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

30:41And candidly, like it's the same thing. It's like, if you're a startup founder, you do want to kind of dress to the level of the room, but you kind of shouldn't show up and like, like you shouldn't have a Rolex, right? It's like very classless, if that makes sense to like show up as a startup founder with a Rolex, right? It's just not, again, it goes back to heart rates, trying too hard. You know, you're not going to trick anyone right is the upshot right yeah this bit of our brand and just expensiveness of the item is such a big one that i think is i think people don't realize just like it could be a pretty cheap thing that if you get tailored in some small way it just looks so much better even if it's not the highest quality item 100 again i would put put differently think about the average person not every person in the world but the average person in the world can look at a suit and be like intuitively that seems like it fits the person or doesn't yeah most people can have no idea what things cost right like if you said like you know what i mean it's just not and like so in some ways it's this weird thing where it's like if you show up at a super misfitting but very expensive item you're like what signal are you setting it's like well you're not very aware right culturally you're not like matching the room you're not showing a lot of sensitivity like to the situation what people actually can prioritize and it's like are you trying to impress me because you have a fancy outfit?

31:59Like what are we talking about? One other tip you have is if you're not sure the level of dress, just ask. Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations, you know, down to like, which forks should I use? You know, 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 a hundred questions about etiquette at a certain point you're like there's no that's not a pig game of ping pong like you're not getting but like it's totally fine to call me 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 is different expectations.

32:52Like people do do things differently. And like your job, you're not expected to know every nuance of every culture you might enter. So maybe as a final question in dress, do you have any just, I don't know, tips for dressing well? I know this is a big question that a professional spend time teaching and charging for. I really, you know, I think the answer is find someone in your universe who you think dresses well. And again, ask them for help. And like what makes sense if that makes you know from that perspective again the well tailored great though that makes a lot of sense the like basics i can say yeah like have jeans that are clean right and like fit you things like that but again 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 great that's a win okay let's talk about dining give us some advice for uh etiquette during dining tip well right uh 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 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 like wine like and then i think look in the terms of asking ideally don't order first right because i think if you see how someone like are we doing starters like what like what how long is this meal going to be like there's a lot of times in dining situations you don't know and the more you let someone else set the tone and then match that tone the better like you kind of want to go middle of the pack to last if that makes sense uh so this yeah so this is in the situation if someone takes you out to dinner like it's a vce uh another family like someone or a partner or whatever whatever it is yeah and look i think i would say in terms of this which i always think is important is like look within reason always offer to pay now you should be turned down right if you go out with a vc right and you're like you know you put a card down 99 % of the time they'll be like i got this like please like this is don't worry about it right and like that's the right vibe on it you do not need to do this if it's a ten thousand dollar dinner if they've ordered a super expensive bottle of wine like there are there are limits to this right but if you go out to a normal dinner in a normal situation, you don't offer to split it.

35:31You just offer to pay for it. Right. And then, you know, you should be declined on that. But there is a little bit of a risk there because someone might not decline you and then you're kind of on the hook for it. But that is, I think, the polite thing and the polite way to approach it. What if they're just like a like a billionaire? I just had dinner with like a very successful VC and I did not feel like offering to pay made sense. Would you still? Yeah, I actually would. I think it depends what the dynamic is. If the billionaire ordered a ten thousand dollar bottle of wine you don't need to offer right if you had a normal meal right i actually think it's great to offer and they'll almost certainly be like of course not right um but i will say you know i'll tell you a funny story which is like when you go out to with dinner to really fancy people right or like someone who's like you're you know there are two interesting dynamics one is it's actually i think especially nice 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 like i'm treating us like this is a conversation and equals and like i'd love to offer or just pay as big the second thing which is important is if you're especially if you're out to dinner with someone who's very very well known you have to tip like crazy because the problem is this is like one thing this is like a this is not in the book this is like a 201 course right but if you go out to someone someone that were like okay they're either known or well it'll be no known and you're making the gesture of buying it not because they obviously don't care about the money it's more like the gesture that's nice that you would offer that you kind of have to tip the way they would tip and they're going to tip like a hundred percent of the bill right because like it's just like the right thing to do and so i do think you like if you're going to do that you really have to tip well got it speaking of tipping my god i hate tipping so much as a concept like obviously people deserve to be paid well and i love that you know they make more money but it's just so convoluted and just like what the hell do i do i never know a lot tip a lot okay just tip a lot like i think 10 20 is the minimum like if you're out in like a situation you know i think you kind of want to tip in my mind to the level of no one you're effectively paying for would bat an eye that you're being stingy is the way i would think about it.

37:4720 % 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 a 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 want to think about the content of the conversation or what the ideas were or the business opportunity. They want to think about, oh my God, that guy tipped an incredible amount. What was that?

