Sam Lessin: Why low heart rate beats hustle in any room

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 call, have an appropriate background. Don't smell like shit.

Lenny Rachitsky 0:08 Tell me why you decided to spend time teaching people proper etiquette.

Sam Lessin 0:13 You have a lot of really young people, they've been holed up in a room coding, and they show up encouraged by Silicon Valley to be, in some ways, abrasive on purpose. You want to be able to show up in a way where people are like, "Okay, this is someone I can work with and trust."

Lenny Rachitsky 0:24 Etiquette is a skill for how to show up in a room with a low heart rate.

Sam Lessin 0:27 You're at the Kleiner Perkins holiday party. You have all the venture capitalists in the world, and all the CEOs. You're at your first company. You feel like, "Oh, my God, this is my shot, and 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 everyone off. You're gonna project totally the wrong vibe.

Lenny Rachitsky 0:46 This isn't your one shot. You'll have other opportunities.

Sam Lessin 0:48 You kind of want to show up with the self-confidence and the calm of abundance. This is part of the story, this is not the entire story. [gentle music]

Lenny Rachitsky 0:58 Today, my guest is Sam Lessin, partner at Slow Ventures, previous VP of Product at Facebook, and two-time founder. This is an unconventional episode that may surprise you in how interesting and useful it is to your life. I asked Sam to come on the pod and talk about proper etiquette. You'll hear the backstory of how Sam got into this stuff, but this is turning into a big thing for him. He's teaching classes around the world. He published a book on proper etiquette. I love his framing for why etiquette matters, that the goal of learning good etiquette is to show up in a room with a low heart rate. And we cover all kinds of social interactions, like introductions, small talk, meals, meetings, and basically all of the most important things you need to know when it comes to etiquette. I personally found these tips really, really useful, and I learned a lot from this conversation and from his book. Sam is also hilarious and so fun, and I hope you enjoy this very unique episode. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get a year free of 19 incredible products, including a year free of Lovable, Replit, Bolt, Gamma, n8n, Linear, Devon, PostHog, Superhuman, Descript, WhisperFlow, Perplexity, Warp, Granola, MagicPad, Andrejcast, ChapAI, Mobbin, and Stripe Atlas. Head on over to lennysnewsletter.com and click Product Pass. With that, I bring you Sam Lessin, after a short word from our sponsors. This episode is brought to you by 10Web, the company that pioneered AI website-building before ChatGPT. In the last three years, over two million websites have been generated with 10Web's vibe-coding platform. 10Web's vibe-coding platform is a powerful way to build websites. Think of it as Lovable for WordPress, front-end and back-end. Users can build any website at any complexity: e-commerce, portfolios, information websites, blogs, and it comes with a WordPress admin panel and thousands of ready-to-use plugins. 10Web also offers website generation as an API as a service for SaaS companies, marketplaces, hosting providers, MSPs, and agencies. SaaS companies can embed it via API, so that users can launch AI-generated sites directly inside of their platform, connected to their own data. Agencies and MSPs can get a white label dashboard to manage clients and resell under their brand. Hosting providers can self-host the API builder on their own infrastructure. Check it out at 10web.io/lenny, and use code Lenny for exclusive free credits and 30% off API or white label solutions. That's the number 10W-E-B.io/lenny. Vibe-coding platform as an API. Today's episode is brought to you by DX, the developer intelligence platform designed by leading researchers. To thrive in the AI era, organizations need to adapt quickly, but many organization leaders struggle to answer pressing questions like: Which tools are working? How are they being used? What's actually driving value? DX provides the data and insights that leaders need to navigate this shift. With DX, companies like Dropbox, Booking.com, Adyen, and Intercom get a deep understanding of how AI is providing value to their developers, and what impact AI is having on engineering productivity. To learn more, visit DX's website at getdx.com/lenny. That's getdx.com/lenny.

Lenny Rachitsky 4:19 [gentle music] Sam, thank you so much for being here, and welcome to the podcast.

Sam Lessin 4:26 Bliss to be here. I'm excited to, to have the conversation.

Lenny Rachitsky 4:29 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.

Sam Lessin 4:39 Useful and interesting? That's so unlikely.

Lenny Rachitsky 4:41 [chuckles] 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?

Sam Lessin 5:01 I really enjoy things at the intersection of hilarious and useful, right? You kind of 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 honest about it, like, you can- it's very hard to cut through the noise these days, so kind of you need humor as a great way to cut through it. But humor just for the sake of being funny is not that useful. Like, there has to be a deeper truth to it. And so, you know, with this etiquette thing that we've gotten into, it started, as many things do, with a tweet that got escalated into an event. It's gotten escalated into a book and a bunch of other stuff. I, I kind of believe that, you know, you should always... There you go, you got it with you. I've got my coffee, too.

Lenny Rachitsky 5:41 Got the book.

Sam Lessin 5:41 It's like, it... There's a, there's a rule, like, you know, you always wanna just double down in life, right? And so I'd say, like, why etiquette? Look, there's a serious, real narrative to, like, why etiquette matters in 2025, um, for founders, almost 2026. Like, one, you know, we talk about software getting commoditized. We talk about all of this fear-mongering and scare people feel about Silicon Valley and AI, and, like, all the things that are going on. The net is, if you wanna do business, and you wanna do business and build great partnerships with-... team members, you know, with companies you wanna do business with, almost with anyone, the reality is etiquette ironically matters a lot, right? There is a deep truth to this, right? You, 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 where they're at, build trust, you know, mirror kind of expected behaviors, these are all, like, tools, right? And so that's the deep truth. The shallow truth is, it's kind of funny to teach Silicon Valley people etiquette, right? Like, the whole narrative for so long has been, "None of this matters, just focus on your product." Saying, "Well, actually, it does matter," and you... You know, I'm wearing a T-shirt. I'm not exactly known as the most high e- etiquette person in the world, 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.

Lenny Rachitsky 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.

Sam Lessin 7:10 Yeah. This is the thing I think about a lot, but it's like, again, I think about... Again, you and I are now old people, right? But like-

Lenny Rachitsky 7:17 Yes

Sam Lessin 7:17 ... you're young.

Lenny Rachitsky 7:17 I feel that. [chuckles]

Sam Lessin 7:18 You, you feel it in your bones. It's like, you're young, right? You're in- you're at the Kleiner Perkins holiday party. You have all the venture capitalists in the world and all the CEOs. You're at your first company. You're young. Maybe you're from a different country. You're like, "Oh, my God," like, "This is my shot," right? Like, "I have all these people I need to talk to, and I need to convince this person of that and make this connection." It becomes very transactional. If you show up like a little Energizer bunny, right, you're 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, come in with a sce- a mindset not of scarcity but of abundance, understand how to give more than you take, understand how to build a relationship, not collect business cards, like, these are things that actually serve you massively well, and I just feel like no one's being honest in teaching founders this, right? Instead, they're saying, "Oh, no, all that matters is your product." I'm like, that, like, the product does matter a lot, but if understanding these rules could be the difference between doing really well and missing a business deal, you know, if you show up with too high a heart rate and you burn a bunch of mild relationship opportunities, like, I don't know why you wouldn't want these skills, right?

Lenny Rachitsky 8:30 Yeah. Is one way to think about it, like, you can be successful not doing any of this, not knowing any of this, and just... You're just, you're hurting yourself. You're making it harder.

Sam Lessin 8:38 Yeah, I think it's just an unnecessary-

Lenny Rachitsky 8:39 Yeah

Sam Lessin 8:39 ... you're creating an unnecessary uphill battle for yourself. I'd also say that, look, this goes back to, like, technical differentiation, where things are at. It is true that if you bring manna from heaven, right, like, you invent something that is literally the next Google or whatever out of pure thought, that sometimes none of this stuff matters, right? Like, if you just- if you fully i- 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, well, not what 99.9% of startups are doing. But if you have that, yeah, you basically can get away with anything. It is true. That doesn't mean you 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. But, like, there are ways in which that can trump all. It's just, like, candidly not the experience of 99.9% of startups.

Lenny Rachitsky 9:30 Awesome. Okay, so let's get into it. There's kind of... You've divided this book into about 10 categories, 10, I don't know, social situations is one way to describe it. So let's just go through each one, and just give us some pieces of advice.

Sam Lessin 9:41 Sure.

Lenny Rachitsky 9:41 And, and something I didn't mention, the reason I'm excited to do this, the reason I reached out to you [chuckles] 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.

Sam Lessin 9:51 Cheers. I mean, again, like, uh, I think the thing for us is, I'm kind of a ship early, ship often guy. So V1, you should buy it now and study it, '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.

Lenny Rachitsky 10:10 Let's do it. Okay, so introductions and entering a room.

Sam Lessin 10:13 Yeah. Be early. [chuckles] That's the first one, right? Like, you know, again, eh, 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, 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 in the room five minutes late, your heart rate's up. If you come in, you had a second to beat in the- take a beat in the, the, in the waiting room. Y- they kept you waiting, right? That, that's the dynamic I think you wanna to cultivate. Now, if you're not late, I'm sorry, if you're not early, just apologize. It doesn't need to be, like, a five-alarm fire. 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, where 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. Something I've seen, I'll, I'll go through a few others that we talk a bunch about in kind of it, is, look, um, you wanna have a strong handshake, firm. Don't crush the person's hand. Again, this is not, you know, practice on your friends, right? You know, you wanna repeat names back, is a really, really valuable thing to think about when you're meeting someone. Say, "Hey, Lenny, it's great to meet you," right? Why? It shows that, like, you're actually trying to remember the person's name, right? Like, a lot of times, people meet a lot of people. It's like, "Nice to meet you," you move on. First, it's gonna be harder for you to remember the person's name. Second, it actually shows like you're meeting them and making an effort, right, to actually connect and say, "Okay, I'm trying to focus on you. You're not just a number to me," right? "You're not just a potential check," or whatever it's gonna be. So there's a bunch of things like that. I'm kind of curious, you know, we can go through a bunch more, but those are some of the ones I would think about.

Lenny Rachitsky 11:52 One that I loved was, if somebody else is late, do not make them feel bad.

Sam Lessin 11:57 Yeah.

Lenny Rachitsky 11:57 Do the opposite of what you're doing, of what you do.

Sam Lessin 11:58 100%, and I think this is like, I've seen this with entrepreneurs, and I, like, I get... Like, I'm a VC. I do get scheduled in, like, 30-minute chunks back-to-back, like, all the time, especially on Zoom. Guess what? I am frequently late. I don't feel good about it, but it happens, right? And a lot of times, founders, most of the time, I'd say, founders know that, like, if I'm late-... I will always apologize. I'll try to email them ahead, et cetera. But then it is what it is, and like, they'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!" And they're like this. And you're like, "It's fine if you feel that way, but it's really not very productive to make a big deal out of it," right? Like, if this is a deal breaker for you that I was a few minutes late, then like, I don't... Then now I feel like I'm wasting the next 25 minutes of my meeting time, 'cause like I'm not... Like, 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?

Lenny Rachitsky 12:51 You had also, uh, some advice on eye contact. Let's hear that one.

