Sam Lessin on Etiquette as a Founder's Tool for Walking Into Any Room With a Low Heart Rate
Lenny's Podcast
Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder. He has also become, somewhat to his own amusement, Silicon Valley's etiquette teacher. In this conversation with Lenny Rachitsky, he explains why he thinks founders should learn the rules of polite behavior. He then works through introductions, conversation, hygiene and dress, dining, tipping, humor, scheduling, email, meetings, and exits. His central claim is that etiquette is not about fussiness. It is a set of tools for building trust quickly and for showing up "in a room with a low heart rate." He says openly that he doesn't always follow these rules himself. His point is that he knows them, and he thinks founders are rarely told they matter.
Why etiquette, and why now
Lessin says he likes projects that sit at the intersection of "hilarious and useful." Humor helps cut through the noise. He also thinks humor only works when there is a deeper truth underneath it. The etiquette project began, as he puts it, with a tweet. The tweet turned into an event, and the event turned into a book (Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook) and a series of classes.
He calls the serious argument the "deep truth." Software is getting commoditized. People are fearful about Silicon Valley and AI, and many worry about losing their jobs. Technology is "no longer some cute sideshow." In that environment, founders are asking people to trust them with their data and their businesses. Knowing how to meet people where they are, build trust, and mirror expected behavior becomes a real business tool. The "shallow truth" is that it is simply funny to teach etiquette to Silicon Valley, a culture that has long insisted nothing matters except the product. Lessin notes he is wearing a t-shirt and is not known as a high-etiquette person, but says he does know the rules.
He grants an exception. If a founder brings "mana from heaven," meaning something like the next Google invented out of pure thought, none of this may matter, and they can "get away with anything." He says that happens very rarely and is not the experience of 99.9% of startups. Even then, he argues, it doesn't mean you should be a jerk, because over time you need to work with great people.
The core idea: low heart rate and abundance, not scarcity
Lessin keeps coming back to one image throughout the conversation. Picture a young founder, possibly from another country, at the Kleiner Perkins holiday party. Every venture capitalist and CEO is in the room. The founder thinks, "Oh my god, this is my shot," and treats every conversation as a transaction to convert. If you show up "like a little Energizer Bunny," he says, you scare people off and project entirely the wrong vibe. He understands why the moment feels high-intensity, but he argues the better approach is to take a beat, give more than you take, build relationships rather than collect business cards, and come in with a mindset of abundance rather than scarcity.
He says he sees scarcity thinking as a uniquely American and uniquely Silicon Valley habit. He compares it to Eminem's "Lose Yourself" and its "one shot, one opportunity" line. He says he likes the song and sometimes listens to it before a big presentation. But even if you privately believe this is your one shot, he argues, you should carry yourself with "the self-confidence and the calm of abundance": this is an opportunity, not the only one; "this is part of the story, this is not the entire story."
A second recurring principle is that the effort you signal often matters as much as the behavior itself. The goal of etiquette is to get out of the way. Your napkin placement, your fragrance, your tip, and your outfit should not be memorable. What the other person should remember is the conversation.
At the end, Lenny reads the book's TL;DR. The goal of all etiquette is building trust and projecting genuine confidence. Maintain an abundance mindset. Remember that you are worthy and have nothing to prove. It is okay to ask questions. Keep your heart rate low.
Introductions and entering a room
The first rule is to be early. Half an hour early is "a little weird." The point is enough buffer that you aren't racing in five minutes late with your heart rate up. Ideally you get to sit in the waiting room for a moment, so that they kept you waiting. If you are late, apologize simply and move on. Lessin says he has watched many people make lateness into a "five alarm fire," coming in flustered, when all that was needed was a brief apology.
The reverse also applies. When someone else is late, don't make them feel bad. Lessin describes his own situation as a VC booked in back-to-back 30-minute blocks, often on Zoom. He says he is frequently late, doesn't feel good about it, always apologizes, and tries to email ahead. Most founders just get into the meeting. Occasionally a founder is indignant. Lessin's reaction is that if a few minutes' lateness is a deal breaker, the remaining 25 minutes now feel wasted because the dynamic is already wrong.
Other introduction basics: a firm handshake that doesn't crush the other person's hand ("practice on your friends"), and repeating the person's name back ("Hey Lenny, it's great to meet you"). Repeating the name helps you remember it. It also shows the person that you are trying to focus on them and that they aren't "just a potential check."
On eye contact, Lessin says people now spend their days glancing across multiple windows. Being present in a conversation is a matter of respect. He acknowledges that some people, including many founders, are neurodivergent and find sustained eye contact hard. He says there is grace for that "to a point," and that visibly trying goes a long way compared with not caring.
Handling partners and forgotten names
If you are with a partner, introduce them first and bring them into the conversation. This also gives you a trick Lessin says he "unfortunately" uses all the time, when you've forgotten the other person's name. The proper form would be "Lenny, please meet my wife Jessica." If you can't remember Lenny's name, flip it: "Jessica, I want to introduce you…" and let it hang. The other person extends their hand, says their name, and you've recovered it. Lessin describes this as using a small amount of plausible deniability, technically slightly imperfect etiquette, in service of better etiquette overall. Socially attuned people may notice what's happening, and that's fine.
A related tool is saying "great to see you" instead of "nice to meet you," because it works whether or not you've met before. Saying "nice to meet you" to someone you've met five or six times is embarrassing for everyone. Lessin says people aren't dumb: someone who hears "great to see you" may suspect you don't remember them, and that is part of "the etiquette dance." He tells a story about his wife. Just before they started dating, he greeted her with a "nice to see you" line because he clearly couldn't remember whether they had met. They had, and she remembered.
Lessin says he has a "clinical problem" with name-face recognition that runs in his family. He partly attributes his early attraction to Facebook to it. It was the first time he could walk around college recognizing people without knowing their names and have "a resource I can study." Lenny says he has the same problem.
Conversation: ping-pong, not interrogation
Lessin's advice for conversations starts with inclusion. He has seen a famous VC or founder walk into a room and a young startup person "waylay" them and try to cordon them off. He argues the more inclusive you are, the more you project the abundance mindset.
Asking questions is good, and far better than launching into a four-minute startup spiel, which he calls self-centered. But questions can be overdone. When someone fires six questions in a row, it feels like an inquisition or like they are extracting information while giving nothing back. His metaphor is ping-pong or tennis: hit the ball back, let them hit it back to you, and don't serve ten balls in a row. The best conversations start when someone offers an idea or a point that the other person can react to, so both are playing together rather than "single player."
He also recommends matching vocabulary. You'd talk differently to a university professor than to a 12-year-old. He says the aim is to make people feel relaxed and good, not to mimic them, and he admits the distinction is subtle.
"Leave them wanting more" is another principle. If you're being transactional about it, the real goal of most interactions is for the other person to walk away thinking you were interesting and that they'd like to talk again. Even better, they might walk across the room and tell someone, "you really should talk to Sam." The bad outcome is that they've heard your entire life story and never need to speak to you again. That is partly a matter of knowing when to excuse yourself.
With famous people, Lessin warns against two failure modes. The first is being "ridiculous," such as walking up to Mark Zuckerberg, whom everyone recognizes, and asking who he is. The second is being sycophantic ("you're the most important person I've ever met"). The better approach is to treat them as people, remember that you're playing an iterative game, and tell yourself this is not your only chance to meet them, even if it actually is. Don't ask for their email and phone number. Let them offer.
Hygiene and dress
On hygiene, Lessin's rule is that your scent should not be noticeable in either direction. Don't douse yourself in perfume or cologne, and don't smell bad. Asked whether the advice applies equally to men and women, he says broadly yes. He adds that a course his team internally calls the "fem etiquette" course is planned for around January or February, because his wife and other women told him there is a lot more that women need to know. He says he can't speak to that material yet.
For dress, he tells a story from his first job out of college as an associate at Bain & Company. He noticed there was a minimum dress code but no maximum. So the associates started "Tuxedo Tuesdays" as a mini rebellion, and as a bonus, nobody would take them to client meetings dressed in tuxedos. He offers it as an example of knowing the rules in order to break them. He adds that rule-breaking should be done "with a lot of cultural understanding."
His practical advice is to look put together and like you made an effort, without overdoing it. A few specific points:
- Dress one level up: not two or three. You can often dial it back, for example by taking off a suit jacket.
- Fit beats brand: "a well-fitting $20 shirt is way better than a misfitting $500 shirt." He argues most people can intuitively tell whether clothes fit, while most can't tell what things cost. An expensive but ill-fitting item signals cultural unawareness and an attempt to impress.
- No status signaling: showing up as a startup founder wearing a Rolex is, in his words, "very classless." He ties this back to trying too hard: "You're not going to trick anyone."
- Ask if you're unsure: he says asking about dress, or even which fork to use, shows confidence and humility. Expectations genuinely differ between places like New York and San Francisco, and no one expects you to know every culture's nuances. Just don't ask a hundred questions.
Asked for general tips on dressing well, he suggests finding someone in your life who dresses well and asking them for help. He jokes that his wife will be chuckling at him being asked about specifics of dress.
His kids and the YC class
Lessin says that working on etiquette made him realize his own children, aged eight, six, and four, have terrible table manners ("you guys eat like animals"). He jokes that he can't be the etiquette guy with kids like that. One result he finds funny: his six-year-old now stands whenever his wife comes to the table. Lessin notes this is arcane and debatable as modern etiquette. He says a more modern version, which the book suggests, is standing for anyone who joins the table. Lenny mentions hearing developmental psychologist Alison Gopnik on Tyler Cowen's podcast describing how children learn to use a fork by experimenting like scientists. Lessin replies that his kids can feed themselves, "it works," but it looks strange.
Before the book, Lessin ran a class specifically for Y Combinator founders. He says part of the motivation was that Garry Tan "got very mad about this," which meant he now had to do it. The class was held at the Four Seasons and handed out certificates of completion. It included tongue-in-cheek elements, such as stylists bringing in models to discuss dress for different events, plus caviar and wine tastings. It also covered the substance: low heart rate, abundance mindset, eye contact, handshakes, and eating in a way that shows respect. Lessin says he doesn't really know what makes Garry Tan mad. He guesses Tan may see it as the wrong thing to focus on, or may object to the gentle joke that YC founders "come out a little bit like animals." Lessin says that isn't their fault. They are often young people who've been holed up coding for months. His example of the kind of small signal he means: a founder who gets a coffee at your office and leaves the cup on the table without asking where to put it.
Dining and tipping
At meals, Lessin's rules include: tip well, split bills evenly rather than tallying who ordered what, make things easy for the waiters, and don't order the most expensive thing on the menu. An investor won't actually care about the cost, he says, but they will notice, and it suggests you're insensitive to what things cost. He also advises not ordering first. Let someone else set the tone on starters, wine, and meal length, then match it. Aim for the "middle of the pack to last."
On paying, he says that within reason you should always offer to pay, not to split. Usually, for example with a VC, you'll be turned down, and that's the right dynamic. He notes you do take the risk of actually being accepted. There are limits. You needn't offer if it's a $10,000 dinner or if the other person ordered a very expensive bottle of wine. Lenny asks about dinner with a billionaire. Lessin thinks offering is especially nice in that case, precisely because such people obviously don't care about the money and nobody ever offers. It signals you see this as a conversation between equals. There is a catch, which he says isn't in the book. If you pay for someone well known, you have to tip the way they would tip, which he suggests might be 100% of the bill.
Lenny says he hates tipping as a concept because it's so convoluted. Lessin's answer is "tip a lot." He calls 20% the minimum, says 30% or sometimes more is fine, and says going far beyond that starts to seem silly. His guiding principle is again that your tip shouldn't be memorable. He recalls people who tipped so extravagantly that a decade later it's the only thing he remembers about the evening. Tipping, he says, is about making everyone feel taken care of so they can relax.
