YouSaid · the spoken record

Sam Lessin

lines on the record: 134
first: 2026-01-15
most recent: 2026-01-15
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“How does it feel, right? Does it feel like you're asking a ton of the person you send us here? 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 these silly, not using emoji, trying to make it readable. Like these are all important things.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Use emojis, try to proofread your stuff, get to the point quickly, assume the person you're reading is busy. Again, I think these are all the types of things that none of this is rocket science from my perspective. But people, it's just good to remember, right? And be on top of it. 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 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“And that's perfectly fine, right? In terms of the way to do it, I just think the key is to make it easy for the person you're trying to do business with, right?”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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 like accepting a cold meeting and showing up to be like you are not the person I expected because it's like I was 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“I'll be honest, I go the other way. I really don't use any of that stuff. Look, I think scheduling is very complicated. This is part of it. I always think of these animals, like 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 like four in the morning my time, right? Or like I'm totally, you know what? I'm going to make it work, right? And like, so I do think like I'm actually kind of against the flat hierarchy, all meetings of the same. That does mean, honestly, I think you probably knock me. It's like my bet is that my calendar moves more than most people's. And I'm sure that feels disrespectful to some. And it is like I want to be really clear, but it's also the reality of trying to balance these things.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“The general story of make the gatekeepers happy and like you is true, but I do the other way to overdo that for what it's worth. It becomes almost too transactional. If you show up with flowers for the EA, you know, like. You better be damn confident in what you're doing, if that makes sense. But. Just like the small things go a long way, like you just make eye contact with them, thank them, respect them, ask, you know, if they bring you a coffee cup, ask them where to put it, what you're done, like don't treat. People who you might who feel like the team or the staff feel that way, make them feel like part of the team at equals.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“You really need to respect EAs and PAs and the whole people. The number one way to look extremely classless is to not respect people who are helping the other person, right? Like this is like the number one thing. Now, you don't need to be so over the top exuberantly. 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 where they schedule and like following up with them and things like that.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Both scheduling, you're getting the numbers right, but then also, really importantly, especially at reasonable times. Like sometimes people like, I want to meet at this time. You're like, you're on EST. That's like four in the morning for me, right? And so I think being respectful of that and just asking, I think is super important. It's not rocket science. It's important. Last point I make, which you make in the book is like,”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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 that like in some ways that 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 that comes up all the time. Look, rescheduling happens when you do it. give notice as much as possible. Once you are asking for rescheduling, you need to be even more accepting of what the other person can do, right? I think is really important. Like 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 besides forget. Like, time zones are really tricky. People screw them up all the time. Check. It's worth the extra check to make sure you're not.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“No bad press and no bad tweets. Yeah, so I think there's a few obvious ones when you're make sure you have availability. 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 like. Make it real like you have to give them real options, you know. The default, I really strongly believe the default should not be calendly. The default in most situations, especially if you recognize the power hierarchy, the business hierarchy. If you're the less senior person, if you are the less busy person,”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, well, like, I think I'd like to say that I'm fairly famous for hating Calendly. I think I'm not overstating it when saying there was a period where Calendly where I personally had driven most of their growth for the month. I got messages from the board because I went on his diatribe about how much I hate calendar and how disrespectful it is. And apparently this was such an internet fervor. I got like millions of engagements that meaningfully drove their month.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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? Like in some ways, like give them their next partner. You know, you're like, oh, like I've enjoyed this conversation. It's super cool. You know, by the way, have you met Steve? Let's go meet Steve. Go talk to Steve for a bit, right? And like, I'll pick you back on. But okay, I'm going to go say hi to my wife. You know, like there's ways to handle it again. The key though is subtlety on these things, right? Like, I think in all things. Like, 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 like plausible deniability to themselves and the community effectively that we've wound down this conversation. I mean, so you have to kind of look for the signs.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm going to go get a drink. Do you want it? And then every once in a while, the person will be like, you're like, if someone says to you in a conversation, they'll wind it down. I was like, I'm going to go grab a drink. Most of the time, that is not an invitation saying, I'd love one too and fall into the bar, right? Like that, that is not so like, I just think you have to kind of recognize the signs effectively when the moment is passing or it's time to move on, et cetera. And then like respect it, that's what I would say.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Just like when the conversation is over, gracefully leave basically the upshot the worst is like the conversation ends and the person just stands there and you're like, uh.