Lenny's Podcast: Product | Career | Growth - How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin

Starting point is 00:00:00 I just feel like no one's being honest and teaching founders of this. Be early. Don't order the most expensive thing on the menu for a video call of an appropriate background. Don't smell like shit. 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 in some ways abrasive on purpose.

Starting point is 00:00:20 You want to go to show up in a way with 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.

Starting point is 00:00:39 If you show up like a little energizer bunny, you're going to scare it 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 Lesson, partner at Suss.

Starting point is 00:01:00 Slow Ventures, previous VPA 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 the 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

Starting point is 00:01:39 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 this very unique episode. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get a year free of 19 incredible products, including a year free of lovable, Replet, Bolt, Gama, N-8, and Linear, Devin, Post,og, Superhuman, Descript, Whisperflow, perplexity, warp, granola, magic pad, and Jurycast, IPR, D, Mobbin, and Strait Atlas. Head on over to Lenny's newsletter.com and click Product Pass. With that, I bring you

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Starting point is 00:04:16 That's getdx.com slash Lenny. Sam, thank you so much for being here. Welcome to the podcast. Blast to be here. I'm excited to 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?

Starting point is 00:04:40 That's so unlikely. That's the Venn diagram that we aim for. I also think it's going to just 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?

Starting point is 00:05:01 I really enjoy things at the intersection of hilarious and useful, right? You kind of need both, right? And hilarious is 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, like, it's very hard to cut through the noise these days. So kind of you need 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 due with a tweet. It got escalated into an event. It's gotten escalated into a book and a bunch of other stuff.

Starting point is 00:05:37 I kind of believe that, you know, you should always, there you got it. You got it with you. I've got my copy 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 of this 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 do business and build great partnerships with team members, you know, with companies you want to do business, almost with anyone, the reality is etiquette ironically matters a lot, right? There is a deep truth to this, right? You especially when you're asked

Starting point is 00:06:20 people to trust you with their data, trust you with their business, you know, this, and when technology is no longer some cute side show, but it's like a major deal. Like people are worried about losing their jobs, like, understand how 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.

Starting point is 00:06:48 I think, well, actually, it does matter. And I'm wearing a T-shirt. I'm not exactly known as the most high etiquette personal, 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,

Starting point is 00:07:03 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, Yeah. This is the thing I think about it. Again, I think about, again, you and I are now old people, right? But like, you're young. I feel that you feel it in your bones. It's like you're young, right? You're in, 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 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 you and I need to convince this person of that and make this connection. It becomes very transatlantic. It becomes very transnational. actionable. If you show up like a little energizer bunny, right, you're going to scare one off. Like, you're going to project totally the wrong vibe. But 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

Starting point is 00:08:01 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, 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. It is one way to think about it. Like, you can be successful not doing any of this, not knowing any of this. It just, you're hurting yourself. You're making it harder. Yeah, it's just an

Starting point is 00:08:38 unnecessary, you're creating an unnecessary uphill battle for some. I'd also say that, look, this goes back to like technical differentiation where things are at. It is true that if you bring mana 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 not what 99.9.9% percent 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 should. You shouldn't be a jerk. And like,

Starting point is 00:09:16 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, and a social situations is one way to describe it. So let's just go through reach one and just give us some pieces of advice. Sure. 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 in your podcast is I was like, wow, this is really interesting. I did not

Starting point is 00:09:50 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 of 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 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.

Starting point is 00:10:29 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 in the room five days late, your heart rates 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 late, I'm sorry, if you're not early, just apologize. It doesn't need to be like a five-a-and-fire rig, and it goes back to this heart-rave thing. You can just apologize simply and move on.

Starting point is 00:10:56 I've seen people screw this up so many times, right? When they come in flustered and all over the place, you're like, it's okay. We understand, right? Like, 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 in kind of it 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 what you're meeting. Someone I 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. Yeah. Do you do the opposite of what you're doing. Of what you do. 100%. And I think this is like, I've seen this with entrepreneurs. And like, I'm a VC. I do get scheduled in like 30 months. minutes 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

Starting point is 00:12:17 time I'd say founders know that like if I'm late, I will always apologize. I'll try to email them ahead, et cetera. 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, they're like, 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, 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?

Starting point is 00:12:48 And so I just think that it's like, don't harp on it. It's okay, you know? You had also some advice on eye contact. Yeah, it's really important. Again, I think the thing of your mind is, especially in the age where everyone's used to be 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.

Starting point is 00:13:07 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 in 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 neurodivergivers in some ways.

Starting point is 00:13:27 So 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 it's 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. So like, look, this happens all the time. And again, in the spirit of I'm not

Starting point is 00:13:57 permitted this either. If you're with your partner, introduce them first, right? bring them into the conversation. One great trick we talk about in the book, which I really unfortunately use all the time, right? Is 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,

Starting point is 00:14:13 whoever you go 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 find someone's name. And like, that's what you're supposed to do, the etiquette is say, Lenny, please meet my wife, Jessica,

Starting point is 00:14:26 you know, and like that's, you know, that's kind of thing. Now, here's the thing. This is where you start betting rules. What if I don't remember? your name, right, if you have your partner with you, you can flip it right and say, Jessica, I want to introduce you and then you kind of like can kind of figure out how to flame it up so that you then, Lenny, extend your hand and say, it's really nice to meet you, Jessica, and you get

Starting point is 00:14:42 to pick up the name again, right, or things like that. So there's, you let it hang. You let it hang, which, by the way, it's a great example of fact that, 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, oh, like, what is proper? What this person is doing?