The two then riff on a product idea: an LLM-driven tipping app where you photograph the bill, it geolocates you, you describe the situation, and it tells you what to tip. It would cover not just restaurants but end-of-year tips for service workers too. Lessin says someone pitching "the 2026 AI-driven tipping calculator" would be hilarious and probably useful, though likely not venture scale. They briefly agree they wouldn't tip someone who installs window shades. Lessin also mentions a Seinfeld episode about a tipping calculator and "Bistromathics" from Life, the Universe and Everything, which he's reading to one of his sons. In that book, the most complicated math in the universe is a restaurant bill.
A few smaller dining tips: if you order a nice wine, offer the sommelier a taste. Remember "B and D": make lowercase b and d shapes with your hands, and the bread plate is on the left and drinks on the right. Rest your knife with the blade pointing inward. Keep your napkin in your lap, not at your neck and not off to the side. Lessin says founders have started sending him videos of themselves dining to get feedback. He recently told one they had done a nice job eating soup, but their napkin should have been in their lap and their knife was pointing the wrong way. Asked about a napkin over one leg versus both, he says only that you don't want your napkin placement to be memorable.
Humor, stories, and winding down
Lessin loves humor but says it can be overdone, and it depends heavily on the audience. His view of why it works: a joke that sits right at the line, or pushes one degree past it, is "the ultimate demonstration of comfort in a space." The risk is asymmetric. A joke everyone laughs at is great. A joke nobody laughs at is a failed high-risk maneuver. Knock-knock jokes don't work with adults, and an off-color joke requires real confidence in the room. You also don't want to be remembered only as the comedian. He keeps a file of favorite jokes, once in Evernote and now in Bear, loosely ranked from least to most offensive, because he forgets them otherwise.
Self-deprecation is safe: "make fun of yourself, not other people." Teasing others signals a high level of familiarity. It can work with a close business partner when everyone is on the same wavelength, but the moment it feels disparaging, it becomes very high risk.
He also recommends having a few short, crowd-pleasing stories ready. The goal is to put others at ease. Nobody should be monologuing, and you shouldn't force the other person to monologue either. When someone tells a story, having one to build on keeps the ping-pong going.
On ending conversations, the worst pattern is when the conversation is clearly over and the person just keeps standing there. He notes that when someone says "I'm going to go grab a drink," it usually isn't an invitation to follow them to the bar. One graceful exit is to connect the person with someone else ("Have you met Steve? Let's go meet Steve"), or to say you're going to say hi to your spouse. His key point is subtlety. Even if everyone knows what's happening, give people plausible deniability that the conversation simply wound down.
Scheduling and the Calendly saga
Lessin describes himself as "fairly famous for hating Calendly." He says he once went on such a widely viewed diatribe about Calendly being disrespectful that it generated millions of engagements. He claims he personally drove most of Calendly's growth for that month, to the point that he got messages from the board.
His rules: if you're the less senior or less busy person, let the other person say when they're free and then make it work on your end. If you do offer times or a link, the options must be real, and one of the first three needs to work. If you ask to reschedule, give as much notice as possible and then accommodate the other person's availability within reason. Double-check time zones, and don't propose times that land at 4 a.m. for the other person.
He also rejects a flat hierarchy of meetings. When someone asks if he's free, the answer depends on who's asking. If a very important person wants to meet at 4 a.m., he'll make it work. He admits this means his calendar probably moves more than most people's, which likely feels disrespectful to some, and he says "it is."
Lenny describes his own approach: asking founders whether they have a Calendly, and if not, offering his own "in case that might make it easier." Lessin says that's perfectly fine. The key is to make it easy for the other person, because if you're the one asking for something, "you do the work." Lenny also tells a story about someone finding his Calendly URL and booking a pitch meeting. Lessin tells a similar one: he has accepted cold meetings from people whose names were one letter off from someone he knew. He adds that once you've committed to the meeting, you do the meeting.
He puts particular weight on respecting executive assistants and personal assistants. He calls disrespecting people who help others "the number one way to look extremely classless." That applies equally to servers. Thank them, follow up with them, and ask where to put your coffee cup. Lenny recalls that during his company's sale to Airbnb, an advisor made a point of building good relationships with Airbnb's EA and office manager. Lessin agrees that making gatekeepers happy works, but warns it can become too transactional. If you show up with flowers for the EA, "you better be damn confident."
Email and communication
Lessin's email advice is to proofread, get to the point quickly, and assume the reader is busy. He compares a ten-paragraph email to a ten-minute monologue in conversation. He acknowledges that some people believe receiving an email creates no obligation to respond. His personal view is that you do owe at least a quick acknowledgment, not a 12-page essay. His test: imagine receiving your own email and ask how it feels.
He advises against emojis in business contexts. In his view, emojis signal a step of familiarity, similar to jokes, "tell them at your own risk." If someone sends you one, you can match it. Lenny says he uses the thank-you hands emoji a lot. Lessin allows that texting is different and says he isn't being dogmatic. He adds that emojis carry cultural connotations and are less legible than clear writing. Lenny notes that emojis can also suggest AI-generated text, because "ChatGPT loves emojis." Getting "spicy," Lessin says that customizing your emoji pack or using unusual emojis is "quite a statement." In his view, it suggests someone who spends time customizing emojis when they could be doing something more interesting. Lenny suggests "finding product market fit," and Lessin adds "or learning etiquette."
He also argues that recipient order carries meaning. If the assistant is first on the "To" line and the CEO is fourth, you've probably done it wrong, because order implies whom you consider most important. He admits he pays slightly more attention to emails where he's listed first. An email sent to many people is almost by definition not that important. The CC line means "you should have a copy, I'm not expecting an immediate response." If you're the fifth CC, you're not expected to reply first, though he says there are times to break that rule. If you're BCC'd, don't reply all.
Lessin says the point is that all of this is invisible stuff that shouldn't occupy 80% of your brain. Doing it intuitively signals a shared "well of knowledge and cultural connection," and that is what makes people trust you. He admits it is a hard ask to expect people to intuitively know unwritten rules. He shares one of his worst mistakes: to check the spelling of someone's name, he put that person in the "To" field of an email that was about them, then hit send. His advice is to never do that.
Meetings, video calls, and leaving
For in-person meetings, arrive 10 to 15 minutes early, not an hour. If you're very early, walk around the block, because otherwise the host feels they're keeping you waiting while you're "six coffees deep with the receptionist." Opening with small talk about the weather or the weekend is useful even though it feels transparent. It signals you're a normal person before switching to business. Lenny mentions a Twitter description of small talk as a TCP/IP handshake. Lessin likes it and says he has always thought of small talk as the old dial-up modem screech, two sides syncing wavelengths.
For video calls: camera on. Lessin says he sometimes violates this "knowingly," aware of what it costs him. Dress appropriately and have an appropriate background. He's not a fan of virtual backgrounds. He won't judge a founder for taking a call from their bedroom, but the bed should be made. A classic founder mistake he sees is leaving the closet open behind them: "I don't want to see your shirts."
Clean up after yourself. Lessin credits his Slow Ventures partner Kevin Colleran with being "maniacal" about this, especially in meetings with LPs, the limited partners the firm raises money from. You take your coffee or Diet Coke, even if you know someone will clean up after you, and you ask where to put it or set it on a side table, acknowledging the mess.
When leaving: stand when people leave the table, and stand to shake hands. Follow up with a short thank-you note. If your phone rings as a meeting ends, send a "calling you right back" reply and walk away, rather than picking up and waving goodbye. Don't make a production of your exit. In large groups, Lessin thinks an "Irish goodbye" is often best, perhaps thanking the host on the way out. Hugging everyone goodbye is "too much."
Where the project is going
Lessin describes the book as a V1 in his "ship early, ship often" style, currently 50 to 60 pages. He expects it to grow to a few hundred pages through later editions, and he wants to credit readers who send in tips. He says classes are planned for the coming year in several places, including New York and Tel Aviv, where he says they've been invited. He notes that outlets like Morning Brew keep making videos about etiquette. He jokes that after good investments and building products, he may end up remembered as "the etiquette guy," and says he is fine with that.
AI Corner: Lettermeme
Lessin says he is skeptical of most AI applications by default. The AI project he has enjoyed most is Lettermeme, a personal news aggregator he built. It takes the newsletters he doesn't have time to read and turns them into daily cartoons, a grid-style front page of what's happening in the world. It's also where the book's cartoons partly came from. Users can pipe in their own trusted newsletters and receive a daily email digest. He built the first version himself end to end with Cursor, DigitalOcean, and Cloudflare, which he says is exactly what vibe coding is good for. He adds that vibe coding "doesn't really scale," so friends who are strong engineers later took the project and improved it in ways he had run out of time for.
Contrarian Corner: seed investors in "AI companies" will lose a lot
Lessin's contrarian view is that seed investors backing companies branded as AI companies will lose "an impossibly large amount of money" in the coming years. He stresses that startups should use AI. Not doing so would be like not using the cloud in 2010 or the internet in 2000. His distinction is between a real business that AI supercharges and a company whose pitch is "we are the AI blank." He thinks the latter are "all going to zero."
His argument has several parts. First, he calls OpenAI "a terrible seed investment." By his account, even at a $500 billion market cap, seed investors have made roughly 25x, which he calls middling at best for the company defining the moment. The reason is that these businesses are so capital-intensive, and seed investing doesn't work in highly capital-intensive businesses. Second, he argues AI is "fundamentally commoditizing," and it is unclear what the lock-in or durable value is. Third, he says people are desperate for something to believe in. He uses SpaceX, a company he says he loves, as an example: if Elon Musk's storytelling can make it worth $1.4 trillion to the public market, large pools of capital may do well riding narrative-driven "religion." For a disciplined seed investor, though, he frames it as a dangerous game of getting out before the narrative collapses.
He places this in a historical frame he calls "terra nova." In his telling, the U.S. thrived for generations on the frontier of the West. His and Lenny's generation had the internet as a "digital terra nova." Since then, every generation has wanted its own. He sees mobile as mostly "more internet." He thinks crypto is the closest thing to a new terra nova, and he places the "AI god" narratives in the same pattern. His conclusion is that AI is incredibly powerful for existing businesses and structures, but "not a great startup opportunity."
What he invests in instead are companies dealing with the cultural and societal implications of AI. He cites Sublime Security and Outtake as examples tied to the theme of the Voight-Kampff test from Blade Runner: determining whether you're dealing with a real person or a bot. He also mentions businesses that AI will disrupt without being AI businesses themselves. His summary: you're going to win because of something else, and AI will be a propellant.
Lightning round
For book recommendations, Lessin names The Ancient City, which he is reading on Marc Andreessen's recommendation (he says he likes to make fun of Andreessen). He also lists Man's Search for Meaning and Area 51: An Uncensored History, which he calls "not very erudite" but great. His one serious pick is Will Durant's The Lessons of History, which he describes as short and the best return on hours invested. He also recommends The Fish That Ate the Whale, about the "Banana King," and The Last Kings of Shanghai, while noting they're longer, more story-driven books. His favorite recent show is Landman. He relays a founder in Midland, Texas complaining that Silicon Valley people now think they understand the energy industry because they watched it, and says he believes it.
His product pick is a dating app, rendered in the transcript as "June Date." He says he doesn't use it because he's happily married. As he describes it, users run a structured prompt through ChatGPT that distills a profile from their chat history, and matching is based on that. He says the profile it generated for him was a "shockingly good description" of who he is. He notes this fits his thesis of businesses with AI implications that aren't AI businesses. He also recounts trying matchmaking among his own newsletter readers with a small LLM. It failed for lack of "liquidity": about a hundred impressive women wrote in, compared with a handful of men, some of whom asked for a "25-year-old hot girlfriend." His newsletter has no sign-up page. People get added if they email him or interact with the LLM chatbot on his website, which is trained on his writing.
Asked for a life motto, he says he doesn't have one. He mentions instead a poster hanging in his gym from a Facebook hackathon after Google+ launched, reading "Carthage must burn." He says that period, working past midnight every night, produced some of his most fun work experiences.