38:17And by the way, I have stories in my own life where like I've been out with people and they've tipped like so much that like a decade later, I remember it. And I'm like, it's fine. They can afford it. It's like, it's like cool that they did that for the server. But honestly, the only thing I remember for the night is how much the person tips. So you're okay. But I think if you're like extremely rich, you do it. Don't even tell anyone basically, but feel free to do it, obviously. Sure. Yeah. I mean, you know, the tip is not a point. The tip is like everyone should feel good about it. Right. Like, and And like, again, there's about, it's about, again, putting people in a sense of ease and comfort.

38:50And you might not like it and it might not be fair in the world. But people are like, everyone's being taken care of. I can be relaxed about this is kind of what you're going for. I recommend your next book after this Femme Kit edition is A Tipping Guide. A Tipping Guide. Well, you know what would be funny is there's a great episode of Seinfeld that's all about the tipping calculator. I don't know if you're a Seinfeld guy. I love Seinfeld. I don't remember that. It was a great tipping episode. I feel like you could honestly have a very funny, modern LLM app that is only about tipping. Imagine a tipping app where it's like, instead of a tipping calculator, you take a picture of the bill, it geolocates where you are, you kind of give it, you're like, this is the situation, and it just tells you what to tip.

39:35Well, a restaurant's one thing, but then it's like the garbage person, a gardener, the person that stalls. Especially this time, end of year, Like, what, at the end of the year? Yeah, exactly. I think no one knows how to tip anymore. I'd soak it. Like, yeah, some guy that, like, installs the shades in our house. Do I tip him? I don't think you tip that person. Okay. Do you tip that person? No, I did not. Because that just, because we already paid a bunch of money for this thing. Yeah, no, I feel like that is weird. I wouldn't tip people like that. That's why we need this book. This is, you're going to make, this is going to be a huge hit.

40:07Well, I think we could fund it. You want to fund it with me? We should fund an app. Talk about YC companies. If someone pitched me in terms of funny but real, if someone pitched me the 2026 AI driven tipping calculator, which gives the social situation and the details and all the things. And it's like, this is how much to tip. That is hilarious and probably quite useful. And probably not venture scale, but I don't care. You know what? It's 2026. It might be. You know, everyone has the problem. Everyone globally has the same problem, which is tipping. Yeah. Just the tokens cost of that. It actually reminds me, I'm reading one of my sons right now, the third book of Hitchhiker's Guide to the Galaxy.

40:45And I don't know if you've read this series. Yes. Do you remember about that? What's Bristomatics? Mathics? So basically the idea is that after the improbability drive, the way they're able to move across the universe very quickly is the most complicated math in the universe, which is the math of your bill at a restaurant. So I think we're on to something. It's in science fiction. Oh, man. One other tip that I just thought of around dining is you had this tip about sommeliers. Give them a sip of your wine if you order something. Yeah, if you order something nice. I'll be very clear again in terms of I don't order a very nice wine.

41:22No sommelier really cares what I'm drinking. But if you are doing that or you're into it, which is great. Again, like think about being generous, right? If they're like, oh, I would love to taste that. I would love to taste. It's great. I love that. I would love to do that. That sounds really nice. yeah okay and one other tip here i wrote down uh b for bread d for drinks tell explain oh bd you just gotta look at your hands right b's and d's for to know which was your bread plate uh right is it kind of the way to think about it and look people get this wrong all the time you sit down at a big table right and you're like ah which is mine you're kind of waiting for someone to pick it up and kind of do the math i'm like okay that's my bread 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 i always drives me nuts um that kind of goes is related is the knife blade goes in right people when they put their knives down right the knife blade goes in because you know like you don't want to like stab your partner next to you but like it's really funny i had an entrepreneur this is not yet a product and people started sending me videos of them like dining or situations and asked for feedback right and i recently had to give feedback to an entrepreneur who was like you did a very nice job eating your soup.

42:32Good job. Your napkin should have been in your lap and your knife is pointed the wrong way. Okay. Napkin actually. Okay. So napkin and lap. Napkin and lap. Not in your neck, not off to the side, you know, napkin and lap. I saw someone who once had a napkin on just one leg versus both legs. Any opinion there? I mean, I don't think you want your napkin placement to be memorable. That's kind of my biggest thing is like, these are not, the point about etiquette is that it gets out of the way, right? It shouldn't be memorable. It's like the Kindle. You don't want to think about the technology. No, you just let the conversation flow.

43:04Yeah. Okay. Amazing. Okay. Speaking of conversation, small talk and humor. Give us some tips. Here's the thing. Humor is great. I love humor. It can be overdone. And again, it shouldn't be the point of things. And also I'd say humor is quite conditional and subtle to the audience. So like in the room you're in, dirty jokes, right? You don't want to tell a dirty joke in the wrong room. but I think the thing about humor is it kind of there's this interesting subtlety to why it's so useful in social settings which is one, it kind of shows the ultimate mastery of a social situation if you're able to tell a joke which is right up to the line or even pushes it one degree to show your own comfort in the space it's the ultimate demonstration of comfort in a space is to tell a joke that's a little over the line or a little off color but not too off color it's like the ultimate thing So if you're really in it and like feeling good, using humor is great.