Starting point is 00:15:00 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 a better etiquette, right? That it's a useful thing to think about as a small cue. I'm so bad 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 like two ways to do this is what you're describing. Either it's like my wife's name's 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 Michelle meet like and then let it hang is that is that Michelle I want to introduce you right or something like something like you know it's something like that or I want to introduce you Michelle you look at them in the eye right and then and then your wife's 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 for this worth I actually have such a clinical problem on name face recognition that's actually runs in our family. I have this whole backstory, which is part, you know, I worked at Facebook for a

Starting point is 00:16:03 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? 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 conversation fronts, 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

Starting point is 00:16:41 walk into the room. And then some young startup person will like waylay them, right? And like kind of almost like block 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, like, low heart rate, you're not like, it's not a scarcity mindset. 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 how to show up at a room and meet with people. You know, another really big one we harp on a lot in the book in kind of a bunch of the panels

Starting point is 00:17:10 is like ask questions, but there's a limit, right? So asking questions is great. You're coming in and says, hey, it's nice to meet you. Let me give you my four minute startup spiel and everything I've into, da, da, da, da, da, is like so self-centered. It kind of misses the point that a conversation is a, 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

Starting point is 00:17:36 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 to 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, someone comes in and gives you an idea

Starting point is 00:18:04 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 it and it goes back and forth where there's openness and they're playing with you, not playing single player, right? It is almost the way I would think about it in a conversation. So it's up here. So it's basically indexed towards asking questions, but not

Starting point is 00:18:20 like 100%. Yeah, consider almost like, 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 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 and jibe. But like I am saying, you know, 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.

Starting point is 00:19:16 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 better you meet someone you're really interested in or whatever.

Starting point is 00:19:33 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 love to hear from them again or meet with them again. Or maybe even better. Everyone's wild. It's like, wow, that's a really interesting person or idea. The person walks across through someone else and says, hey, you really should talk to Lenny.

Starting point is 00:19:52 Shut to Sam. Like that's kind of like you want to leave them being like, that's interesting. And I 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.

Starting point is 00:20:07 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?

Starting point is 00:20:26 I'll go so far 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 you the Eminem song when he talks about like,

Starting point is 00:20:40 I have one shot, one opportunity. I think it's, oh Eminem, yeah, yeah, yeah. It's a great song. It's a great song. Great beat. Everyone's 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?

Starting point is 00:21:06 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.

Starting point is 00:21:24 You get so much 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're 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 in, he is and you're like, hi, I'm Sam and who are you? You're like, what are you doing? Like, it's

Starting point is 00:21:54 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 to just, 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 have talk to them again, right? Now, going up and me 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.

Starting point is 00:22:28 Maybe one last tip is the, as you actually start with this one of, in this line of great to see you when you meet someone versus like nice to see you again. Again, Lenny, you and I probably use this all the time, I bet, because I honestly, again, we go to my name phase or whatever. It's really difficult social situation to put someone in. It just think about from their perspective. If you go up to someone and say, hey, it's really great. It's great to meet. you like we've met five times. It's like quite embarrassing, right? And for them, for you, for everyone. So the more I like love, in fact, I, my wife, my wife of many, many years I've dated since college has a really funny story about this, which is the first time right before we started dating,

Starting point is 00:23:04 I went up to her. And I basically did a nice to see you line, right? And 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. saying like, oh, like, not knowing if I've met someone before or not, she's like, how can you? 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

Starting point is 00:23:29 because it works, whether you meet them or not. Yeah, and again, it's one of those things where here's the thing. People are dumb. If you go around saying, nice to see you to everyone, they're like, there's a small percentage of this person doesn't remind me who I remember who I am. And there are other ways or keep, but like, that's okay. Like, that's part of the etiquette dance to some degree

Starting point is 00:23:47 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.

Starting point is 00:24:01 One is just like subtle fragrance. Yeah. Don't smell like shit. Right. Like it's like don't overpower it. You know, you shouldn't smell like you just douse yourself in perfume, right? Or cologne or whatever it is. But like you also shouldn't smell bad.

Starting point is 00:24:14 Right. And like it's again, your scent should not be noticeable is almost the way I would put it, you know, in any direction. It's not, you're not, there's, there's, there's no advantage to that. That's 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?

Starting point is 00:24:33 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 are 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 Freig was one I would say, I don't think you want your fragrance to be memorable for anyone, no matter what your gender is.

Starting point is 00:24:59 Awesome. This is good. Let me take two tangents here real quick. One is, I heard you told the story on your podcast about your kids and the impact this has had on them. Maybe share a story. Well, look, here's a funny thing. I literally have realized in doing this.

Starting point is 00:25:13 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 8-year-old, a 6-year-old, and a 4-year-old. And, like, I'm like, wow, you guys, you guys eat like animals. Like, you know, you don't know how to use a fork or knife properly. Again, it's not like at 4 or 6. It's not like stopping them well in life.

Starting point is 00:25:31 I'm like, you, I can't be the etiquette guy if you guys are reading like. So I've been, I've been putting it. And some of them has 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 at the table,

Starting point is 00:25:51 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. Then 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 meal, whether it's a man or woman, you stand up as like a modern way of thinking about that. That might be better is what I would say. I will say that it's an ongoing, somewhat hilarious to be at our dinner table. I'm just trying to get them to, like, not use a fork in knife like animals right now, but we're working on it. We're working on.