Sam Lessin 12:54 Yeah, it's really important. A- again, I think the thing to keep in mind is, especially in an age where everyone's used to being in front of computer screens and looking at six different windows at the same time, again, people are taking their time to meet with you. Or at a party, they're, like, taking their time to, like, listen to you. And it's just a matter of respect to be like: I'm actually here in this conversation. I'm not off on my screen. I'm not, like, glancing around the room. Now, look, there are some people, we all know this, who are, like, literally neuro- quite neurodivergent, and that's very str- hard for them. Like, that happens, and I... A lot of founders have, like, neurodivergence in some ways, so, like, there is grace in this to a point, but it's a thing you should make at least an effort. I think one of the most important things about all this stuff is, what matters in some ways is the signaling of the effort as much as the actual thing, right? I think is a really big overarching theory. So it's like, look, if you have trouble with this, but you're really trying, that goes a long way, versus just being like, whatever.

Lenny Rachitsky 13:48 Uh, maybe a final tip there is around partners, introducing the partner, saying hi to their partner. Share that one.

Sam Lessin 13:53 Yeah. Yeah, so like, look, this happens all the time, and again, in the spirit of I'm not perfect at this either, if you're with your partner, introduce them first, right? Like, yeah, you know, bring them into the conversation. One great trick we talk about in the book, which I really unfortunately use all the time, right, is this whole thing... Let's pretend you're with your partner or with someone who's a friend. It doesn't have to be a romantic partner, whoever you're with. You're gonna forget someone's name, right? And what you really should do is-

Lenny Rachitsky 14:18 All the time. All the time.

Sam Lessin 14:19 You're gonna forget someone's name, and like, that's what you're supposed to do. The etiquette is, you say, "Lenny, please meet my wife, Jessica." You know, and like, that's, you know, th- that's kind of thing. Now, here's the thing. This is where you start bending the rules. What if I don't remember your name, right? If you have your partner with you. You can flip it around and say, "Jessica, I want to introduce you," and then you kind of like, can kind of figure out how to frame it up so that you then, Lenny, extend your hand and say, "It's really nice to meet you, Jessica," and you get to pick up the name again, right? Or things like that. So there are some-

Lenny Rachitsky 14:45 The way you put it there is you let it hang.

Sam Lessin 14:46 You let it hang-

Lenny Rachitsky 14:46 That's the phrase you got.

Sam Lessin 14:47 Which by the way-

Lenny Rachitsky 14:48 I love that

Sam Lessin 14:48 ... it's a great example of the fact that like, if you're really in tune socially, you, you kind of know what's going on, right? [chuckles] Like, you know what I mean? Like, y- 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.

Lenny Rachitsky 15:14 Well, I am so bad at remembering names. I, like, I think I have a medical issue where-

Sam Lessin 15:18 Oh, yeah

Lenny Rachitsky 15:19 ... I just can't remember names. So this tip [chuckles] is so good, and just to reinforce it. So there's almost, like, two ways to do this, is what you're describing. Either it's like, my wife's name is Michelle, so it's like: "Hey, Michelle. Uh, meet my wife, Michelle." And then they're like, "Oh, I'm Bob. Nice to meet you, Michelle." Or it's, uh, like, make it a little more awkward of just like: "Uh, Michelle, meet, um..." Like, like, and then let it hang. Is that, is that the tip there?

Sam Lessin 15:41 "Michelle, I want to introduce you," right?

Lenny Rachitsky 15:42 Oh.

Sam Lessin 15:42 Or something like that.

Lenny Rachitsky 15:43 I want to introduce you.

Sam Lessin 15:43 Or like, you know, something like that.

Lenny Rachitsky 15:45 Okay.

Sam Lessin 15:45 Or, "I want to introduce you to Michelle."

Lenny Rachitsky 15:46 Okay.

Sam Lessin 15:46 You look at them in the eye, right?

Lenny Rachitsky 15:47 Yeah.

Sam Lessin 15:48 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.

Lenny Rachitsky 15:53 Yeah.

Sam Lessin 15:53 Look, I also, fort worth, I actually have such a clinical problem on name-face recognition that's actually runs in our family. I have this whole backstory, which is, part... You know, I worked at Facebook for a 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.

Sam Lessin 16:20 I think a lot of people do.

Lenny Rachitsky 16:21 Okay, let's move on to conversations. Give us some tips.

Sam Lessin 16:25 So, I mean, on the conversation front, I mean, I think the key, again, is to welcome people into the conversation. Like, consider it, you know, y- there's... Especially, you see this happen sometimes, especially when there's weird power dynamics at play. Um, you know, you'll see some famous VC or founder walk into the room, and then some young startup person will, like, waylay them, right? And, like, kind of almost, like, flock them off, right? And they're, like, really excited to talk to this person, but you're like, there's a bunch of people around, and like, the more you can be inclusive, again, low heart rate. You're not like... It's not a scarcity mindset, it's an abundance mindset. Like, I think that's kind of like the, the tome to think about in terms of like, 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 a limit, right? So asking questions is great. You're coming in and says, "H- hey, it's nice to meet you. Let me give you my four-minute startup spiel and everything I'm into, da, da, da, da." Is, like, so self-centered, it kind of misses the point that a conversation is a, is a give and a get, and it should be an exchange. And so when you go in with a mindset of, "I should ask questions," that- that's great. There is doing it too much, right? Which is, when it's done in a forced way... Sometimes I feel this, where 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, 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 that you haven't- it's like a game of ping pong. Like, then you can kind of react to it, and it goes back and forth, where there's openness and they're playing with you. Not playing single player, right, is almost the way I would think about it in a conversation.

Lenny Rachitsky 18:17 So the tip here, [clears throat] so it's basically index towards asking questions, but not, like, 100%, you asking questions.

Sam Lessin 18:21 Yeah, consider almost like... Put it this way, imagine you're playing ping pong.... right?

Lenny Rachitsky 18:25 Mm-hmm.

Sam Lessin 18:25 Or tennis, or whatever you want. 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 10 balls at them in a row, or like... You know what I mean? Or like, uh, you know, or that, that's kind of, like, not the vibe you wanna go for.

Lenny Rachitsky 18:41 Yep. Awesome.

Sam Lessin 18:42 Look, we talk a lot about matching, matching vocabulary. You're gonna meet a lot of different people. You know, y- you wanna make people feel good and welcome. You know, I'm not saying that, you know, you should walk into a room and start talking in jive. But, like, I am saying, like, if you're speaking to a university professor versus a 12-year-old, if they're using a certain level of vocabulary or words, like, again, the point is to meet people where they're at in a way that makes them feel relaxed and good, not try to, like, mirror them, if that makes sense. But there is a subtlety that I think really matters to it.

Lenny Rachitsky 19:16 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.

Sam Lessin 19:25 Yes. This is important. I mean, I think in the end of the day, like most interactions, let's pretend 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." The person who walks across the room to someone else and say, "Hey, you really should talk to Lenny. You should talk to Sam." Like, that's kind of like... You wanna leave them being like, "That's interesting, and I'd like to continue this or expand it," not, "I just heard this entire person's life story. I never need to talk to them again," right? And so I do think there's, you know, again, like, leave them wanting more, right, I think is important. And that, that is partially about knowing when to excuse yourself gracefully, as much as it is about when to enter.

Lenny Rachitsky 20:12 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-

Sam Lessin 20:20 I've had this conversation-

Lenny Rachitsky 20:21 Yeah

Sam Lessin 20:21 ... with so many, and I think it's a uniquely American, and honestly, a uniquely Silicon Valley thing, right? I'll go, I'll go so far as to say that. Which is, look, we're used to... Especially if you're young, and these are big opportunities or big moments, people are kind of used to this, like, environment of scarcity. It, like, reminds me of the Eminem song where he talks about, like, "I have one shot, one opportunity," you know?

Lenny Rachitsky 20:43 I think it's... Oh, Eminem. Yeah, yeah, yeah.

Sam Lessin 20:44 It's a great song.

Lenny Rachitsky 20:45 Okay, yes.

Sam Lessin 20:45 It's a great song.

Lenny Rachitsky 20:46 Yes. [chuckles]

Sam Lessin 20:46 It's a 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 kind of want to show up with the self-confidence and the calm 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 keep focusing on low heart rate, engagement, eye contact, you get so much of the way there.

Lenny Rachitsky 21:26 You also have a tip about how to handle famous people that you might meet?

Sam Lessin 21:29 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 would basically say. But also, like, you... Not being ridiculous is almost the way I would frame it in this conversation, right? Which, the ridiculous is, like, if you go up to Mark Zuckerberg, and everyone knows what he looks like and who he is, and you're like: "Hi, I'm Sam," and "Who are you?" 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 just... Again, it's, it's about grace as much as anything else, right? And recognizing that they're people. And again, you're playing an iterative game, and the best thing you can do is say, "This is not my only..." As much as it might actually be, "This is not my only opportunity to meet Mark." And in an ideal world, when I walk away, people will be like, "That was a pretty nice person." Like, "Maybe I wanna talk to them again," right? Uh, now, going up and being like: "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.

Lenny Rachitsky 22:28 Maybe one last tip is the- this, you actually start with this one, of, this line of, "Great to see you-

Sam Lessin 22:32 Yeah

Lenny Rachitsky 22:32 ... when you meet someone, versus, like, "Nice to see you" again.

Sam Lessin 22:34 I... Well, again, Lenny, you and I probably use this all the time, I bet, because I honestly... Again, we go by name, face, whatever. It's a really difficult social situation to put someone in. It just... Think about from their perspective. If you go up to someone and say: "Hey, it's really great... It's great to meet you," and you're like, "We've met five times," it's, like, quite embarrassing, right? And for them, for you, for everyone. And so the more... I, like, love it. In fact, I- my wife, my wife of many, many years, who I've dated since college, has a really funny story about this, which is the first time, right before we started dating, I went up to her, and I basically did a "nice to see you" line, right? 'Cause... And I very clearly couldn't remember if we had met before, and we had, and she remembered. And so for me, this is an important one, right, to keep in mind.

Lenny Rachitsky 23:17 My wife is constantly making fun of me of saying, like, "Oh," like, and not knowing if I've met someone before or not. She's like: "How can you... Like, I don't, [chuckles] I don't know what to do with you." So that's a great one. So the line there is, "Great to see you"-

Sam Lessin 23:29 Great to see you

Lenny Rachitsky 23:29 ... because it works whether you've met them or not. You remember them or not.

Sam Lessin 23:31 Yeah, and again, it's one of those things where, here's the thing: people are dumb. If you go around saying, "Nice to see you" to everyone, they're like, "There's a small percentage chance this person doesn't remind me who I- uh, remember who I am."

Lenny Rachitsky 23:41 Right, right. [chuckles]

Sam Lessin 23:41 Right? And there are other ways to keep... But, like, that's okay. Like, that's part of the etiquette dance to some degree, is like-

Lenny Rachitsky 23:47 Yeah

Sam Lessin 23:48 ... that's fine. What's not fine is, "It's so nice to meet you," and, like, we've met six times, right? [chuckles]

Lenny Rachitsky 23:54 Yep.

Lenny Rachitsky 23:55 Okay, um, let's talk hygiene. There's a couple there that stood out to me. Uh, tell me if I'm missing a- any that you think are really important. One is just, like, subtle fragrance.