On podcasting, he describes More or Less, co-hosted with his wife and with Dave and Brit Morin. He and his wife are the default contrarians, the Morins think everything is amazing, and his wife, who runs The Information, prompts them with what's happening in the news. He says it's like talking to friends for an hour a week, posted fairly raw. They'd do it even if no one listened. It isn't huge, has no growth strategy, and isn't paid. What surprised him is how useful it has been. People in the industry he cares about pick up pieces of it and bring them up, and sometimes an entrepreneur shows up after an episode with a better idea than the one the hosts discussed.
I just feel like no one's being honest in teaching founders this. Be early. Don't order the most expensive thing on the menu. For a video call, have an appropriate background. Don't smell like...
Tell me why you decided to spend time teaching people proper etiquette.
You have a lot of really young people. They've been holed up in a room coding and they show up encouraged by Silicon Valley to be somewhat abrasive on purpose. You want to be able to show up in a way where people are like, "Okay, this is someone I can work with and trust."
Etiquette is a skill for how to show up in a room with a low heart rate. You're at the Kleiner Perkins holiday party. You have all the venture capitalists in the world and all the CEOs. You're at your first company. You're like, "Oh my god, this is my shot, but I need to convince this person of that and make this connection." It becomes very transactional. If you show up like a little Energizer Bunny, you're going to scare folks off. You're going to project totally the wrong vibe. This isn't your one shot. You'll have other opportunities. You kind of want to show up with the self-confidence and the calm of abundance. This is part of the story. This is not the entire story.
Today my guest is Sam Lessin, partner at Slow Ventures, previous VP of product at Facebook and two-time founder. This is an unconventional episode that may surprise you in how interesting and useful it is to your life. I asked Sam to come on the pod and talk about proper etiquette. You'll hear the backstory of how Sam got into this stuff, but this is turning into a big thing for him. He's teaching classes around the world. He published a book on proper etiquette. I love his framing for why etiquette matters: that the goal of learning good etiquette is to show up in a room with a low heart rate. And we cover all kinds of social interactions like introductions, small talk, meals, meetings, and basically all of the most important things you need to know when it comes to etiquette. I personally found these tips really, really useful and I learned a lot from this conversation and from his book. Sam is also hilarious and so fun and I hope you enjoy this very unique episode.
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Sam, thank you so much for being here and welcome to the podcast.
Blast to be here. I'm excited to just have the conversation.
This is going to be a very different kind of conversation. I suspect this is actually going to be really, really useful and really, really interesting to a lot of people.
Useful and interesting. That's so unlikely. That's the Venn diagram that we aim for.
I also think it's just going to be a lot of fun. So I really appreciate you doing this. I want to give you the opportunity to set the stage for why we're chatting through this. Just tell me why you decided to spend time on teaching people proper etiquette and why should people pay attention to this? Why is this important?
I really enjoy things at the intersection of hilarious and useful, right? You kind of need both, right? And hilarious just because you should have fun in life. We should be working on things that are fun and interesting. Also, candidly, if we're being more honest about it, it's very hard to cut through the noise these days. So humor is a great way to cut through it. But humor just for the sake of being funny is not that useful. There has to be a deeper truth to it.
And so, you know, with this etiquette thing that we've gotten into, it started, as many things do, with a tweet that got escalated into an event. It's gotten escalated into a book and a bunch of other stuff. I kind of believe that, you know, you should always... There you go. You got it with you. I've got my coffee, too. There's a rule like, you know, you always want to just double down in life, right?
And so, I'd say, like, why etiquette? Look, there's a serious real narrative to why etiquette matters in 2025 for founders, almost 2026. One, you know, we talk about software getting commoditized. We talk about all the fear-mongering and how scared people feel about Silicon Valley and AI and all the things that are going on. The net is, if you want to do business and build great partnerships with team members, with companies you want to do business with, almost with anyone, the reality is etiquette ironically matters a lot, right? There is a deep truth to this, right? Especially when you ask people to trust you with their data, trust you with their business. And when technology is no longer some cute sideshow but is a major deal, and people are worried about losing their jobs, understanding how to meet people where they're at, build trust, you know, mirror kind of expected behaviors, these are all tools, right? So that's the deep truth.
The shallow truth is it's kind of funny to teach Silicon Valley people etiquette, right? The whole narrative for so long has been none of this matters, just focus on your product, and saying, well, actually it does matter. And, you know, I'm wearing a t-shirt. I'm not exactly known as the most high-etiquette person in the world, but I do know the rules, right? And I think it's fun and funny as well, and I think those things are both important.
I'm going to get into the actual rules, but just to follow that thread, you had a really great line somewhere that etiquette is almost a skill for how to show up in a room with a low heart rate.
Yeah, this is the thing I think about a lot. Again, you and I are now old people, right? But like...
Yes.
You're young.
I feel that.
You feel it in your bones. It's like you're young, right? You're at the Kleiner Perkins holiday party. You have all the venture capital in the world and all the CEOs. You're at your first company. You're young. Maybe you're from a different country. You're like, "Oh my god, this is my shot, right? I have all these people I need to talk to and I need to convince this person of that and make this connection." It becomes very transactional. If you show up like a little Energizer Bunny, right, you're going to scare off... you're going to project totally the wrong vibe. But I can understand why it'd be a high-intensity moment in a lot of ways.
I think understanding how to show up, take a beat, come in with a mindset not of scarcity but of abundance. Understand how to give more than you take. Understand how to build a relationship, not collect business cards. These are things that actually serve you massively well. And I just feel like no one's being honest in teaching founders this, right? Instead, they're saying, "Oh, no. All that matters is your product." I'm like, yeah, the product does matter a lot, but if understanding these rules can be the difference between doing really well and missing a business deal, you know, if you show up with too high a heart rate and you burn a bunch of mild relationship opportunities, I don't know why you wouldn't want these skills, right?
Yeah. That is one way to think about it. You can be successful not doing any of this, not knowing any of this, and you're just hurting yourself. You're...
You're creating an unnecessary uphill battle for yourself. I'd also say that, look, this goes back to technical differentiation and where things are at. It is true that if you bring manna from heaven, right, like you invent something that is literally the next Google or whatever out of pure thought, that sometimes none of this stuff matters, right? If you fully have that, that's it, you know. That literally happens. It happens very, very rarely, but it does happen. It is not what 99.9% of startups are doing, but if you have that, yeah, you basically can get away with anything.
That doesn't mean you should. You shouldn't be a jerk, and candidly, over the course of history, you need to work with great people and you'll be more successful if you show up with good etiquette and rules and context. But there are ways in which that can trump all. It's just candidly not the experience of 99.9% of startups.
Awesome. Okay. So let's get into it. You divided this book into about 10 categories, 10 social situations is one way to describe it. So let's just go through each one and just give us some pieces of advice. And something I didn't mention, the reason I'm excited to do this, the reason I reached out to you to do this, this wasn't you pitching me, "Hey, let's talk about this on your podcast," is I was like, "Wow, this is really interesting. I did not know these things."
Cheers. I mean, again, I think the thing for us is I'm kind of a ship-early, ship-often guy. So V1, you should buy it now and study it because it's good and it's going to be a limited edition. You know, the funny part about doing this is people come back with a bunch of other things we should cover, right? So I suspect that eventually this will evolve beyond it. But I think, you know, we're starting with some good stuff.
Let's do it. Okay, so introductions and entering a room.
Yeah, be early. That's the first one, right? Again, I say this as someone who, I'll be honest, like hypocrisy, you know, I live with hypocrisy. I'm frequently not early, right? But you should be early, right? And you don't need to be half an hour early. That's a little weird. But, you know, making sure that you have some buffer time so that, again, think about low heart rate. If you come racing into the room five minutes late, your heart rate's up. If you come in and you had a second to take a beat in the waiting room, they kept you waiting, right? That's the dynamic I think you want to cultivate.
Now, if you're not early, just apologize. It doesn't need to be a five-alarm fire. Again, it goes back to this heart rate thing. You could just apologize simply and move on. I've seen people screw this up so many times, right? Where they come in flustered and all over the place. You're like, "It's okay. We understand, right?" So I think that's another really kind of obvious one, but an important one.
I'll go for a few others that we talk a bunch about. Look, you want to have a strong handshake, firm. Don't crush the person's hand. Again, you know, practice on your friends, right? You want to repeat names back. That's a really, really valuable thing to think about when you're meeting someone. Say, "Hey, Lenny, it's great to meet you." Right? Why? It shows that you're actually trying to remember the person's name, right? A lot of times people meet a lot of people. It's like, "Nice to meet you," and you move on. First, it's going to be harder for you to remember the person's name. Second, it actually shows you're meeting them and making an effort, right, to actually connect and say, "Okay, I'm trying to focus on you. You're not just a number to me, right? You're not just a potential check, or whatever it's going to be." So there's a bunch of things like that. I'm kind of curious, you know, we can go through a bunch more, but those are some of the ones I would think about.
One that I loved was if somebody else is late, do not make them feel bad. Do the opposite of what you do.
100%. And I've seen this with entrepreneurs. I'm a VC. I do get scheduled in 30-minute chunks back-to-back all the time, especially on Zoom. Guess what? I am frequently late. I don't feel good about it, but it happens, right? And most of the time, I'd say, founders know that if I'm late, I will always apologize. I'll try to email them ahead, etc. But then it is what it is, and we kind of get right into it.
Every once in a while you'll have some founder who is super indignant about it, right? It's fine if you feel that way, but it's really not very productive to make a big deal out of it, right? If this is a deal breaker for you that I was a few minutes late, then now I feel like I'm wasting the next 25 minutes of my meeting time because this is going to be the wrong dynamic, right? And so I just think, don't harp on it. It's okay, you know.
Yeah. And also some advice on eye contact. Share that one.
It's really important. Again, I think the thing to keep in mind is, especially in an age where everyone's used to being in front of computer screens and looking at six different windows at the same time, people are taking their time to meet with you, or at a party they're taking their time to listen to you. And it's just a matter of respect to be like, I'm actually here in this conversation. I'm not off on my screen. I'm not glancing around the room.
Now, look, there are some people, we all know this, who are literally quite neurodivergent, and that's very hard for them. That happens. A lot of founders have neurodivergence in some ways. There is grace in this, to a point, but it's a thing you should at least make an effort on. I think one of the most important things about all this stuff is that what matters, in some ways, is the signaling of the effort as much as the actual thing, right? I think that's a really big overarching theory. So, look, if you have trouble with this but you're really trying, that goes a long way versus just being like, whatever.
Maybe a final tip there is around partners: introducing the partner, saying hi to their partner. Share that.
Yeah. Yeah. So, look, this happens all the time. And again, in the spirit of I'm not perfect at this either. If you're with your partner, introduce them first, right? Like, bring them into the conversation. One great trick we talk about in the book, which I really unfortunately use all the time, right? Is there this whole thing, let's pretend you're with your partner or with someone who's a friend. It doesn't have to be romantic partner, whoever you're with. You're going to forget someone's name, right? And what you really should do is
All the time, all the time.
You're going to forget someone's name. And what you're supposed to do, the etiquette, is say, "Lenny, please meet my wife Jessica." You know, that kind of thing. Now, here's the thing. This is where you start bending rules. What if I don't remember your name? Right? If you have your partner with you, you can flip it around and say, "Jessica, I want to introduce you." And then you can kind of figure out how to frame it up so that you then, Lenny, extend your hand and say, "It's really nice to meet you, Jessica." And you get to pick up the name again, right? Or things like that. So the way you put it there is you let it hang. That's
You let it hang, by the way. I love it.
It's a great example of the fact, if you're really in tune socially, you kind of know what's going on, right? Like, you know what I mean? You're not an idiot. You know that, oh, what is proper, what this person is doing, there's a gap between it, there's a reason. But it's at least enough plausible deniability of semi-bad etiquette that leverages the social situation to be a better etiquette, right? It's a useful thing to think about as a small cue.
I am so bad at remembering names. I think I have a medical issue, I just can't remember names, so this tip alone is so good.