44:02You 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 got to be pretty confident before you tell it. Right. In space. the last thing you want like a joke that everyone laughs at is great a joke that no one laughs at is a it's like a huge risk maneuver you failed right and like it's not the point so it's a great tool i love it like i think everyone should have their file of jokes i do i don't know about you like i have like a evernote it's not ever done 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 because like i forget the jokes but like you know you kind of want to use humor sparingly and smartly this is your next book this uh list of jokes list of jokes ranked by like social situation and like level of extremeness everyone's gonna be telling you same jokes oh man 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 funny there's a funny joke about people who know all the jokes i'll leave it i'll leave you hanging and wanting more for our next podcast conversation abundance okay uh you also recommend self-deprecating uh as a make fun of yourself not other people yeah i mean that's 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 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.

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46:29They'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. Also, so you said you had this kind of list of jokes that you, because I can't remember. I have zero jokes in my head. I'm like, okay, here, I'm going to get one. So I should make a list. Make a list. I got some good ones for you.

47:00Okay, I'll borrow some. You also recommend having some stories, some crowd-pleasery kind of stories to tell. Yeah, you want to have some easy stories that are, again, like it shouldn't be 10 minutes. Right. But again, I think the thing about it is like, imagine that the whole game in these social settings, again, is putting other people at ease, making them feel like you understand them and the room and you're a trustworthy person and on the same wavelength. And in some ways, think about it as like, who's carrying the conversation. It shouldn't be your monologue. You shouldn't force them to monologue either.

47:29Right. That's where questions come in and back and forth. Having a fun build on story. They tell a story. You have a story to tell. Like, again, I really think of it as like a conversation or these social interactions as a ping pong game, right? And like you kind of want to have a few of those in your arsenal. Your last tip in that section was how to wind down a conversation, just the importance of realizing it's time to wind down. Any tips for how to do that? Yeah, just like when the conversation is over, gracefully leave. It's basically the upshot. The worst is like the conversation ends and the person just stands there and you're like, uh, I'm going to go get a drink, you know, or do you want it?

48:02And then once in a while, the person will be like, you're like, if someone says to you in a conversation and they're winding down. It's like, I'm going to go grab a drink. Most of the time, that is not an invitation to say, I'd love one too and follow them to the bar, right? Like that is not, so like I just think you have to kind of recognize the signs effectively when the moment is passing or it's time to move on, et cetera. And then like respect it. That's what I would say. I use that one all the time. Is there any other ways you find useful to wind down a conversation just to get out of a conversation?

48:32Well, I think the other thing people do frequently, which again is totally fine if done respectfully is bring someone else into the conversation right like in some ways like give them their next partner you know you're like oh like i've enjoyed this conversation it's super cool you know i 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 okay i'm gonna go say hi to my wife you know like there's ways to handle it again like the key though is subtlety on these things right like i think in all things like you want to basically let people feel respected as much as anything else.

49:04So if you're too overt about it, right, you don't give them, even if everyone kind of knows what's going on, the key is to give them like plausible deniability to themselves and the community effectively that like we've wound down this conversation. I mean, so you have to kind of look for the signs. Awesome. Okay. There's four more sections. The next one is scheduling etiquette. Give us some advice. Oh, well, like I think I'd like to say that I'm fairly famous for hating Calendly. um there is a i actually i i think i'm not overstating it when saying there was a period where calendar where i personally had driven most of their growth for the month i got messages from the board because i went on this diatribe about how much i hate countly and how disrespectful it is and apparently this was such an internet fervor i got like millions of engagements that meaningfully drove their month um wow no no bad press no bad press and no bad tweets yeah so I think like, look, there's a few obvious ones.

49:59Make 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, I really strongly believe the default should not be Calendly. The default in most situations, especially if you recognize the power hierarchy, the busyness hierarchy. If you're the less senior person, if you are the less busy person, you should let the other person tell you when they're free. and then make it work on your end, right? Is what I would say. And it's fine if the first slot doesn't work, but one of the first three really needs to, right?

50:33So I think that like in some ways that it's important to kind of respect that. It's better to ask what they can do and then move your schedule. If you really can't and you're going to use a scheduling agent or something, it just needs to actually have real options is basically, I think, that comes up all the time. Look, rescheduling happens. When you do it, give notice as much as possible. 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 worth the extra check to make sure you're not both scheduling uh you're getting the numbers right but then also really importantly at like reasonable times like sometimes people like i want to meet at this time you're like you're on est you're where that's like four in the morning for me right and so like i think being respectful of that and just asking i think is super important it's not rocket science it's important last point i make which you make in the book is like you really need to respect eas and pas and the whole people like this is the the number one look way to look extremely classless is to not respect people who are helping the other person, right?