Sam Lessin 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 doused yourself in perfume, right, or cologne, or whatever it is. But, like, you also shouldn't smell bad, right? And like, it's again, your scent should not be noticeable, is almost the way I would put it, um, you know, i- in any direction. Uh, it's, it's not... You're not... There's, there's, there's no advantage to that, [chuckles] is basically what I would say.

Lenny Rachitsky 24:27 ... 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.

Sam Lessin 24:33 So it's an interesting question. I think broadly in this book, the answer is broadly yes. I will say that there is probably in January or February going to be a, what, what we've internally been calling the Fem etiquette course-

Lenny Rachitsky 24:46 Mm.

Sam Lessin 24:46 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 fragrance one, I would say, I don't think you want your fragrance to be memorable for anyone, no matter what your gender is.

Lenny Rachitsky 24:59 Awesome. This is good. Let me take two chang- 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.

Sam Lessin 25:09 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 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, you guys eat like animals. Like, you just, you know, you're- you don't know how to use a fork or a knife properly." Again, it's not like at four or six, it's not, like, stopping them well in life. But, like, you- I can't be the etiquette guy if you guys are eating like... So I've, I've been putting it- and some of them, it's been really cute. Others have been really funny, like my six-year-old has started standing whenever my wife comes to the table, which is kind of arcane, um, from an etiquette perspective. You could 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-

Lenny Rachitsky 25:55 That is so funny

Sam Lessin 25:56 ... don't judge me yet, but in a year you can judge me on my children's etiquette. Then there might have to be a children's etiquette book.

Lenny Rachitsky 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. That's like a modern way of thinking about that.

Sam Lessin 26:09 That might be better, is what I would say. I will say the, the... it's a, it's an ongoing, somewhat hilarious debate at our dinner table.

Lenny Rachitsky 26:15 [chuckles]

Sam Lessin 26:15 I'm just trying to get them to, like, not use a fork and knife like animals right now, but we're, we're working on it. We're working on it.

Lenny Rachitsky 26:21 I was just, uh... Speaking of that, I was just listening to Tyler Cowen had Ale- Alison Gopnik on-

Sam Lessin 26:25 Okay

Lenny Rachitsky 26:25 ... his 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.

Sam Lessin 26:36 Right.

Lenny Rachitsky 26:36 Yeah.

Sam Lessin 26:36 Like, to be clear, they're able to feed themselves. It works.

Lenny Rachitsky 26:38 [chuckles]

Sam Lessin 26:38 But it's like, you look at it, and it's like-

Lenny Rachitsky 26:40 Yeah

Sam Lessin 26:40 ... "What are you doing?"

Lenny Rachitsky 26:41 Yeah, yeah. Okay, the other tangent is, you didn't share the, uh, class you actually taught to founders already, so maybe share a little bit about this class you taught.

Sam Lessin 26:49 Yeah, so I mean, the- before the book, yeah, we did a, we did a class specifically initially for YC founders, right? Uh, partially because YC, Garry Tan, got very mad about this, so I'm like, "Well, now I have to do it," right? Because 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 some very fancy Vogue Spashure 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, how to have an abundance mindset. You know, basic skills, like look people in the eye, shaking hands. You know, how to eat, like, that shows that you're being respectful, things like that. Um-

Lenny Rachitsky 27:40 Why do you think Garry Tan was so mad at it? Is it because he's like: "This is a waste of time, not worth it," versus, like, "Just build a thing that's successful?"

Sam Lessin 27:46 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 YC founders do come out a little bit like animals, right? There's like, having met with many of them, like, it's not their fault. They're, like, young kids. They've been holed up in a room coding, and that's all they've been thinking about for months or whatever. And so, like, when they show up at your office to pitch you, and, you know, they get a coffee or something, and then they, like, leave it on the table and don't ask you where to put it, it's a subtle sign of, like, not being aware of your broader environment that you may or may not know. But, like, I think it's valuable. Maybe they're like: "This is the wrong thing to focus on." I just think it's funny as much as anything else.

Lenny Rachitsky 28:28 I love it. Okay, so on the hygiene thing, is there anything else?

Sam Lessin 28:31 I think the hygiene stuff, I mean, you should get the book. I think it's, like, fairly obvious hygiene stuff, like, don't be covered in schmutz. You know what I mean? Like, show respect, try to anticipate how the room is going to be dressed, and, like, don't massively overdress or underdress. It's like, if you show up to a business casual thing in a tuxedo, you know, you're, you're, like, you're kind of trying to stand out. Don't be memorable from that perspective, but you also don't want to be memorable in the other direction, as like, wow, that, that person, like, really has no respect for the room.

Lenny Rachitsky 28:59 This actually, you're getting to the next category, which is dress, which I'm excited about.

Sam Lessin 29:02 Yes. Yeah, I mean, dress, like, look, I gotta say, again, in terms of know the rules, but don't always follow them, when I- my first job out of college, I was an associate at Bain & Company, right? This is, like, a consulting firm, and there was, like, a business casual, and I kind of came up with the snarky realization that there was a minimum dress code but there wasn't a maximum dress code. So I started in the office as somewhat of a mini rebellion in the consulting firm, what we called Tuxedo Tuesdays, where all the associates would wear tuxedos to work, which then meant we didn't have to go to the client meetings because they would never take us to client meetings in tuxedos. So it was like, okay, like, you know, again, you know the rules to break them. It was fun. But I, you know, I do think from a dress perspective, again, I think the real thing is, like, look put together, look like you cared, look like you made some effort, but you don't, don't overdo it, is basically the upshot of the most simple way to dress. Unless, 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.

Lenny Rachitsky 29:57 Uh, so here's a couple tips that I love. So one is just dress one level up. That's a really simple tip.

Sam Lessin 30:01 It's an easy way to win. Not two, not three, but one.

Lenny Rachitsky 30:05 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-

Sam Lessin 30:10 Sure

Lenny Rachitsky 30:10 ... a little less formal, yeah.

Sam Lessin 30:11 100%.

Lenny Rachitsky 30:12 And then you talk about fit of the item versus the brand.

Sam Lessin 30:16 100%. Like, like, at the end of the day, fit is everything, right? I say this is... Again, you guys, all your listeners have to understand, part of my joy at doing this is there is some level of hypocrisy in it, right? 'Cause, like, but, 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 $20 shirt is way better than a misfitting $500 shirt, right? Uh, uh, and candidly, like, it's the same thing as like-... if you're a startup founder, you do wanna kind of dress to the level of the room, but you kinda shouldn't show up in, like... Like, you shouldn't have a Rolex, right? It's, like, very classless, if that makes sense, to, like, show up as a startup founder with a Rolex, right? Uh, it's just not... Again, it goes back to heart rate, trying too hard. You know, you're not gonna trick anyone, right? [chuckles] Is the upshot, right?

Lenny Rachitsky 31:06 Yeah. This bit of a 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.

Sam Lessin 31:20 100%. I mean, again, eh, I, I would put, put differently, think about the average person, not every person in the world. 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.

Lenny Rachitsky 31:33 Yeah.

Sam Lessin 31:34 Most people can have no idea what things cost, right? Like, if you said, like... You know what I mean? Like, it's just not-

Lenny Rachitsky 31:38 Mm.

Sam Lessin 31:38 And, like, so in some ways, it's this weird thing, where it's like, if you show up in a super misfitting but very expensive item, you're like, "What signal are you sending?" It's like, well, you're not very aware, right, culturally. You're not, like, matching the room. You're not showing a lot of sensitivity, like, to the situation, what people actually can prioritize. And it's like, are you trying to impress me because you have a fancy outfit? Like, what, what are we talking about?

Lenny Rachitsky 32:01 One other tip you have is, if you're not sure the level of dress, just ask.

Sam Lessin 32:04 Yeah. This is a big thing in general, which is I think people are afraid to ask in all sorts of situations, you know, e- down to, like, "Which forks should I use?" You know, and, you know, or, "What's the expect..." Like, it is absolutely fine to ask. In fact, if anything, it shows a level of confidence, and calm, and humility to ask if you don't know, right? So I actually think this is a great example. There's absolutely nothing wrong with asking about dress, about etiquette, about expectations. You know, I don't... Again, it goes back to this whole give to get. If you get someone on the phone and you ask them 100 questions about etiquette, at a certain point, you're like, there's no... That's not a ping 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 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, to know every nuance of every culture you might enter.

Lenny Rachitsky 32:58 So maybe as a final question in dress, do you have any just, I don't know, tips for dressing well? I know this is a big question that professionals spend time teaching and charging for.

Sam Lessin 33:10 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. The- that makes a lot of sense. The, like, basics I can say, yeah, like, have jeans that are clean, right, and, like, fit you, things like that. But again, eh, 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.

Lenny Rachitsky 33:39 Great. [chuckles] This is- [chuckles] That's

Lenny Rachitsky 33:42 a win. Okay, let's talk about dining. Give us some advice for, uh, etiquette during dining.

Sam Lessin 33:49 Tip well, right? Uh, y- don't, don't not tip, don't tip badly. You know, don't be super stingy about, you know, okay, who ordered the flambé? You know, like, split bills evenly. Make things easy for waiters. Um, in general, it's don't order the most expensive thing on the menu. Does it really matter, especially to, like, an investor, do they really care? No, they don't really care, but they do notice. And you're like, ah, you're the type of person that, like, is truly insensitive to what things cost, even if it doesn't actually matter, right? So I think there are things like that. Same thing with wine. Like, and then I think, look, in the terms of asking, ideally, don't order first, right? Because I think if you see how someone... Like, are we doing starters? Like, what, like, 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 wanna go middle of the pack to last, if that makes sense. Uh, so-

Lenny Rachitsky 34:48 So this, this-

Sam Lessin 34:49 Yeah.

Lenny Rachitsky 34:49 So this isn't a situation if someone takes you out to dinner, like it's a VC, another found- like, someone invites you to dinner.

Sam Lessin 34:54 Or a partner, or whatever, whatever it is.

Lenny Rachitsky 34:56 Yeah.

Sam Lessin 34:56 Yeah.

Lenny Rachitsky 34:56 Awesome.

Sam Lessin 34:56 And look, I, I think, uh, what we say, say, in terms of this, which I obviously think is important, is, like, look, within reason, always offer to pay. Now, you should be turned down, right? If you go out with a VC, right, and you're like... You know, you put a card down, 99% of the time they're gonna be like, "I got this." Like, "Please," like, "This is... Don't worry about it," right? And, like, that's the right vibe on it. You do not need to do this if it's a $10,000 dinner, if they've ordered a super expensive bottle of wine. Like, there are, there are limits to this, right? But if you go out to a normal dinner in a normal situation, 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, 'cause 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.

Lenny Rachitsky 35:44 What if they're just, like, a, like a billionaire? I just had dinner with, like, a very successful VC, and I did not feel like offering to pay made sense. Would you still-

Sam Lessin 35:52 It depends what... Yeah, I actually would. I think it depends what the dynamic is.

Lenny Rachitsky 35:56 Mm.

Sam Lessin 35:56 If the billionaire ordered a $10,000 bottle of wine- [chuckles] ... you don't need to offer, right? If you had a normal meal, right, I actually think it's great to offer.

Lenny Rachitsky 36:06 Mm.

