How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin

0:00 I just feel like no one's being honest in teaching founders this. Be early. Don't Order the most expensive thing on the menu. For a video called 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 someone abrasive on purpose. You want to be able to show up in a way where people like okay, this is someone I can work with and trust. Etiquette is a skill for how to show up in a room with a low heart rate. You're at the Kleiner Perkins holiday party you have All the venture capitalists in the world and all the CEOs, you're 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, and it becomes very transactional. If you show up like a little energizer bunny. You're gonna scare vote off. You're gonna project totally the wrong vibe. This isn't your one shot. You'll have other opportunities. You kinda wanna show up with the self-confidence and the calm.

0:53 Of abundance. This is part of the story, this is not the entire story. Today my guest is Sam Lesson, partner at Slow Ventures, previous VPA product at Facebook, and two time founder. This is an unconventional episode. That may surprise you, and how interesting and useful it is to your life. I asked Sam to come on the pot and talk about proper etiquette.

1:15 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 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.

1:48 And I hope you enjoyed this very unique episode. If you enjoyed 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 nineteen incredible products. Including a year free of lovable replit, bold, gamma, N8, and Linear Devin Post Hawk, Superhuman Descript, Whisperflow, Perplexity, Warp Grenola, Magic Pattern, Drey Cast, IPRD, Mobbin and Stripe Atlas. Head on over to Lenny's newsletter.com and click product pass.

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4:16 That's get dx.com slash line. Sam, thank you so much for being here and welcome to the podcast. Blast to be here. I'm excited to to have the conversation. This is gonna be a very different kind of conversation. Uh, I suspect this is actually gonna be really, really useful and really, really interesting to a lot of people.

4:39 Useful and interesting? That's so unlikely. That's the Venn diagram that we that we aim for. Uh, I also think it's gonna just be a lot of fun. So uh I really appreciate you doing this. I wanna give you the opportunity to set the stage for for why we're chatting through this. Just tell me why you decided to spend time on teaching people proper etiquette and why should people pay attention to this? Why is this important? I really enjoy things at the intersection of

5:04 Hilarious and useful. Right. You kinda need both, right? And hilarious just'cause you should have fun in life. We should be working on things that are fun and interesting. Also, candidly, if we're being More

5:15 Honest about it. Like you can't it's very hard to cut through the noise these days. So kinda 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 to do with a tweet.

5:32 They got escalated into an event. It's gotten escalated into a book and a bunch of other stuff. I I kinda believe that, you know, you should always there you go, you got it with you. I've got my coffee, too. It's like It there's there's a rule like you know, you always want to just double down in life, right? And so I'd say like why add a kid look There's a serious real narrative to like why etiquette matters in twenty twenty five. I'm for founders, almost twenty twenty six. Like one.

5:55 You know. We talk about software getting commoditized. We talk about all this fearmongering and scared people feel about Silicon Valley and AI and like all the things that are going on. Then that is if you wanna do business and you wanna do business and build great partnerships with Team members.

6:11 you know, with companies you want to do business with almost with anyone. The reality is etiquette ironically matters, right? There is a deep truth to this, right? You especially when you're asking people to trust you with their data. Trust you with their business. You know, this and and when technology is no longer some cute sideshow, but it's like a major deal. Like people are worried about losing their jobs. Like Understanding how to meet people.

6:32 Where they're at, build trust. You know, mirror kind of expected behaviors. These are all like tools, right? So th 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.

6:48 Saying well, actually It does matter. And You you know, I'm wearing a T shirt, I'm not exactly known as the most high Etiquette personal, but I do know the rules, right? And I think like that's kind of there's some there's some it's fun and funny as well. And I think those things are both important.

7:02 I'm gonna get into the actual rules, but just to follow that thread. You had a really great line somewhere that Etiquette is almost a skill for how to show up in a room with a low heart rate. Yeah. This is the thing about a lot is like again, I think about Again. You and I are now old people.

7:16 Right, but like you're young. I feel that you you feel it in your bones. It's like you're young. Right. You're in You're the Kleiner Perkins holiday party. You have

7:26 All the venture capitals in the world and all the CEOs. You're your first company, you're young, maybe you're from a different country. Like oh my god, like this is my shot. Right, like I have all the people I need to talk to, and I need to convince this person of that and make this connection. It becomes very transactional. If you show up like

7:42 A little energizer bunny. Right. You're gonna scare everyone off. Like you're gonna s project totally the wrong vibe. And I 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.

7:56 Coming with a ske a mindset not of scarcity but of abundance. Understand how to give more than you take. Understand how to build a relationship, not collect business cards, like These are things that actually serve you massively well. And I just feel like no one's being honest in teaching founders this. Right. Instead they're saying, Oh no, all that matters is your

8:13 All right. Like 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

8:22 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. Th is one way to think about it, like you can be successful. not doing any of this, not knowing any of this, it just

8:36 You're just h you're hurting yourself. You're Yeah, I think it's just an unnecessary you're creating an unnecessary pop out of his own. I'd also say that look. This goes back to like technical differentiation where things are at. It is true. Then if you bring mana from heaven, right, like you invent something That is

8:52 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 it that's it. You know, it's like it's literally like that happens. It happens very, very rarely. But it does happen. It is about what ninety nine point nine percent of startups are doing. But if you have that Yeah, you basically can get away with anything. It is true.

9:13 That doesn't mean you should. You shouldn't be a jerk and like candidly over the course of history you need to work with great people and like You'll be more successful if you show up with Good etiquette and rules and context. There are ways in which that can trump all it's just like candidly not the experience. Of ninety nine point nine percent of startups.

9:30 Awesome. Okay, so let's get into it. There's kind of you divided this book into about ten categories, ten and a social situations is one way to describe it. So let's just go through each one and just give us some pieces of advice. Sure. And and something I didn't mention, the reason I'm excited to do this, the reason I reached out to you to do this, this wasn't you like pitching me, hey, let's talk about this on your podcast. is I was like, wow, this is really interesting. I did not know these things. Cheers. I mean again, like I I think the thing for us is I'm kind of a ship early, ship often guy. So

9:55 V one You should buy it now and study it'cause it's good. And it's gonna be like a limited edition, you know. There's a bunch of the funny part about doing this is people come back with a bunch of other things we should cover, right? So I I suspect. that eventually this will evolve beyond it. But I think the good you know, we're starting with some good stuff. Let's do it. Okay, so introductions and entering a room.

10:13 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 I live with hypocrisy. I'm frequently not early.

10:25 Right? But you should be early. Right. Um and you don't need to be half an hour early. That's a little weird. But you know, making sure that you have Some buffer time. So that again, think about low heart rate. If you come in racing the room five minutes late, your heart rate's up.

10:37 If you come in You had a second to beat in the to take a beat in the the in the waiting room. They kept you waiting, right? That that's the dynamic I think you wanna Now if you're not late, I'm sorry, if you're not early. Just apologize. It doesn't need to be like

10:51 A five one five again, it goes back to this heart rate thing. You can just apologize simply. And move on. 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 uh so I think that's kind of a r another really Kind of obvious one, but an important one.

11:07 Something I've seen, I I'll go for a few others that we talk about. About in kind of it is Look. Um You want to have a strong handshake?

11:14 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 it a really really valuable thing to think about when you're beating someone, say?

11:25 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. He's like Nice to meet you, you move on. First it's gonna be harder for you to remember the person's name.

11:36 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. Or whatever it's gonna be. 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.

11:52 One that I loved was If somebody else is late. Do not make them feel bad. Yeah. Do the opposite of what you're doing of what you're doing. And I think this is like I've seen this with entrepreneurs and like I get like I OBC.

12:04 I do get scheduled in like thirty minute chunks back to back. Like all the time, especially on Zoom. Guess what? I am frequently late. I don't feel good about it. But it happens, right? And

12:15 A lot of times founders most of the time I'd say founders know that like if I'm late I will always apologize. I'll try to email them ahead, et cetera. But then it is what it is. And like we're the 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 like

12:32 It's fine. If you feel that way. But it's really not very productive. to make a big deal out of it, right? Like if this is a deal breaker for you that I was a few minutes late. Then like I don't then now I feel like I'm wasting the next twenty five minutes of my meeting time'cause like I'm not like

12:46 This is gonna be the wrong dynamic, right? And so I just think there's like don't don't harp on it. It's okay, you know. You had also uh some advice on eye contact. It's really important. Again, I think the thing here Especially in an age where everyone's used to be in front of computer screens. And looking at six different windows at the same time.