51:52Like this is like the number one thing. Now you don't need to be so over the top, you don't want to overdo it, but there should be this deep well of like respect for anyone who's helping you, whether that's a server or a PA or an EA or whatever. This needs to come with an extra gesture of respect. That means say thank you with a schedule and like follow up with them and things like that. 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 if they like you, it helps.

52:30It helps lubricate the thing. The general story of like, make the gatekeepers happy and like you is true. But I do the other ways to overdo that for what it's worth. It becomes almost too transactional. If you show up with flowers for the EA, you know like you better be damn confident like in what you're doing if that makes sense but um just like the small things go a long way like you just you know make eye contact with them thank them respect them you know ask you know if they bring you a coffee cup ask them where to put it when you're done like don't treat people who you might who feel like the team or the staff feel that way make them feel like part of the team at equals the Calendly stuff I feel like that's its own separate book of Calendly etiquette.

53:12Yeah, Calendly is one of my favorite episodes of going hyperviral on something hilarious. So one thing that Calendly does is you can 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. Look, I'll be honest. I go the other way. I don't use any of that stuff. And look, I think scheduling is very complicated. This is part of it. I always give these examples. is 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 for the morning my time right or like i'm totally you know what i'm gonna make it work right and like so i do think like i'm actually kind of against the like flat hierarchy all meetings are the same that are that does mean honestly i think you probably knock me is like my bet is that my calendar moves more than most people's.

54:08And I'm sure that feels disrespectful to some. And it is. Like, I'm going to be really clear. But it's also the reality of trying to balance these things. The other flaw with 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 I was like, it was on my calendar. I'm like, what is that? The funny one I've had is there are people whose names are very similar to other people I know. And every once in a while, I've ended up like accepting a cold meeting and showing off to me like, you are not the person I expected because it's like, I was like, oh, your name is off by one letter.

54:41That's cool. That's not a thing to call out, by the way, from an etiquette perspective. Once you're committed to the meeting, you're doing the meeting, even if it's the wrong person. Oh, man. Okay. Well, one last question with Calendly. Something I try to do, I'm curious to get your take, is like, okay, someone went like a founder, I'm meeting with a founder, and the way I approach it is like, okay, do you have a Calendly or something I could use to book a meeting with you? If not, in parentheses, here's my calendar in case that might make it easier. Yeah. I think that's perfectly fine, right, in terms of the way to do it.

55:11I just think the key is to make it easy for the person you're trying to do business with, right? And not make them feel like they have to do the work if they don't want to. No, you do the work. Like, basically, you're asking for something, you do the work is the upshot. Okay, sweet. Moving on to the next topic, communication. Don't use emojis. Try to proofread your stuff. Get to the point quickly. Assume the person you're reading is busy. Like, again, I think these are all the types of things that like none of this is rocket science from my perspective. But people, it's just good to remember, right, and be on top of it.

55:43You know, I do think people have different things on this. I personally do think that on things like email, you kind of do have an SLA to respond. There are some people I know who are like, email does not mean I have to respond. You send me an email, you may or may not get a response. It's completely up to me. I have no contract to respond to your email. I personally go the other way, which 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.

56:15But again, I don't I just think it's like if you read an email, I'm sorry, if you write an email, imagine you're receiving it. How does it feel? Right. Does it feel like you're asking a ton of the person you sent us here? If you send them 10 paragraphs, it's annoying. right you're like okay i have to read all this what am i going to find time like this is like you're asking a lot it's kind of like a monologue in a conversation you've just said i'm going to spend 10 minutes talking at you right and so i do think keeping it short and to the point you know not being silly not using emoji trying to make it readable like these are all important say more about the emoji piece like is your advice just no emojis if it's a business i think emojis emoji from my perspective is very it's like a it's like quite a step of familiarity if that makes sense if you uh from a business context look if someone sends you a smiley face 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 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 awesome okay i do use emojis i use like the thank you hands one a lot and look i think text is different i think people might have slightly different takes on this and so i wouldn't say anything i'm saying here is dogmatic but i'm just saying that like again emojis are not highly legible to most people they can mean lots of different things they usually have cultural connotation to them 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 and emojis sometimes kind of implies use ai to generate this thing because jgbt loves emojis totally and i'll say like look i mean there's a whole you want to get you want to get spicy for a second yes i don't know how i feel about people who have like invested too much in their emojis right so you get people who have like changed the colors of their emojis from the default or whatever i'm not saying not to do it i'm just saying it's quite a statement is my view that you've invested in your emoji pack or like using special emojis people haven't seen before or like it's like again it's a subtlety and you got to understand the room and like the culture and like what you're responding to but i i i do think that people read more into that than people want to be read into it you know it's crazy now i don't know if you've seen this you can like create your own emojis now in ios and emojis or so it's like a whole new world just like and again it's like if you choose to use those, you are going way out on a limb, right?

