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 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 people 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 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. Like 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. It's like 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 like why etiquette matters in 2025 for founders, almost 2026. Like one, you know, we talk about software getting commoditized. We talk about all the fear-mongering and scared people feel about Silicon Valley and AI and like all the things that are going on. The net is, if you want to do business and you want to build great partnerships with team members, you know, 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. You know, and when technology is no longer some cute sideshow but is like a major deal, like people are worried about losing their jobs, like understand how to meet people where they're at, build trust, you know, mirror kind of expected behaviors. These are all like tools, right? So that's the deep truth. The shallow truth is it's kind of funny to teach Silicon Valley people etiquette, right? Like the whole narrative for so long has been none of this matters, just focus on your product. Saying, well, actually it does matter. And you, 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 like that's kind of... there's some... 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. Is like again, I think... you and I are now old people, right? But like...
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, like this is my shot, right? Like 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, like you're going to project totally the wrong vibe. And I can understand why you'd be like 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. Like 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, like 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, like I don't know why you wouldn't want these skills, right?'
Yeah. That is one way to think about it. Like, you can be successful not doing any of this, not knowing any of this, and you're just hurting yourself.
You're creating an unnecessary uphill battle for yourself. I'd also say that, look, this goes back to like 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? Like if you just... if you fully... that's it, you know, it's like... it's literally like that happens. It happens very, very rarely, but it does happen. It is about not what 99.9% of startups are doing, but if you have that, yeah, you basically can get away with anything. It is true that doesn't mean you shouldn't be a jerk. And like candidly, over the course of history, you need to work with great people and like you'll be more successful if you show up with good etiquette and rules and context. But like there are ways in which that can trump all. It's just like candidly not the experience of 99.9% of startups.
Awesome. Okay. So let's get into it. There's kind of... you divided this book into about 10 categories, 10, I don't know, 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 like 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, like 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 like a limited edition. You know, there's a bunch of... 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 the good, 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? Like, you know, again, I say this as someone who, I'll be honest again, 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 in racing into the room five minutes late, your heart rate's up. If you come in, 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 like 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?' Like, so I think that's kind of another really kind of obvious one, but an important one. Something I've seen, I'll go for a few others that we talk a bunch about, is look, you want to have a strong handshake, firm, don't crush the person's hand. Again, this is not... you know, practice on your friends, right? You know, you want to repeat names back is 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 like you're actually trying to remember the person's name, right? Like a lot of times people meet a lot of people. It's like, 'Nice to meet you.' You move on. First, it's going to be harder for you to remember the person's name. Second, it actually shows like 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 for 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 think this is like... I've seen this with entrepreneurs and like I get... like I'm a VC. I do get scheduled in like 30-minute chunks back-to-back like all the time, especially on Zoom. Guess what? I am frequently late. I don't feel good about it, but it happens, right? And a lot of times founders, most of the time I'd say founders know that like if I'm late, I will always apologize. I'll try to email them ahead, etc. But then it is what it is. And like we kind of get right into it. Every once in a while you'll have some founder who like is super indignant about it, right? They're like, 'Oh...' It's fine if you feel that way, but it's really not very productive to make a big deal out of it, right? Like if this is a deal breaker for you that I was a few minutes late, then like I don't... then now I feel like I'm wasting the next 25 minutes of my meeting time because like I'm not... like this is going to be the wrong dynamic, right? And so I just think there's like, 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. Again, people are taking their time to meet with you or at a party. They're like taking their time to like listen to you. And it's just a matter of respect to be like, I'm actually here for this conversation. I'm not off on my screen. I'm not like glancing around the room. Now, look, there are some people, we all know this, who are like literally quite neurodivergent. And that's very hard for them. Like that happens. And a lot of founders have like neurodivergence in some ways. Like there is grace in this to a point, but it's a thing you should make at least an effort. I think one of the most important things about all this stuff is what matters in some ways is the signaling of the effort as much as the actual thing, right? I think is a really big overarching theory. So it's like, 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, like 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, yeah, you know, 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's this whole thing, let's pretend you're with your partner or with someone who's a friend. It doesn't have to be a 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 like what you're supposed to do, the etiquette is say, 'Lenny, please meet my wife Jessica.' You know, and like that's, 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 kind of like 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 like if you're really in tune socially, you kind of know what's going on, right? Like you know what I mean? Like you're not an idiot. Like you know that, oh, like what is proper, what this person is doing, there's a gap between it, there's a reason. The reason is, but it's at least enough plausible deniability of like semi-bad etiquette that leverages the social situation to be better etiquette, right? That it's a useful thing to think about as a small hack.