Sam Lessin 36:06 And they'll almost certainly be like, "Of course not," right? [chuckles] 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 your, you know... There are two interesting dynamics. One is, it's actually, I think, especially nice to offer, and even sometimes pay, because the reality is, if you think about it, they obviously don't care about the money. But no one does that, right? Like, they're like, "Well, clearly you should pay." And so the more you're like, "Oh, no, like, I, like, I'm treating us like this is a conversation in equals, and, like, I'd love to offer or just pay as big." The second thing, which is important, is if you're, especially if you're out to dinner with someone who's very, very well-known-... you have to tip like crazy. Because the problem is, this is like one thing, this is like a- this is not in the book, this is like a 201 course, right? But if you go out to dinner with someone that were like, okay, they're either known or relatively known, known, and you're making the gesture of buying it, not 'cause they obviously don't care about the money, it's more like the gesture that's nice that you would offer that. You kinda have to tip the way they would tip, and they're gonna tip like 100% of the bill, right? Because like, it's just like the right thing to do. And so I do think you... Like, if you're gonna do that, you really have

Sam Lessin 37:15 to tip well.

Lenny Rachitsky 37:16 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 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 the-

Sam Lessin 37:29 Just tip a lot.

Lenny Rachitsky 37:29 [chuckles] Tip a lot. Okay.

Sam Lessin 37:30 Just tip a lot.

Lenny Rachitsky 37:31 [chuckles]

Sam Lessin 37:31 Like, I think 10, 20% is the minimum.

Lenny Rachitsky 37:34 Yeah.

Sam Lessin 37:34 Like, if you're out in like a, a situ... You know, I think you kinda wanna tip, in my mind, to the level of no one you're effectively paying for would bat an eye that you're being stingy, is the way I would think about it. 20% feels like the minimum, 30% sometimes, like more seems a little bit silly, but it's not... It is a squirrely topic, and I just- I don't... Again, let me put it this way. I don't think you want your tip to be memorable, is almost the way to put it. Like, this is not a thing to focus on. When you think- when the person that you're out to dinner with thinks back on their dinner, on the dinner a month later, they wanna think about the content of the conversation, or what the ideas were, or the business opportunity. They wanna 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 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, "It'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 remember for the night is how much the person tips.

Lenny Rachitsky 38:34 S- so you're s- okay, but I think if you're like extremely rich, you do it, don't even tell anyone, basically, but feel free to do it, obviously.

Sam Lessin 38:40 Sure, yeah. I mean, you don't want to... 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, 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.

Lenny Rachitsky 38:58 I recommend your next book after this, uh, Fami- Fem- Femiquette? Femiquette, uh, edition, is a tipping guide.

Sam Lessin 39:05 A tipping guide. Well, you know what would be funny, is like there's a great episode of, um, Seinfeld that's all about the tipping calculator. I don't know if you're a Seinfeld guy.

Lenny Rachitsky 39:12 I love Seinfeld. I don't remember that.

Sam Lessin 39:14 It's a great tipping... It's a great tipping episode.

Lenny Rachitsky 39:16 Mm.

Sam Lessin 39:16 Uh, I feel like you could honestly, like, have a very funny, like, modern LLM app that is only about tipping.

Lenny Rachitsky 39:23 I would-

Sam Lessin 39:23 Like, imagine like a tipping app-

Lenny Rachitsky 39:24 Pay money for that

Sam Lessin 39:24 ... where it's like- [chuckles]

Lenny Rachitsky 39:26 Yes.

Sam Lessin 39:26 It's like, instead of a tipping calculator, you take a picture of the bill-

Lenny Rachitsky 39:30 Yes

Sam Lessin 39:30 ... it geolocates where you are. You kinda give it, be like, "This is the situation," and it's like, it just tells you what to tip.

Lenny Rachitsky 39:35 Well, what, like, the tip... Like, a restaurant's one thing, but then it's like the garbage person, uh, a gardener, the-

Sam Lessin 39:41 Well, especially-

Lenny Rachitsky 39:42 person that installs-

Sam Lessin 39:42 ... especially this time, end of year, like we're at the end of year.

Lenny Rachitsky 39:45 Yeah, exactly.

Sam Lessin 39:45 Like, I, I think no one knows how to tip anymore.

Lenny Rachitsky 39:47 I'd so... Like, yeah, some guy that de- like, installs the shades in our house, do I tip him?

Sam Lessin 39:52 Do you... I don't think you tip that person.

Lenny Rachitsky 39:53 Okay.

Sam Lessin 39:54 I, I actually- Do you tip that person?

Lenny Rachitsky 39:55 No, I, I did not, 'cause that just-

Sam Lessin 39:57 I feel like-

Lenny Rachitsky 39:57 'Cause we already paid a bunch of money for this thing, and like-

Sam Lessin 39:58 Yeah, no, I, I feel like that is weird.

Lenny Rachitsky 40:00 Maybe.

Sam Lessin 40:01 I wouldn't tip-

Lenny Rachitsky 40:02 Okay

Sam Lessin 40:02 ... people like that.

Lenny Rachitsky 40:03 Yeah, that's, that's why we need this book. This is... You're gonna make- this is gonna be a huge hit or sell well.

Sam Lessin 40:07 Well, we could fund it. You wanna fund it with me? We should fund an app.

Lenny Rachitsky 40:10 I'm, I'm, I'm-

Sam Lessin 40:10 Talk about YC companies.

Lenny Rachitsky 40:11 Yeah.

Sam Lessin 40:11 If someone pitched me in terms of funny but real-

Lenny Rachitsky 40:14 Yes

Sam Lessin 40:14 ... if someone pitched me the 2026 AI-driven tipping calculator-

Lenny Rachitsky 40:20 Yes

Sam Lessin 40:20 ... which gives the 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.

Lenny Rachitsky 40:28 And probably not venture scale, but I don't care. I invest in lots of odd things.

Sam Lessin 40:31 You know what? It's 2026, it might be. You know, everyone has the problem.

Lenny Rachitsky 40:35 Mm. [chuckles]

Sam Lessin 40:35 Everyone globally has the same problem, which is tipping.

Lenny Rachitsky 40:38 Yeah, just the tokens, uh, cost of that.

Sam Lessin 40:40 It actually reminds me, I'm reading one of my sons right now, the third book of Hitchhiker's Guide to the Galaxy.

Lenny Rachitsky 40:45 Mm-hmm.

Sam Lessin 40:46 And I don't know if you've read the series.

Lenny Rachitsky 40:47 Yes, yes.

Sam Lessin 40:48 It's, it's a poor substitute. Do you remember about the, what's, uh, Bristomatics, Mathics?

Lenny Rachitsky 40:53 No. Yeah.

Sam Lessin 40:53 So basically, the idea is that after the improbability drive, the way they're able to move across the universe quickly is the most complicated math in the universe, which is the math of your bill at a restaurant. [chuckles] So I think we're onto something. It's in science fiction.

Lenny Rachitsky 41:08 [chuckles] Oh, man. One other tip that I just ha- thought of is, uh, around dining, is you have this tip about sommeliers. Give them a sip of your wine if you order something really well.

Sam Lessin 41:16 Yeah, yeah, if you, if you order something nice. That... I'll be honest, be very clear again, in terms of, I don't order a very nice wine.

Lenny Rachitsky 41:22 Yeah.

Sam Lessin 41:22 No sommelier really cares what I'm drinking. But i- if you are doing that or you're into it, which is great, again, like, think about being generous, right? If they're like: "Oh, I would love to taste that," like, "Let them have a taste." It's great.

Lenny Rachitsky 41:33 I love that.

Sam Lessin 41:34 You know?

Lenny Rachitsky 41:34 I would love to do that. That sounds really nice.

Sam Lessin 41:36 Yeah.

Lenny Rachitsky 41:36 Yeah. Okay, and one other tip here I wrote down, uh, B for bread, D for drinks. Tell, [chuckles] explain that.

Sam Lessin 41:40 Oh, B, D, you just gotta look at your hands, right? Bs and Ds for, to know which was your bread plate, uh, right, is a kinda the way to think about it. And look, people get this wrong all the time. You sit down at a big table, right, and you're like: "Uh, which is mine?" And you're kinda waiting for someone to pick it up and kinda do the math, and like, "Okay, that's my bread." Um, but that's, the B and D is useful. Uh, also, like, look, forks and knives, like, just knowing what side they go on, knowing... One thing that always drives me nuts, um, that kinda goes, is related, is the knife blade goes in, right? People, when they put their knives down, right, the knife blade goes in, w- because you don't like, you don't wanna like stab your partner next to you. But like, it was really funny, I had an entrepreneur... This is not yet a product, and people have started sending me videos of them like dining or in situations and asked for feedback, right?

Lenny Rachitsky 42:27 [chuckles]

Sam Lessin 42:27 And I recently had to give feedback to an entrepreneur who was like, "You did a very nice job eating your soup. Good job. Your napkin should have been in your lap, and your knife is pointed the wrong way." [chuckles]

Lenny Rachitsky 42:37 [chuckles] Okay, napkin, actually. Okay, so napkin in lap.

Sam Lessin 42:40 Napkin in lap.

Lenny Rachitsky 42:42 Okay, not like-

Sam Lessin 42:42 Not in your lap, not off to the side, you know-

Lenny Rachitsky 42:45 Yeah

Sam Lessin 42:45 ... napkin in lap.

Lenny Rachitsky 42:46 ... I saw someone have once had a napkin on just one leg versus both legs. Any opinion there?

Sam Lessin 42:50 I mean, I don't think you want your napkin placement to be memorable.

Lenny Rachitsky 42:54 Okay. [chuckles]

Sam Lessin 42:54 That's kind of... My biggest thing is, like, these are not... The point about etiquette is that it gets out of the way, right?

Lenny Rachitsky 42:58 Yeah, yeah.

Sam Lessin 42:58 It shouldn't be memorable, you know?

Lenny Rachitsky 42:59 It's like the Kindle. You don't want to think about the technology.

Sam Lessin 43:02 No, just y- you just... It let the conversation flow.

Lenny Rachitsky 43:04 Yeah,

Lenny Rachitsky 43:05 okay. Amazing. Okay, uh, speaking of conversation, small talk and humor, give us some tips.

Sam Lessin 43:10 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 then also, I'd say humor is quite conditional and subtle to the c- to the audience. So like, in the, the, the room you're in, dirty jokes, right? You tell a dirty... You don't want to tell a dirty joke in the wrong room. Uh, you... But I think the thing to think about humor is it kind of... There's this interesting subtlety to why it's so useful in social settings, 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, is to tell a joke that's a little over the line or a little off-color, but not too off-color. It's like the ultimate thing. So like, if you're really in it and, like, feeling good, using humor is great. You should not be remembered as only the comedian. And again, like, the level of jokes that you're playing with is, like, a very subtle thing, right? So you don't want to tell a knock-knock joke, right, when, like, with adults, right? But the off-color sex joke that is hilarious, you, you, you've gotta be pretty confident before you tell it, right, in the space. Uh, the last thing you want... Like, if you have a joke that everyone laughs at, is great. A joke that no one laughs at is a hu- it's like a huge risk maneuver. You've failed, right? And, like, it's not the point. So it's a great tool. I love it. Like, I think everyone should have their file of jokes. I do. I don't know about you. Like, I have, like, a Evernote... It's not Evernote anymore. It's like a Bear of, like, my favorite jokes, and I- they're loosely ranked and from least offensive to most offensive, um-

Lenny Rachitsky 44:49 [chuckles]

Sam Lessin 44:49 ... 'cause, like, I forget the jokes. But like, you know, you kinda wanna use humor sparingly and smartly.