Starting point is 00:26:21 I was just speaking of that. I was just listening to Tyler Cohen had Allison Gopnik on this 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 and tell something works. Right. Like to be clear, they're able to feed themselves.

Starting point is 00:26:38 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 didn't share the class you actually taught to founders already. So maybe share a little bit about this class you talk.

Starting point is 00:26:49 Yeah, so, I mean, before the book, we did a, we did a class specifically, initially for YC founders, right? Partially because YC, Gary Tang got very mad about this. I'm like, well, now I have to do it, right? Because that's very funny. But, but yeah, we basically, you know, we gave them all certificates of completion. But we did a class. We hosted it.

Starting point is 00:27:06 It was at the four seasons. We did some stuff that was fun and a little bit irreverent. Like we had some very fancy Wilkesbash for people come in with models and show, talk about dress at different types of events. 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 with a low heart rate, how to have an abundance mindset, you know, basic skills, like with people with the eye, shaking

Starting point is 00:27:34 hands, you know, how to eat like that shows that you're being respectful, things like that. Why do you think Gary 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, don't really understand what makes Gary 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 and cheat. 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 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

Starting point is 00:28:06 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'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

Starting point is 00:28:44 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,

Starting point is 00:29:01 which I'm excited about. Yeah, I mean, just like, look, I got to say, again, in terms of know the rules, but don't always follow them. When I, my first job at a college, I was an associate at bating 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 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 tuxed.

Starting point is 00:29:32 So it was 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 you don't, 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.

Starting point is 00:30:01 It's an easy way to win. Not two, not three, but one. And oftentimes you can reduce that. Like if you have a suit on, you can take off the jacket and you're less, a little less formal. A hundred percent. And then you talk about fit of the item versus the brand? 100%. Like in the end of the day, fit is everything, right?

Starting point is 00:30:19 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, 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 misfooting $500 shirt, right? And candidly, like, it's the same thing.

Starting point is 00:30:42 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 rates, trying to hard.

Starting point is 00:31:02 You know, you're not going to trick anyone, right? Is the upshot, right? Yeah, this bit of our brand and just expensiveness of the item is such a big one that I think is, 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. I would have put differently. Think about the average person, not every person in the world, but the average person in the

Starting point is 00:31:26 world can look at a suit and be like intuitively, that seems like it fits the person or doesn't. Most people can't 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 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.

Starting point is 00:31:55 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. 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,

Starting point is 00:32:32 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 pick game of ping pong. Like, you're not getting, but like, 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 do things differently.

Starting point is 00:32:53 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. professional spend time teaching and charging for it. I really, you know, I think the answer is find someone in your universe who you think dress as 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, though 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, my wife listens to this podcast episode and here's

Starting point is 00:33:35 me being asked about specifics of dress, she's going to be chuckling. Correct. That's a win. Okay. Let's talk about dining. Give us some advice for etiquette during dining. Tip well, right? Don't not tip, don't tip, don't tip badly.

Starting point is 00:33:55 You know, 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, it's 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 like is truly insensitive to what things cost, even if it doesn't actually matter, right?

Starting point is 00:34:22 So I think there are things like that, same thing like 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 what, 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 of someone takes you out to dinner, like, it's a VC, another family, like someone invites you to dinner.

Starting point is 00:34:54 Or a partner or whatever, whatever it is. Yeah. And look, I think I would say it's in terms of this, which I always 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. If they've ordered a super expensive bottle of wine, like there are, there are limits to this, right? But if you go out to a normal dinner in a normal situation,

Starting point is 00:35:30 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're kind of 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, 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,

Starting point is 00:36:08 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 with dinner to really fancy people, right, or like someone who's like, you're, you know, there are two interesting that it was. 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, it's, 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 big. The second thing, which is important is if you're, especially if you're

Starting point is 00:36:41 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 of the someone with someone like, okay, they're either known or well until you're known and you're making the gesture of buying it, not because they obviously don't care of 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,

Starting point is 00:37:17 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. A lot. Tip a lot. Okay. Just tip a lot. Like I think 10, 20. 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 squirrelly topic. And I just, I don't, again, this way, I don't think you want your tip to be memorable. It's almost way to put

Starting point is 00:38:01 it. Like, this is not a. thing to focus on. When the person who out to dinner with thinks back on their dinner 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 want to think about, oh my God, I tipped an incredible amount of 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, 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.

Starting point is 00:38:34 So you're okay, but I think if you're like extremely rich, you do it, don't even tell anyone basically, but feel free to do it, obviously. Sure. Yeah. I mean, you don't really, this is not a point. The tip is like everyone should feel good about it, right? 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.

Starting point is 00:38:53 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, uh, famic, famic. Femiket. Edition is a tipping guide. A 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.

Starting point is 00:39:12 I love Seinfeld. I don't remember that. There's a great tipping. It'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, it's like, instead of a tipping calculator, you take a picture of the bill, if you locates 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 the tip. Well, like, the tip, like a restaurant's one thing, but then it's like the garbage person,

Starting point is 00:39:40 a gardener, the person that stalls. Especially this time, end of year, like what at the end of year? Like, I think no one knows how to tip anymore. I'd so, like, yeah, some guy that, like, installs those shades in our house. Do I, do you tip that person? I actually, do you tip that person? No, I did not, because that just, because we already paid a bunch of money for this thing. Yeah, no, I feel like that is weird.