58:50That people are going to be receptive to that and not be like, this is a person who spent a lot of their time customizing their emoji pack when they probably should be doing something more interesting. They should be finding product market fit. Yeah. Or learning etiquette. The other tip you had that I'd love, which is think about the order of the emails when you're emailing somebody. Yeah. I do think you kind of want to think about you know there is a connotation to who you send it to and who you cc and the order in which people know 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 and because the implication there is you who you think is most important comes first like who's first to mind who are you really sending this to you know what i mean is almost the way i think 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 mildly pay more attention to it than when i'm the fifth right because in my head i'm like okay well like this is really 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 would put it and so you have to be really careful with 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.

1:00:09Right. And like, I do think people sometimes miss that. Like the CC line is very, very valuable. It means, hey, you should have a copy of this. This is not really to you. I'm not expecting an immediate response. Right. I even think there's even a subtlety, like who responds that like if you send an email to 10 people CC 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 again you can break this rule like there are times to break it there's a subtlety to it but it wasn't really sent to you right like and so there's a whole language to who you send to and who you cc and the order that like again it's very subtle but it's worth understanding so true man any you would think nobody sees all these little things in the gmail thread but you do they're just right there you see them and i think people this is the whole thing about etiquette is like it's all this invisible stuff yeah that you don't need to spend like all in some ways the whole story of doing this well is it should not occupy 80 of your brain right what you're saying is i've got this we're on the same wavelength my heart rate is low i'm doing it properly and i'm doing it with like intuitively almost right which is a hard ask right because what we're basically saying is like these are unknown things but intuitively you should just know them and that is actually what you're signaling is like you can trust me because intuitively there's this well of knowledge and cultural connection and whatever that we can we can share effectively and if uh your bcc definitely do not reply all yeah i mean i i have some unbelievably funny faux pas from my history with ccbcc two lines um i one of the worst etiquette slash 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 a being smart proofreading thing proofread proofread and don't send emails to people about them that they're not supposed to see and it's like gmail makes it too easy to do that because it adds them automatically if you like talk if you add their name no for me it was more just like the way to check the spelling of someone's name is not to put them in the two field ever yeah oh yeah okay oh man well you're still you're still kicking so I'm still kicking okay uh two more uh meeting etiquette yeah I mean again we've talked about arriving a little bit early you should do that don't arrive up too too early 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 because then all of a sudden it feels like this person's been near a long time like this feels like even though they're not scheduled like we're leaving them hanging you're six coffees deep with the receptionist like you don't want that right like 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 other 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 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 normal you're like signaling like oh i know that we should start with a normal conversation if that makes sense right i don't know if you saw this on twitter someone described small talk as like the tcpip acc handshake i love it it's a great description i always i always describe it as like imagine the modem crash from when we were kids on a 14-4 you know like that old modem crash like that's that's what small talk is it's a modem crash we're trying to hit the wavelengths you know etc is like so that you're ready to talk so they already really communicate yeah um for meetings virtual ones camera on like and again I say this as someone who sometimes violates this, right?

1:04:13I violate it knowingly. I violate it knowing what it costs me, but you really should have your camera on, right? And again, like you should dress appropriately for a video call. You should have an appropriate background. You know, if you have your bed in your background, it should be nicely made. You know what I mean? Like in some ways it's like doing the easy stuff is the key in some way. And I go a step further. I actually, this is less a hard rule. I actually really don't love virtual backgrounds for the same reason. I'm like, look, I'm not gonna judge you if you're in your bedroom, if you're a startup founder, it's fine.

1:04:47But 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'll be on a call and like their closets open. And I'm like, it's not a big deal. but like do you see your own self picture here like can you just close your closet i don't want to see your shirts you know like that that type of stuff i think goes further than people realize awesome uh one other tip you had was clean up after yourself if you're in a real meeting this is actually the easiest way and this by the way is for my partner kevin collard but the easiest way to come off badly is to not offer to put your coffee cup in the kitchen right and like honestly we do this 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 that coke even if you know full well someone's going to come in and clean up after you you make a point of asking where we can put it or putting on the side table, et cetera, and acknowledging that there is a mess.