Lenny Rachitsky 44:54 This is your next book, this, uh, list of jokes.

Sam Lessin 44:56 List of jokes, l- ranked by, like, social situation-

Lenny Rachitsky 44:59 [chuckles]

Sam Lessin 44:59 ... and, like, level of extremeness.

Lenny Rachitsky 45:01 [chuckles] Yes.

Sam Lessin 45:02 Yeah.

Lenny Rachitsky 45:02 Everyone's gonna be telling the same jokes. Oh, man. Mm.

Sam Lessin 45:05 Well, there is a, there is a funny joke about that, right? Which is the whole the prisoners... I won't even tell it. It's a funny... There's a funny joke about people who know all the jokes. I'll leave it at that.

Lenny Rachitsky 45:14 Okay. We'll leave it-

Sam Lessin 45:14 I'll leave you hanging and wanting more for our next podcast conversation.

Lenny Rachitsky 45:18 Abundance. Okay, uh, you also recommend self-deprecating, uh, as a-

Sam Lessin 45:22 Make fun of yourself-

Lenny Rachitsky 45:23 ... a joke

Sam Lessin 45:23 - not other people.

Lenny Rachitsky 45:24 Yeah.

Sam Lessin 45:25 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... You know, if you're there with your business partner and you're really feeling the vibe, and you... Again, it can be quite effective, but the second it feels disparaging or people aren't on the same wavelength, it's a very high-risk maneuver. Making fun of yourself is always fine. [upbeat music]

Lenny Rachitsky 45:50 Here's a puzzle for you: What do OpenAI, Cursor, Perplexity, Vercel, Plat, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, SCIM, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. 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.com to make your app enterprise-ready today. You 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, and I'm like, "Okay, here, I'm gonna get one," so I should make a list. [chuckles]

Sam Lessin 46:58 Make a list!

Lenny Rachitsky 46:58 Okay.

Sam Lessin 46:58 I got, I got some good ones for you.

Lenny Rachitsky 47:00 Okay, [chuckles] I'll have to borrow some. Uh, you also recommend having some stories, some crowd-pleasery kind of stories to tell.

Sam Lessin 47:05 Yeah, you wanna have some easy stories that are, again, like, it shouldn't be 10 minutes, right? But again, I think the thing to think about is, like, imagine that the whole game in these social settings, again, is putting other people at ease, making them feel like you understand them and the room, and you're a trustworthy person and on the same wavelength. And in some ways, think about it as, like, who's carrying the conversation? It shouldn't be your monologue. You shouldn't force them to monologue either, right? And that's where questions come in and back and forth. Having a fun build on story. They tell a story, you have a story to tell. Like, again, I really think of it as like a conversation or these social interactions as a ping-pong game, right? And, like, you kind of want to have

Sam Lessin 47:42 a few of those in your arsenal.

Lenny Rachitsky 47:43 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?

Sam Lessin 47:49 Yeah, just like, when the conversation is over, gracefully leave [chuckles] is basically the upshot.

Lenny Rachitsky 47:53 Mm, mm. [chuckles]

Sam Lessin 47:53 You know, people... The, the worst is, like, the conversation ends, and the person just stands there, and you're like, "Uh, I'm gonna go get a drink," you know? Or, "Do you want to...?" And then every once in a while, the person will be like... You're like, if someone says to you in a conversation to wind it down, is 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 follow 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 the moment is passing or it's time to move on, et cetera, um, and then, like, respect it, uh, is what I would say.

Lenny Rachitsky 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 to get out of a conversation when you're like-

Sam Lessin 48:32 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, i- in some ways, like, give them their next partner. You know, you'll be like, "Oh," like, "I've enjoyed this conversation. It's super cool, you know, uh, you know, by the way, have you met Steve?"...Let's go meet Steve. Go talk to Steve for a bit, right? And like, "I'll pick you back up." And then they're like: "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 in, in all things. Like, you wanna basically let people feel respected as much as anything else. So if you're, if you're too overt about it, right, um, 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 kind

Sam Lessin 49:20 of look for the signs.

Lenny Rachitsky 49:21 Awesome. Okay, uh, there's four more sections. Uh, the next one is scheduling etiquette. Give us some advice.

Sam Lessin 49:26 Oh, well, like, I think I'd like to say that I'm fairly famous for hating Calendly. Um, eh, there was a, a... I actually, I, I think I'm not overstating it when saying there was a period with Calendly 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 Calendly and how disrespectful it is, and apparently, this was such an internet fervor, I got, like, millions of engagements, that it meaningfully drove their month. Um-

Lenny Rachitsky 49:51 Wow!

Sam Lessin 49:52 ... so they thanked me for it.

Lenny Rachitsky 49:52 No pr- no bad press.

Sam Lessin 49:53 No bad press, and no bad tweets. Yeah, so I think, like... Look, there's a few obvious ones. When you're sched- 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. You know, the defa- I really strongly believe the default should not be Calendly. The default in most situations, especially if you recognize the power hierarchy or the busyness hierarchy, if you're the less senior person, if you are the less busy person, you should let the other person tell you when they're free, and then make it work on your end, right? Uh, is what I would say. And it's fine if the first slot doesn't work, but the, one of the first three really needs to, right? So I think that, like, in some ways, that it's important to kind of respect that. It's better to kind of 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... And it comes up all the time. Um, look, rescheduling happens. When you do it, give notice as much as possible. 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 but sometimes forget. Like, 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 are like: "I want to meet at this time." You're like: "You're on EST, you're what... That's, like, 4:00 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 we make in the book, is like, you really need to respect EAs and PAs and the whole people. Like, this is the n- the number one look, way to look extremely classless is to not respect people 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. Like, you don't want to overdo it, but there should be this deep well of, like, respect for anyone who's helping you, whether that's a server or a PA or an EA or whatever. There... This needs to come with an extra gesture of respect. That means saying thank you when they schedule, and, like, following up with them, and things like that.

Lenny Rachitsky 52:14 There's a... I'll tell a story. When we were selling our company to Airbnb, we had this guy helping us sell the company, and he made it a big point to build a good relationship with the EA and office manager at Airbnb because they- if they like you, they'll... You know, it helps. It helps you-

Sam Lessin 52:30 Yeah, I mean, like-

Lenny Rachitsky 52:30 ... get the thing

Sam Lessin 52:31 ... make, the, the general story of, like, make the gatekeepers happy and like you is true, but I, I, I do think there are ways to overdo that, for what it's worth.

Lenny Rachitsky 52:38 Yeah.

Sam Lessin 52:38 It becomes almost too transactional. If you show up with flowers for the EA, [chuckles] you know, like, eh, you better be damn confident, like, in what you're doing, if that makes sense. But-

Lenny Rachitsky 52:47 Yeah, yeah

Sam Lessin 52:47 ... um, just, like, the small things go a long way. Like, you just to, you know, make eye contact with them, thank them, respect them, you know, ask... You know, if, 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, in, who feel like the team or the staff, feel that way. Make them feel like part of the team and equals.

Lenny Rachitsky 53:08 The Calendly stuff, I feel like that's its own separate book of-

Sam Lessin 53:11 It's its own-

Lenny Rachitsky 53:11 ... Calendly etiquette.

Sam Lessin 53:12 Yeah, the Calendly-

Lenny Rachitsky 53:13 There's so many-

Sam Lessin 53:13 Look, Calendly-

Lenny Rachitsky 53:15 So many nuances

Sam Lessin 53:15 ... the, the Calendly is one of my favorite, my favorite episodes of going hyperviral on something hilarious.

Lenny Rachitsky 53:20 So one thing that Calendly 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 feels like a good solution.

Sam Lessin 53:27 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, you know, I always give these examples. It's like, "When are you free?" It totally depends on who's asking. If Barack Obama, or I don't know, I won't say Donald Trump, someone wants to meet with me, and it's, like, 4:00 in the morning my time, right, or, like, I'm totally with Sam doing something really important, 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, da, da, da. That does mean, honestly, I think you'd probably knock me, is like, my bet is that my calendar moves more than most people's, and I'm sure that feels disrespectful to some, and it is. Like, I wanna be really clear. But it's also the reality of trying to balance these things.

Lenny Rachitsky 54:16 The other, uh, flaw with Calendly I've realized, someone once figured out my Calendly URL and just booked a meeting with me, like a founder wanting to pitch me, and then I was like, it was on my calendar. I'm like, "What the-"

Sam Lessin 54:26 The funny one I've had is there are people whose names are very similar to other people I know.

Lenny Rachitsky 54:32 Mm.

Sam Lessin 54:32 And every once in a while, I've ended up, like, accepting a cold meeting and showing up-

Lenny Rachitsky 54:36 Yeah [chuckles]

Sam Lessin 54:36 ... and being like: "You are not the person I expected." Because it's like, I was like-

Lenny Rachitsky 54:40 Yeah

Sam Lessin 54:40 ... "Oh, your name is off by one letter."

Lenny Rachitsky 54:41 Yeah.

Sam Lessin 54:41 "That's cool." [chuckles] 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.

Lenny Rachitsky 54:49 Oh, man, okay. Uh, well, well, one last question on Calendly. Something I try to do, I'm curious to get your take, is like, okay, someone want, like a founder, I'm meeting with a founder-... and, uh, I'm- the way I approach it is like, "Okay, do you have a Calendly or l- or something I could use to book a meeting with you? If not, in parentheses, here's my Calendly in case that might make it easier."

Sam Lessin 55:08 Yeah.

Lenny Rachitsky 55:08 What do you think about that?

Sam Lessin 55:08 I think that's perfectly fine, right, in terms of-

Lenny Rachitsky 55:10 Yeah

Sam Lessin 55:10 ... the way to do it. I just think, again, the key is to make it easy for the person you're trying to do business with, right?

Lenny Rachitsky 55:14 And not make... Yeah, and not make them feel like they have to do the work if they don't want to.

Sam Lessin 55:18 Right. No, you do the work.

Lenny Rachitsky 55:19 You do the work.

Sam Lessin 55:19 Like, basically, you're asking for something, you do the work-

Lenny Rachitsky 55:22 Yeah

Sam Lessin 55:22 ... is the gunshot.

Lenny Rachitsky 55:23 Okay, sweet. Moving on to the next topic: communication.

Sam Lessin 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 on things like email, you kind of do have an SLA to respond. There are some people I know who are like, "Email does not mean I have to respond. You send me an email, you may or may not get a response. It's completely up to me. I have no contract to respond to your email." I, I personally go the other way, which is I feel like from an etiquette perspective, like, I don't owe you a 12-page essay, but I do owe at least an acknowledgement quickly, right, of what you've sent. Like, you don't want to leave people hanging. But again, I 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 sent it to? If you send them 10 paragraphs, it's annoying, right? You're like: "Okay, I have to read all this. When am I going to find time?" Like, this is like you're asking a lot. It's kind of like a monologue in a conversation. You've just said, "I'm going to spend 10 minutes talking at you," right? And so I do think keeping it short and to the point, you know, not being silly, not using emoji, trying to make it readable, like, these are all important things.