13:04 Again, people are taking their time to meet with you. Or at a party, they're like taking their time to like listen to you. And It's just a matter of respect. To be like I'm actually here in this conversation. I'm not off on my screen. I'm not like glancing on the room. No look. There are some people

13:19 We all know this who are like literally neuro quite neurodivergent, and that's very str hard for them. Like that happens. And I a lot of founders have like neurodivergents in some ways. 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.

13:38 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. I maybe a final tip there is around partners.

13:50 Introducing the partner, saying hi to their partner. Sure that was. Yeah, so like look, this happens all the time and again In the spirit of I'm not permitted to this either. If you're with your partner Introduce them first. Right.

14:01 They yeah, you know, bring them into the conversation. One great trick we talk about in the book, which I really unfortunately use all the time, right? Is there this whole thing Let's pretend you're with your partner or with someone who's a friend. It doesn't have to be romantic partner, whoever you're with. You're gonna forget someone's name. Right. And what you really should do is All the time. All the time. A good friends' name. And like that's what you're supposed to do. The etiquette is

14:23 Say Lenny. Please meet my wife Jessica. You know, and like that's you know, the that's kinda thing. Here's the thing. This is where you start betting rules. What if I don't remember your name?

14:32 Right, if you have your partner with you. You can flip it right and say, Jessica I wanna introduce you and then you kinda 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 to pick up the name again, right? Or things like that. So you let it hang. It's a great example of the fact like If you're really in tune socially.

14:52 Yeah. You kinda know what's going on. Right. Like you know what I mean? Like i you're not an idiot. Like you know that oh, like uh what is proper, what this person is doing. There's a gap between it, there's a reason. The reason is But it's 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 it's a useful thing to think about as a small cue.

15:14 What I am so bad at remembering names that like I think I have a medical issue or 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. Uh meet my wife Michelle. And then they were like um Bob.

15:33 Nice to meet you Marshall. Or it's uh like make it a little more awkward of just like Uh Michelle Mead, um Like And then let it hang. Michelle, I wanna introduce you, right? Or something like that. Or like you know something like that. Or I wanna introduce you to Michelle. You look at them in the eye, right? And then and then your wife will be like, Hi, I'm Michelle Remind me your name, or it's nice to meet you, or whatever it ends up being. Look, I also for the sort, I actually have such a clinical problem.

15:57 on name face recognition that's actually runs in our family. I have this whole backstory. We just Part you know, I worked at Facebook for a long time, was really into it early on. No kidding. I think part of my early attraction to the platform was it was the first time you walk around college and you're like, I know these people, I just don't remember their names. You're like, Oh my God, there's a resource I can study, right? 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.

16:21 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, you there's especially you see this happen sometimes. Especially when there's weird power dynamics at play. Um Yeah, you'll see

16:39 some famous V C or founder 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 and be like There's a bunch of people around and like the more you can be inclusive, again, low heart rate You're not like it's not a scarcity mindset, it's an abundance mindset. Like I think that's kind of like the the tone to think about in terms of like

17:01 what a conversation is and like how to how to show up in a room and and meet with people. Um You know, another really big one we we harp on a lot in the book. in in kind of a bunch of the panels is like Ask questions. But there's

17:14 A limit. Right. So asking questions is great. You're coming in and says he hey, it's nice to meet you. Let me give you my four minute startup spiel and everything I've been to da da is like so self centered. It kinda 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 that's great. There is

17:33 Doing it too much. Right, which is when it's done in a forced way. Sometimes I feel this. You 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.

17:55 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. Or has a point or sparks something, then you have it's got a game of ping pong. Like then you can kind of react to it. It goes back and forth.

18:11 Where there's openness and they're playing with you. Not playing single player. It is almost the way I would think about it. So it's up here. So it's basically indexed towards asking questions, but not like a hundred percent. Yeah, consider put it this way, imagine you're playing ping pong. Right, or tennis, or whatever you want.

18:26 Like Hit the ball back. Right, that's the question. Right, and then 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 ten balls at them in a row.

18:36 Or like you know what I mean? Or like uh you know that that's kinda like not the vibe you want to go for. Yep. Awesome. Look, we talk a lot about matching matching vocabulary. You're gonna meet a lot of different people.

18:47 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 like If you're speaking to a university professor versus a twelve year old, if they're using a certain level of vocabulary words, like

19:03 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

19:12 mirror them, if that makes sense. But there is a subtlety that I think really matters to it. Cool. There's a few more I'll point out real quick. Um Connecting to this idea of asking questions, not trying to give your whole spiel Constantly this idea of leaving them wanting more. Yes.

19:26 This is important. I mean I think In the end of the day, like most interactions, let's say you meet someone you're really interested in or whatever. If we're being transactional about it. What's the real goal? The real goal is to leave people in a position where they're like, Wow, that was a really interesting person. I'd love to hear from them again or meet with them again. Or maybe even better, every once in a while this will happen is like Wow, that's a really interesting person or idea.

19:48 the person who walks across the room somewhere and say, Hey, you really should talk to Lenny. Just a Sam. Like that's kinda like You wanna leave them being like that's interesting. I like to continue this or expand it. Not

19:59 I just heard this entire person's life story. I never need to talk to them again. Right. And so I do think there's, you know, again, like leave them wanting more, right? I think is important. And that that is partially by 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. Uh, 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 uh honestly a uniquely Silicon Valley thing, right? I'll go so far to say that, which is

20:28 Look. We're used to especially if you're young and these are big opportunities or big moments. People are kind of used to this like environment of scarcity. It like reminds me of the M M song when he talks about like a one shot, one opportunity I think it's Oh M Yeah. It's a great song. It's a great song.

20:46 Great beat. Every once in a while before a big presentation, you gotta 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 kinda want to show up.

21:03 В тексе конфиденц а на кам. Of abundance, right? Being like this is not gonna 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

21:20 Keep focusing on low heart rate. Engagement, eye contact. You get so much of the way there. You also have a tip about how to handle famous people that you might meet? Uh, 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.

21:39 But also like You not being ridiculous is almost the way I would frame it in this conversation, right? Which the ridiculous is like if you go up to Mark Zuckerberg. knows what he looks like and who he is.

21:50 Hi, I'm Sam, and who are you? You're like, What are you doing? Like it's like ridiculous, right? On the other hand, going up and being like, You're the most important person I've ever met. is wrong, right? And so there's a way to again it's it's about grace as much as anything else, right? And recognizing that there are people And again You're playing an iterative game.

22:08 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. Pretty nice person. Like Maybe I wanna talk to them again, right? Uh now going up and be like

22:22 I need your email address and phone number. It's like no, let let him offer it. You know, like that that type of stuff I think matters. Maybe one last tip is the this you actually start with this one of this line of great to see you when you meet someone versus like nice to see you. Well again, Lenny, you and I probably use this all the time, I bet, because I honestly again we go by name, face, whatever. It's really difficult social situation to put someone in. It just think about from their perspective. If you go up to someone And say

22:47 Hey, it's really great. It's great to meet you. You're like we've met five times. It's like quite embarrassing, right? And for them, for you, for everyone's the more I like love in fact I w 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, I went up to her And I basically did a nice to see you line, right? Cause and I very clearly couldn't remember if we had met before, and we had.

23:13 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 of saying like oh and like not knowing if I've met someone before or not. She's like, How can you like I don't I don't know what to do with you. So that's a great one. So the line there is great to see you because it works whether you meet them or not. Yeah. And again, it's one of those things where here's the thing.

23:33 People are dumb. If you go around saying nice to see you to everyone. Like There's a small percentage chance this person doesn't remind me who I remember who I am. Right. And there are other ways or to but like that's okay. Like that's part of the etiquette dance to some degree. Is like that's fine. What's not fine is It's so nice to meet you and like we've met six times.