And just to reinforce it, so there's almost two ways to do this, is what you're describing. Either it's like, my wife's name is Michelle. So it's like, "Hey, meet my wife, Michelle." And then they're like, "Oh, I'm Bob. Nice to meet you, Michelle." Or make it a little more awkward of just like, "Michelle, meet..." and then let it hang. Is that the
"Michelle, I want to introduce you," right? Or something like that, you know. Or "I want to introduce you to Michelle." You look at them in the eye, right? And then your wife will be like, "Hi, I'm Michelle. Remind me your name," or "It's nice to meet you," or whatever it ends up being. Look, I actually have such a clinical problem on name-face recognition, that actually runs in our family. I have this whole backstory, which is, you know, I worked at Facebook for a long time, was really into it early on. No kidding, I think part of my early attraction to the platform was it was the first time, you walk around college and you're like, I know these people, I just don't remember their names. You're like, oh my god, there's a resource I can study, right? And this was a very valuable social thing for me. So I'm with you. I have the same problem, I think a lot of people do.
Okay, let's move on to conversations. Give us some tips.
So, on the conversations front, I think the key again is to welcome people into the conversation. Consider it, you know, especially, you see this happen sometimes, especially when there's weird power dynamics at play. You'll see some famous VC or founder walk into the room and then some young startup person will waylay them, right? And kind of almost block them off, right? And they're really excited to talk to this person, but you're like, there's a bunch of people around, and the more you can be inclusive, again, low heart rate, it's not a scarcity mindset, it's an abundance mindset. I think that's kind of the tone to think about in terms of what a conversation is and how to show up in a room and meet with people.
Another really big one we harp on a lot in the book and in a bunch of the panels is ask questions, but there's a limit, right? So asking questions is great. You're coming in, it says, "Hey, it's nice to meet you. Let me give you my four-minute startup spiel and everything I'm into" is so self-centered. It kind of misses the point that a conversation is a give and a get and it should be an exchange. And so when you go in with a mindset of I should ask questions, that's great. There is doing it too much, right? Which is when it's done in a forced way. Sometimes I feel this. You'll meet someone and you feel like it's the inquisition, or all they're trying to do is extract information from you and giving you nothing in return, right? Like, this happens sometimes.
And so I think again this is about balance. This is about low heart rate. I do think questions are a great tool to engage someone. But don't make it six questions in a row, and make sure there's always, in some ways, a give to get, right? The best conversations are, someone comes in and gives you an idea or has a point or sparks something, then it's like a game of ping pong, then you can kind of react to it and it goes back and forth, where there's openness and they're playing with you, not playing single player, right? That's almost the way I would think about it in a conversation.
So the tip here, it's basically index towards asking questions, but not 100%.
Yeah. Consider, almost put it this way. Imagine you're playing ping pong, right? Or tennis or whatever you want. Hit the ball back, right? That's the question, right? And they'll hit it back to you and then you hit it back to them, right? That's kind of what the flow should be. If you hit 10 balls at them in a row, or, you know what I mean, that's kind of not the vibe you want to go for.
Yep. Awesome.
Look, we talk a lot about matching vocabulary. You're going to meet a lot of different people. You want to make people feel good and welcome. I'm not saying that you should walk into a room and start talking in J, but I am saying, if you're speaking to a university professor versus a 12-year-old, if they're using a certain level of vocabulary words, again, the point is to meet people where they're at in a way that makes them feel relaxed and good, not try to mirror them, if that makes sense. But there is a subtlety that I think really matters to it.
Cool. There's a few more I'll point out real quick. Connecting to this idea of asking questions, not trying to give your whole spiel constantly. This idea of leaving them wanting more.
Yes, this is important. I think at the end of the day, most interactions, let's say you meet someone you're really interested in or whatever. If we're being transactional about it, what's the real goal? The real goal is to leave people in a position where they're like, "Wow, that was a really interesting person. I'd love to hear from them again or meet with them again." Or maybe even better, every once in a while this will happen, like, "Wow, that's a really interesting person or idea." The person walks across the room and says, "Hey, you really should talk to Lenny. Talk to Sam." You want to leave them being like, "That's interesting. I'd like to continue this or expand it." Not, I just heard this entire person's life story, I never need to talk to them again, right? And so I do think, again, leave them wanting more, right? I think is important. And that is partially about knowing when to excuse yourself gracefully as much as it is about when to enter.
And again, this comes back to this idea of abundance. This isn't your one shot. You'll have other opportunities. People don't want to feel like you're just on them, just trying to
I've had this conversation with so many, and I think it's a uniquely American and honestly a uniquely Silicon Valley thing, right? I'll go so far as to say that, which is, look, especially if you're young and these are big opportunities or big moments, people are kind of used to this environment of scarcity. It reminds me of the Eminem song where he talks about one shot, one opportunity. Oh, Eminem. Yeah. It's a great song. It's a great song.
Great beat. Every once in a while before a big presentation, you've got to listen to it and pump yourself up, right? But actually, again, in terms of putting people at ease and building relationships and etiquette, even if in your heart of hearts you're like, "This really is my one shot," you kind of want to show up with the self-confidence and the calm of abundance, right? Being like, "This is not going to be my only opportunity. This is an opportunity. I'm excited to be here. I'm engaged." Right? This is part of the story. This is not the entire story. And I think if you kind of remind yourself of that, you remind yourself that it's okay to not know everything, you keep focusing on low heart rate, engagement, eye contact, you get so much of the way there.
You also have a tip about how to handle famous people that you might meet.
I mean, there's so many ways. There's a bunch of tips about, I think, generally famous people, but I think there's this thing which is not being sycophantic, is what I basically say, but also not being ridiculous, is almost the way I would frame it in this conversation, right? The ridiculous is, if you go up to Mark Zuckerberg, and everyone knows what he looks like and who he is, and you're like, "Hi, I'm Sam, and who are you?" Like, what are you doing? It's ridiculous, right? On the other hand, going up and being like, "You're the most important person I've ever met" is wrong, right? And so there's a way. Again, it's about grace as much as anything else, right? And recognizing that they're people. And again, you're playing an iterative game. And the best thing you can do is say, "This is not my only," as much as it might actually be, "This is not my only opportunity to meet Mark." And in an ideal world, when I walk away, he's like, "That was a pretty nice person. Maybe I want to talk to them again." Right? Now, going up and being like, "I need your email address and phone number," it's like, no, let him offer it. That type of stuff I think matters.
Maybe one last tip is this. You actually start with this one, of this line of "great to see you" when you meet someone versus "nice to see you."
Well, again, Lenny, you and I probably use this all the time, I bet. Because honestly, again, we go by name, face, whatever. It's a really difficult social situation to put someone in. Just think about it from their perspective. If you go up to someone and say, "Hey, it's great to meet you," and they're like, "We've met five times," it's quite embarrassing, right? For them, for you, for everyone. In fact, my wife of many, many years, who I've dated since college, has a really funny story about this, which is, right before we started dating, I went up to her and I basically did a "nice to see you" line, right? Because I very clearly couldn't remember if we had met before, and we had, and she remembered. And so for me this is an important one, right, to keep in mind.
My wife is constantly making fun of me for not knowing if I've met someone before or not. She's like, "I don't know what to do with you." So that's a great one. So the line there is "great to see you," because it works whether you've met them or not.
Yeah. And again, it's one of those things where, here's the thing, people aren't dumb. If you go around saying "nice to see you" to everyone, they're like, there's a small percentage chance this person doesn't remember who I am, right? And there are other ways, but that's okay. That's part of the etiquette dance to some degree, that's fine. And what's not fine is "It's so nice to meet you" and we've met six times, right?
Yep. Okay, let's talk hygiene. There's a couple there that stood out to me. Tell me if I'm missing any that you think are really important. One is just subtle fragrance.
Yeah. Don't smell, right? Don't overpower it. You shouldn't smell like you just doused yourself in perfume, right? Or cologne or whatever it is. But you also shouldn't smell bad, right? Again, your scent should not be noticeable, is almost the way I would put it, in any direction. There's no advantage to that, is basically what I would say.
By the way, this is a good question. Does this advice apply equally to men and women? Is there anything, maybe as we go through it?
So, it's an interesting question. I think broadly in this book, the answer is broadly yes. I will say that there is probably, in January or February, going to be what we've internally been calling the fem etiquette course, because my wife and other women have said this is good, but there's a bunch of other stuff that women need to know. And so I can't speak to that yet. The fragrance one, I would say, I don't think you want your fragrance to be memorable for anyone, no matter what your gender is.
Awesome. Let me take two tangents here real quick. One is, I heard you told a story on your podcast about your kids and the impact this has had on them. Maybe share a story there.
Well, look, here's the funny thing. I literally have realized in doing this, I love my children, they have terrible manners, right? There's certain things they're not bad at, but broadly speaking, I have an 8-year-old, a six-year-old, and a four-year-old, and I'm like, "Wow, you guys eat like animals. You don't know how to use a fork or knife properly." Again, it's not like at four or six it's stopping them in life. But I'm like, I can't be the etiquette guy if you guys are like this. So some of it has been really cute. Others have been really funny. My six-year-old has started standing whenever my wife comes to the table, which is kind of arcane from an etiquette perspective. You can argue about whether it's actually even really etiquette anymore or not. But if you're being really formal, when a woman comes to the table, you stand, right? It's very funny to have the six-year-old do that. So in our household, don't judge me yet, but in a year you can judge me on my children's etiquette. It might have to be a children's etiquette book.
So good. I think actually at the end you say that whenever anyone joins you for a meal, whether it's a man or woman, you stand up, as a modern way of thinking about
That might be better, is what I would say. I will say it's an ongoing, somewhat hilarious debate at our dinner table. I'm just trying to get them to not use a fork and knife like animals right now, but we're working on it. We're working on it.
I was just listening to Tyler Cowen, who had Alison Gopnik on his podcast, and she studies kids, and her whole thing is how kids learn like scientists, and she has a whole thing about how they figure out how to use a fork by just experimenting until something works.
Right, to be clear, they're able to feed themselves, it works, but you look at it and it's like, what are you doing?
Yeah, yeah. Okay, the other tangent is, you didn't share the class you actually taught to founders already. So maybe share a little bit about this class you taught.
Yeah. So before the book, we did a class specifically, initially, for YC founders, right? Partially because YC's Garry Tan got very mad about this. I'm like, "Well,
now I have to do it, right?" Because that's very funny. But yeah, we basically, you know, we gave them all certificates of completion, but we did a class. We hosted it was at the Four Seasons. We did some stuff that was fun and a little bit irreverent, like we had some very fancy wolves basher people come in with models and show talk about dress at different types of events and things like that, which was kind of tongue-in-cheek, but a lot of fun. We also did like caviar and wine tasting type stuff, but then we also spent a lot of time focusing on like the actual meat of the matter, right? Which is things like how to show up with a low heart rate, how to have an abundance mindset, you know, basic skills like look people in the eye, shaking hands, you know, how to eat like that shows that you're being respectful, things like that.
Why do you think Garry Tan was so mad at it? Is it because he's like this is a waste of time, not worth it, versus like just build a thing that's successful?
I don't know. I mean, I don't really understand what makes Garry Tan mad and it's fine, but like from my perspective, I think, yeah, I think he's just like in some ways, again, to be clear, it's a little tongue-in-cheek. We're a little bit making fun of the fact that YC founders do come out a little bit like animals, right? There's like having met with many of them, and it's not their fault. They're like young kids. They've been holed up in a room coding and that's all they've been thinking about for months or whatever. And so like when they show up at your office to pitch you and you know they get a coffee or something and then they like leave it on the table and don't ask you where to put it. It's a subtle sign of like not being aware of your broader environment that you may or may not know. But like I think it's valuable. Maybe they're like this is the wrong thing to focus on. I just think it's funny as much as anything else.
I love it. Okay. So on the hygiene thing, is there anything else?
I think the hygiene stuff, I mean you should get the book. I think it's like fairly obvious hygiene stuff, like don't be covered in schmutz, you know what I mean? Like show respect. Try to anticipate how the room is going to be dressed and like don't massively overdress or underdress. It's like if you show up to a business casual thing in a tuxedo, you know, you're like you're kind of trying to stand out. Don't be memorable from that perspective, but you also don't want to be memorable in the other direction. It's like, wow, that person like really has no respect for the room.