I am so bad at remembering names. I like... I think I have a medical issue, so I just can't remember names. So this tip alone is so good.
And just to reinforce it, so there's almost like 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, Michelle, meet my wife, Michelle.' And then they're like, 'Oh, I'm Bob. Nice to meet you, Michelle.' Or it's like make it a little more awkward of just like, 'Uh, Michelle, meet, um, like...' and then let it hang. Is that the...
'Michelle, I want to introduce you,' right? Or something like that, you know, something like that. Or 'I want to introduce you to Michelle.' You look at them in the eye, right? And then your wife would 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 also... I actually have such a clinical problem on name-face recognition that actually runs in our family. I have this whole backstory, which is part... you know, I worked at Facebook for a long time, was really into it early on. 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? Like, and this was like 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, I mean, on the conversations front, I mean, I think the key again is to welcome people into the conversation. Like consider it, you know, there's especially... you see this happen sometimes, especially when there's weird power dynamics at play. You know, you'll see some famous VC or founder walk into the room and then some young startup person will like waylay them, right? And like kind of almost like flock them off, right? And they're like really excited to talk to this person, but you're like, there's a bunch of people around and like the more you can be inclusive, again, low heart rate, you're not like... it's not a scarcity mindset, it's an abundance mindset. Like I think that's kind of like the tone to think about in terms of like what a conversation is and like how to show up in a room and meet with people. Um, you know, another really big one we harp on a lot in the book in kind of a bunch of the panels is like ask questions, but there's a limit, right? So asking questions is great. If you're coming in and it's like, 'Hey, hey, it's nice to meet you. Let me give you my four-minute startup spiel and everything I'm into,' that is like 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 like 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 like 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? Like if you can come in... the best conversations are coming in, someone comes in and gives you an idea or has a point or sparks something, then you have... it's like a game of ping pong, like then you can kind of react to and it goes back and forth where there's openness and they're playing with you, not playing single player, right? Is almost the way I would think about it in a conversation.
So the tip here, so it's basically index towards asking questions, but not like 100%.
Yeah. Consider almost... put it this way. Imagine you're playing ping pong, right? Or tennis or whatever you want. Like 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? Like that's kind of what the flow should be. If you hit 10 balls at them in a row or like, you know what I mean? Or like, you know, that's kind of like 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 know, you want to make people feel good and welcome. You know, I'm not saying that, you know, you should walk into a room and start talking in jargon, but like I am saying like if you're speaking to a university professor versus a 12-year-old, if they're using a certain level of vocabulary words, like again, the point is to meet people where they're at in a way that makes them feel relaxed and good, not try to like 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 mean, I think in the end of the day, like 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 who walks across the room says, 'Hey, you really should talk to Lenny. Talk to Sam.' Like that's kind of like 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 there's, you know, again, like 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, we're used to, especially if you're young and these are big opportunities or big moments, people are kind of used to this like environment of scarcity. It like reminds me of the Eminem song where he talks about like a 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 got to listen to it and pump yourself up, right? But like, 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. I mean, there's a bunch of tips about, I think, you know, generally famous people, but like I think there's this thing which is like not being sycophantic is what I basically say, but also like you not being ridiculous is almost the way I would frame it in this conversation, right? Which the ridiculous is like 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?' Like it's like 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, I'm like, 'That was a pretty nice person. Like, 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.' You know, like that type of stuff I think matters.
Maybe one last tip is this. You actually start with this one, this line of 'great to see you' when you meet someone versus like 'nice to see you guys.'
Well, again, Lenny, you and I probably use this all the time, I bet. Because I 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 really great, it's great to meet you,' and you're like, 'We've met five times.' It's like quite embarrassing, right? And for them, for you, for everyone. The more I like... In fact, my wife, my wife of many, many years who I've dated since college, has a really funny story about this, which is the first time, 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 saying like, oh, like not knowing if I've met someone before or not. She's like, 'How can you... 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 like that's okay. Like that's part of the etiquette dance to some degree is like that's fine. And what's not fine is 'it's so nice to meet you' and like 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 like subtle fragrance.