1:05:59I feel that. Final topic is exiting and leaving. What are some tips? You should stand when people leave the table, right? Not ridiculously. By the way, you should stand when you're shaking hands. It's just what you do, right? And like it shows that you're aware of it. Follow up with gratitude. Like you should send people thank you notes, even if they shouldn't be long. It shouldn't be ridiculous. us 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 etc like this is kind of like the kind of obvious stuff in terms of exiting and how you think about it like even if someone if someone rings you right and you're like and the meeting's over and you're over time you're like i gotta pick up this call you hit the button 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 think like there's stuff like that um that would just keep in mind they'll said like don't make a production of your exiting just like just leave yeah yeah i mean again like i don't like you know yes i think that's really true it's i mean there's even a point like there are lots of scenarios where i think an irish goodbye is the best goodbye but you just kind of disappear like any large group setting i think is great maybe you think one person on the way out of the host right 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 it's too much i love that okay we got through everything is there anything else that you think might be important there's so much other stuff i mean again i go back to this whole thing which is like you know these are all fun tips i love the cartoons we iterated them a bunch we have more to do like 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 because like there'll be a second version of the book and then a third and like i actually really want to like cite the people who contribute to it like the book is what like 50 60 pages it will be a few hundred eventually and i think there's a lot more to come and we're going to be doing classes next year all over the country and actually world we'll be we got we invited to do we're going to do one in Tel Aviv.

1:08:13Wow. We're going to do one. We're certainly doing one in New York and a few other places and, you know, it'll be fun. This is, oh my God, you got a whole new life forming here. I, 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 going to be ultimately remembered as like the etiquette guy? That's kind of hilarious. That's what we're doing here.

1:08:42I'm into it. I'm fine with that. So let's read. You have the TLDR at the beginning. I'll just read this real quick and add anything that we're missing. So this is just like what to do if you do nothing else. Remember the goal of all etiquette is essentially building trust and project genuine confidence. Always maintain an abundance mindset. Remember that you are worthy and have nothing to prove and that it's okay to ask questions. And keep your heart rate low. That's the point. if nothing else. If you remember those points, you will be served well. There we go. Okay, I'm going to take us to close out, make this more of a regular episode.

1:09:16I'm going to take us to two recurring segments on the podcast, AI Corner and Contrarian Corner. I don't know if I told you I was going to ask you these questions, but I'm going to go for it. All right, lay it on me. I love Contrarian Corner. And AI Corner, it depends what you mean by that. So the question on AI Corner is just, what's one way you found AI useful in your work or life that might be helpful for people to hear? 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 is partially where the cartoons for this came from is I built a little personal news aggregator called Letter Meme that basically takes all the newsletters I don't have time to read and turns them into daily cartoons.

1:09:56Like 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 because there's all these smart newsletters. You don't have time to read any of them. so I pipe them all in except Lenny's newsletter but keep going what? except Lenny's newsletter sure of course that one I don't put in the aggregator of course of course I don't do that but it's great so I'm super into it and that's lettermeme.com I'm checking it out I love this I love this so this is AI generated aggregates all the important newsletters and creates a little summary and a cartoon yeah and you can make your own so like for me I actually I'm looking at this now there's actually one thing that got messed up on this we need to change but the yeah The 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 and you pipe your own newsletters into it.

1:10:42So it's like whatever you actually trust and pay attention to. Genius. And how did you build this? Was the Vibe Coded? Did you have an engineer help you? Well, both actually. Like I actually, the Vibe Coding thing, this is exactly what Vibe Coding is good for is like, this is like, you know, cursor and digital ocean and Cloudflare will get you a long way in terms of just like building this stuff on the fly. And so I built the first version of this myself 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 in a few ways that I honestly ran out of time to work on.

1:11:15Well, let's go to Contrarian Corner. This could be an entire podcast conversation with you, I suspect. But just like what's something you want to share that you believe that most other people don't believe? I think that the venture capital, the seed venture capitalists who invest in companies that are branded as AI companies are going to lose an impossibly large amount of money in the coming years. And that doesn't mean that I don't think you should be using AI to build things. I actually think you absolutely should. It's kind of like not using AI in your startup is the equivalent of not using the cloud in like 2010 or like not using the internet in like 2000.

1:11:52It'd be insane. Like, of course, you're going to use these tools. But there's a difference between a great business that you're using AI to supercharge or make better or just as a piece of infrastructure. that's not an AI business, this is a business, right? And I'm very into those versus like all of these companies that come out, whether that say we are the AI blank. I just, I think they're all going to zero. Even, you know, my kind of argument from a seed perspective is like, look, is open AI a good investment or not? 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.

1:12:29That'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 consumption. So if you're trying to employ$100 billion, the market is fragmented. You know, people want to dream a dream. People like want religion. They want belief. Like there's a bunch of reasons why you can like squint and justify it. 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?