Starting point is 00:40:00 I wouldn't tip. people like that. That's why we need this book. You're going to make, it's going to be a huge hit. Well, I mean, we can fund it.

Starting point is 00:40:08 You want to fund it with me? We should fund an app. Talk about YC companies. If someone pitched me in terms of funny but real, if someone pitched me the 2026 AI driven tipping calculator,

Starting point is 00:40:19 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,

Starting point is 00:40:30 but I don't care. You know what? It's 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 this series. Yes. Yes. Do you remember about what's Bristomatics, mathics? 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. Oh, man. What other tip that I just thought of around dining is you have this tip about Somalia is give

Starting point is 00:41:14 them a sip of your wine if you order something. Yeah, yeah. If you order something nice, I'll be very clear again in terms of I don't order a very nice wine. Yeah. 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?

Starting point is 00:41:29 If they're like, oh, I would love to taste that. I like, I love 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. Tell, explain. Oh, BD. You just got to look at your hands, right? Bs and D's for which was your bread, right? Is it 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, ah, 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 is useful. Also, like, look, forks and knives, like just knowing what side they go on. Knowing one thing I always drive 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 have 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

Starting point is 00:42:31 job eating your soup. Good job. Your napkin should have been at your lap and your knife is pointed out of the wrong way. Okay, napkin actually. Okay, so napkin and lap. Napkin and lap. Not in 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 out of the way, right? It shouldn't be memorable. It's like the Kindle. You don't want to think about the technology. No, it just let the conversation flow.

Starting point is 00:43:04 Yeah. Okay. Amazing. Okay. Speaking of conversation, small talk and humor. Give us some tips. Here's the thing. Humor's great.

Starting point is 00:43:13 I love humor. It can be overdone. And again, it shouldn't be the points 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.

Starting point is 00:43:29 But I think the thing that, 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 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? 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 if you're really in it and like feeling good, you're, you're, really in it and like feeling good, Using humor is great.

Starting point is 00:44:02 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, you got to be pretty confident before you tell it, right? In space. The last thing you want, like a joke that everyone laughs at is great.

Starting point is 00:44:28 A joke that no one laughs at is a huge. 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 an 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. 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 of this list of jokes. Lest of jokes. Ranked by like social situation and like level of extremeness.

Starting point is 00:45:01 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 that.

Starting point is 00:45:14 I'll leave you hanging and wanting more for our next podcast conversation. Abundance. Okay. You also recommend self-deprecating as a joke. Make fun of yourself, not other people. Yeah. I mean, 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.

Starting point is 00:45:33 And if you're there with your business partner and you're really feeling the vibe and you're 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 fine. Here's a puzzle for you. What do open AI, cursor, perplexity, Versel, Platt, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, skim, Rback, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS.

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Starting point is 00:46:50 Also, so you said you had this kind of list of jokes that you were, Because I can't remember. I have zero jokes in my head. 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.

Starting point is 00:47:00 I'll have to borrow. So you also recommend having some stories of crowd pleaserie kind of stories to tell. 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 we're about it is like imagine that the whole game in these social settings, again, is putting other people at ease, making it 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.

Starting point is 00:47:31 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. 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?

Starting point is 00:47:49 Yeah, just like when the conversation is over, Grace, leave, basically the upshot. The worst is like the conversation ends and the person just stands there and you're like, I'm going to go get a drink. You know, do you want it? And then once in a while the person will be like,

Starting point is 00:48:03 you're like, if someone says to you in a conversation to 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, like, I love one too and fall up to the bar, right? Like that is not. So like, I just think you have to kind of recognize the signs effectively when

Starting point is 00:48:19 the moment is passing or, It's time to move on, et cetera. And then, like, respect it. That's what I would say. I use that one all the time. Is there any other ways you find useful to wind down a conversation? Just say to get out of a conversation. Well, I think the other thing people do frequently, which, again, is totally fine,

Starting point is 00:48:35 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.

Starting point is 00:48:52 And they're like, okay, I'm going to go say hi to my wife. You know, like there's ways to handle it. Again, like 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 like we've wound down this conversation.

Starting point is 00:49:19 I mean, 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, like, I think I'd like to say that I'm fairly famous for hating Callendly. There is a, I actually, I think I am not overstating it when saying there was a period where Caledity where I personally had driven most of their growth for the month. I got messages from the board because I went on this diatribe about how much I hate Cali and how disrespectful it is. And apparently, this was such an internet fervor. I got like millions of engagements that it meaningfully drove their month. So they thank you for it. No bad press.

Starting point is 00:49:53 No bad press. No bad tweets. Yeah. So I think like, look, there's a few obvious ones. Make sure you have availability. You know, like 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.

Starting point is 00:50:10 You know, the default, I really strongly believe the default should not be callingly. The default in most situations, especially if you recognize the power hierarchy or 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 slot 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 it comes up all the time.

Starting point is 00:50:49 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 is really important. Like, if you're asking the reschedule, you basically, within reason, need to make it work for them, right? Is what I would say. And then look, I think, like, there's, like, obvious stuff that people should notice and just forget. Like, time sounds are really tricky. People screw them up all the time.

Starting point is 00:51:16 Check. It's worth the extra check to make sure you're not. both scheduling, you're getting the numbers right, but then also really importantly, especially at like reasonable times. Like sometimes people like, I want to meet this time. You're like, you're on EST, you're where, that's like four in the morning for me, right?