23:52 Right. Yeah. Okay, um let's talk hygiene. There's a couple there that stood out to me. Uh, tell me if I'm missing any that you think are really important. One is just like subtle fragrance.

24:04 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, right? And like it's again Your scent should not be noticeable.

24:17 Is almost the way I would put it. Um you know, i in any direction. Uh it's it's not you're not There's there's there's no advantage to that, is basically what I would say. By the way, this is a good uh question. Does this advice apply both equally to men and women? Is there anything that as maybe as we go through it. So it's an interesting question. I think broadly in this book the answer is broadly yes. I will say that There is probably in January or February going to be a

24:42 What we Internally 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. Um, and so I I can't speak to that yet. I think the frag was one I would say. I don't think you want your freighters to be memorable for anyone, no matter what your gender is. Awesome.

25:00 This is a good let me take two tangent tangents here real quick. One is uh there I heard you told a story on your podcast about your kids and the impact this has had on them. Maybe share a story there. Well, I look here's the funny thing. I I literally have realized in doing this I love my children. They have terrible manners. Right. And like there's a certain things they're like not bad at, but broadly speaking, I have an eight year old, a six year old, and a four year old. And like I'm like, wow, you guys

25:24 You guys eat like animals. Like you just you know, you're you don't know how to use a fork or knife properly. Again, it's not like At four or six is not like stopping them well in life. I'm like you I can't be the etiquette guy if you guys are eating like so I've I mean for some of them as being really cute. Others have been really funny, like My six year old has started standing whenever my wife

25:41 comes to the table. Which is kind of arcane, um, from an etiquette perspective. You can argue about whether it's actually even really etiquette anymore or not. But if you're being really formal, when a woman comes to the table, you stand, right? It's very funny to have the 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. There might have to be a children's etiquette book.

26:01 So good. I think actually at the end you say that uh whenever anyone joins you for a meal, whether it's a man or woman, you stand up as like a modern way of thinking about it. That might be better, is what I would say. I will say the the it's uh it's an ongoing somewhat hilarious debate at our dinner table. I'm just trying to get them to like not use a fork and knife like animals right now, but we'll we're working on it. We're working on it. I was just uh speaking that I was just listening to Tyler Coven had Alice Alison Gopnick on podcast and she studies kids And she her whole thing is how kids learn like scientists. And she has a whole thing about how they figure out how to use a fork by just like experimenting until something works.

26:36 Right. Like to be clear, they're able to feed themselves. It works. But it's like you look at it and it's like, What are you doing? Yeah. Okay, the other tangent is you didn't uh share the uh class you actually taught to founders already, so maybe share a little bit about this Classy time. So I mean the before the book, we did a we did a class specifically initially for Y C founders, right? Uh partially because Y C Gary Tan got very mad about this. I'm like, Well now I have to do it, right?'Cause that that's very funny. But um But um but yeah we basically you know we gave them all certificates of completion, but we did a class. We hosted it, it was at the four seasons. We did some stuff that was fun and a little bit irreverent, like we had

27:11 Some very fancy Wilkes Basher people come in with models and show up talk about dress at different types of events and things like that, which was kind of tongue in cheek, but but a lot of fun. Um we also did like caviar and wine tasting type stuff. But then we also spent a lot of time focusing on like the actual meat of the matter, right? Which is Things like how to show up with a low heart rate. I have an abundance mindset.

27:32 you know, basic skills like looking people in the eye, shaking hands, you know, how to eat, like this shows that you're being respectful, things like that. Um Well, I do 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? Uh I don't know. I mean, I don't really understand what makes Garry Tan mad, and it's fine. But like from my perspective, I think, yeah, I think he's just like in some ways, again, to be clear, it's a little tongue in cheek. We're a little bit making fun of the fact that Y C 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.

28:05 And that's all they've been thinking about for months or whatever. And so like When they show up at your office. To pitch you. And you know, they get a coffee or something and then they like leave it on the table and don't ask you where to put it. It's a subtle sign of like not being aware of your broader environment that you may or may not know, but like

28:22 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 I mean you should get the book. I think it's like fairly obvious Hiding stuff like Don't be covered in schmutz. You know what I mean? Like show respect.

28:39 Try to anticipate How the room is gonna be dressed. And like don't massively overdress or underdress. It's like if you show up To a business casual thing at a tuxedo. You know, you're you're like

28:51 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 that person like really has no respect for the room. This actually you're getting into the next category, which is dress, which I'm excited about. Yeah, I mean dress. Like look, I gotta say, again. In terms of know the rules, but don't always follow. When I my first job out of college, I was an associate at Bating Company, right? This is like a consulting firm. And there was like a business casual. Yeah. I kind of came up with the snarky realization that there was a minimum dress code, but there wasn't a maximum dress code.

29:19 So I started in the office as somewhat of a mini rebellion 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 tuxedos. So it was like a 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

29:40 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 the most simple way to dress. Unless unless you're trying to very intentionally break a rule, right? Um which maybe you are, but I think you should do that with a lot of Cultural understanding, let's put it that way. Uh, so here's a couple tips that I love. So one is just dress one level up.

30:00 That's a really simple tip. It's an easy way to win. Not two, not three, but one. And oftentimes you can like reduce that. Like if you have a suit on, you could like take off the jacket and you're less a little less formal in the air. A hundred percent. And then you talk about fit of the Item versus the brand. Hundred percent.

30:16 Like like at the end of the day, fit is everything, right? 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. Cause like but which is great. Like you gotta 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 Twenty dollar shirt.

30:37 is way better. than a misfitting five hundred dollar shirt. Right. And candidly, like it's the same thing as like If you're a startup founder You do want to kinda dress to the level of the room. But

30:49 You kinda shouldn't show up and like Like you shouldn't have a Rolex. Right. It's like very classless, if that makes sense, to like show up as a startup founder with a Rolex, right? Uh it's just not again, it goes back to heart rates. Trying too hard. You know, you're not gonna

31:02 Trick anyone, right? Is the upshot, right? Yeah. This bit of her 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. Uh, it just looks so much better, even if it's not the highest quality item. A hundred per yeah, I I I would put put differently.

31:23 Think about the average person, not every person in the world, but the average person in the world Can look at a suit. And be like intuitively. That seems like it fits the person or doesn't. Yeah.

31:34 people can have no idea what things cost, right? Like if you said like you know what I mean, like it's just not In some ways it's this weird thing where it's like if you show up in a super misfitting But very expensive item. You're like, what signal are you sending? It's like, well, you're not very aware, right? Culturally, you're not like matching the room, you're not showing a lot of sensitivity. Like to the situation what people actually can prioritize. And it's like are you trying to impress me because you have

31:58 Of fancy outfits? Like what what are we talking about? One other tip you have is if you're not sure the level of dress, just ask. Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations, you know. Down to like Which forks should I use? You know, and you know, or what's the expected like it is absolutely fine to ask.

32:18 If act if anything. It shows a level of confidence and calm. And humility to ask if you don't know. Right. So I actually think this is a great example. There's absolutely nothing wrong with asking About dress, about etiquette, about expectations. You know, I don't

32:32 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 pig game of ping pong. Like you're not getting but like it's totally fine to call and be like, Hey, like what's You know, what's this gonna look like and by the way, it's important because

32:48 In New York versus San Francisco. There's different expectations. Like people do do things differently. And like your job, you're you're not expected to ha to know every nuance of every culture you might enter. So maybe as a final question in dress, do you have any just I don't know, tips for dressing well? I know this is a big question that a professional spend time Teaching and

33:09 Charging for it. I really you know, I think the answer is find someone in your universe who you think dresses well. And again, ask them for help and like what makes sense if that makes uh you know from that perspective. Again. The well tailored Great.

33:23 Th that makes a lot of sense. The like basics I can say. Yeah, like have genes that are clean. Right, and like fit you. Things like that. But again, uh when my wife listens to this Podcast episode. and hears me being asked about specifics of dress, she's gonna she's gonna be chuckling.

33:39 Yeah. That's a win. Okay. Let's talk about dining. Give us some advice for uh etiquette during dining.

33:49 Tip well. Right. Uh don't Don't not tip, don't tip badly. Yeah.