1:13:06The money plowers are going to do great with all this narrative driven religion is what I would put it. But if you're a disciplined seed investor, I guess my contrary take would be run away from things that are AI companies. Because even if you look smart for the moment, you're playing a dangerous game of get out before the narrative collapses. Wow, I love this. Okay, I want to follow this through a little bit. So you're saying because of the dilution that goes along with these companies. It's like they're too capital. If they work, they're too capital intensive. Like seed investing does not work in highly capital intensive businesses.

1:13:38So like that's not going to happen. Two, they're fundamentally commoditizing in all sorts of ways. It's very unclear what the lock-in or value is on any of these things, right? And so it's just like the whole dynamic is off. And the thing is people are desperate right now for things to believe in. like if you think about the history you know we've done so well as a country with terra nova like the u.s was amazing for so many years because we had the west and if you were going to 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 reverberated like you know my generation your generation we were blessed because we had the internet the internet was digital terra nova and like we got to build fortunes and do amazing stuff and new work in this like new world that was created but It was effectively the same thing as the West all over again, right?

1:14:23And ever since then, whether it's mobile, which again, if you look at the math on it, everyone wants it to be disruptive in Terra Nova. Not really. It's just more internet, right? Or like crypto, which by the way, I think crypto is 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? But the story has to be real, right? And I think, unfortunately, this time, this is a classic example of AI is a powerful tool. It's incredibly powerful for existing businesses and existing structures.

1:14:56It's not a great startup opportunity. So what is it you look for? Do you invest? Do you? Yeah. What do you look for when you're investing in a startup? Well, I won't invest in things that I would consider an AI startup. I'll invest in things that use AI, right? For me, I think I'm really interested in the cultural implications of AI or the new businesses that need to exist because it is a force 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 Great Blade Runner, which was the test they basically ran.

1:15:25Are you a real or are you a bot? The turtle? The turtle on their back? Yeah. There's a whole set of companies that are like implications of AI and how do you manage it 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? 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 an interesting way so i think there's a lot of opportunity but again i think there's a i at least draw a distinction between if you're trying to be i mean certainly a foundation model company but like any of these things that are like we're gonna win because ai i'm like yeah you're gonna win because of something else right and ai is gonna be a propellant to it sam you're a fascinating human.

1:16:10I feel like we could talk for hours. Is there anything, before we get to our very exciting lightning round, anything else you wanted to share? I'm happy to be here. I love your work. It's good to be on your podcast. Happy to bullshit whenever. No, we're good. Okay, well with that, we've reached our very exciting lightning round. I've got five questions for you. Five questions. I'm ready. Five questions. What are two or three books that you find yourself recommending most to other people? Ooh, okay. So let me pull up my list because I got to pull up my Kindle for this. One is I'm reading right now.

1:16:41I got to admit, I like to make fun of Mark Andreessen a lot, but he recommended a book called The Ancient City, which is fascinating. And so I'm in the middle of that right now. I'm really enjoying it. Man's Search for Meaning is great. I'm just going through. What have I read recently? You know, it's great. Area 51, an uncensored history of the top secret military base. Not very erudite. Great book. And then I honestly think the one serious one i'll make a recommendation on is uh lessons from history is like one of my favorite books ever um i would really really really recommend it's a short read um but i would lessons from history by alan durant is like probably the most approachable non-obvious book i love i did that one on audible and it's you just listen to it all like not like in a it's a short read it's not a long book i honestly think from a few hours hours of investment to intellectual return my one real answer right now would be that i could give you a thousand others from i you know there are things like the banana king have you heard this one have you seen this one oh my god this is so good what's it called it so the fish that ate the whale incredible book uh so is um the last kings of shanghai if you know that one like these are all like amazing books but they're longer and there are more stories just every one of the podcasts should go read will durant okay i love it uh favorite recent movie or tv show that you've really enjoyed oh i gotta say i mean recent i think landman is fabulous have you watched landman yeah yeah i think it's great episodes i'm like really into it that would be my most recent take what's interesting about that show is now uh tech companies are all super into energy and i talked to it i talked to well i'll funny story which i talked to a founder who's in uh midland texas and it was just kind of part of the show and it's so classic and typical he's like all these silicon value people and now think they understand the energy industry because they watched landman he's like so there's all he's like i'm like it's like wild but i totally believe it like because i know too many venture capitalists like oh i now understand this because i watched landman and he's like it's totally a thing yeah i would feel that okay favorite product that you recently discovered they love could be like a gadget could be an app could be clothing okay i'll pitch you know i'll pitch people on this is a little self-serving but um i will pitch people on june date so okay i actually don't use this product because i'm happily married but this is cool and here's the basic idea is if you think about so much of ai right now this goes back to like what businesses do you overhaul that are interesting that have AI implications but are not AI.