Starting point is 00:51:31 And so like I think being respectful of that and just asking, I think it's super important. It's not rocket science, it's important. Last point I make, which you make in the book is like, you really need to respect EA's and PA's and the whole people. Like this is 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.

Starting point is 00:51:54 Now, you don't really be so over the top exuberantly. You don't want to overdo it, but there should be this deep well of like 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 like falling up with them and things like that. There's a, I'll tell a story when we were selling our company to Airways. 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 they, if they like you,

Starting point is 00:52:29 it helps. It helps. It helps lubricate the thing. The general story of like make the gatekeepers happy and like you is true. But I do the other 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, like, you better be damn confident, like 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. You know, ask, you know, if they bring you a coffee cup, ask them where to put it when you're done. Like, don't treat people who you might, who feel like the team or the staff feel that way.

Starting point is 00:53:05 Make them feel like part of the team equals. The Calumlee stuff, I feel like that's its own separate book of Cali etiquette. Yeah. Cali, look, Cali only is one of my favorite, my favorite episodes. of going hyper viral on something hilarious. So one thing that Cali only does is you can like embed, I don't do this yet, but I should. It feels like just embedding your times in the email. It feels like a good solution.

Starting point is 00:53:27 Look, I'll be honest. I go the other way. Like I really, I don't use any of that stuff. Like, and look, I think scheduling is like very complicated. This is part of it is, you know, I always think of these emails. It's 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,

Starting point is 00:53:47 Trump. Someone wants to meet with me and it's like for the morning my time, right? Or like I'm totally absolutely based on doing something. 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 like flat hierarchy all meetings are the same. That does mean honestly. I think you probably knock me is 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'm going to be really clear. But it's also the reality of trying to balance these things. The other flaw. with Cali, I realized someone once figured out my calendarly URL and just booked a meeting with me, like a founder.

Starting point is 00:54:24 And I was like, it was on my calendar. I'm like, 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 me 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 adequate perspective. And once you're committed to the meeting, you're doing the meeting even if it's the wrong person. Oh, man.

Starting point is 00:54:49 Okay. Well, one last question with Cali. Something I try to do, I'm curious to get your take is like, okay, someone went like a founder. I'm meeting with a founder. And the way I approach it is like, okay, do you have a calendar or something I could use to book a meeting with you? If not in parentheses, here's my Calenly in case that might make it easier. Yeah. That's perfectly fine, right, in terms of the way to do it.

Starting point is 00:55:11 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 not 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 appshot. Okay, sweet. Move it on to the next topic.

Starting point is 00:55:25 Communication. Don't use emojis. Try to proof read 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, 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.

Starting point is 00:55:43 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 are 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

Starting point is 00:56:07 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 don't, 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 us here?

Starting point is 00:56:26 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 and 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 into the point, you know, not being silly, not using emoji, trying to make it readable.

Starting point is 00:56:46 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 emojis, emoji for my perspective is very, it's like a, it's like quite a step of familiarity,

Starting point is 00:56:57 if that makes sense. If you, uh, from a business context, look, if someone sends you a smiley face, you can respond with it. Like you can kind of like match.

Starting point is 00:57:06 Again, it goes back to this matching vocabulary and language. Like I'm not saying you should be totally cut and dry. But it's kind of, I would say emojis almost feel like jokes. me, which is like, tell them at your own risk and they're probably not worth it, you know? Awesome. Okay.

Starting point is 00:57:21 I do use emojis. I use like the thank you hands one a lot. 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.

Starting point is 00:57:41 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. And emojis sometimes kind of implies use AI to generate this thing because JetGPD loves emojis. Totally. And I'll say like look, I mean there's a whole, we 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.

Starting point is 00:58:14 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.

Starting point is 00:58:39 in iOS and emojis or so. It's like a whole new world and just infinite images. 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 spent a lot of their time

Starting point is 00:58:55 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 love, 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 know, there is a connotation to who you send it to and who you CC and the order in which it people know.

Starting point is 00:59:18 Now, I don't want to like overstate this, but put differently, it's like, if you're saying the email and the first person on the email is the assistant and the fourth person on the email as 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 mind? Well, who are you really sending this to? You know what I mean? is almost the way I think and who's kind of included. So like, if I look at an email and I'm the first person in the two, right?

Starting point is 00:59:45 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 the 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? It's almost the way I would put it. And so you have to be really careful with management of that.

Starting point is 01:00:01 I think even the who do you send it to and who do you CC, there's a language to 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 subtle to, like, who responds then? Like, if you send an email of 10 people, CC'd to the whole nine yards, you know, there is a subtle etiquette to, like, when you respond. Like, if you're the fifth CC on an email, you're not expected to be the first response.

Starting point is 01:00:37 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 see C and the order that like, again, it's very subtle, but is worth understanding. So true. Man, any, you would think nobody sees all these little things in the Gmail thread. But you do.

Starting point is 01:00:57 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. Yeah. 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.

Starting point is 01:01:13 My heart rate is low. I'm doing it properly. And I'm doing it with 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,

Starting point is 01:01:26 you can trust me because intuitively there's this well of knowledge and cultural connection and whatever that we can, we can share effectively. And if your BCC definitely do not reply all. Yeah. I mean, I have some unbelievably funny faux pauses from my history with CCBCC two lines. One of the worst etiquette slash mistakes I ever made, never, ever, put someone you're talking about who's not on an email in the two line to check the spelling of their name and then hit send.

Starting point is 01:01:57 That's a bad idea, right? So whatever you're doing, that's not a good etiquette thing. That's just like a being smart. Proof-reading thing. Proof-read, proof-read. for free 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 if you add them no for me it was more just like the way to check the spelling of someone's

Starting point is 01:02:18 name is not to put them in the two field ever yeah oh yeah oh yeah I'm still kicking so it wasn't so bad I'm still kicking I'm still kicking okay okay uh two more meeting etiquette yeah I mean again we've talked about arriving a little bit you should do that. Don't arrive up 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 off. 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. Like so I think you want to be like 10 to

Starting point is 01:02:59 15 minutes early. You do not want to be much earlier than that. We talked about meeting other 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 is 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. It's kind of like. And again, it's it's almost a signal of like, I am here for business, but I am like a normal person. and like I'm willing to have like a normal,

Starting point is 01:03:36 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 describes small talk as like the TCIP ACC handshake. I love it.

Starting point is 01:03:46 It was a great description. I always described it as like, imagine the modem crash from when we were kids on a 144. We go do do do do do do do do do 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.

Starting point is 01:04:01 And so that you're ready to talk. So they're ready to talk. Yeah. For meetings, virtual ones, camera on. And again, I say this is someone who sometimes violates this, right? I violate it knowingly. I violate it knowingly 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. I go a step further. I,

Starting point is 01:04:34 I actually, 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 closets open.

Starting point is 01:05:01 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.

Starting point is 01:05:22 And this is, by the way is for my partner to Kevin Collard. 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 if you think about it, we work for LPs, limited partners, right? Like that's who we raise money from and then deployed 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 that

Starting point is 01:05:49 Coke. Even if you know full well, someone's going to come in and clean up after you, then you make a point of asking where we can put it or putting it on the side table, et cetera, acknowledging that there is a mess. I feel that. final topic is exiting and leaving what are some tips you should stand where people leave the table right not ridiculously by the way you should you're going to stay on 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

Starting point is 01:06:15 you're aware of it um follow up with gratitude like you should send people thank you notes even if it shouldn't be long it shouldn't be ridiculous but like we met I got something out of it like thank you for taking your time is like oh always appreciated, is what I would say. Obviously, there's stuff like, don't take calls, et cetera. 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, if someone rings you, right?

Starting point is 01:06:42 And you're like, and the meeting's over and you're over time, 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 would just keep in mind. Also, like, don't make a production of your exiting.

Starting point is 01:06:59 Just like, just exit. Yeah, yeah. I mean, again, I don't like, you know, yes. I think that's really true. It's, I mean, there's even a point to like, there are lots of scenarios where I think an Irish goodbye is the best goodbye, but you just kind of disappear. Like any large group setting, I think is great. Maybe you think one person on the way out of the host, right?

Starting point is 01:07:17 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 they think might be important to share anything? There's so much other stuff.

Starting point is 01:07:31 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 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

Starting point is 01:07:46 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.

Starting point is 01:08:10 We're going to be we got, we invited to do what. 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, uh, my God, that you got a whole new life forming here. I, I, you know, the funny thing is this stuff. The etiquette's story is obviously, pretty fun. And so, like, people like morning brew, 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 ultimately remembered as

Starting point is 01:08:38 like the etiquette guy? That's kind of hilarious. That's what we're doing here. I'm into it. I'm into it. I'm fine with that. So I'll read a you have the TLDR 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

Starting point is 01:09:18 podcast, AI Corner and Contrarian Corner. I don't know if I told you I was going to ask you these questions. I'm going to go for me. I love Contrarying Corner. An AI corner depends what you mean by that. So the question in AI corner is just, what's one way you found AI useful in your worker life that might be helpful for people to hear? So look, I'm by default pretty skeptical of most AI applications.

Starting point is 01:09:40 I will say the thing that I've had the most fun with AI and I find great is actually partially where the cartoons where this came from is I built a little personal news aggregator called Letter Mem 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 the world as a front page in cartoons.

Starting point is 01:10:00 And I actually love it. It's like the best way I get an overview because there's all these smart newsletters. You don't know time to read any of them. So I pipe them all in. Except Lenny's newsletter. But keep going. And what?

Starting point is 01:10:10 Except Lenny's new letter. Sure. Of course. That one I don't put in the aggregator. Of course. I don't do that. But it's great. So I'm super into it.

Starting point is 01:10:19 And that's lettermeem.com. I love this. I love this. So this is A. generated aggregates all the important newsletters and creates a little summary and a cartoon. Yeah, and you can make your own. So like for me, I actually, I'm looking at this now, there's actually one thing that got messed up on this we need to change. But the, yeah, the, the idea is you basically get an email digest once a day and it's continuously updated like

Starting point is 01:10:39 what's going on in the world and you pipe-your-own newsletters into it. So it's like whatever you actually trust and pay attention to. Genius. And how did you build this? Was the vibe-coded? Do you have an engineer help you? Well, both actually. Like I actually, the vibe-coding thing, this is exactly what vibe coding is good for. This is like, you know, cursor and digital ocean and cloud flare will get you a long way in terms of just like 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.

Starting point is 01:11:07 And so the reality is after a certain point, I had some friends who are great engineers just take it and like up level it in a few ways that I honestly ran out of time to work on. Well, let's go to a contrarian corner. This could be an entire podcast conversation with you, I suspect. but just like 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 your startup is the equivalent of not using the cloud in like 20.

Starting point is 01:11:50 2010 or like not using the internet in like 2000. It would be insane. Like, of course we'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 the business. Right.

Starting point is 01:12:04 And I'm very into those versus like all of these companies that come out, whether they're, that say we are the AI blank. I just, I think they're all going to zero. Even, you know, my kind of argument from a seed perspective is like, look, is open AI a good investment or not? to terrible seed investment, right? The way the numbers baked out, even at a $500 billion market cap

Starting point is 01:12:25 when all of a sudden none, the seed investors have made something like 25 times their money. That's insane, right? If you think about it, like that's basically the worst, it's like a middling at best seed investment for like the company that is defining the moment.

Starting point is 01:12:39 And the reason is because these things are so capital consumption. So if you're trying to employ $100 billion, 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. You know what?

Starting point is 01:12:55 If the storytelling of Elon allows SpaceX, which, by the way I love, I think Space is an awesome company. But if all of a sudden that actually can be worth $1.4 trillion to the public market, guess what? The money plowers are going to do great with all this narrative-driven religion, is what I would put it. But if you're a disciplines-eat investor, I guess my contrary intake 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

Starting point is 01:13:23 before the narrative collapses. Wow, I love this. Okay, I want to follow this third a little bit. So is the, you're saying, because of the dilution that goes along with these companies. It's like they're too capital. If they work, they're too capital-intensive. Like seed investing does not work in highly capital-intensive businesses.

Starting point is 01:13:38 Like, 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. things, right? And so it's just like the whole dynamic is off. And the thing is people are desperate right now for things to believe in. Like if you think about the history, you know, we've done so well as a country with Terra Nova. Like the US was amazing for so many years. Because you had the West. And if you were going to work hard, you would like go West and you do great. And like there was all this opportunity, a lot of opportunity. We've had reverberated

Starting point is 01:14:09 like, you know, my generation, your generation. We were blessed because we had the internet. The internet was digital Terra Nova. And like we got to build fortunes. and do amazing stuff and new work in this new world that was created. But it was effectively the same thing as a West all over again, right? And ever since then, whether it's mobile,

Starting point is 01:14:27 which again, if you look at the math on it, everyone wants to be disruptive in Terra Nova. Not really, it's just more internet, right? Or like crypto, which, by the way, I think crypto's amazing. I think it's the closest thing to Terra Nova. But to now the AI God narratives, every generation is desperate

Starting point is 01:14:42 for their Terra Nova story with good reason. 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? Do you invest, yeah, what do you look for when you're investing in AI startup? Well, again, I won't invest in the thing I would consider an AI startup. I'll invest in things that use AI, right? 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,

Starting point is 01:15:15 whether it's sublime security or outtake, things like that, that are basically all around the theme of the Voicomf test from Great Blade Runner, which was the test they basically ran to are you a real or are you a bot? Like that's a huge problem. The turtle on their back? Yeah, there's a whole set of companies that are like implications of AI and how do you manage it

Starting point is 01:15:35 and handle it as a society. I think there's a lot to do there. There's a lot to do in cultural shifts from AI, right? There's all sorts of interesting trends to follow there. Like there's there's all sorts of businesses that will be disrupted. They're like not AI businesses. They're businesses that will be disrupted in an interesting way. So I do there's a lot of opportunity.

Starting point is 01:15:54 But again, I think there's a, I at least draw a distinction between if you're trying to be, I mean, certainly a foundation model company, but like any of these things that are like, we're going to win because of AI. I'm like, yeah, 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.

Starting point is 01:16:13 Is there anything before we get to our very exciting lightning round, anything else you wanted to share? Oh, look, I'm happy to be here. Like, I love your work. It's good to be on your podcast. Happy to bullshit whenever. No, we're good. Okay. Well, with that, we've reached our very exciting lightning round.

Starting point is 01:16:27 I've got five questions for you. Five questions. 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 got to admit, I like to make fun of Mark and Reese.

Starting point is 01:16:43 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. Mansearch for meeting is great. I'm just going through. What have I read recently? You know, it's great. Area 51, an uncensored history of the top secret

Starting point is 01:17:01 military base. Not very erudite. Great book. And then I honestly think the one serious one I'll make a recommendation on is Lessons from History is like one of my favorite books. ever. I would really, really, really recommend. It's a short read. But I would, Lessons from History by Alan Durant is like probably the most approachable, non-obvious book I love. I did that one on Audible and it's, you just listen to it all like not like in a couple hours. It's a short read. It's not

Starting point is 01:17:32 a long book. I honestly think for me, hours of investments to intellectual return. My one real answer right now would be that I could give you a thousand others from I, you know, There are things like the Banana King. Have you heard this one? Have you seen him for this one? Oh my God. This is so good. What's it called?

Starting point is 01:17:49 So the fish that ate the whale. Incredible book. So is The Last Kings of Shanghai. If you know that one. These are all like amazing books. But they're longer and there are more stories. Just every one of the podcasts should go read Will Durant. Okay.