33:56 Бі супер стін. about, you know, okay, who ordered the flambe? You know, like splillly, make things easy for waiters. Um In general it's Don't Or the most expensive thing on the menu.

34:09 Does it really matter? Especially to like an investor, do they really care? No. Really care, but they do notice and you're like, ah, you're the type of person that like

34:18 is truly insensitive to what things cause even if it doesn't actually matter, right? So I think there are things like that. Same like wine. Like And then I think look in the terms of asking Ideally. Don't order first.

34:30 Right. Because I think if you see how someone like are we doing starters, like what like what how long is this meal gonna 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 kinda want to go middle of the pack to last, if that makes sense. Uh this yeah, so this isn't the situation if someone takes you out to dinner, like it's a V C another found like someone invites a partner or whatever. Whatever it is. Yeah. And look, I I think I the thing is like in terms of this, which I always think is important is like look.

35:01 Within reason. Always offer to pay. Now You should be turned down, right? If you go out with a V C Right.

35:10 And you're like You know, you put a card down. Ninety nine percent 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 ten thousand dollar 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,

35:29 Your normal situation. You don't offer to split it. You just offer to pay for it, right? And then You know. you should be declined on that. But you there is a little bit of a risk there because someone might not decline you and then you kind of are on the hook for it. But that that is, I think, the 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 V C and

35:49 I did not feel like offering to pay made sense. Would you still yeah, I actually w I think it depends What the dynamic is. If the billionaire ordered a ten thousand dollar bottle of wine You don't need to offer. Right. If you had a normal meal Right.

36:05 I actually think it's great to offer. And they'll almost certainly be like, Of course not, right? Um But I will say, you know, I'll tell you a funny story, which is like when you go out to a r with dinner to really fancy people, right? Or like someone who's like you're, you know. There are two interesting dynamics. One is It's actually, I think, especially nice.

36:23 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 clearly you should pay. And so the more you're like oh no, I like I 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.

36:40 Is if you're especially if you're out to dinner. With someone who's very, very well known. You have to tip. Like crazy. Because the problem is this is like one thing, this is like a this is not in the book. This is like a two oh one course, right?

36:53 But If you go out the side with someone that were like, Okay, they're either Known or relatively known known, and you're making the gesture of buying not'cause they obviously don't care about the money, it's more like the gesture that's nice that you would Offer that.

37:05 You kinda have to tip the way they would tip. And they're gonna tip like a hundred percent 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 gonna do that, you really have to tip well. Got it. Speaking of tipping, my God, I hate tipping so much as a concept. Like uh obviously people deserve to be paid well and

37:22 I love that, you know, they make more money, but it's just so convoluted and just like what the hell do I do? I never know. Tip a lot. Tip a lot. Okay. Just tip a lot. Like I think ten twenty percent's the minimum like if you're out in like a a situ. I think you kinda want to tip in my mind. to the level of No one you're effectively paying for

37:43 would bat an eye that you're being stingy. is the way I would think about it. Twenty percent feels like the minimum. Uh thirty percent sometimes like more Seems a little bit silly. But it's not it is a squirrely topic and I just I don't this way. I don't think you want your tip to be memorable.

38:01 Is almost the way to put it. Like this is not a thing to focus on. Like when you think when the person that you're 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, that guy tipped an incredible amount. What was that? And by the way, I I have stories in my own life.

38:20 Where like I've been out with people. And they've tipped like So much that y like a decade later I remember it. And I'm like, that's fine, they can afford it. It's like it's like Cool that they did that for the server, but it honestly the only thing I've over for the night is how much the person tips.

38:34 So you're s okay, but I think if you're like extremely rich, do you do it Don't even tell anyone basically, but feel free to do it, obviously. Sure. Yeah. I mean you don't really think the tip is not a point. The tip is like everyone should feel good about it, right? Like and like again There's about It's about again putting people in a sense of ease and comfort.

38:50 And you might not like it and it might not be fair in the world, but people are like Everyone's being taken care of. I can be relaxed about this is kinda what you're going for. I recommend your next book after this uh Femic femicit? Femicate? Uh

39:03 Addition is a tipping guide. A tip and guide. Well you know what would be funny is like there's a great episode of um Seinfeld. It's all about the tipping calculator. I don't know if you're a Seinfeld guy. I love Seinfeld. I don't remember. Uh I feel like you could honestly like Have a very funny Like modern L app.

39:21 That is only about tipping. Like imagine like a tipping app. Where it's like Instead of a tipping calculator. Yeah, you take a picture of the bill. Yeah.

39:31 You kinda give it, you're like, This is the situation and it's like it just tells you what's a tip. Well what like the tip like a restaurant's one thing, but then it's like the garbage person Uh a gardener, the end of year. Like what at the end of year? Like I I think no one knows how to tip anymore. I'd so can like yeah, some guy that del like installs the shades in our house. Do I tip I don't think you tip that person. I actually Do you tip that person? No, I I did not. Yeah, no, I I feel like that Is weird. Okay.

40:03 Like that. That's that's why we need this book. This is you're gonna make you're just gonna be a huge hit. Why we can fund it. You wanna fund it with me? We should fund an app. Talk about Y C companies. If someone pitched me in the terms of funny but real If someone pitched me. The twenty twenty six AI driven tipping calculator.

40:20 Which gives a social situation. And the details and the all the things. And it's like this is how much to tip. That is hilarious and probably quite useful. And probably not venture scale, but I don't care. I revisited the twenty twenty six, it might be. You know, everyone has the problem. Everyone globally has the same problem, which is dipping.

40:37 Yeah, just the tokens, uh 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. It's important. Do you remember? About that with uh Bristomattox. Mathics. So basically the idea is that after the improbability drive

40:55 the way they're able to move across the universe 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.

41:09 Oh man. One other tip that I just ha thought of as uh around dining is yeah, this tip about Somalia is give'em a sip of your wine if you order something. Yeah, if you if you order something nice. I'll be able to be very clear again in terms of I don't order a very nice wine. Yeah. No somebody really cares what I'm drinking, but I if you are doing that or you're into it, which is great.

41:27 Again, like think about being generous, right? If they're like oh I would love to taste that like 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, uh B for bread, D for drinks. Tell explaining. Oh, B D. You just gotta look at your hands, right? Bs and D's for to know w which was your bread plate, uh, right, is a kind of the way to think about it. Look, people get this wrong all the time. You sit down at a big

41:50 table, right? And you're like uh Which is my the kind of waiver someone to pick it up and kinda do the math. I'm like, okay, that's my bread. Um but that's the B and D is useful. Uh also like look Forks and knives.

42:02 Like just knowing what side they go on. Knowing one thing I always drives me nuts. Um that kind of goes is related. Is the knife blade goes in. Right. People when they put their knives down

42:13 Right. The knife plate goes in for because you don't like you don't want to like stab your partner next to you. But like it was really funny, I had An entrepreneur. This is not yet a product that 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 job eating your soup.

42:32 Good job. Your napkin should have been in your lap. And your knife is pointed the wrong way. Okay napkin actually. Okay, so napkin and lap. Napkin and lap.

42:42 Not in your neck. Not off to the side. Yeah, nap it and lap. I saw someone had 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.

42:54 That's kinda my biggest thing is like these are not the point about etiquette is that it gets you out of the way, right? It shouldn't be memorable. Like the Kindle. You don't want to think about the technology. No, just you just let the conversation flow. Yeah. Okay, amazing. Okay. Uh speaking of conversation, small talk and humor. Give us some tips. Here's the thing. Humor's great. I love humor. It can be overdone. And again, it shouldn't be the point of things. And I also say humor is quite conditional and subtle to the to the audience. So like

43:22 In the the 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. Uh

43:29 You but I think the thing with the thing about humor is it kind of There's this interesting subtlety to why it's so useful in social studies, which is one It kind of shows the ultimate mastery of a social s 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.

43:49 It's to tell a joke. It's a little over the line. Or a little off colour. But not too off colour. Thing. So if you're really in it.

43:59 And like feeling good. Using humor is great. You should not be remembered as only the comedian. And again, like the level of jokes. that you're playing with is like a very subtle thing, right? So you don't wanna tell

44:11 A knock knock joke. Right. When like with adults Right. The off colour sex joke that is hilarious.