1:19:23So everyone's got this like old virtual girlfriend, loneliness, you're going to chat with your friend, da da da, like whatever, fine. These guys came out and what they do, they're like, look, if we're really trying to match up humans, like call it Tinder 2.0, one of the best sources of information to do that is their chat GPT histories. So this app is kind of built around the premise of distilling, you ask chat GPT a structure prompts that they've designed. It pulls out an unbelievably good profile of who you are. And then you basically match with people based on like what you're actually asking ChatGPT about and the implications of who you are.

1:19:59And the fun part is I haven't obviously done dates on it. Not for me, but I have pulled my profile from like, wow, this is like shockingly good description of who I actually am. And so I think that's like a really fun business. that's it's like that prompt that the chat gpt folks once had of just like draw visualize my space based on everything you know about me and it's it was like holy moly it's a lot it's pretty good and so so in this dating app i love this idea it's so good so do people read that are they able to see that as your profile or you know it's it's a little abstracted from that and like but it's like the matching and the core thing is like based on it and it's like again i'm like i was like wow like this is good like and it's goes on dates for you okay so it's like it simulates what the date might be like between you two potentially i guess yeah your ai goes on dates for you receives one high match each one carefully sighted wow so fun it's good i i get if you're single i tried with my newsletter at one point i was like oh you know honestly the people who read my newsletter are pretty weird and specific and so hey why don't i just like offer a matchmaking service where I'm like, okay, if you read my newsletter, really, you're here.

1:21:06Tell me who you are. I will like build a little LLM and try to match with people. Didn't work for me because candidly, you know what happened? Way too many qualified women and not enough men. I just don't have the liquidity. Like I have a hundred great women who wrote in me like, Hey, this is what I'm looking for. This is who I am. You're like, you were an amazing person. And then like the four guys you write in are like, I want a 25 year old hot girlfriend. You're like, ah, this is not going to work but june date might have the liquidity to make it work by the way your newsletter is awesome tell people where to find it while we're on that you i 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 perfect if you send me an email lesson at gmail i'm fine like then i you get if i respond you get automatically added i basically just like that's how i like people i'm interacting with get added or i'll just add you but i it's actually funny there's not i oh you know you can do actually they'll get you on it is if you're you go to wlesson.com l-e-s-s-i-n.com i have my little like bought 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 okay i love i love this contrarian growth strategy no no you can't really sign up okay that's great okay two more questions uh you have a favorite life motto that you find yourself coming back to often in work or in life?

1:22:32No, but I will say that I have Hanging in My Gym, which I love from the Facebook hackathon after the launch of Google+. This is going way back in history. They made great posters, which was Carthage Must Burn. And it was just like this great moment in work time when it was like, okay, game on. Like Google's coming for us. Like let's, and I had some of the most fun work experiences. we were working literally 24 hours a day. Like past midnight every night was in that period. And I love that poster. So Carthage must burn. How about that? Great. Final question. You are a fellow podcaster. I really enjoy your podcast called More or Less.

1:23:15It's very cleverly named because of Lesson and with the Moors. We love our last name. We also like my wife and I are contrarians and hate everything by default. And the Moors like think everything is amazing. So it kind of works from a dynamic perspective. I love it. Dave Morin, but just to be clear. And your wife, she runs the information. So she's good at prompting us whether it's actually going on in the world and then we just bullshit about it. So what's something you've learned from that experience? I don't know. Any surprises about podcasting? So here's the thing. I think people, it's kind of a weird podcast in some ways because honestly, I don't think any of us are highly filtered.

1:23:48And it's kind of just like talking to your friends for an hour a week, which I want to do. I love them more. We don't live that close to them. So it's kind of fun to just have that time set aside and then cut it up and post on the internet pretty raw um here's the funny thing about it it's fun it serves our purposes way more than i actually expected it to which is we enjoyed 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 the industry seem to pick up pieces they like from it and like talk to us about it so it's like a great conversation starter 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 uh is what i would say um you know even the fact that it's like you know is i don't know i'm not sure if that's your experience too but like and i think your podcast is probably much larger than ours but um it's like weirdly listened to and useful by the people that like we care about um and it's fun despite despite the fact that, you know, it's not like a, I don't know, it's not all in or something.

1:24:59Yet. I don't think it ever will be. It's like way too niche, you know, like, but we have fun. I mean, I would, I would happily do it with my friends if no one was listening. 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 sam you're awesome this was such a fun chat it's 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 for check out i'm basically just less my look our venture firm is called slow venture is slow.co um i'm sam lesson i'm kind of lesson everywhere whether it's like twitter or instagram or whatever you used.

1:25:49Or just lesson at Gmail is my last name is my email address and I do read it. So I don't know. I appreciate you having me on. It's always fun to see you. It's been too long. And I don't know. Come hang out in the pool house sometime. Okay. I love this as an excuse to hang out. Sam, thank you so much for being here. Hey, great to see you. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast.

1:26:24You can find all past episodes or learn more about the show at Lenny's podcast.com. See you in the next episode.