Lenny Rachitsky 56:47 Say more, say more about the emoji piece. Like, is your advice just no emojis if it's a business email?

Sam Lessin 56:51 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... Like, if someone sends you a smiley face, you can respond with it. Like, you can kind of like match... Again, it goes back to this matching vocabulary and language. Like, I'm not saying you should be totally cut and dry, but it's kind of why I would say emojis almost feel like jokes to me, which is like, tell them at your own risk, and they're probably not worth it, you know?

Lenny Rachitsky 57:20 Awesome. Okay, I do use emojis. I use like the pr- the thank you hands one a lot, and...

Sam Lessin 57:25 Look, I think-

Lenny Rachitsky 57:25 Yeah

Sam Lessin 57:25 ... text is different. I think people might have slightly different takes on this, and so I wouldn't say anything I'm saying here is dogmatic. But I'm just saying that like, again, emojis are not highly legible to most people. They can mean lots of different things. They usually have cultural connotation to them, and, like, I would say that, like, they're kind of harder to read than just a well-worded, simple, to-the-point email. Um, and I think you just want to come across as, like, a literate, to-the-point, simple, clear person.

Lenny Rachitsky 57:54 And emojis sometimes kind of implies you used AI to generate this thing, 'cause ChatGPT loves emojis.

Sam Lessin 57:59 Totally. And I'll say, like, look, I mean, there's a whole... We want to get, we want to get spicy for a second.

Lenny Rachitsky 58:04 Yes.

Sam Lessin 58:05 I don't know how I feel about people who have, like, invested too much in their emojis, right? So you get people who have, like, changed the colors of their emojis from the default or whatever. I'm not saying not to do it. I'm just saying it's quite a statement, in my view, that you've invested in your emoji pack or, like, using special emojis people haven't seen before or, like... It's like, again, it's a subtlety, and you've got to 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.

Lenny Rachitsky 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-

Sam Lessin 58:40 Yeah

Lenny Rachitsky 58:40 ... animojis or so. It's like a whole new world and just infinite emojis.

Sam Lessin 58:43 Like, again, it's like, if you choose to use those, you are going way out on a limb, right-

Lenny Rachitsky 58:50 Mm-hmm

Sam Lessin 58:50 ... that people are going to be receptive to that and not be like, "This is a person who spends a lot of their time customizing their emoji pack when they probably should be doing something more interesting."

Lenny Rachitsky 58:58 They should be finding product-market fit.

Sam Lessin 59:00 Yeah, or learning etiquette.

Lenny Rachitsky 59:01 Mm. [chuckles] The other tip you had that I love, which is, uh, think about the order of the emails when you're emailing somebody.

Sam Lessin 59:09 Yeah, I, I do think you kind of want to think about, you know... There is a connotation to who you send it to and who you CC, and the order in which people... Now, now, I, you know, I don't want to, like, overstate this, but put differently, it's like, if you're sending an email, and the first person on the email is the assistant and the fourth person on the email is the CEO, you've probably done it wrong.

Lenny Rachitsky 59:30 And 'cause the implication there is you- who you think is most important comes first. Like, who's first to, to, to mind?

Sam Lessin 59:34 Well, who are you really sending this to? You know what I mean?

Lenny Rachitsky 59:37 Yeah.

Sam Lessin 59:37 It's almost the way I think.

Lenny Rachitsky 59:38 Yeah.

Sam Lessin 59:38 And, like, who's kind of included? So, like, 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?

Lenny Rachitsky 59:48 Mm, yeah.

Sam Lessin 59:48 'Cause in my head, I'm like: "Okay, well, like, this is really to Kevin, and, like, I'm on it." Like, if you see an email sent to many, many, many people, almost by definition, it's not that important, right, is almost the way I put it. And so you have to be really careful with managing that. I think even the, the who do you send it to and who do you CC, there's a language to that, that, like, from an etiquette perspective, to understand, right? And, like, I, I do think people sometimes miss that. Like, the CC line is very, very valuable. It means, "Hey, you should have a copy of this. This is not really to you. I'm not expecting an immediate response," right? I even think there's even a subtlety, like, who responds then. Like, if you send an email to 10 people, CC'd to the whole nine yards, you know, there is a subtle etiquette to, like, when you respond. Like, if you are the fifth CC on an email, you're not expected to be the first response.

Lenny Rachitsky 1:00:37 [chuckles]

Sam Lessin 1:00:37 A- 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 is a whole language to who you send to and who you CC and the order that, like... Again, it's very subtle, but it's worth understanding.

Lenny Rachitsky 1:00:51 So true. Man, any- you would think nobody sees all these little things in the Gmail thread, but you do. They're just right there, and you're like-

Sam Lessin 1:00:57 You see them

Lenny Rachitsky 1:00:58 ... "I see them right there."

Sam Lessin 1:00:58 And I think people... This is the whole thing about etiquette, is like, it's all this invisible stuff.... that you don't need to spend, like, all, like, the- in some ways, the whole story of doing this well is it should not occupy 80% of your brain, right? What you're saying is, "I've got this. We're on the same wavelength. My heart rate is low. I'm doing it properly, and I'm doing it with, like, intuitively almost," right? Which is a hard ask, right? 'Cause what we're basically saying is, like, these are unknown things, but intuitively you should just know them, and that is actually what you're signaling, is like, "You can trust me," because intuitively there's this well of knowledge and cultural connection and whatever that we can, we can share effectively.

Lenny Rachitsky 1:01:33 And if, uh, your BCC, definitely do not reply all.

Sam Lessin 1:01:36 Yeah, I mean, I, I have some unbelievably funny faux pas from my history with CC, BCC, to lines. Um, I... One of the worst etiquette/mistakes I ever made, never, ever, ever put someone you're talking about who's not on an email in the To line to check the spelling of their name and then hit Send. That's a bad idea, right? So whatever you're doing, that's not even an etiquette thing. That's just, like, uh, being smart.

Lenny Rachitsky 1:02:04 Proofreading thing.

Sam Lessin 1:02:04 Proofread. Proofread, and don't send emails to people about them that they're not supposed to see. [chuckles]

Lenny Rachitsky 1:02:10 And it's like Gmail makes it too easy to do that because it adds them automatically if you, like, uh, talk-

Sam Lessin 1:02:14 If you add them

Lenny Rachitsky 1:02:14 ... if you have their name.

Sam Lessin 1:02:15 No, for me, it was more just like-

Lenny Rachitsky 1:02:16 Yeah

Sam Lessin 1:02:16 ... the way to check the spelling of someone's name-

Lenny Rachitsky 1:02:18 Yeah

Sam Lessin 1:02:18 ... is not to put them in the To field, ever.

Lenny Rachitsky 1:02:20 Yeah. [chuckles] Oh, yeah. I... [chuckles] Okay. Oh, man. Well, you're still, you're still kicking, so it wasn't-

Sam Lessin 1:02:26 Still kicking

Lenny Rachitsky 1:02:27 ... so bad.

Sam Lessin 1:02:27 I'm

Sam Lessin 1:02:28 still kicking.

Lenny Rachitsky 1:02:29 [chuckles] Okay, great. Okay, uh, two more. Uh, meeting etiquette.

Sam Lessin 1:02:33 Yeah, I mean, again, we've talked about arriving a little bit early. You should do that. Don't arrive up too, too early. Like, you shouldn't, again, like, if you're an hour early, walk around the block. It's fine to walk around the block. You don't want to sit in someone's office, 'cause then all of a sudden it feels like this person has been here a long time. Like, this almost feels like even though they're not scheduled, like we're leaving them hanging. You're six coffees deep with the receptionist. Like, you don't want that, right? Like, um, so I think you want to be, like, 10 to 15 minutes early. You do not want to be much earlier than that. Um, we talked about meeting on their convenience. I do think it's fine to 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, the pleasantry of like, "The weather is nice," or, "How was your weekend?" Or like something that kind of cuts, cuts the air a little bit and then you kind of flip into business is, like, a good thing. Even though it, like, feels transparent, it's still useful, right, is what I would say. Uh, to kind of like... And again, it's, it's almost a signal of like, "I am here for business, but I'm, like, a normal person, and, like, I'm willing to have, like, a nor-," you're like signaling like: Oh, I know that we should start with a normal conversation, if that makes sense, right? Um-

Lenny Rachitsky 1:03:41 I don't know if you saw this on Twitter. Someone described small talk as like the TCP/IP ACK handshake.

Sam Lessin 1:03:45 I love it.

Lenny Rachitsky 1:03:46 Yeah.

Sam Lessin 1:03:46 It's a great description. I always, I always describe it as like, imagine the modem crash from when we were kids on a-

Lenny Rachitsky 1:03:51 Yeah

Sam Lessin 1:03:51 ... 14.4, where it goes, doo, doo, doo, doo-

Lenny Rachitsky 1:03:53 Mm-hmm

Sam Lessin 1:03:53 ... doo, doo, doo, doo, doo. You know, like, that old modem crash. Like, that's, that's what small talk is. It's a modem crash.

Lenny Rachitsky 1:03:58 Mm-hmm.

Sam Lessin 1:03:58 We're trying to hit the wavelengths, you know, et cetera, is, like, the way I would-

Lenny Rachitsky 1:04:01 I mean, so that you're ready to talk-

Sam Lessin 1:04:03 Yeah

Lenny Rachitsky 1:04:03 ... so that you're ready to really communicate. Yeah.

Sam Lessin 1:04:04 Yeah. Um, for meetings, Z- virtual ones, camera on. Like, and again, I say this as someone who sometimes violates this, right? I violate it knowingly. I violate it knowing what it costs me, but you really should have your camera on, right? 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. 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 in your bedroom, if you're a startup founder. It's fine, but I would like to see that your bed is made. Or, like, I'll give you another one that's classic that I see with founders all the time: Close your closet. Like, people will get on Zoom calls and they will, you know, be on a call, and, like, their closet's open, and I'm like, it's not a big deal, but, like, do you see your own self pictured 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.

Lenny Rachitsky 1:05:16 Awesome. Uh, one other tip you had was clean up after yourself if you're in a real meeting, just-

Sam Lessin 1:05:20 A hundred... This is actually-

Lenny Rachitsky 1:05:21 Put your cup away

Sam Lessin 1:05:21 ... the easiest way, and this, by the way, is from my partner, Kevin Colleran, but the easiest way to come off badly is to not offer to put your coffee cup in the kitchen, right? And, like, honestly, we do this. 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 maniacal about this, which is no matter who's in the room, if we're with an LP, you take the coffee, you take the Diet Coke, even if you know full well someone's going to come in and clean it up after you, and you make a point of asking where we can put it or putting it on the side table, et cetera, and acknowledging

Sam Lessin 1:05:58 that there is a mess.

Lenny Rachitsky 1:05:59 I feel that. Final topic is exiting and leaving. What are some tips?

Sam Lessin 1:06:05 You should stand when people leave the table, right? Not ridiculously. By the way, you should... You're gonna stand when they leave the table. 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. Um, follow up with gratitude. Like, you should send people thank you notes, even if... They shouldn't be long, they shouldn't be ridiculous, but like, "We met, I got something out of it," like, "Thank you for taking your time," is, like, always appreciated, 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, and you're like, and the meeting's over, and you're over time, and 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 pick up 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 I would just keep in mind.