44:19 You You you've got to be pretty confident before you tell it, right? In space. Uh the last thing you want, like if you like a joke that everyone laughs at Is great. A joke that Noah laughs at?

44:30 is a huge it's like a huge risk maneuver you failed, right? And like it's not the point. So it's a great tool. I love it. Like, I think everyone should have their file of jokes. I do. I don't know about you, but like I have like a Evernote. It's not ever there anymore. It's like a bear. Of like my favorite jokes.

44:44 And I they're loosely ranked and from least offensive to most offensive. Um 'Cause like I forget the jokes, but like, you know, you kinda want to use humor sparingly and smartly. This is your next book this uh list of jokes. List of jokes l ranked by like social situation and like level of extremeness. Oh man. Well there is a there is a funny joke about that, right, which is the whole

45:08 The prisoners. I won't even tell it. It's a funny there's a funny joke about People who know all the jokes. I'll leave it at that. I'll leave you hanging and wanting more for our next podcast conversation. Abundance.

45:19 Okay. Uh you also recommend self deprecating uh as a make fun of yourself, not other people. Yeah. I mean that's it it's just like you can make fun of yourself as much as you want, right? Um Again, making fun of other people. shows an incredible level of familiarity. Right. And if it's if it w you know, if you're there with your business partner.

45:37 And you're really feeling the vibe and you the again it can be quite effective. But The second it feels disparaging. Where 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.

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46:11 WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed stage startup trying to land your first enterprise customer, or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready and unlocking growth. They're essentially stripe for enterprise features. Visit WorkOS.com to get started, or just hit up their Slack support where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best, with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workOS dot com to make your app Enterprise ready today. Also so you said you had this kind of list of jokes that you'cause I I can't remember. I have zero jokes in my head that I'm like, Okay, here I'm gonna get one. So I should make a list. Make a list. I g I got some good ones for ya. Okay, I'll I'll have to borrow some. Uh you also recommend having some stories, some crowd pleasery kind of stories to say. Yeah, you wanna have some easy stories that are again like

47:07 It shouldn't be ten minutes. Right. But Again, I think the thing to think about is like imagine that the whole game In these social settings. Again, it's putting other people at ease.

47:16 Making them feel like you understand them and the room and you're a trustworthy person on the same wavelength. And in somebody's think about it as like who's carrying the conversation. It shouldn't be your monologue. You shouldn't force them to monologue either, right? That's where questions come in and back and forth. Having a fun build on story. They tell a story, you have a story to tell.

47:35 Like Again, I really think of it as like a conversation or these social interactions is a ping pong game. Right. And like you kinda wanna have a few of those in your arsenal. Your last tip in that section was how to wind down a conversation, just the importance of realizing it's time to wind down any tips for how to do that. Yeah, just like when the conversation is over, gracefully leave and basically the upshot. The the worst is like the conversation ends and the person just stands there. Are you like uh

47:59 I'm gonna go get a drink. You know, do or do you want it and then w once a while the person is will be like you're like If someone says to you in a conversation to why it's like I'm gonna go grab a drink. Most of the time That is not an invitation to say, like, I'd love one too, and fall them to the bar. Right. Like that that is not so like I just think you have to kind of recognize the signs effectively when

48:19 The moment is Passing Or it's time to move on. Et cetera, um and then like respect it. Uh.

48:27 I I use that one all the time. Is there is there any other ways you find useful to wind down a conversation, just gonna get out of a conversation. Well, I I think I think the other thing people do frequently, which again is totally fine if done respectfully, is bring someone else into the conversation, right? Like in 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, I you know, by the way, have you met Steve? Let's go meet Steve.

48:49 Go talk to Steve for a bit, right? And like I'll pick you back up. I'm gonna and okay, I'm gonna go say hi to my wife. You know, like there's there's ways to handle it. Again, like The key though is subtlety on these things, right? Like I think of in all things. Like you wanna basically let people feel respected as much as anything else. So if you If you're too overt about it. Right. Um

49:08 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. I mean, so you have to kinda look for the signs. Awesome. Okay. Uh there's four more sections. Uh 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 Calendly.

49:30 Um there is a I actually I I think I'm not overstating it when saying there was a period where calendar 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 countly and how disrespectful it is. And apparently This was such an internet fervor. I got like millions of engagements that immediately drove their month. Um bad press. No bad press. And no bad tweets. Yeah. So I think like

49:57 Look. There's a few obvious ones. Well, you just gotta 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.

50:10 You know. The default I really strongly believe the default should not be Cal only. The default in most situations, especially If you recognize that power hierarchy, the business hierarchy. If you're the less senior person

50:21 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? Uh is what I would say. And it's fine if the first law doesn't work, but the f one of the first three really needs to, right? So I think that like in some ways, That it's important to kinda respect that. It's better to uh ask what they can do and then move your schedule. If you really can't and you're gonna use a scheduling agent or something. It just needs to actually have real options is basically I think that comes up all the time.

50:48 Um Look. Rescheduling happens. When you do it. Give notice as much as possible.

50:55 Uh 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 to reschedule You basically within reason need to make it work for them, right? Uh is what I would say. And then look, I I think like there's like obvious stuff that people should know with forget, like

51:13 Time zones are really tricky. People screw them up all the time. Check. It's a it's worth the extra check to make sure you're not Both scheduling uh you're getting the numbers right, but then also really importantly, scheduling at like reasonable times. Like sometimes people like I want to meet at this time, you're like, You're on

51:28 E S T, you're what that's like four in the morning for me, right? And so like I think being respectful of that and just asking, I think is super important. It's not rocket science, it's important. Last point I make which you make in the book is like You really need respect. Yeah, it is.

51:42 And PAs and the whole people like this is the The number one look way to look extremely classless. І на who are helping the other person. Right. Um like this is like the number one thing. Now you don't need to be so over the top exuberant, you don't want to overdo it.

51:59 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. There this needs to come with an extra gesture of respect. That means saying thank you when they schedule and like follow up with them and things like that. There's a I'll tell a story when we were selling our company to Airbnb.

52:18 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. Airbnb because They if they like you, they'll Yeah, it helps. It helps the thing. The the general story of like make the gatekeepers happy and life you is true. But I I

52:36 I do think there are ways to overdo that for what it's worth, it becomes almost too transactional. Maybe shop. With flowers for the EA. You know, like You better be damn confident, like in what you're doing, if that makes sense. But um just like the small things go a long way. Like you just you know, make eye contact with them, thank them, respect them. You know ask you know

52:55 If a 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 in who feel like the team or the staff feel that way, make them feel like Part of the team it equals. The Calendly stuff. I feel like that's its own separate book of Calendly Etiquet. Yeah, the Calendly look Calaces.

53:16 My favorite episodes of going hyperviral on something hilarious. So one thing that Kelly 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. Look, I'll be honest, I go the other way. Like I I really um I don't use any of that stuff. Like um and and look, I think scheduling is like very complicated. This is part of it is

53:37 You know, I always think of these yellows like When are you Free. It totally depends on who's asking. If Barack Obama or I don't know

53:46 I won't say Donald Trump. Someone wants to meet with me. And it's like four in the morning my time. Right. Or like I'm totally with Salem Disney with the point, you know what? I'm gonna 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 that you probably knock these like

54:04 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 gonna be really clear. But it's also the reality of trying to balance these things. The other uh flaw with Callie I've realized someone once

54:19 figured out my Calendly URL and just booked a meeting with me. Like a founder wanting to pitch me in 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 and be like, You are not the person I expected because it's like I was like, Oh, your name is off by one letter. Yeah.

54:42 Yeah. That's not a thing to call out, by the way, from an etiquette perspective. Once you're committed to the meeting, you're doing the meeting, even if it's the wrong person. Oh man. Okay. Uh well one last question on Cowley. Something I try to do, I'm curious to get your take. Is like, okay, someone w like a founder, I'm meeting with a founder. And Uh

54:59 Um the way I approach it is like, Okay, do you have a calendarly or lake or something I could use to book a meeting with you? If not in parentheses, here's my count only in case that might make it easier. Yeah. I that's perfectly fine, right? In terms of the the way to do it. I just think it 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 a young shot. Okay, sweet. Moving on to the next topic, communication.