This actually you're getting into the next category, which is dress, which I'm excited about.
Yeah. I mean dress, like look, I got to say again in terms of know the rules but don't always follow them. My first job out of college I was an associate at Bain & Company, right, this is like a consulting firm, and there was like a business casual and I kind of came up with the snarky realization that there was a minimum dress code but there wasn't a maximum dress code. So, I started in the office as somewhat of a mini rebellion in the consulting firm, what we called tuxedo Tuesdays, where all the associates would wear tuxedos to work, which then meant we didn't have to go to the client meetings because they would never take us to client meetings in tuxedos. So, it's like, you know, again, you know the rules to break them. It was fun. But I, you know, I do think from a dress perspective, again, I think the real thing is like look put together, look like you cared, look like you made some effort, but don't overdo it is basically the upshot of the most simple way to dress. Unless you're trying to very intentionally break a rule, right? Which maybe you are, but I think you should do that with a lot of cultural understanding. Let's put it that way.
So, here's a couple tips that I love. So, one is just dress one level up as a really simple tip.
It's an easy way to win. Not two, not three, but one.
And oftentimes you can like reduce that. Like if you have a suit on, you could like take off the jacket and you're a little less formal.
Yeah, 100%.
And then you talk about fit of the item versus the brand.
100%. Like at the end of the day, fit is everything, right? I say this is again, you guys, all your listeners have to understand part of my joy at doing this is there is some level of hypocrisy in it, right? Which is great. Like you got to have a little bit of that in your life in terms of how I myself behave sometimes. But look, at the end of the day, like a well-fitting $20 shirt is way better than a misfitting $500 shirt, right? And candidly, like it's the same thing. It's like if you're a startup founder, you do want to kind of dress to the level of the room, but you kind of shouldn't show up in like, like you shouldn't have a Rolex, right? It's like very classless, if that makes sense, to like show up as a startup founder with a Rolex, right? It's just not, again it goes back to heart rate, trying too hard. You know, you're not going to trick anyone, right? Is the upshot, right?
Yeah. The fit over brand and just expensiveness of the item is such a big one that I think people don't realize, just like it could be a pretty cheap thing that if you get tailored in some small way it just looks so much better even if it's not the highest quality item.
100%. I mean again I would put it differently: think about the average person, not every person in the world, but the average person in the world can look at a suit and be like intuitively that seems like it fits the person or doesn't. Yeah. Most people have no idea what things cost, right? Like if you said like, you know what I mean? Like it's just not. And like so in some ways it's this weird thing where it's like if you show up in a super misfitting but very expensive item, you're like what signal are you sending? It's like, well, you're not very aware, right, culturally, you're not like matching the room. You're not showing a lot of sensitivity like to the situation, what people actually prioritize. And it's like, are you trying to impress me because you have a fancy outfit? Like what are we talking about?
One other tip you have is if you're not sure the level of dress, just ask.
Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations, you know, down to like which forks should I use, you know, or what's the expect, like it is absolutely fine to ask. In fact, if anything it shows a level of confidence and calm and humility to ask if you don't know, right? So I actually think this is a great example. There's absolutely nothing wrong with asking about dress, about etiquette, about expectations. You know, again it goes back to this whole give to get. If you get someone on the phone and you ask them a hundred questions about etiquette, at a certain point you're like that's not a game of ping pong. Like you're not g, but like it's totally fine to call, be like hey, like what's this going to look like? And by the way it's important because in New York versus San Francisco there's different expectations, like people do do things differently, and like your job, you're not expected to know every nuance of every culture you might enter.
So maybe as a final question in dress, do you have any just, I don't know, tips for dressing well? I know this is a big question that a professional spends time teaching and charging for.
I really, you know, I think the answer is find someone in your universe who you think dresses well and again ask them for help and like what makes sense from that perspective. Again the well-tailored, great, that makes a lot of sense. The like basics I can say, yeah, like have jeans that are clean, right, and like fit you, things like that. But again, when my wife listens to this podcast episode and hears me being asked about specifics of dress, she's going to be chuckling.
Great, that's a win. Okay, let's talk about dining. Some advice for etiquette during dining?
Tip well, right? Don't not tip. Don't tip badly, you know, don't be super stingy about, you know, okay, who ordered the flambé, you know, like split bills evenly. Make things easy for waiters. In general, it's don't order the most expensive thing on the menu. Does it really matter? Especially to like an investor. Do they really care? No, they don't really care, but they do notice and you're like, ah, you're the type of person that like is truly insensitive to what things cost, even if it doesn't actually matter, right? So, I think there are things like that. Same wine. Like and then I think, look, in the terms of asking, ideally don't order first, right? Because I think if you see how someone, like are we doing starters, like how long is this meal going to be, like there's a lot of times in dining situations you don't know, and the more you let someone else set the tone and then match that tone the better. Like you kind of want to go middle of the pack to last, if that makes sense.
So this, yeah, so this is in the situation if someone takes you out to dinner, like it's a VC, another founder, like someone invites you.
Partner or whatever, whatever it is. Yeah. And look, I think I always say in terms of this, which I obviously think is important, is like look, within reason, always offer to pay. Now, you should be turned down, right? If you go out with a VC, right, and you're like, you know, you put a card down, 99% of the time they'd be like, I got this. Like, please, don't worry about it, right? And like that's the right vibe on it. You do not need to do this if it's a $10,000 dinner, or if they've ordered a super expensive bottle of wine, like there are limits to this, right? But if you go out to a normal dinner in a normal situation, you don't offer to split it. You just offer to pay for it, right? And then, you know, you should be declined on that. But there is a little bit of a risk there because someone might not decline you and then you kind of are on the hook for it. But that is, I think, the polite thing and the polite way to approach it.
What if they're just like a billionaire? I just had dinner with like a very successful VC and I did not feel like offering to pay made sense. Would you still?
Yeah. I actually would. I think it depends what the dynamic is. If the billionaire ordered a $10,000 bottle of wine, you don't need to offer, right? If you had a normal meal, right, I actually think it's great to offer. And they'll almost certainly be like, "Of course not." Right? But I will say, you know, I'll tell you a funny story, which is like when you go out to dinner with really fancy people, right? Or like someone who's like you're, you know, there are two interesting dynamics. One is it's actually I think especially nice to offer and even sometimes pay, because the reality is if you think about it, they obviously don't care about the money, but no one does that, right? Like they're like well clearly you should pay. And so the more you're like oh no, like I'm treating us like this is a conversation of equals, and like I'd love to offer or just pay, is big. The second thing, which is important, is especially if you're out to dinner with someone who's very, very well-known, you have to tip like crazy, because the problem is, this is like one thing, this is not in the book, this is like a 201 course, right? But if you go out with someone like, okay, they're either known or relatively known and you're making the gesture of buying it, not cuz, they obviously don't care about the money, it's more like the gesture that's nice that you would offer that, you kind of have to tip the way they would tip, and they're gonna tip like 100% of the bill, right? Because like it's just like the right thing to do. And so I do think if you're gonna do that, you really have to tip well.
Got it. Speaking of tipping, my god, I hate tipping so much as a concept. Like obviously people deserve to be paid well. And I love that, you know, they make more money, but it's just so convoluted and just like what the hell do I do? I never know.
Tip a lot.
Tip a lot. Okay.
Just tip a lot. Like I think 10, 20% is the minimum. Like if you're out in like a situ, you know, I think you kind of want to tip, in my mind, to the level of no one you're effectively paying for would bat an eye that you're being stingy, is the way I would think about it. 20% feels like the minimum. 30% sometimes. Like more seems a little bit silly, but it is a squirrely topic and I just, again, let me put it this way. I don't think you want your tip to be memorable is almost a way to put it. Like this is not a thing to focus on. When the person that you're out to dinner with thinks back on the dinner a month later, they want to think about the content of the conversation or what the ideas were or the business opportunity. They don't want to think about, oh my god, that guy tipped an incredible amount, what was that? And by the way, I have stories in my own life where like I've been out with people and they've tipped like so much that like a decade later I remember it, and I'm like that's fine, they can afford it, like it's cool that they did that for the server, but honestly, the only thing I remember from the night is how much the person tipped.
So you're just, okay, but I think if you're like extremely rich, do you do it? Don't even tell anyone basically, but feel free to do it obviously.
Sure. Yeah. I mean, the tip is not a point. The tip is like everyone should feel good about it, right? And like again, it's about again putting people in a sense of ease and comfort, and you might not like it and it might not be fair in the world, but people are like everyone's being taken care of, I can be relaxed about this, is kind of what you're going for.
I recommend your next book after this fem ficit fee edition is a tipping guide.
A tipping guide. Well, you know what would be funny is there's a great episode of Seinfeld. It's all about the tipping calculator. I don't know if you're a Seinfeld guy.
I love Seinfeld. I don't remember.
There's a great tipping episode. I feel like you could honestly like have a very funny like modern LLM app that is only about tipping. Like imagine like a tipping app where it's like, instead of a tipping calculator, you take a picture of the bill, it geolocates where you are, you kind of give it, you're like this is the situation, and it just tells you what to tip.
Well, what, like the tip, like a restaurant's one thing, but then it's like the garbage person, a gardener, the
Especially this end of year, like we're at the end of year, like I think no one knows how to tip anymore.
It's so like, yeah. Some guy that like installs the shades in our house. Do I
Do you? I don't think you tip that person. I actually, do you tip that person?
No, I did not, just because we already paid a bunch of money for this thing.
Yeah. No, I feel like that is weird. I wouldn't tip people like that.
Yeah, that's why we need this book. You're going to make it, it's going to be a huge hit.
We could fund it. You want to fund it with me? We should fund an app. Talk about YC companies. If someone pitched me, in the terms of funny but real, if someone pitched me the 2026 AI-driven tipping calculator, which takes the social situation and the details and all the things and it's like this is how much to tip, that is hilarious and probably quite useful.
And probably not venture scale, but I don't care.
2026 it might be, you know, everyone has the problem. Everyone globally has the same problem, which is tipping.
Yeah. Just the tokens cost of that. It actually reminds me, I'm reading one of my sons right now the third book of Hitchhiker's Guide to the Galaxy, and I don't know if you've read the series. It's important. Do you remember about the, what's Bistromathics
mathematics? So basically the idea is that after the improbability drive, the way they're able to move across the universe is the most complicated math in the universe, which is the math of your bill at a restaurant. So I think we're on to something. It's in science fiction.
Oh man. What other tip that I just thought of around dining is you had this tip about sommeliers. Give them a sip of your wine if you order something.
Yeah. If you order something nice, that I'll be very clear again in terms of
I don't order a very nice wine. Yeah.
No sommelier really cares what I'm drinking. But if you are doing that or you're into it, which is great, again, think about being generous, right? If they're like, "Oh, I would love to taste that." Like a taste. It's great.
I love that. I would love to do that. That sounds really nice.
Yeah.
Yeah. Okay. And one other tip here. I wrote down B for bread, D for drinks. Explain that.
Oh, B and D, you just got to look at your hands, right? B's and D's, so which was your bread plate, right, is kind of the way to think about it. And look, people get this wrong all the time. You sit down at a big table, right? And you're like, which is mine? You're kind of waiting for someone to pick it up and kind of do the math. I'm like, okay, that's my bread. But that's the B and D, it's useful. Also, look, forks and knives, just knowing what side they go on, knowing, one guy always drives me nuts, that kind of goes, is related, is the knife blade goes in, right? People, when they put their knives down, right, the knife blade goes in, because you don't want to stab your partner next to you.
But it was really funny. I had an entrepreneur, this is not yet a product thing, people started sending me videos of them dining or in situations and asking for feedback, right? And I recently had to give feedback to an entrepreneur, who's like, "You did a very nice job eating your soup. Good job. Your napkin should have been in your lap." And your knife is pointed the wrong way.
Okay. Napkin, actually. Okay. So, napkin in lap.
Napkin in lap. Not at your neck,
not off to the side, you know. Napkin in lap.