Yeah. Don't smell like [__], right? Like it's like don't overpower it. You know, you shouldn't smell like you just doused yourself in perfume, right? Or cologne or whatever it is. But like you also shouldn't smell bad, right? And like it's again, your scent should not be noticeable is almost the way I would put it. Um, you know, in any direction. Uh, it's not... you're not... there's no advantage to that is basically what I would say.
By the way, this is a good question. Does this advice apply both equally to men and women? Is there anything that as 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 a what we've internally been calling the femme 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 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. This is a good... 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? And like there's certain things they're like not bad at, but broadly speaking, I have an 8-year-old, a 6-year-old, and a 4-year-old. And like 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 in life. I'm like, I can't be the etiquette guy if you guys are eating like... So I've been put... and some of them have been really cute. Others have been really funny. Like my 6-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 6-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 like a modern way of thinking about it.
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. We're working on it.
I was just speaking... I was just listening to Tyler Cowen 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 like experimenting until something works.
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, yeah. Okay, the other tangent is you did share the class you actually taught to founders already, so maybe share a little bit about this class you taught.
Yeah, so I mean, 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, it was at the Four Seasons. We did some stuff that was fun and a little bit irreverent, like we had some very fancy Wall Street banker 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 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 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. When I, 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, 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 you 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? Um, 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.
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? Because like, but 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, in 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, 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 of your 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 setting? 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 can 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 expectation. 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, I don't, 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, there's no, that's not a game of ping pong. Like you're not, but like it's totally fine to call and be 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's 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.
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 professionals spend 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, 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 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. Um, 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. And then I think look, in terms of asking, ideally don't order first, right? Because I think if you see how someone, like are we doing starters? 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 the better. Like you kind of want to go middle of the pack to last if that makes sense.
So this, yeah, so this 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, 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 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? Um.
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 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 in equals and like I'd love to offer or just pay as a 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 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 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 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 you, like if you're going to 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.
Just tip a lot. Like I think 10, 20% is the minimum. Like if you're out in like a situation, 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's not, it is a squirrely topic. And I just, I don't, again, let me put it this way. I don't think you want your tip to be memorable is almost the 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 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 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 it, don't even tell anyone basically, but feel free to do it obviously.
Sure. Yeah. I mean, you don't really, the tip is not a point. The tip is like everyone should feel good about it, right? Like and like again, it's about 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 fancy 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's like 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 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, 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. This is, 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 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 and probably not venture scale, but I don't care. In 2026 it might be, you know, everyone has the problem. Everyone globally has the same problem which is tipping.
Yeah. Just the token 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 Bistroatics 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. No sommelier 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 a taste, it's great.
I love that. I would love to do that. That sounds really nice.
Yeah. Okay. And one other tip here. I wrote down B for bread, D for drinks. Explain that.
Oh, BD, you just got to look at your hands, right? B's and D's for, 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, uh, 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. Um, but that's the B and D is useful. Uh, also like look, forks and knives, like just knowing what side they go on, knowing, one guy always drives me nuts, um, 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 know, like 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 thing, people started sending me videos of them like dining or situations and ask 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 and lap.
Napkin and lap. Not at your neck, not off to the side, you know. Napkin and 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 like 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, 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 about humor is it kind of, 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 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 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 got to be pretty confident before you tell it, right? In space. Uh, the last thing you want, like 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 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, but like I have like an Evernote, it's not Evernote anymore, it's like a Bear of like my favorite jokes and they're loosely ranked from least offensive to most offensive. Um, because like I forget the jokes, but like you know, you kind of want to use humor sparingly and smartly.
This is your next book. This list of jokes.
List of jokes ranked by like social situation and like 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. It's a funny, 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, that's it, it's just like you can make fun of yourself as much as you want, right? Um, again, making fun of other people shows an incredible level of familiarity, right? And if it, you know, if you're there with your business partner and you're really feeling the vibe and you, 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 that you, 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-pleasing kind of stories to tell.
Yeah, you want to have some easy stories that 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 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 like 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. Like again, I really think of it as like a conversation or these social interactions is a ping-pong game, right? And like 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?