55:27 Don't use emojis. Try to proofread your stuff. Get to the point quickly, assume the person you're reading is busy. Like the again, I 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. Um You know, I I I I do think people have different things on this. I personally do think That

55:49 on things like email. You kinda do have an SLA to respond. There's some people I know who 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 I personally go the other way. Which is I feel like

56:05 From an educate perspective, like I don't owe you A twelve page essay. But I do owe at least an acknowledgement quickly. Right, of what you've said. Like you don't want to leave people hanging.

56:15 But again, I don't I 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 send it to? If you send them ten paragraphs.

56:28 It's annoying, right? You're like, Okay, I have to read all this. What am I gonna 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 gonna spend 10 minutes talking at you. Right. And so I do think keeping it short and to the point. You know, not being silly, not using emoji, trying to make it readable. Like these are all say more about the emoji piece. Like is your advice just no emojis if it's a business. I think emojis emoji from my perspective is very it's like a it's like quite a step of familiarity, if that makes sense. If you uh from a business context Look, if someone sends you a smiley face.

57:03 you can respond with it. Like you can kind of like match again, it goes back to this matching vocabulary and language. Like I'm not saying You should be totally cut and dry. But It's kinda like I would say emojis almost feel like jokes to me, which is like Tell them at your own risk.

57:18 And they're probably not worth it. You know? Awesome. Okay. I do use emojis. I use like the pr the thank you hands one a lot. And look, I think text is different. takes on this. And so I I wouldn't say anything I'm saying here is dogmatic.

57:32 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.

57:42 And like I would say that like they're kinda harder to read than just a well worded, simple to the point email. Um And I think you just want to come across as like a literate, to the point, simple, clear person. Emoji sometimes.

57:55 Kind of implies use AI to generate this thing'cause Jet GPT loves emojis. Totally. I also like look, I mean there's a whole we wanna get we wanna get spicy for a second. Yes. I don't know how I feel about People who have like invested too much in the emojis. Right. So you get people who have like changed

58:11 The colours their emojis from the default or whatever. I'm not saying not to do it. I'm just saying it's quite a statement. Is my view that you've invested in your emoji pack? Or like using special emojis people haven't seen before, or like It's like

58:25 Again. It's a subtlety. And you gotta understand the room and like the culture and like what you're responding to. But I I I do think that people read more into that than people want to be read into it.

58:36 You know what's crazy now? I don't know if you've seen this. You can like create your own emojis now in IOS. Yeah. And emojis or so. It's like a whole new world in just infinite of it. If you choose to use those You are going way out on a limb. Right. That people are gonna be receptive to that and not be like

58:53 This is a person who spent a lot of their time customizing their emoji pack when they probably should be doing something more interesting. They should be finding product market fit. Yeah, or learning etiquette. Mm-hmm. The other tip you had that I love, which is uh think about the order of the emails when you're emailing somebody. Yeah, I I do think you kind of

59:11 Wanna think about You know, there is a connotation to who you send it to. And who are you C C. And the order in which people now I you know. I don't want to like overstate this.

59:21 But put differently it's like If you're in an email on the first person on the email is the assistant and the fourth person on the email is the CEO, you've probably done it wrong. And'cause the implication there is You who you think is most important comes first, like who's first t to mind. You know what I mean? Who's kind of included? So like

59:40 If I look at an email And I'm the first person in the two. Right. Candidly I I mildly pay more attention to it than when I'm the fifth. Right,'cause in my head I'm like, Okay, well like

59:51 This is really to Kevin and like I'm on it. Like if you see an email sent to many, many, many people Almost by definition it's not that important. Right, is almost the way I put it. And so you have to be really careful with the edge of that. I think even the the Who do you hand to and who do you C C There's a language to that.

1:00:06 that like from an etiquette perspective to understand, right? And like I I do think people sometimes miss that. Like the CC line is very, very valuable. It means Hey, you should have a copy this. This is not really to you. I'm not expecting an immediate response. Right. I even think there's even a subtlety like who responds then. Like if you send an email to ten people. C C to The whole lot of yards.

1:00:26 You know, there is a subtle ad. See like When you respond. Like if you are the fifth C C on an email. You're not expected to be the first response. Again, you can break this rule. Like there are times to break it. There's a subtlety to it, but it wasn't really sent to you, right? Like and so there's a whole language to who you send to and who you C C in the order that like

1:00:48 Again, it's very subtle. But it's worth understanding. So true. Man, any You would think nobody sees all these little things in the

1:00:56 Gmail thread, but you do. They're just right there and you'll get the thing. I think people this is the whole thing about Etiquette is like it's all this invisible stuff. Yeah. You don't need to spend like all the in some ways the whole story of doing this well Is it should not occupy eighty percent of your brain. Right. What you're saying is I've got this, we're on the same wavelength, my heart rate is low, I'm doing it properly, and I'm doing it with like Intuitively almost, right? Which is a hard ask, right? Because what we're basically saying is like

1:01:20 These are unknown things. But intuitively you should just know them. And that is actually what you're signaling is like you can trust me'cause intuitively there's this well of knowledge and cultural connection and whatever that we can we can share effectively. And if uh your B C C definitely do not reply all. Yeah, I mean I I have some unbelievably funny faux pas from my history.

1:01:41 With C C B C Two lines. Um I one of the worst Etiquette slash Mistakes I ever made. Never ever.

1:01:51 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. That's a bad idea, right? So whatever you're doing, that's not even an etiquette thing. That's just like a Be smart.

1:02:04 Proofreading thing. Proofread. Proofread. And don't send emails to people about them that they're not supposed to see. Yeah. And it's like Gmail makes it too easy to do that'cause it adds them automatically if you like talk if you add them. No, for me it was more just like the the way to check the spelling of someone's name is not to put them in the two field ever. Yeah. Oh yeah. I don't bad okay. Oh man. Well you're still you're still kicking, so bad.

1:02:27 I'm still kicking. Okay, uh two more. Uh meeting etiquette. Yeah, I mean, again, we've talked about arriving a little bit early. You should do that. Don't arrive up too too early.

1:02:39 Like you shouldn't again, like if you're an hour early Walk around the block. It's fine to walk around the block. You don't want to sit in someone's office. Cause then all of a sudden it feels like this person's been here a long time. Like this feels like even though they're not scheduled, like we're leaving them hanging. Six coffees deep. with the receptionists, like you don't want that, right? Like uh

1:02:57 So I think you wanna be like ten to fifteen minutes early. You do not want to be much earlier than that. Um We talked about meaning other convenience. I do think it's fine. Just start with a little bit of small talk. Right. Uh you know, there are times it's not, or times people are running behind, but like

1:03:13 The pleasantry of like The weather is nice, or how is your weekend? Or like something that kind of cuts cuts the air a little bit and then you kinda flip into business is like a good thing, even though it like feels transparent is still useful. Right, is what I would say. Uh kinda like and again, it's it's almost a signal of like I am here for business.

1:03:32 But I'm like a normal person. And like I'm willing to have like a nor you're like signaling like, oh, I know that we should start with a normal conversation, if that makes sense. Right. I don't know. If you saw this on Twitter, someone described small talk as like the T C P I P Ac handshake. I love it. I always I always describe it as like Imagine the modem crash from when we were kids on a fourteen four. You know, like that old modem crash. Like that's that's what small talk is. It's a modem crash. We're trying to hit the wave lights. You know, et cetera. Yeah.

1:04:05 Uh For meetings virtual ones. Camera on. Like and again, I say this as someone who sometimes violates this, right? I violate it knowingly, I violate it knowing what it costs me. But

1:04:17 You really should have your camera on, right? Um 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 ways and I I go a step further.

1:04:34 I actually this is this is less Uh a hard rule. I actually really don't love virtual backgrounds for the same reason. I'm like, look. I'm not gonna judge you if you're your bedroom, if you're a startup founder. It's fine.

1:04:47 But I would like to see that your bad 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

1:04:57 People will get on Zoom calls and they'll you know be on a call and like their closets open and I'm like It's not a big deal, but like Do you see your own self picture here? Like can you just close your closet? I don't want to see your shirts. You know, like that that type of stuff I think goes further than people realize. Awesome.