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, you want to have some easy stories that are again like it shouldn't be 10 minutes, right? But again, I think the thing about it is like imagine that the whole game in these social settings 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 like who's carrying the conversation. It shouldn't be your monologue. You shouldn't force them to monologue either, right? 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. Like, again, I really think of it as like a conversation or these social interactions as a ping-pong game, right? And like you kind of want to have a few of those in your arsenal.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“It's just like 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 and 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 fine.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“There is a funny joke about that, right? Which is the whole. Prisoners, I won't even tell it. It's a funny, there's a funny joke about people who know all the jokes.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Is like a very subtle thing, right? So you don't want to tell a knock knock joke, right, when like with adults, right? But the off-color sex joke that is hilarious, you've got to be pretty confident before you tell it, right, in space. The last thing you want, like I think a joke that everyone laughs at is great, a joke that Noah laughs at is like a huge risk maneuver you failed, right? And like it's not the point. So it's a great tool. I love it. Like I think everyone should have their file of jokes. I do. I don't know about you. Like I have like a Evernote. It's not Evernote anymore. It's like a bear of like my favorite jokes. And they're loosely ranked and from least offensive to most offensive. Because like I forget the jokes. But like, you know, you kind of want to use humor sparingly and smartly.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Here's the thing Humor's 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 like 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 to think about humor is it kind of there's this interesting subtlety to why it's so useful in social studies, which is one it kind of shows the ultimate mastery of a social situation. If you're able to tell a joke which is right up to the line or even pushes it one degree to show your own comfort in the space, right? So the ultimate demonstration of comfort in a space is to tell a joke that's a little over the line or a little off color, but not too off color. It's like the ultimate thing. So like if you're really in it and like feeling good using humor is great, you should not be remembered as only the comedian. And again, like the level of jokes that you're playing with.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, BD, you just got to look at your hands, right? B's and D's for to know which was your breadplate is kind of the way to think about it. Look, people get this wrong all the time. You sit down at a big table, right? And you're like, which is mine that 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&D is useful. Also, like, look, forks and knives, like just knowing what side they go on, knowing women 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 like stab your partner next to you. But like it was really funny, I had an entrepreneur. This is not yet a product. People started sending me videos of them like dining or in situations and asked for feedback, right? And I recently had to give feedback to an entrepreneur who was like, you did a very nice job eating your soup. Good job. Your napkin should have been in your lap.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah. If you were to say nice, I'll be very clear again in terms of Order a very nice wine No Somalia really cares what I'm drinking. But if you are doing that or you're into it, which is great, again, like think about being generous, right? If they're like, oh, I would love to taste that, like it's great”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“So, basically, the idea is that after the improbability drive, the way they're able to move across the unit very quickly 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Actually, reminds me, I'm reading one of my sons right now, the third book of Hitchhiker's Guide to the Galaxy. I don't know if you've read this series. Yes, yes. Do you remember what's a Bristow Mattox?”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“You know what? It's 2026, it might be. You know, everyone has the problem, everyone globally has the same problem, which is tipping.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“If someone pitched me the 2026 AI driven tipping calculator, which gives 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“It's like instead of a tippy 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's like, it just tells you what's a tip.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“There's a great tipping episode. I feel like you could honestly have a very funny modern LLM app that is only about tipping. Like imagine a tipping app where it's like.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Tipping guide. Well, you know what would be funny is like there's a great episode of Seinfeld that's all about the tipping calculator. I don't know if you're a Seinfeld guy.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. Yeah, I mean, you know what? If it's not a point, the tip is like everyone should feel good about it, right? Like, and like, again, there's about, 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Almost the way to put it, like this is not a thing to focus on when you think when the person out to dinner with thinks back on their dinner a month later, they want to think about the content of the conversation or what the ideas were or the business opportunity. They 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, it's fine. They can afford it. It's like cool that they did that for the server, but honestly, the only thing I remember for the night is how much the person tips.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Just tip a lot. I think 20% is the minimum. Like, if you're out in a situation, 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's not it is a squirrely topic. And I just, I don't, again, put it I don't think you want your tip to be memorable.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Tip the way they would tip, and they're going to 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 going to do that, you really have to tip well.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“But I will say, I'll tell you a funny story, which is like when you go out with dinner to really fancy people, right? Or like someone who's like, 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 and equals and like I'd love to offer or just pay as big. The second thing which is important is if you're, 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 like a, this is not in the book. This is like a 201 course, right? But if you go out and start with someone that were like, okay, they're either known or relatively known known and you're making the gesture of buying it not because 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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?”