Lenny Rachitsky 1:06:57 They also said, like, don't make a production of your exiting. Just, like, just exit-

Sam Lessin 1:07:00 Just leave

Lenny Rachitsky 1:07:00 ... you know?

Sam Lessin 1:07:00 Yeah, yeah.

Lenny Rachitsky 1:07:01 Don't be like, "I gotta go."

Sam Lessin 1:07:01 I mean, again, I don't like... Y- you know, yes, I think that's really true. It's, I mean, there's, there's even a, a, a point to, like, y- there are lots of scenarios where I think an Irish goodbye is the best goodbye.... where you just kind of disappear. Like, any large group setting I think is great. Maybe you thank one person on the way out, or the host-

Lenny Rachitsky 1:07:16 [chuckles]

Sam Lessin 1:07:17 ... right? But like, you know, the, the, "I am leaving now," right? Like, "Let me kind of say goodbye to everyone and hug everyone," it's too much.

Sam Lessin 1:07:24 It's too much. [chuckles]

Lenny Rachitsky 1:07:26 I love that. Okay, we got through everything. Is there anything else that you think might be important to share anything-

Sam Lessin 1:07:30 There's so much other stuff. I mean, again-

Lenny Rachitsky 1:07:32 Mm

Sam Lessin 1:07:32 ... I go back to this whole thing, which is like, you know, these are all fun tips. I love the cartoons. We iterated on them a bunch. We have more to do.

Lenny Rachitsky 1:07:38 Mm.

Sam Lessin 1:07:38 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. 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 wanna like cite the people who contribute to it. Like, the book is what? Like 50, 60 pages. It, it will be a few hundred eventually, and I think there's a lot more to come, and we're gonna be ch- 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.

Lenny Rachitsky 1:08:13 Wow!

Sam Lessin 1:08:13 We're gonna do one, uh... We're certainly doing one in New York and a few other places, and, you know, it'll be fun.

Lenny Rachitsky 1:08:18 This is, uh, oh, my God, that you got a whole new life forming here.

Sam Lessin 1:08:22 I, I, y- you know, the funny thing is, this stuff, the etiquette story is obviously pretty fun, and so, like, people like Morning Brew just, like, keep making videos about this, and, like, there's this whole etiquette thing going on, and I'm like, "Oh, my God, I've done some pretty good investments in my life, built some cool products. Am I gonna be ultimately remembered as, like, the etiquette guy?" That's kind of hilarious. Uh-

Lenny Rachitsky 1:08:41 That's what we're doing here. This is-

Sam Lessin 1:08:42 I'm into it, though. I'm into it.

Lenny Rachitsky 1:08:43 Okay.

Sam Lessin 1:08:43 I'm fine with that. [chuckles]

Lenny Rachitsky 1:08:45 So I'll read, uh... You have a tl;dr at the beginning. I'll just read this real quick and add anything-

Sam Lessin 1:08:48 Yeah, sure

Lenny Rachitsky 1:08:48 ... that we're missing. So this is just, like, what to do if you do nothing else. "Remember the goal of all etiquette is essentially building trust and project genuine confidence. 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."

Sam Lessin 1:09:06 That's the point. If nothing else, if you remember those points, you will, you will be served well.

Lenny Rachitsky 1:09:11 There we go. Okay, I'm gonna take us to closeout, make this more of a [chuckles] regular episode. I'm gonna take us to two recurring segments on the podcast, AI Corner and Contrarian

Lenny Rachitsky 1:09:20 Corner. I don't know if I told you I was gonna ask you these questions-

Sam Lessin 1:09:22 All right

Lenny Rachitsky 1:09:22 ... but I'm gonna go for it.

Sam Lessin 1:09:23 Lay it on me.

Lenny Rachitsky 1:09:23 So-

Sam Lessin 1:09:24 I love Contrarian Corner.

Lenny Rachitsky 1:09:25 [chuckles] AI Corner-

Sam Lessin 1:09:25 And AI Corner, depends what you mean by that.

Lenny Rachitsky 1:09:28 So the question in AI Corner is just, what's one way you've found AI useful in your work or life that might be he- helpful for people to hear?

Sam Lessin 1:09:34 So look, I'm by default, pretty skeptical of most AI applications. I will say, the thing that I've had the most fun with with AI, and I find great, is it- actually, it's partially where the cartoons for this came from, is I built a little personal news aggregator called Lettermeme, that basically takes all the newsletters I don't have time to read and turns them into daily cartoons. Like, so I have a grid of, like, what's going on in the world as 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, and then continuously-

Lenny Rachitsky 1:10:07 Except Lenny's Newsletter, but keep going.

Sam Lessin 1:10:09 Uh, what? Except Lenny's Newsletter-

Lenny Rachitsky 1:10:11 Except Lenny's, of course

Sam Lessin 1:10:11 ... sure, of course.

Lenny Rachitsky 1:10:11 Of course.

Sam Lessin 1:10:11 That one I don't put in the aggregator, although-

Lenny Rachitsky 1:10:13 Of course.

Sam Lessin 1:10:13 Of course I don't do that. Um, but, uh, it's great. Uh, so I'm super into, uh, into it, uh-

Lenny Rachitsky 1:10:19 And that's lettermeme.com. We'll check it out.

Sam Lessin 1:10:21 Lettermeme.com.

Lenny Rachitsky 1:10:21 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.

Sam Lessin 1:10:28 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 to, like, what's going on in the world-

Lenny Rachitsky 1:10:41 Amazing

Sam Lessin 1:10:41 ... and you pipe your own newsletters into it, so it's like whatever you actually trust and pay attention to.

Lenny Rachitsky 1:10:45 Genius. And y- how did you build this? Was it vibe-coded? Did you have an engineer help you?

Sam Lessin 1:10:49 Well, both actually. Like, I actually... The vibe-coding thing, this is exactly what vibe-coding is good for, is like-

Lenny Rachitsky 1:10:54 Yeah

Sam Lessin 1:10:54 ... this is like, you know, Cursor and DigitalOcean, 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 end-to-end. But then, vibe-coding also doesn't really scale, and so the reality is, after a certain point, I had some friends who are great engineers just take it and, like, up-level it in a few ways

Sam Lessin 1:11:13 that I honestly ran out of time to work on.

Lenny Rachitsky 1:11:15 Well, let's go to Contrarian Corner. Uh, this could be an entire podcast conversation [chuckles] with you, I suspect. But just, like, what's something you wanna share that you believe that most other people don't believe?

Sam Lessin 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, i- e- and that doesn't mean that I don't think you should be using AI to build things. I actually think you absolutely should. It's kind of like not using AI in your startup is the equivalent of not using the cloud in, like, 2010, or, like, not using the internet in, like, 2000. It would be insane. Like, of course you're gonna use these tools. But there's a difference between a great business that you're using, uh, 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, all of these companies that come out, whether... Th- that say, "We are the AI blank," um, I just, I think they're all going to zero. Uh, even, you know, my, my kind of argument of this from a seed perspective is like, look, is OpenAI a good investment or not? It's a terrible seed investment, right? The way the numbers baked out, even at a $500 billion market cap, when all is said and done, the seed investors have made something like 25 times their money. That's insane, right? If you think about it, like, that's basically the worst... It's like a middling at best seed investment for, like, the company that is defining the moment. And the reason is because these things are so capital consumptive. So if you're trying to deploy $100 billion, the market is fragmented, you know, people want to dream a dream, people, like, want religion, they want belief. Like, there's, there's, there's a bunch of reasons why you can, like, squint and justify. You know what? If the storytelling of Elon allows SpaceX, which by the way, I love, I think SpaceX is an awesome company. But if all of a sudden that actually can be worth $1.4 trillion to the public market, guess what? The money powers 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 contrarian take would be run away-... 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.

Lenny Rachitsky 1:13:26 Wow, I love this. Okay, I wanna follow this thread a little bit. So is the- you're saying because of the dilution that goes along with these companies?

Sam Lessin 1:13:32 There's so many reasons.

Lenny Rachitsky 1:13:32 Mm.

Sam Lessin 1:13:32 It's, like, they're too capital- They're- if they work, they're too capital intensive.

Lenny Rachitsky 1:13:35 Mm.

Sam Lessin 1:13:35 Like, seed investing does not work in highly capital-intensive businesses, so, like, that's not gonna happen. Two, they're fundamentally commoditizing in all sorts of ways. It's very unclear what the lock-in or value is on any of these things, right? And so 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, 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 would, like, go west, and you'd do great, and, like, there was all this opportunity, land of opportunity. We've had reverberating, like, you know, my generation and your generation, we were blessed because we had the internet. The internet was digital Terra Nova, and, like, we got to build fortunes and do amazing stuff and new work, be in this, like, new world that was created, but it was effectively the same thing as the West all over again, right? And ever since then, whether it's mobile... Which again, if you look at the math on it, everyone wants to be disruptive and 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, right? And I think unfortunately this time, this is a classic example of AI is a powerful tool. It's incredibly powerful for existing businesses and existing structures. It's not a great startup opportunity.

Lenny Rachitsky 1:14:58 So what is it you look for? Do you invest- do you... Yeah, what do you look for when you're investing in an AI startup, if anything? Or do you at all?

Sam Lessin 1:15:02 Uh, well, again, I won't invest in anything that I would consider an AI startup. I'll invest in things that use AI, right?

Lenny Rachitsky 1:15:07 Yeah. Yeah.

Sam Lessin 1:15:07 Like, for me, I think I'm really interested in the cultural implications of AI or the new businesses that need to exist because it is a force in the world. So we've done a lot, whether it's Sublime Security or Outtake, things like that, that are basically all around the theme of the Voight-Kampff test from Blade Runner, which was the test they basically ran to say, "Are you a real or are you a bot?" Right?

Lenny Rachitsky 1:15:27 Like the turtle?

Sam Lessin 1:15:27 Like, that's a huge problem, like-

Lenny Rachitsky 1:15:28 The turtle on their back?

Sam Lessin 1:15:30 Yeah, [chuckles] it's, 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? There's a lot to do there, and there's a lot to do in cultural shifts from AI, right? Um, we- you know, there's all sorts of interesting trends to follow there. Like, there's, there's all sorts of businesses that will be disrupted. They're, like, not AI businesses, they're businesses that'll be disrupted in interesting ways. 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," I'm like, "Yeah, you're gonna win 'cause of something else," right? "And AI is gonna be a propellant to it."

Lenny Rachitsky 1:16:09 Sam, you're a fascinating human. [chuckles] 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 share?

Sam Lessin 1:16:18 Oh, look, I'm happy to be here. Like, I love your work. It's good to be on your podcast.

Lenny Rachitsky 1:16:22 I appreciate it.

Sam Lessin 1:16:22 Happy to bullshit whenever. But no, we're good. [chuckles]

Lenny Rachitsky 1:16:25 Okay, well, with that, we've reached our very exciting lightning round.

Sam Lessin 1:16:27 Okay.

Lenny Rachitsky 1:16:27 I've got five questions for you.

Sam Lessin 1:16:29 Five questions, I'm ready.

Lenny Rachitsky 1:16:30 Five questions. What are two or three books that you find yourself recommending most to other people?

Sam Lessin 1:16:35 Ooh, okay, so let me pull up my list, 'cause I, I, I gotta pull up my Kindle for this.