Starting point is 01:18:03 I love it. Favorite recent movie or TV show that you've really enjoyed? I got to say, I mean, recent, I think Landman is fabulous. Have you watched Landman? Yeah, yeah. I think it's great. I'm like 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 I talked to it. I talked to, well, I'll tell you a funny story, which I talked to a founder who's in

Starting point is 01:18:30 Midland, Texas, and it was just kind of part of the show. And it's so classic and typical. He's like all these Silicon Valley people and now think they understand the energy industry because they watched landman. He's like, so there's all, he's like, I'm like, it's like,

Starting point is 01:18:44 it's like, it's like, like, because I know too many venture capitalists. Like, oh, I now understand this

Starting point is 01:18:49 because I watch land man. And he's like, it's totally a thing. Yeah. I would feel that. Okay. Favorite product that you recently discover they love could be like a gadget,

Starting point is 01:18:59 could be an app, could be clothing. Okay, I'll pitch, you know, I'll pitch people on. This is a little self-serving. But,

Starting point is 01:19:06 um, 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 is if you think about so much of AI right now, this goes back to like what businesses do you overhaul that are interesting, that I'm AI implications but are not AI.

Starting point is 01:19:23 So everyone's got this like old virtual girlfriend, loneliness. You're going to chat with your friend that I like, whatever, fine. These guys came out. And what they do, they're like, look, if we're really trying to match up humans, like call it Tinder 2.0, what are the best sources of information to do that is their chat GPT histories? So this app is kind of built around the premise of distilling, you ask chat GBT a structure prompts that they've designed. It pulls out an unbelievably good profile of who you are. And then you basically match with people based on like what you're actually asking chat GPD about and the implications of who you are.

Starting point is 01:19:58 And the fun part is I haven't obviously done dates on it. Not for me. But I have pulled my profile from like, wow, this is like shockingly good description of who I actually am. And so I think that's like a really fun business. That's like that prompt that the chat GPT folks once had of just like draw, visualize my space based on everything you know about me. And it's it was like, holy moly. It's a lot.

Starting point is 01:20:22 It's pretty good. And so in this dating app, I love this idea. It's so good. So do people read that? Are they able to see that as your profile or it's like private? It's a little abstracted from that. But it's like the matching and the core thing is like based on it. And it's like, again, I'm like, I was like, wow.

Starting point is 01:20:37 Like this is good. And it goes on dates. for you. Okay, so it's like, it simulates what the date might be like between you two, potentially. I guess. Yeah. Your AI goes on dates for you, receives one match. Each one carefully is like, wow, so fun. It's good. I get it. 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 like offer a matchmaking service where I'm like, okay, if you read my newsletter, really, you're here, tell me who you are. I will like build a little LLM and trying to

Starting point is 01:21:10 match with 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 like I have 100 great women who murdered me like hey this is what I'm looking for this who I am you're like you were an amazing person and then like the four guys you write in are like I want a 25 year old hot girlfriend you 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 that topic You actually can't. Like, I just kind of like, there's no way to sign up for it.

Starting point is 01:21:42 If you send me an email. Perfect. If you send me an email, Lesson at Gmail, I'm fine. Like, then I, you get, if I respond, you get automatically added. I basically just, like, that's how I, like, people I'm interacting with get added. Or I'll just add you. But I, it's actually funny. There's not, I, I, oh, what you know what you can do actually, that'll get you on it is if you go to W.

Starting point is 01:22:02 lesson.com, W-L-E-S-Zion.com. I have my little, like, bought app that, like, includes, like, a little L-L-L-L-M that kind of is 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.

Starting point is 01:22:19 But, no, there's not like a sign-up page for it. Okay, I love this contrarian growth strategy. No, no, you can't really sign up. Okay, that's great. Okay, two more questions. You have a favorite life motto that you find yourself coming back to often in work or in life?

Starting point is 01:22:32 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 like this great moment in work time when it was like, okay, game on. Like Google's coming for us. Like let's, and I had some of the most fun work experiences. We were working literally 24 hours a day.

Starting point is 01:23:00 Like past midnight every night. 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 Lesson and with the Moors, Dave Moran. We love our last thing. We also like my wife and I are contraries 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 it's Dave Morin, but Morton, just to be clear. And your wife, she runs the information. Yeah. So she's going to be. prompting us with it to actually going out of the world

Starting point is 01:23:34 and then we just bullshit 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

Starting point is 01:23:50 friends for an hour a week, which I want to do. Like, I love them more. 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 serves our purposes way more than I actually expect it to which is we enjoy doing it

Starting point is 01:24:10 which is the most important part. We would do it if no one was listening. And weirdly like a lot of our friends and people we care about 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.

Starting point is 01:24:22 It's like I don't like it's not a huge podcast. It's big enough. But it's I actually think the thing that's been most surprising to you about it is that even though like we don't really have growth strategies. and we're not trying to blow it up and we don't get paid for it.

Starting point is 01:24:34 It's like weirdly useful is what I would say. You know, even the fact that it's like, you know, I don't know. I'm not sure if that's your experience too, but like, and I think your podcast is probably much larger than ours. But it's like weirdly listened to

Starting point is 01:24:48 and useful by the people that like we care about. And it's 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 like way too niche, you know, like, but we have fun. I mean, I would, I would happily do it with my friends if no one was listening.

Starting point is 01:25:09 And then it's like, that'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 bullshit about something. And then some entrepreneur shows up as 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. It's very different for my regular podcast. I think people will find this extremely interesting and useful.

Starting point is 01:25:31 as I thought and also fun. Two final questions where can folks find you online if they want to reach out? I'm basically just less. Look, our venture firm is called Slow Venture is SlowVenture. I'm Sam Lesson. I'm kind of lesson everywhere, whether it's like Twitter or Instagram or whatever you used.

Starting point is 01:25:49 Or just lesson at Gmail is 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.

Starting point is 01:26:01 time. 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 Lenny's Podcast.com. See you in the next episode. Thank you.

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