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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 put a card down 99% of the time, they'll be like, I got this, like, please, like, this is, 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, 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, you know, 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, right, don't not tip, don't tip badly. Don't be super stingy about, you know, okay, who ordered the flambay? You know, like split bills evenly, make things easy for waiters. In general, don't order the most expensive thing on the menu. Does it really matter, especially 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 is truly sensitive to what things cost, even if it doesn't actually matter, right? So I think there are things like that. Same with wine. 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, what like, what, 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“I really 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 if that makes you know from that perspective again the well tailored great that makes a lot of sense the like basics i can say yeah like have genes 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 gonna she's gonna be chuckling”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations. Down to like, which forks should I use? 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. 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 pick game of ping pong. But it's totally fine to call me like, hey, like, what's, you know, what's this going to look like? And by the way, it's important because in New York versus San Francisco, there is different expectations. Like people do things differently. And like your job, you're not expected to know every nuance of every culture you might enter.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“People can have no idea what things cost, right? Like, if you said, like, you know what I mean? It's just not, and like, so in some ways, it's this weird thing where it's like if you show up at 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 to the situation, what people actually can prioritize. And it's like, are you trying to impress me because you have a fancy outfit? What are we talking about?”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“I would have put differently. Think about the average person, not every person in the world, but the average person in the world can look at a suit. Do like intuitively that seems like it fits the person who doesn't”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“100%. Like at the end of the day, fit is everything, right? I say this 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? Because great. Like you got to have a little bit. You're a startup founder, you do want to kind of address to the level of the room, but you kind of shouldn't show up and 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 rates, trying too hard. You know, you're not going to trick anyone, right? Is the upshot, right?”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, like, look, I gotta say again, in terms of know the rules, but don't always follow them. When I my first job out of college, I was an associate at bathing 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 and a consulting firm, what we call 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 and tuxedos. So it was like, you know, you know the rules to break them. It was fun. But 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 you don't overdo it is basically the upshot, the most simple way to address. 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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'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 really has no respect for their room.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't know. I mean, I don't really understand what makes Gary Tan mad, and it's fine, but from my perspective, I think, yeah, I think he's just, 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. I guess that their fault, they're like young kids, they've been hold up in a room coding, and that's all they've been thinking about for months or whatever. And so 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.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I mean, before the book, we did a class specifically initially for YC founders, right? Partially because YC, Gary's hang got very mad about this. So I'm like, well, now I have to do it, right? Because that's very funny. But yeah, we basically gave them all certificates of completion. But we did a class. We hosted it. It was at the four seasons. We did some stuff that was fun and a little bit irreverent. Like we had some very fancy woke spash for people come in with models and show a 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 the actual meat of the matter, right? Which is things like how to show up at a low heart rate, how to have an abundance mindset, you know, basic skills, like looking people at the eye, shaking hands, you know, how to eat like the shows that you're being respectful, things like that.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Right, like to be clear, they're able to feed themselves. It works. But it's like you look at it, and it's like, what are you doing? Yeah.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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 like not use a fork and knife like animals right now, but we're working on it.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, look, here's the funny thing I literally have realized in doing this, I love my children, they have terrible manners, right? And like there's a certain things they're like not bad at, but broadly speaking, I have an eight-year-old, a six-year-old, and a four-year-old. And I'm like, wow, you guys eat like animals. Like, you just, you know, you don't know how to use a fork or knife properly. Again, it's not like at four or six, it's not like stopping them well in life. I'm like, you, I can't be the etiquette guy if you guys are reading like. So some of them 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 or my children's etiquette.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a what we 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. I think the frag was one I would say, I don't think you want your fragrance to be memorable for anyone, no matter what your gender is.”
2026-01-15 · Lenny's Podcast · How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · IDENTIFIED FROM THE TRANSCRIPT · source