1:05:16 Uh, one other tip you had was clean up after yourself if you're in a real meeting. This is actually a couple of the easiest way. And this, by the way, is for my partner Kevin Coller. But the easiest way To come off badly. Is to not

1:05:30 Offer. To put your coffee cup in the kitchen. Right. And like honestly, we do this. Like we because like if you think about it, we work for LPs, limited partners, right? Like that's who we raise money from and then deploy it from. And my partner Kevin, even more than me, has this thing. Which is he is

1:05:44 maniacal about this, which is no matter who's in the room, if we're with an L P You take the coffee, you take the coke, even if you know full well someone's gonna come in and clean that for you. You make a point. Of asking where we can put it. Putting on the side table, et cetera, and acknowledging that there's a mess.

1:05:59 I feel that. Final. Topic is exiting and leaving. What are some tips? You should stand when people leave the table. Right. Not ridiculously, by the way, you should go stand with the table.

1:06:10 Stand and shake hands. Don't be sitting when you're shaking hands. It's just what you do, right? And like it shows that you're aware of it. Uh follow up. with gratitude, like you should send people thank you notes. Even if they shouldn't be long. It shouldn't be ridiculous. But like we met

1:06:25 I got something out of it. Like Thank you for taking your time. It's like always appreciated. Uh is what I would say. Um Obviously there's stuff like don't take calls, et cetera. Like this is kind of like the the kind of obvious stuff in terms of exiting and how you think about it. Like even if someone if someone rings you. Right.

1:06:42 And you're like and the meeting's over and you're over time, you're like, I gotta pick up this call. You hit the button that says I'm calling you right back. And then walk away. Don't just become the phone and like wave. You know, is what I would say. Um Yeah, and I I think like there's stuff like that, um that would just keep in mind. They also had like don't make a production of your exiting just like just exiting. Yeah, yeah. I mean again like I don't like

1:07:02 You know, yes, I think that's really true. It's I mean there's there's even a a point like it There are lots of scenarios where I think an Irish goodbye is the best goodbye. We just kinda disappear. Like any large group setting I think is great. Maybe you take one person on the way out of the host, right? But like

1:07:18 Yeah, the the I am leaving now, right? Like let me kind of say goodbye to everyone and hug everyone, it's too much. Yeah. I love that. Okay, we got through everything. Is there anything else that you think might be important to share? So much other stuff. I mean again, I go back to this whole thing, which is like, you know, these are all fun tips.

1:07:35 I love the cartoons. We iterated them a bunch. We have more to do. Like I we're having a lot of fun with this, and I think it is providing a lot of value to people, which is great. Like that's kind of my goal is to both have fun and actually provide value. And help people. That intersection is great.

1:07:49 There's a thousand other tips. And like so for the biggest thing for me is when you have more or think of them, send them to us. Cause 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 fifty, sixty pages. it it will be a few hundred eventually. And I think there's a lot more to come. And we're gonna be t doing classes next year all over the country. And actually world. We'll be we we got we invited to do we're gonna do one in Tel Aviv. We're gonna do one uh we're certainly doing New York and a few other places and you know, it'll be fun. This is uh my God.

1:08:21 A whole new life forming here. I I you know the funny thing is this stuff the etiquette story is obviously Pretty fun. And so like think people like Morning Brew who just like keep making videos about this and like there's this whole etiquette thing going on. And like

1:08:33 Oh my god, I've done some pretty good investments in my life, built some cool products. Am I gonna be ultimately remembered as like the etiquette guy? That's kind of hilarious. Uh that's where we're doing it. I'm into it, though. I'm into it. I'm fine with that. So I'll read uh you have a 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.

1:08:51 Remember the goal of all etiquette is essentially building trust and project genuine confidence. Uh 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 point.

1:09:07 If nothing else. If you remember those points, you will you will be served well. There we go. Okay. I'm gonna take us to close out, make this more of a s regular episode, I'm gonna take us to two recurring segments on the podcast, AI Corner and Contrarian Corner. I don't know if I told you I was gonna ask you these questions, but I'm gonna go. I love contrary and corner. An AI corner, depends what you mean by that. So the question at 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

1:09:37 Pretty skeptical of most AI applications. I will say the thing that I've had the most fun with with AI and I find great is actually partially where the cartoons for this came from is I built A little personal news aggregator called Letter Meme. That basically takes all the newsletters I don't have time to read.

1:09:53 And turns them into daily cartoons. Like so I have a grid of like what's going on. The world's a front page in cartoons. And I actually love it. It's like the best way I get an overview. Cause there's all these smart newsletters, you don't have time to read any of them. So I pipe them all in. Except Lady Newsletters. But keep going.

1:10:10 Except like that one I don't put in the aggregator, although I don't do that. Um But uh it's great. Uh so I'm super into uh into it. Uh and that's letter meme.com. I'm checking it out. I love this. I love this. So this is AI generated. S 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 uh Yeah, the the uh the idea is you basically get an email digest once a day and it's continuously updated of like 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 the how did you build this? Was the vibe coded? Did 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 cloudflare 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 and to end.

1:11:04 But then vibe coding also doesn't really scale. And so the reality is after a certain point, I had some friends who are great engineers just take it and like up level it in a few ways that I honestly ran out of time to work on. Well let's go to contrarian corner. Uh, this could be an entire podcast conversation with you, I suspect. But just like what's something. You wanna share that you believe that most other people don't believe.

1:11:25 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. Um And that doesn't mean that I don't think you should be using AI to build things. I actually think you absolutely should. It's kind of like Not using AI in your startup is the equivalent of not using the cloud.

1:11:49 in like twenty ten, or like not using the internet. in like two thousand it'd be insane. Like of course we're gonna use these tools. But there's a difference between a great business That you're using I AI to supercharge or make better or just as a piece of infrastructure. That's not an AI business. This is a business, right? And I'm very into those versus like.

1:12:06 all of these companies that come out whether that that say we are the AI blank Uh. I just I think they're all going to zero. Uh, even you know, my kind of argument is from a seed perspective is like, look. Is open AI a good investment or not?

1:12:19 It's a terrible seed investment. Right. The way the number's baked out, even at a five hundred billion dollar market cap, when all said and done. The seed investors have made something like twenty five 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.

1:12:36 For like the company that is defining the moment. And the reason is because these things are so capital consumptive. So If you're trying to employ a hundred billion dollars The market is fragmented. You know, y people want to dream a dream, people like want religion, they want belief. Like th there's there there's a bunch of reasons why you can like squint and justify You know what? If the storytelling of Elon

1:12:57 allows SpaceX, which by the way I love. I think SpaceX is an awesome company. But if all of a sudden that actually can be worth one point four trillion dollars to the public market, guess what? The money plowers are gonna do great with all this narrative driven. Uh religion is what I would put it. But if you're a disciplined seed investor. I guess my contrary take would be run away.

1:13:16 From things that are AI companies. Uh,'cause even if you look smart for the moment, you're you're playing a dangerous game of get out. Uh Before the narrative collapses. Wow, I love this. Okay, I want to follow this through 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. So like that's not gonna happen.

1:13:40 Two. They're fundamentally commoditizing in all sorts of ways. It's very unclear what the lock in or value is on any of these things, right? And so It's just like the whole dynamic is off, and the the thing is people are desperate right now. For things to believe in. Like

1:13:54 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'cause we had the West, and if you were gonna work hard, you could like go west and you do great, and like there was all this opportunity later of opportunity. We've had reverberate to like you know my generation, your generation.

1:14:12 We were blessed. Because we have the internet. The internet was digital Terra Nova. And like we got to build fortunes and do amazing stuff and new work, being this like 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 Which again, if you look at the math on it.

1:14:29 Everyone wants it 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 for their Terra Nova story with good reason. Right, like but but the story is it has to be real.

1:14:47 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. is not a great start up opportunity. So what is it you look for? Do you inv do you what do you look for when you're investing in AS D Uh well again, I won't invest in things that 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 of the world. So

1:15:14 We've done a lot. Whether it's to live security or outtake. All around the theme of the Void Kampf test from Great Blade Runner, which was the test they basically ran to the are you a real or are you a bot? Right. Turtle on their back?