I saw someone once had a napkin on just one leg versus both legs. Any opinion there?
I mean, I don't think you want your napkin placement to be memorable.
That's kind of my biggest thing, is these are not, the point about etiquette is that it gets you out of the way, right? It shouldn't be memorable.
Like the Kindle, you don't want to think about the technology.
No, you just let the conversation flow.
Yeah. Okay. Amazing. Okay. Speaking of conversation, small talk and humor, give us some tips.
Here's the thing. Humor is great. I love humor. It can be overdone. And again, it shouldn't be the point of things. And also, I'd say humor is quite conditional and subtle to the audience. So, in the room you're in, dirty jokes, right? Do you tell a dirty, you don't want to tell a dirty joke in the wrong room. But I think the thing about humor is there's this interesting subtlety to why it's so useful in social settings, which is, one, it kind of shows you the ultimate mastery of a social situation if you're able to tell a joke which is right up the line, or even pushes it one degree, to show your own comfort in the space, right? It's the ultimate demonstration of comfort in a space to tell a joke that's a little over the line or a little off color, but not too off color. It's the ultimate thing. So if you're really in it and feeling good, using humor is great. You should not be remembered as only the comedian.
And again, the level of jokes that you're playing with is a very subtle thing, right? So, you don't want to tell a knock-knock joke, right, with adults, right? But the off-color sex joke that is hilarious, you got to be pretty confident before you tell it, right, in a space. The last thing you want, a joke that everyone laughs at is great. A joke that no one laughs at is a huge risk maneuver. You've failed, right? And it's not the point.
So, it's a great tool. I love it. I think everyone should have their file of jokes. I do. I don't know about you, but I have an Evernote, it's not Evernote anymore, it's a Bear of my favorite jokes, and they're loosely ranked from least offensive to most offensive. Because I forget the jokes, but you kind of want to use humor sparingly and smartly.
This is your next book. This list of jokes.
List of jokes, ranked by social situation and level of extremeness.
Everyone's going to be telling these same jokes.
Oh man.
Well, there is a funny joke about that, right? Which is the whole, the prisoners. I won't even tell it. There's a funny joke about people who know all the jokes.
I'll leave it at that. I'll leave you hanging and wanting more for our next podcast conversation.
Abundance. Okay. You also recommend self-deprecating as a
make fun of yourself, not other people.
Yeah. I mean, it's just, you can make fun of yourself as much as you want, right? Again, making fun of other people shows an incredible level of familiarity, right? And if you're there with your business partner and you're really feeling the vibe, again, it can be quite effective, but the second it feels disparaging or people aren't on the same wavelength, it's a very high-risk maneuver. Making fun of yourself is always fun.
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Also, so you said you had this kind of list of jokes, because I can't remember. I have zero jokes in my head that I'm like, "Okay, here, I'm going to get one." So, I should make a list.
Make a list. I got some good ones for you.
Okay, I'll have to borrow some. You also recommend having some stories, some crowd-pleaser kind of stories to tell.
Yeah, you want to have some easy stories that, again, shouldn't be 10 minutes, right? But again, I think the thing is, imagine that the whole game in these social settings, again, is putting other people at ease, making them feel like you understand them and the room and you're a trustworthy person and on the same wavelength. And in some ways, think about it as who's carrying the conversation. It shouldn't be your monologue. You shouldn't force them to monologue either, right? And that's where questions come in, and back and forth, having a fun build-on story. They tell a story, you have a story to tell. Again, I really think of a conversation or these social interactions as a ping-pong game, right? And you kind of want to have a few of those in your arsenal.
Your last tip in that section was how to wind down a conversation. Just the importance of realizing it's time to wind down. Any tips for how to do that?
Yeah, just when the conversation is over, gracefully leave, basically, is the upshot. The worst is the conversation ends and the person just stands there and you're like, "I'm going to go get a drink," you know, or "Do you want," and then every once in a while the person will be like, if someone says to you in a conversation, they wind it down, it's like, "I'm going to go grab a drink." Most of the time that is not an invitation to say, "I'd love one too," and follow them to the bar, right? That is not. So I just think you have to kind of recognize the signs effectively when the moment is passing or it's time to move on, etc., and then respect it. That's what I would say.
I use that one all the time. Are there any other ways you find useful to wind down a conversation? Just going to get out of a conversation.
Well, I think the other thing people do frequently, which again is totally fine if done respectfully, is bring someone else into the conversation, right? In some ways, give them their next partner, you know, be like, "Oh, I've enjoyed this conversation. It's super cool. By the way, have you met Steve? Let's go meet Steve. Go talk to Steve for a bit," right? "And I'll pick you back up. Okay, I'm going to go say hi to my wife." There are ways to handle it. Again, the key though is subtlety on these things, right? I think in all things you want to basically let people feel respected as much as anything else. So if you're too overt about it, right, you don't give them, even if everyone kind of knows what's going on, the key is to give them plausible deniability to themselves and the community, effectively, that we've wound down this conversation. So you have to kind of look for the signs.
Awesome. Okay. There's four more sections. The next one is scheduling etiquette. Give us some advice.
Oh, well, I think I'd like to say that I'm fairly famous for hating Calendly. I actually think I'm not overstating it when I say there was a period where I personally had driven most of Calendly's growth for the month. I got messages from the board, because I went on this diatribe about how much I hate Calendly and how disrespectful it is. And apparently this was such an internet fervor, I got millions of engagements that meaningfully drove their month. Thank, no bad press.
No bad press. No bad tweets. Yeah. So, I think, look, there's a few obvious ones. Make sure you have availability, you know. If you ask someone to schedule with you, it's not always wrong to be like, here's my availability, or here's a link, but make it real. You have to give them real options. I really strongly believe the default should not be Calendly. The default in most situations, especially if you recognize the power hierarchy, the busyness hierarchy, if you're the less senior person, if you are the less busy person, you should let the other person tell you when they're free and then make it work on your end, right? Is what I would say. And it's fine if the first thought doesn't work, but one of the first three really needs to, right? So, I think in some ways it's important to kind of respect that it's better to ask what they can do and then move your schedule. If you really can't and you're going to use a scheduling agent or something, it just needs to actually have real options, is basically, I think, a thing that comes up all the time.
Look, rescheduling happens. When you do it, give notice as much as possible. Once you're asking for rescheduling, you need to be even more accepting of what the other person can do, right? I think that's really important. If you're asking to reschedule, you basically, within reason, need to make it work for them, right? Is what I would say.
And then look, I think there's obvious stuff that people should know but sometimes forget. Time zones are really tricky. People screw them up all the time. Check. It's worth the extra check to make sure you're getting the numbers right, but then also, really importantly, scheduling at reasonable times. Sometimes people are like, "I want to meet at this time," and you're like, you're on EST, that's like 4 in the morning for me, right? And so I think being respectful of that and just asking is super important. It's not rocket science. It's important.
Last point I make, which you make in the book, is you really need to respect EAs and PAs and the whole, like, this is the number one way to look extremely classless, is to not respect people who are helping the other person, right? This is the number one thing. Now, you don't need to be so over-the-top, you don't want to overdo it, but there should be this deep well of respect for anyone who's helping you, whether that's a server or a PA or an EA or whatever. This needs to come with an extra gesture of respect. That means saying thank you when they schedule and following up with them and things like that.
I'll tell a story. When we were selling our company to Airbnb, we had this guy helping us sell the company, and he made it a big point to build a good relationship with the EA and office manager at Airbnb, because if they like you, it helps you get the thing.
The general story of make the gatekeepers happy and like you is true, but I do think there are ways to overdo that, for what it's worth. It becomes almost too transactional. If you show up with flowers for the EA, you know, you better be damn confident in what you're doing, if that makes sense. But yeah, just the small things go a long way. You just, you know, make eye contact with them, thank them, respect them. If they bring you a coffee cup, ask them where to put it when you're done. Don't treat people who you might, and who feel like the team or the staff, feel that way. Make them feel like part of the team, as equals.
The Calendly stuff, I feel like that's its own separate book of Calendly etiquette.
Yeah, look, the Calendly one is one of my favorite episodes of going hyper viral on something hilarious.
So, one thing that Calendly does is you can embed, I don't do this yet, but I should. It feels like just embedding your times in the email feels like a good
Look, I'll be honest. I go the other way. I don't use any of that stuff. And look, I think scheduling is very complicated. Part of it is, I always think of these, when are you free? It totally depends on who's asking. If Barack Obama, or I don't know, I won't say Donald Trump, someone wants to meet with me and it's four in the morning my time, right? I'm totally news. You know what? I'm going to make it work, right? And so I'm actually kind of against the flat hierarchy, all meetings are the same. That does mean, honestly, I think you probably knock me, my bet is that my calendar moves more than most people's, and I'm sure that feels disrespectful to some, and it is, I want to be really clear, but it's also the reality of trying to balance these things.
The other flaw with Calendly I've realized: someone once figured out my Calendly URL and just booked a meeting with me, like a founder wanting to pitch me, and then it was on my calendar.
The funny one I've had is there are people whose names are very similar to other people I know
and every once in a while I've ended up accepting a cold meeting and showing up being like, you are not the person I expected, because it's like, oh, your name is off by one letter.
That's cool.
That's not a thing to call out, by the way, from an etiquette perspective. Once you're committed to the meeting, you're doing the meeting, even if it's the wrong person.
Oh man. Okay. Well, one last question with Calendly. Something I try to do, curious to get your take, is
like okay someone want like a founder. I'm meeting with a founder and I'm the way I approach it is like okay do you have a Calendly or something I could use to book a meeting with you? If not, in parenthesis, here's my Calendly in case that might make it easier.
Yeah I think that's perfectly fine. Right. In terms of the way to do it I just think again the key is to make it easy for the person you're trying to do business with. Right.
And not make Yeah. And that make them feel like they have to do the work if they don't want to.
No, you do the work. Like basically, you're asking for something, you do the work is the upshot.
Okay, sweet. Moving on to the next topic. Communication. Don't use emojis.
Try to proofread your stuff. Get to the point quickly. Assume the person you're reading is busy. Like, again, I think these are all the types of things that like none of this is rocket science from my perspective. But people, it's just good to remember, right? And be on top of it.
You know, I do think people have different things on this. I personally do think that on things like email, you kind of do have an SLA to respond. There's some people I know who are like, "Email does not mean I have to respond. You send me an email, you may or may not get a response. It's completely up to me. I have no contract to respond to your email." I personally go the other way, which is I feel like from an etiquette perspective, like I don't owe you a 12-page essay, but I do owe at least an acknowledgement quickly, right, of what you've sent? Like you don't want to leave people hanging.
But again, I just think it's like if you read an email, I'm sorry, if you write an email, imagine you're receiving it. How does it feel? Right? Does it feel like you're asking a ton of the person you sent it to? If you send them 10 paragraphs, it's annoying, right? You're like, "Okay, I have to read all this. What am I going to find time? Like this is like you're asking a lot." It's kind of like a monologue in a conversation. You've just said I'm going to spend 10 minutes talking at you, right? And so I do think keeping it short and to the point, you know, not being silly, not using emoji, trying to make it readable, like these are all important things.
Say more about the emoji piece. Like is your advice just no emojis if it's a business?
I think emoji from my perspective is very it's like quite a step of familiarity if that makes sense. From a business context, like look, if someone sends you a smiley face, you can respond with it. Like you can kind of like match. Again, it goes back to this matching vocabulary and language. Like I'm not saying you should be totally cut and dry, but I would say emojis almost feel like jokes to me, which is like tell them at your own risk and they're probably not worth it, you know?
Awesome. Okay. I do use emojis. I use like the thank you hands one a lot. And
Look, I think text is different. I think people might have slightly different takes on this and so I wouldn't say anything I'm saying here is dogmatic but I'm just saying that like again emojis are not highly legible to most people. They can mean lots of different things. They usually have cultural connotation to them and like I would say that like they're kind of harder to read than just a well-worded simple to the point email. And I think you just want to come across as like a literate, to the point, simple, clear person.