Lenny Rachitsky 1:16:39 Sweet.

Sam Lessin 1:16:40 Uh, one is, I'm reading right now... I gotta admit, I like to make fun of Marc Andreessen a lot, but he recommended a book called The Ancient City, which is fascinating, and so I'm in the middle of that right now. I'm really enjoying it. Um, Man's Search for Meaning is great. Uh, I'm just going through. What have I read recently? You know what's great? Area 51: An Uncensored History of the Top Secret Military Base. Not very erudite, great book. And then I, 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, uh, I would really, really, really recommend it. It's a short read, um, but I would- Lessons from History by Alan Durant is, like, probably the most approachable, non-obvious book I love.

Lenny Rachitsky 1:17:28 I did that one on Audible, and it's... You just listen to it all, like, not- like, in a couple hours.

Sam Lessin 1:17:32 It's a short read.

Lenny Rachitsky 1:17:32 Yeah.

Sam Lessin 1:17:32 It's not a long book. I, I honestly think from a-

Lenny Rachitsky 1:17:34 A few hours

Sam Lessin 1:17:35 ... hours of investment-

Lenny Rachitsky 1:17:37 Yeah

Sam Lessin 1:17:37 ... to intellectual return-

Lenny Rachitsky 1:17:39 Yeah

Sam Lessin 1:17:39 ... my one real answer right now would be that. I could give you a thousand others from... I, you know, there are things like The Banana King. Have you heard of this one? Have you seen this one?

Lenny Rachitsky 1:17:48 No.

Sam Lessin 1:17:48 Oh my God-

Lenny Rachitsky 1:17:48 Mm

Sam Lessin 1:17:48 ... 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, you go read Will Durant.

Lenny Rachitsky 1:18:02 Okay, I love it. Uh, favorite recent movie or TV show that you've really enjoyed?

Sam Lessin 1:18:07 Oh, I gotta say, I mean, recent, I think Landman is fabulous.

Lenny Rachitsky 1:18:11 Mm-hmm.

Sam Lessin 1:18:11 Have you watched Landman?

Lenny Rachitsky 1:18:12 Yeah, yeah.

Sam Lessin 1:18:13 I think it's great.

Lenny Rachitsky 1:18:13 I've watched the latest episodes, yeah.

Sam Lessin 1:18:14 I, I'm, like, really into it. That would be my most recent take.

Lenny Rachitsky 1:18:17 What's interesting about that s- show is now, uh, tech companies are all super into energy and, you know, data centers.

Sam Lessin 1:18:25 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 which is kind of part of the show, and it's so classic and typical. He's like, "All these Silicon Valley people now think they understand the energy industry because they watched Landman."

Lenny Rachitsky 1:18:42 [chuckles]

Sam Lessin 1:18:42 He's like, "So there's all..." He's like... I'm like, "It's, like, wild," but I totally believe it, like, 'cause I know too many venture capitalists who are like, "Oh, I now understand this 'cause I watched Landman," and he's like-

Lenny Rachitsky 1:18:51 Yeah

Sam Lessin 1:18:51 ... "This is totally a thing." Uh.

Lenny Rachitsky 1:18:52 Yeah, I've, I would feel that. [chuckles] Okay, favorite product that you recently discovered that you love? Could be like a gadget, could be an app, could be clothing, could be-

Sam Lessin 1:19:02 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. 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, whole virtual girlfriend, loneliness, you're gonna chat with your friend, da, da, da. Like, whatever, fine. These guys came out, and what they do is they're like: "Look, if we're really trying to match up humans, like call it Tinder 2.0, what are the best sources of information to do that? Is their ChatGPT histories." So this app is kind of built around the premise of distilling... You ask ChatGPT a structured prompt that they've designed. It pulls out an unbelievably good profile of who you are, and then you basically match with people based on, like, what you're actually asking ChatGPT about and the implications of who you are, and things like that. And, like, you know, the fun part is, I haven't obviously gone dates on it, again, not for me, but I have pulled my profile from it. Like, wow, this is like shockingly good description of who I actually am. And so I think that's, like, a really fun business.

Lenny Rachitsky 1:20:12 That's- it's like that prompt that the ChatGPT 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-

Sam Lessin 1:20:21 It's pretty good.

Lenny Rachitsky 1:20:21 You know a lot.

Sam Lessin 1:20:22 It's pretty good.

Lenny Rachitsky 1:20:22 And so, so in this dating app... I love this idea. It's so good. So do, do people read that? Are they able to see that as your profile, or it's, like, private?

Sam Lessin 1:20:29 I, you know, it's, it's, it's a little abstracted from that-

Lenny Rachitsky 1:20:31 Okay, okay, okay, okay

Sam Lessin 1:20:32 ... and, like, but it's like the matching and the core thing is, like, based on it, and it's like-

Lenny Rachitsky 1:20:35 Yeah

Sam Lessin 1:20:35 ... again, I'm like, I was just like: "Wow! Like, this is good." Like-

Lenny Rachitsky 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.

Sam Lessin 1:20:44 I guess. I mean-

Lenny Rachitsky 1:20:45 Yeah. Your AI goes on dates for you, receives one high match, each one carefully selected. Wow, it's so fun.

Sam Lessin 1:20:51 It's good. I, I get it-

Lenny Rachitsky 1:20:52 What a world

Sam Lessin 1:20:52 ... if you're single. I tried with my newsletter at one point. I was like: "Oh, you know, honestly, the people who read my newsletter are pretty weird and specific, and so, hey, why don't I just, like, offer a matchmaking service?" Where I'm like: "Okay, if you read my newsletter, really, and you're here, tell me who you are. I will, like-

Lenny Rachitsky 1:21:09 Yeah

Sam Lessin 1:21:09 ... build a little LLM and try to match you with people." Didn't work for me because candidly, you know what happened? Way too many qualified women and not enough men. I just don't have the liquidity. Like, I have 100 great women who wrote in to me like: "Hey, this is what I'm looking for, this is who I am." You're like, "You are an amazing person." And then, like, the four guys who write in are like, "I want a 25-year-old hot girlfriend." You're like, "Ah, this is not gonna work."

Lenny Rachitsky 1:21:32 Mm.

Sam Lessin 1:21:32 But June Date might have the liquidity to make it work.

Lenny Rachitsky 1:21:35 By the way, your newsletter is awesome. Tell people where to find it while we're on that topic.

Sam Lessin 1:21:38 You actually can't. Like, I just kind of like... There's no way to sign up for it. Um, if you send me an email-

Lenny Rachitsky 1:21:44 Perfect. [chuckles]

Sam Lessin 1:21:45 If you send me an email, lessin@gmail, I'm fine... Like, then I- you get- if I respond, you get automatically added.

Lenny Rachitsky 1:21:52 Mm.

Sam Lessin 1:21:52 I basically just, like, that's how I... Like, people I'm interacting with get added, or I'll just add you.

Lenny Rachitsky 1:21:56 Contrarian.

Sam Lessin 1:21:56 But I-

Lenny Rachitsky 1:21:57 [chuckles]

Sam Lessin 1:21:57 ... It's actually funny, there's not, I... Oh, well, you know what you can do actually, that will get you on it, is if you go to wlessin.com, L-E-S-S, wlessin.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. 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 for it.

Lenny Rachitsky 1:22:21 Okay, I love, I love this contrarian growth strategy. "No, nah, you can't really sign up." [chuckles] Okay, that's great. Okay, two more questions: Uh, do you have a favorite life motto that you find yourself coming back to often in work or in life?

Sam Lessin 1:22:32 No, but I will say that I have hanging in my gym, which I love, from the Facebook Hackathon after the launch of Google Plus, this is going way back in history, they made great posters, which was, 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. Like, let's..." And I had some of the most fun work experiences. We were working literally 24 hours a day. Like, past midnight every night was in that period, and I love that poster. So, Carthage must burn. How about that? [chuckles]

Lenny Rachitsky 1:23:08 [chuckles] Great. Final question: You are a fellow podcaster. Uh, I really enjoy your podcast. It's called More or Less. It's very cleverly named because of Lessin and the Moors, Dave Morin.

Sam Lessin 1:23:18 We love our last names. We also, like, my wife and I are contrarians and hate everything by default, and the Morins, like, think everything is amazing, so it kind of works from a dynamic perspective.

Lenny Rachitsky 1:23:27 I love it. And it's Dave Morin, Brit Morin, just to be clear, and your wife, she runs the Information.

Sam Lessin 1:23:31 Yeah, so she's good at prompting us what's actually going on in the world, and then we just bullshit about it.

Lenny Rachitsky 1:23:36 So what's, uh, what's something you've learned from that experience? I don't know, any surprises about podcasting basically?

Sam Lessin 1:23:40 So here's the thing. I think people, like... It's kind of a weird podcast in some ways because honestly, I don't think any of us are highly filtered, and it's kind of just like talking to your friends for an hour a week, which I want to do. Like, I love the Morins. We don't live that close to them, so it's kind of fun to just, like, have that time set aside and then cut it up and post it on the internet pretty raw. Um, here's the funny thing about it: It's fi- It, it serves our purposes way more than I actually expected it to, which is we enjoy doing it, which is the most important part. We would do it if no one was listening. And weirdly, like, a lot of our friends and people we care about in 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, we don't get paid for it, it's, like, weirdly useful, [chuckles] uh, is what I would say. Um, y- you know, even the fact that it's like... You know, it's, I don't know. I'm not sure if that's your experience, too, but, like... And I think your podcast is probably much larger than ours, but, um, it's, like, weirdly listened to and useful by the people that, like, we care about. Um, and it's fun, despite the fact that, you know, it's not like a, I don't know, it's not All In or something. [chuckles]

Lenny Rachitsky 1:24:59 Yet. Uh-

Sam Lessin 1:25:00 I don't think it ever will be. It's, like, way too niche, you know?

Lenny Rachitsky 1:25:03 Yeah. Yeah.

Sam Lessin 1:25:03 Like, um, but we have fun. Again, I would, I would happily do it with my friends if no one was listening, and then it's like, that's kind of wild that a bunch of people that we actually do care about find the pieces that are interesting, and it actually is helpful from a business perspective because you bullshit about something, and then some entrepreneur shows up and is like: "Hey, by the way, here's a better idea." You're like, "That's great."

Lenny Rachitsky 1:25:23 Sam, you're awesome. This was such a fun chat. [chuckles] Very different from my regular podcast. I think people will find this extremely interesting and useful, as I thought, and also fun. Two final questions. Where can folks find you online if they want to reach out, check out your fun-

Sam Lessin 1:25:36 Yeah, I'm basically just Less-

Lenny Rachitsky 1:25:37 What should people know?

Sam Lessin 1:25:37 My... Look, our venture firm is called Slow Ventures, slow.co. Um, I'm Sam Lessin. I'm kind of Lessin everywhere, whether it's, like, Twitter or Instagram or whatever you use. Um, or just lessin@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. Uh, and I don't know, come hang out in the pool house sometime.

Lenny Rachitsky 1:26:02 Okay. [chuckles] I love, I love this, like, this as an excuse to hang out. Sam, thank you so much for being here.

Sam Lessin 1:26:07 Hey, great to see you.

Lenny Rachitsky 1:26:09 Bye, everyone. [upbeat music] Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode!