on the problem of telling humans from bots. He draws a line between foundation-model companies and anyone claiming "we're going to win because AI"; in his view, you win because of something else, with AI as a propellant.