An emoji sometimes kind of implies used AI to generate this thing because ChatGPT loves emojis.
Totally. I also like look I mean there's a whole you want to get spicy for a second?
Yes.
I don't know how I feel about people who have like invested too much in their emojis, right? So you get people who have like changed the colors of their emojis from the default or whatever. I'm not saying not to do it. I'm just saying it's quite a statement is my view that you've invested in your emoji pack or like using special emojis people haven't seen before or like it's like again it's a subtlety and you got to understand the room and like the culture and like what you're responding to. But I do think that people read more into that than people want to be read into it.
You know what's crazy now? I don't know if you've seen this. You can like create your own emojis now in iOS and emojis are so
It's like a whole new world. Just in
Again it's like if you choose to use those you are going way out on a limb right that people are going to be receptive to that and not be like this is a person who spends a lot of their time customizing their emoji pack when they probably should be doing something more interesting.
They should be finding product market fit.
Yeah or learning etiquette.
The other tip you had that I loved which is think about the order of the emails when you're emailing somebody.
Yeah I do think you kind of want to think about you There is a connotation to who you send it to and who you CC and the order in which people know. Now you know I don't want to like overstate this but put differently it's like if you're sending an email and the first person on the email is the assistant and the fourth person on the email is a CEO you've probably done it wrong.
And because the implication there is who you think is most important comes first, like who's first to put to mind.
Who are you really sending this to, you know what I mean, is almost the way I think and like who's kind of included. So like if I look at an email and I'm the first person in the to, right? Candidly, I mildly pay more attention to it than when I'm the fifth, right? Because in my head, I'm like, "Okay, well, like this is really to Kevin and like I'm on it." Like if you see an email sent to many many many people, almost by definition, it's not that important, right? Is almost the way I would put it. And so, you have to be really careful with managing that.
I think even the who do you send it to and who do you CC, there's a language to that that like from an etiquette perspective to understand, right? And like I do think people sometimes miss that. Like the CC line is very very valuable. It means, hey, you should have a copy of this. This is not really to you. I'm not expecting an immediate response, right? I even think there's even a subtlety like who responds then. Like if you send an email to 10 people CC'd, the whole nine yards, you know, there is a subtle etiquette to like when you respond. Like if you are the fifth CC on an email, you're not expected to be the first response. Again, you can break this rule. Like, there are times to break it. There's a subtlety to it, but it wasn't really sent to you, right? Like, and so there's a whole language to who you send to and who you CC and the order that like again, it's very subtle, but is worth understanding.
So true, man. And you would think nobody sees all these little things in the Gmail thread, but you do. They're just right there.
You see them. And I think people, this is the whole thing about etiquette is like it's all this invisible stuff that you don't need to spend like all in some ways the whole story of doing this well is it should not occupy 80% of your brain, right? What you're saying is I've got this, we're on the same wavelength, my heart rate is low, I'm doing it properly, and I'm doing it like intuitively almost, right? Which is a hard ask, right? Because what we're basically saying is like these are unknown things, but intuitively you should just know them. And that is actually what you're signaling is like you can trust me because intuitively there's this well of knowledge and cultural connection and whatever that we can share effectively.
And if you're BCC, definitely do not reply all.
Yeah. I mean I have some unbelievably funny faux pas from my history with CC, BCC, to lines. One of the worst etiquette slash mistakes I ever made. Never ever ever put someone you're talking about who's not on an email in the to line to check the spelling of their name and then hit send. That's a bad idea, right? So, whatever you're doing, that's not even an etiquette thing. That's just like a being smart.
Proofreading thing.
Proofread. Proofread and don't send emails to people about them that they're not supposed to see.
And it's like Gmail makes it too easy to do that because it adds them automatically if you like talk.
No, for me it was more just like the way to check the spelling of someone's name is not to put them in the to field ever.
Yeah. Oh, bad. Okay. Oh, man. Well, you're still kicking, so
I'm still kicking.
Great. Okay. Two more. Meeting etiquette.
Yeah. I mean, again, we've talked about arriving a little bit early. You should do that. Don't arrive too too early. Like, you shouldn't again like if you're an hour early, walk around the block. It's fine to walk around the block. You don't want to sit in someone's office because then all of a sudden it feels like this person has been here a long time. Like this feels like even though they're not scheduled, like we're leaving them hanging. You're six coffees deep with the receptionist. Like you don't want that, right? So I think you want to be like 10 to 15 minutes early. You do not want to be much earlier than that.
We talked about meeting at other's convenience. I do think it's fine to start with a little bit of small talk, right? You know there are times it's not or times people running behind but like the pleasantry of like the weather is nice or how was your weekend or like something that kind of cuts the air a little bit and then you kind of flip into business is like a good thing even though it like feels transparent is still useful right is what I would say. And again it's almost a signal of like I am here for business but I'm like a normal person and like I'm willing to have like a norm you're like signaling like oh I know that we should start with a normal conversation if that makes sense. Right.
I don't know if you saw this on Twitter. Someone described small talk as like the TCP/IP ACK handshake.
I love it. It's a great description. I always describe it as like imagine the modem crash from when we were kids on a 14.4, you know, like that old modem crash. Like that's what small talk is. It's a modem crash. We're trying to hit the wavelengths, you know, etc.
So that you're ready to talk, so that you're ready to really communicate.
Yeah. Yeah. For meetings, virtual ones, camera on. Like, and again, I say this as someone who sometimes violates this, right? I violate it knowingly. I violate it knowing what it costs me, but you really should have your camera on, right? And again, like you should dress appropriately for a video call. You should have an appropriate background. You know, if you have your bed in your background, it should be nicely made. You know what I mean? Like, in some ways, it's like doing the easy stuff is the key in some way.
And I go a step further. This is less a hard rule. I actually really don't love virtual backgrounds for the same reason. I'm like, look, I'm not going to judge you if you're in your bedroom, if you're a startup founder. It's fine, but I would like to see that your bed is made or like I'll give you another one that's classic that I see with founders all the time. Close your closet. Like people will get on Zoom calls and you'll be on a call and like their closet's open. And I'm like it's not a big deal, but like do you see your own self picture here? Like can you just close your closet? I don't want to see your shirts, you know? Like that type of stuff I think goes further than people realize.
Awesome. One other tip you had was clean up after yourself if you're in a real meeting.
This is actually the easiest way, and this, by the way, is for my partner Kevin Colleran, but the easiest way to come off badly is to not offer to put your coffee cup in the kitchen, right? And like honestly, we do this because like if you think about it, we work for LPs, limited partners, right? Like that's who we raise money from and then deploy it from. And my partner Kevin, even more than me, has this thing, which is he is maniacal about this, which is no matter who's in the room, if we're with an LP, you take the coffee, you take the Diet Coke, even if you know full well someone's going to come in and clean it back for you, and you make a point of asking where we can put it or putting it on the side table, etc., and acknowledging that there is a mess.
I feel that. Final topic is exiting and leaving. What are some tips?
You should stand when people leave the table, right? Not ridiculously, by the way. You should go stand with the table. Stand to shake hands. Don't be sitting when you're shaking hands. It's just what you do, right? And like it shows that you're aware of it.
Follow up with gratitude. Like you should send people thank you notes. Even if they shouldn't be long, they shouldn't be ridiculous, but like we met, I got something out of it. Like thank you for taking your time is like always appreciated, is what I would say.
Obviously there's stuff like don't take calls, etc. Like this is kind of like the kind of obvious stuff in terms of exiting and how you think about it. Like even if someone rings you, right, and the meeting's over and you're over time, you're like, I got to pick up this call. You hit the button that says, I'm calling you right back and then walk away. Don't just pick up the phone and like wave, you know, is what I would say. Yeah, and I think like there's stuff like that that I would just keep in mind.
You also had like don't make a production if you're exiting, just like just leave.
Yeah. Yeah. I mean, again, I don't like, you know, yes. I think that's really true. I mean there's even a point to like there are lots of scenarios where I think an Irish goodbye is the best goodbye, where you just kind of disappear. Like any large group setting I think is great. Maybe you thank one person on the way out, the host, right? But like you know the "I am leaving now," right? Like let me kind of say goodbye to everyone and hug everyone. It's too much. It's too much.
I love that. Okay, we got through everything. Is there anything else that you think might be important to share?
There's so much other stuff. I mean, again, I go back to this whole thing, which is like, you know, these are all fun tips. I love the cartoons. We iterated on them a bunch. We have more to do. Like, we're having a lot of fun with this, and I think it is providing a lot of value to people, which is great. Like, that's kind of my goal is to both have fun and actually provide value and help people.
That intersection is great.
There's a thousand other tips and like so the biggest thing for me is when you have more or think of them, send them to us because like there'll be a second version of the book and then a third and like I actually really want to like cite the people who contribute to it. Like the book is what like 50, 60 pages. It will be a few hundred eventually and I think there's a lot more to come and we're going to be doing classes next year all over the country and actually world. We got invited to do we're going to do one in Tel Aviv.
Wow.
We're going to do one we're certainly doing one in New York and a few other places and you know it'll be fun.
This is oh my god you got a whole new life forming here.
You know the funny thing is this stuff, the etiquette story is obviously pretty fun and so like I think people like Morning Brew who just like keep making videos about this and like there's this whole etiquette thing going on and I'm like oh my god I've done some pretty good investments in my life, built some cool products, am I going to be ultimately remembered as like the etiquette guy? That's kind of hilarious. That's what we're doing here. I'm into it. I'm fine with that.
So you have the TL;DR at the beginning. I'll just read this real quick and add anything that we're missing. So this is just like what to do if you do
Nothing else. Remember the goal of all etiquette is essentially building trust and project genuine confidence. Always maintain an abundance mindset. Remember that you are worthy and have nothing to prove and that it's okay to ask questions and keep your heart rate low. That's the points. If nothing else, if you remember those points, you will be served well.
There we go. Okay, I'm going to take us to close out, make this more of a regular episode. I'm going to take us to two recurring segments on the podcast: AI Corner and Contrarian Corner. I don't know if I told you I was going to ask you these questions, but lay it on me.
I love... depends what you mean by that.
So the question in AI Corner is just what's one way you found AI useful in your work or life that might be helpful for people to hear.
So look, I'm by default pretty skeptical of most AI applications. I will say the thing that I've had the most fun with, with the AI, and I find great, is actually partially where the cartoons for this came from, is I built a little personal news aggregator called Lettermeme that basically takes all the newsletters I don't have time to read and turns them into daily cartoons. So I have a grid of what's going on in the world as a front page in cartoons, and I actually love it. It's the best way I get an overview, because there's all these smart newsletters. You don't have time to read any of them. So, I pipe them all in.
Except... keep going.
And what? Except of course that one I don't put in the aggregator. Although, of course, I don't do that. But it's great. So I'm super into it.
And that's lettermeme.com. Check it out. I love this. I love this. So, this is AI generated. Aggregates all the important newsletters and creates a little summary and a cartoon.
Yeah. And you can make your own. So, for me, I'm actually looking at this now. There's actually one thing that got messed up on this we need to change. But the idea is you basically get an email digest once a day and it's continuously updated, what's going on in the world, and you pipe your own newsletters into it. So, it's whatever you actually trust and pay attention to.
Genius. And how did you build this? Was it vibe coded? Did you have an engineer help you?
Well, both actually. The vibe coding thing, this is exactly what vibe coding is good for. You know, Cursor and DigitalOcean and Cloudflare will get you a long way in terms of just building this stuff on the fly, and so I built the first version of this myself end to end. But then vibe coding also doesn't really scale, and so the reality is after a certain point I had some friends who are great engineers just take it and uplevel it in a few ways that I honestly ran out of time to work on.
Well, let's go to Contrarian Corner. This could be an entire podcast conversation with you, I suspect, but just what's something you want to share that you believe that most other people don't believe?