1:15:30 Yeah, it's like there's a whole like set of companies that are like implications of AI and how do you manage it and handle it as a society. I think there's a a lot to do there. I use a lot to do in cultural shifts from AI, right? Um Wh you know, there's all sorts of interesting trends to follow there. Like There's there's all sorts of businesses.

1:15:47 That will be disrupted. They're like not AI businesses, they're businesses that will be disrupted interesting way. So I think there's a lot of opportunity. 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 gonna win cause AI.

1:16:04 I'm like, yeah, you're gonna win because of something else, right? And AI is gonna be a propellant to it. Sam, you're a fascinating human. I feel like I I could we could talk for hours. Is there anything before we get to our very exciting lightning round, anything else you wanted to look I'm happy to be here. 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 let me run five questions for you. Five questions. I'm ready. Five questions. What are two or three books that you find yourself recommending most to other people? Ooh, okay. So let me pull up my list'cause I I I gotta pull up my Kindle for this.

1:16:39 Uh one is I'm reading right now, I gotta admit. I like to make fun of Mark Andreessen a lot. But he recommended a book called The Ancient City. Which is fascinating. And so I'm in the middle of that right now. I'm really enjoying it. Um Man search for meeting is great.

1:16:53 Uh I'm just going through. What have I read recently? You know what's great? Area fifty one. An uncensored history of the top secret military base. Not very Ariadite.

1:17:03 Great book. And then I I honestly think the one serious one I'll make a recommendation on is uh lessons from history. Is like One of my favorite books ever. Um I would really, really, really recommend. It's a short read.

1:17:18 Um, 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

1:17:29 You can just listen to it all, like not like in a shower. It's not a long book. I honestly think for me hours of an investment Yeah. 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.

1:17:46 Have you heard this one? Have you seen this one? Oh my God, this is so good. What's it called? It's the fish that ate the whale. Incredible book. Uh so is um The Last Kings of Shanghai. If you know that one. Like these are all like amazing books, but They're longer and there are more stories. Just every one of the podcasts should go read Wilderand.

1:18:02 Okay. I love it. Uh, favorite recent movie or TV show that you've really enjoyed? Oh, I gotta say, I mean recent I think Landman is fabulous. Have you watched Landman? Yeah, yeah, yeah. I think it's great episodes. I I'm like really into it. That would be my most recent take. What's interesting about that. Mm. Show is now uh

1:18:20 Tech companies are all super into energy and the I talked to I talked to well I'll tell you a funny story, which I talked to a founder Who's in uh Midland, Texas. And it was just kind of part of the show. And it's so classic and typical. He's like

1:18:38 All these select value people and now think they understand the energy industry because they watch the land map. He's like so there's all he's like I'm like it's like wild, but I totally believe it like because I know too many venture capitalists are like Oh, I now understand this because I watched Landman and he's like this totally a thing. Uh. I I would feel that. Okay.

1:18:55 Favorite product that you really discover that you love. Could be like a gadget, could be an app. Could be clothing. Could Okay, I'll pitch you know, I'll pitch people on. This is a little self serving. But um I will pitch people on June date.

1:19:10 So okay. I actually don't use this product'cause 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 have AI implications but are not AI. So Everyone's got this like old virtual girlfriend, loneliness, you're gonna chat with your friend, da da da like whatever, fine.

1:19:30 These guys came out. And what they do is like look, if we're really trying to match up humans, like call it Tinder two point oh One of 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 asked ChatGPT a structure prompts that they've designed. It pulls out an unbelievably good profile of who you are.

1:19:52 And then you basically match with people. based on like what you're actually asking chat GPT about and the implications of who you are. And you know the fun part is I haven't obviously done dates on it. Yeah, not for me. But I have pulled my profile from like wow, this is like shockingly good description.

1:20:09 Of who I actually am. And so I think that's like a really fun business. That's it'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. You know a lot. It's pretty good. And so so in this dating app, I love this idea. It was so good. So the the people read That are they able to see that as your profile or it's it's a little abstracted from that. And like is 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. Like this is good. Like

1:20:39 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 high match, each one carefully Wow, so fun. It's good. I I get 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.

1:21:00 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 L M and try to match these people. Didn't work for me because candidly you know what happened.

1:21:14 Way too many qualified women. And not enough men. I just don't have the liquidity. Like I have Hundred Great women who murdered. Hey, this is what I'm looking for. This is who I am. You're like, you were an amazing person.

1:21:25 And then like The four guys you write in are like I want a twenty five year old hot. girlfriend like ah this is not gonna work. But June Dave might have the liquidity to make it work. By the way, your newsletter's awesome. Tell people where to find it while we're on that topic.

1:21:39 can't like I just kinda like there's no way to sign up for it. Um If you send me an email perfect. If you send me an email, lessen at Gmail. I'm fine with 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.

1:21:56 But I it's actually funny. There's not I Oh well, you know you can do actually that'll get you on it. is if you go to W lesson dot com L E S W L E S I dot com. I have my little like bot app that like includes like a little LLM that kind of is trained on my writing just because I was having fun building it.

1:22:13 If you enter your email address there. And talk to it. It will add you. Um but No, there's not like a sign up page. Okay. I love I love this contrarian growth strategy. No, you can't really sign up.

1:22:25 Okay. That's great. Okay, two more questions. Uh you have a favorite life motto. that you find yourself coming back to often in work or in life. No, but I will say that I have Hangy in my gym, which I love. From the Facebook hackathon. after the launch of Google Plus. This is going way back in history.

1:22:43 They made great posters. Which was uh 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.

1:22:55 Like let's and I had w some of the most fun work experiences. We were working literally twenty four hours a day. Like Past midnight every night was in that period, and I love that poster. So Carthage must burn. How about that?

1:23:08 Great. Final question. You are a fellow podcaster. Uh I really enjoy your podcast called More or Less. It's very cleverly named because of lesson and with the Moors. We love Orless. We also like my wife and I are contrarians and hate everything by default and the Morens like think everything's amazing. So it kinda works from a dynamic perspective. I love it. And Dave More, but Morein just to be clear.

1:23:29 And your wife, she runs the information. So she's good at prompting us with it to actually going on the world and then we just bullshit about it. So what's uh 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 kinda just like talking to your friends for an hour a week, which I wanna do. Like I love the mortars. We don't live that close to them, so it's kinda fun to just like have that time set aside and then cut it up and post on the internet pretty raw. Um

1:24:00 Here's the funny thing about it. It's Fine it serves our purposes. Way more Then

1:24:07 I actually expect it to, which is we enjoy doing it, which is the most important part. We would do it if no one was listening. And Weirdly, like a lot of our friends and people we care of the industry seem to pick up the pieces they like from it and like talk to us about it. So it's like a great conversation starter. Um So it's like weird. It's like I don't like it's not a huge podcast. It's big enough, but it's it's I actually think the thing that's been most surprising to me about it is that Even though like we don't really have growth strategies and like we're not trying to blow it up and like

1:24:33 We don't get paid for it. It's like Weirdly Useful. Uh is what I would say. Um, you know, even the fact that it's like, you know, is 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.

1:24:46 But um It's like weirdly listened to and useful by the people that like we care about, um and is fun. Despite the fact that You know. It's not like a

1:24:56 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 um but we have fun. I mean I would I would happily do it with my friends if no one was listening. And

1:25:09 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 is like, Hey, by the way Here's a better idea. You're like, that's great. Sam, you're awesome. This was such a fun chat. Very different from my regular podcast. I think people will find this extremely interesting and Useful, as I thought, and also fun.

1:25:33 Two file questions, where can folks find you online if they want to reach out? Check out the channel. Look, our venture firms called slow ventures, slow dot co. Um, I'm Sam Lesson. I'm kinda lesson everywhere, whether it's like Twitter or Instagram or whatever you use. Um Or just less than Gmail is my last name, is 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.

1:25:58 Uh Yeah, I don't know. Come hang out in the pool house sometime. Okay. I love I love this this as an excuse to hang out. Sam, thank you so much for being here. Hey, great to see ya.

1:26:09 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'sPodcast.com. See you in the next episode.

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