I think that the venture capital, the seed venture capitalists who invest in companies that are branded as AI companies are going to lose an impossibly large amount of money in the coming years. And that doesn't mean that I don't think you should be using AI to build things. I actually think you absolutely should. It's kind of like not using AI in your startup is the equivalent of not using the cloud in 2010 or not using the internet in 2000. It would be insane. Of course you're going to use these tools. But there's a difference between a great business that you're using AI to supercharge or make better, or just as a piece of infrastructure. That's not an AI business. This is a business, right? And I'm very into those, versus all of these companies that come out that say, "We are the AI blank." I just think they're all going to zero.
Even, you know, my kind of argument about this from a seed perspective is, look, is OpenAI a good investment or not? It's a terrible seed investment, right? The way the numbers baked out, even at a $500 billion market cap, when all said and done the seed investors have made something like 25 times their money. That's insane, right? If you think about it, that's basically the worst. It's a middling at best seed investment for the company that is defining the moment, and the reason is because these things are so capital consumptive. So if you're trying to deploy 100 million dollars... The market is fragmented. You know, people want to dream a dream. People want religion. They want belief. There's a bunch of reasons why you can squint and justify. And you know what? If the storytelling of Elon allows SpaceX, which by the way I love, I think SpaceX is an awesome company, but if all of a sudden that actually can be worth 1.4 trillion dollars to the public market, guess what? The money powers are going to do great with all this narrative-driven religion is what I would put it. But if you're a disciplined seed investor, I guess my contrary take would be run away from things that are AI companies. Because even if you look smart for the moment, you're playing a dangerous game of get out before the narrative collapses.
Wow, I love this. Okay, I want to follow this story a little bit. So you're saying because of the dilution that goes along with...
It's like, if they work, they're too capital intensive. Seed investing does not work in highly capital intensive businesses. So that's not going to happen. Two, they're fundamentally commoditizing in all sorts of ways. It's very unclear what the lock-in or value is on any of these things, right? And so the whole dynamic is off. And the thing is people are desperate right now for things to believe in. If you think about the history, you know, we've done so well as a country with terra nova. The US was amazing for so many years because we had the West, and if you were going to work hard, you could go west and you'd do great, and there was all this opportunity, land of opportunity. We've had it reverberate. My generation, your generation, we were blessed because we had the internet. The internet was digital terra nova, and we got to build fortunes and do amazing stuff and new work, being in this new world that was created, but it was effectively the same thing as the West all over again, right? And ever since then, whether it's mobile, which again if you look at the math on it, everyone wants it to be disruptive, terra nova, not really, it's just more internet, right? Or crypto, which by the way I think crypto is amazing, I think it's the closest thing to terra nova, but to now the AI god narratives, every generation is desperate for their terra nova story, with good reason, right? But the story has to be real, right? And I think unfortunately this time this is a classic example of: AI is a powerful tool. It's incredibly powerful for existing businesses and existing structures. It's not a great startup opportunity.
So what is it you look for? Yeah, what do you look for when you're investing in an AI startup?
Well, again, I won't invest in what I would consider an AI startup. I'll invest in things that use AI. Right. Yeah, for me I think I'm really interested in the cultural implications of AI, or the new businesses that need to exist because it is a force in the world. So we've done a lot, whether it's Sublime Security or Outtake, things like that, that are basically all around the theme of the Voight-Kampff test from the great Blade Runner, which was the test they basically ran: are you real or are you a bot, right? That's a huge problem.
A turtle on their back.
Yeah. There's a whole set of companies that are implications of AI, and how do you manage it and handle it as a society. There's a lot to do there, and there's a lot to do in cultural shifts from AI, right? There's all sorts of interesting trends to follow there. There's all sorts of businesses that will be disrupted. They're not AI businesses. They're businesses that will be disrupted in interesting ways. So I think there's a lot of opportunity, but again, I at least draw a distinction between, if you're trying to be, I mean certainly a foundation model company, but any of these things that are "we're going to win because AI," I'm like, no, you're going to win because of something else, right? And AI is going to be a propellant to it.
Sam, you're a fascinating human. I feel like we could talk for hours. Is there anything, before we get to our very exciting lightning round, anything else you wanted to...
Look, I'm happy to be here. I love your work. It's good to be on your podcast. Happy to whenever. But no, we're good.
Okay. Well, with that, we've reached our very exciting lightning round. I've got five questions for you.
Five questions. I'm ready.
Five questions. What are two or three books that you find yourself recommending most to other people?
Ooh. Okay. So, let me pull up my list, because I got to pull up my Kindle for this. One is, I'm reading right now, I gotta admit I like to make fun of Marc Andreessen a lot, but he recommended a book called The Ancient City, which is fascinating. And so I'm in the middle of that right now. I'm really enjoying it. Man's Search for Meaning is great. I'm just going through what have I read recently. You know what's great? Area 51, an uncensored history of the top secret military base. Not very erudite. Great book. And then I honestly think the one serious one I'll make a recommendation on is The Lessons of History. It's one of my favorite books ever. I would really, really, really recommend it. It's a short read. But I would say The Lessons of History by Will Durant is probably the most approachable non-obvious book I love.
I did that one on Audible and you just listen to it all in a couple hours.
It's a short read. It's not a long book. I honestly think from a few hours of investment to intellectual return, my one real answer right now would be that. I could give you a thousand others. You know, there are things like...
The Banana King. Have you heard of this one? Have you seen this one?
Oh my god, this is so good. What's it called? The Fish That Ate the Whale. Incredible book. So is The Last Kings of Shanghai, if you know that one. These are all amazing books, but they're longer and they're more stories. Just, everyone on the podcast should go read Will Durant.
Okay. I love it. Favorite recent movie or TV show that you've really enjoyed.
Oh, I gotta say, recent, I think Landman is fabulous. Have you watched Landman?
Yeah. Yeah.
I'm really into it. That would be my most recent take.
What's interesting about that show is now tech companies are all super into energy. And you know...
I talked to... well, I'll tell you a funny story. I talked to a founder who's in Midland, Texas, which is kind of part of the show. And it's so classic and typical. He's like, "All these Silicon Valley people now think they understand the energy industry because they watched Landman." I'm like, it's wild, but I totally believe it, because I know too many venture capitalists who are like, "Oh, I now understand this because I watched Landman." And he's like, "This is totally a thing."
Yeah. I would feel that. Okay. Favorite product that you recently discovered that you love. Could be a gadget, could be an app, could be clothing, could be...
Okay, I'll pitch, you know, this is a little self-serving, but I will pitch people on June Date. So, okay, I actually don't use this product because I'm happily married, but this is cool. And here's the basic idea: if you think about so much of AI right now, this goes back to what businesses do you overhaul that are interesting, that have AI implications but are not AI. So everyone's got this whole virtual girlfriend, loneliness, you're going to chat with your friend, whatever, fine. These guys came out and what they do is they're like, look, if we're really trying to match up humans, call it Tinder 2.0, one of the best sources of information to do that is their ChatGPT histories. So this app is kind of built around the premise of distilling. You ask ChatGPT a structured prompt that they've designed. It pulls out an unbelievably good profile of who you are, and then you basically match with people based on what you're actually asking ChatGPT about and the implications of who you are. And the fun part is, I obviously haven't done dates on it, again, not for me, but I have pulled my profile, and I was like, wow, this is a shockingly good description of who I actually am. And so I think that's a really fun business.
It's like that prompt that the ChatGPT folks once had of just, visualize my space based on everything you know about me, and it was like, holy moly, a lot.
It's pretty good.
And so in this dating app, I love this idea. This is so good. So do people read that? Are they able to see that as your profile or something?
It's a little abstracted from that, but the matching and the core thing is based on it, and again, I was like, wow, this is good.
And it goes on dates for you. Okay. So it simulates what the date might be like between you two, potentially.
I guess.
Yeah. "Your AI goes on dates for you. Receive one high match each week, carefully..." Wow. So fun.
It's good. Again, if you're single. I tried with my newsletter at one point. I was like, oh, you know, honestly the people who read my newsletter are pretty weird and specific, and so, hey, why don't I just offer a matchmaking service where I'm like, okay, if you read my newsletter, you're here, tell me who you are, I will build a little LLM and try to match these people. Didn't work for me because, candidly, you know what happened? Way too many qualified women and not enough men. I just don't have the liquidity. I have a hundred great women who write in being like, "Hey, this is what I'm looking for. This is who I am." You're like, "You are an amazing person." And then the four guys who write in are like, "I want a 25-year-old hot girlfriend." You're like, "Ah, this is not going to work." But June Date might have the liquidity to make it work.
By the way, your newsletter is awesome. Tell people where to find it while we're on the topic.
You actually can't. There's no way to sign up for it. If you send me an email... perfect. If you send me an email, lessin@gmail, I'm fine. Then if I respond, you get automatically added. That's basically how people I'm interacting with get added, or I'll just add you. But it's actually funny, there's not... Oh, well, you know what you can do actually that'll get you on it is if you go to wlessin.com, I have my little bot app up that includes a little LLM that is kind of trained on my writing, just because I was having fun building it. If you enter your email address there and talk to it, it will add you. But no, there's not a signup page.
Okay. I love this contrarian growth strategy. No, you can't really sign up. Okay, that's great. Okay, two more questions. Do you have a favorite life motto that you find yourself coming back to often in work or in life?
No, but I will say that I have hanging in my gym, which I love, from the Facebook hackathon after the launch of Google Plus, this is going way back in history, they made great posters, which was "Carthage must burn." And it was just this great moment in work time when it was like, okay, game on, Google's coming for us, let's go. And I had some of the most fun work experiences. We were working literally 24 hours a day, past midnight every night, in that period, and I love that poster. So, Carthage must burn. How about that?
Great. Final question. You are a fellow podcaster. I really enjoy your podcast called More or Less. It's very cleverly named because of Lessin and the Morins.
We love our Lessin. We also, like, my wife and I are contrarians and hate everything by default, and the Morins, like, think everything is amazing. So it kind of works from a dynamic perspective.
I love it. And Dave Morin, Brit Morin, just to be clear, and your wife, she runs The Information.
Yeah. So she's good at prompting us with what's actually going on in the world and then we just about it.
So what's something you've learned from that experience? I don't know, any surprises about podcasting?
So, here's the thing. I think people, like, it's kind of a weird podcast in some ways because honestly, I don't think any of us are highly filtered, and it's kind of just like talking to your friends for an hour a week, which I want to do. Like, I love the world. We don't live that close to them. So it's kind of fun to just, like, have that time set aside and then cut it up and post on the internet pretty raw.
Here's the funny thing about it. It's fine. It serves our purposes way more than I actually expected it to, which is we enjoy doing it, which is the most important part. We would do it if no one was listening. And weirdly, a lot of our friends and people we care about in the industry seem to pick up pieces they like from it and, like, talk to us about it. So it's like a great conversation starter.
So it's, like, weird. I don't, like, it's not a huge podcast. It's big enough, but I actually think the thing that's been most surprising to me about it is, even though we don't really have growth strategies and we're not trying to blow it up and we don't get paid for it, it's weirdly useful, is what I would say. You know, even the fact that it's, you know, I don't know. I'm not sure if that's your experience too, and I think your podcast is probably much larger than ours, but it's weirdly listened to and useful by the people that we care about, and is fun
despite the fact that
you know, it's not like a, I don't know, it's not All-In or something
yet. I don't think it ever will be. It's way too niche, you know. But we have fun. I mean, I would happily do it with my friends if no one was listening. And then it's kind of wild that a bunch of people that we actually do care about find the pieces that are interesting. And it actually is helpful from a business perspective because you about something and then some entrepreneur shows up and is like, hey, by the way, here's a better idea. You're like, that's great.
Sam, you're awesome. 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. Two final questions. Where can folks find you online if they want to reach out for check?
Look, our venture firm is called Slow Ventures, slow.co. I'm Sam Lessin. I'm kind of Lessin everywhere, whether it's Twitter or Instagram or whatever you use. Or just lessin@gmail, my last name, is my email address, and I do read it. So I don't know. I appreciate you having me on. It's always fun to see you. It's been too long. And I don't know, come hang out in the pool house sometime.
Okay. I love this as an excuse to hang out. Sam, thank you so much for being here.
Hey, great to see you. Bye, everyone.
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
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