How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin
87 min
•Jan 15, 20265 months agoSummary
Sam Lessin, partner at Slow Ventures and former VP of Product at Facebook, discusses why etiquette matters in business and provides practical guidance on social interactions, dining, meetings, and communication. He frames etiquette as a skill for showing up in any room with a low heart rate, building trust, and projecting genuine confidence—essential for founders and professionals navigating high-stakes business environments.
Insights
- Etiquette is not about rigid rules but about signaling respect and awareness; the goal is to make others feel comfortable and build trust, not to be memorable for following conventions
- Scarcity mindset in social interactions (treating every meeting as 'your one shot') undermines relationship-building; abundance mindset and leaving people wanting more creates better long-term opportunities
- Small, invisible signals—from email CC ordering to napkin placement to offering to pay—compound to either build or erode credibility, often without conscious awareness from others
- Most AI-branded startups will fail because AI is a tool for existing businesses, not a defensible startup opportunity; the real opportunities are in businesses disrupted by AI or cultural implications of AI
- Etiquette serves as a proxy for self-awareness and cultural sensitivity; violations signal lack of awareness more than malice, making effort and humility more valuable than perfection
Trends
Growing recognition that soft skills and social intelligence are competitive advantages in tech, especially as founders seek to build trust with investors and partnersShift from 'move fast and break things' culture toward intentional relationship-building and long-term partnership strategies in venture and startup ecosystemsIncreased focus on founder education beyond product and fundraising, including communication, presentation, and interpersonal skillsAI being repositioned from standalone business opportunity to infrastructure/tool for existing business models, with venture capital potentially overinvesting in 'AI companies'Rise of personal brand and thought leadership through unconventional content (etiquette guides, cartoons, podcasts) as differentiation strategy for VCs and operatorsDating and matching applications leveraging AI to create better user profiles and compatibility matching based on conversational data and behavioral patternsRenewed interest in cultural and historical literacy as founders recognize that understanding context and nuance improves business outcomes
Topics
Etiquette as a business skill and competitive advantageBuilding trust and credibility through social interactionsFounder education and soft skills developmentDining etiquette and business mealsVirtual and in-person meeting protocolsEmail communication and professional correspondenceDress codes and personal presentationSmall talk and conversation dynamicsScheduling and calendar managementAI investment thesis and startup opportunitiesAbundance vs. scarcity mindset in networkingHiring and working with executive assistantsHumor and storytelling in professional settingsTipping culture and service industry respectPersonal branding and thought leadership
Companies
Facebook
Sam Lessin was VP of Product at Facebook; he was attracted to the platform early because it solved his name-face reco...
Slow Ventures
Sam Lessin is a partner at this venture firm; he invests in companies using AI as infrastructure, not 'AI companies'
Y Combinator
Sam taught an etiquette class to YC founders at the Four Seasons, which sparked the broader etiquette project
Airbnb
Referenced as an example of a company acquisition where relationship-building with gatekeepers (EAs, office managers)...
OpenAI
Sam argues that even OpenAI was a poor seed investment despite its success, illustrating why AI companies are capital...
Kleiner Perkins
Referenced as a prestigious VC firm whose holiday parties represent high-stakes networking opportunities for young fo...
10Web
Sponsor offering AI website building and VibeCoding platform; Sam used it to build his Letter Meme product
DX
Sponsor providing developer intelligence platform for measuring AI impact on engineering productivity
WorkOS
Sponsor offering enterprise-ready APIs for SSO, SCIM, RBAC, and audit logs for B2B SaaS companies
Sublime Security
Portfolio company at Slow Ventures; example of a business addressing AI implications (email security in age of AI)
Outtake
Portfolio company at Slow Ventures; another example of business built around implications of AI rather than AI itself
SpaceX
Referenced as example of narrative-driven company that benefits from storytelling and belief, despite capital intensity
Dropbox
Customer of DX platform; uses it to measure AI impact on developer productivity
Booking.com
Customer of DX platform; uses it to measure AI impact on developer productivity
Intercom
Customer of DX platform; uses it to measure AI impact on developer productivity
June Date
Dating app Sam recommends; uses AI to create detailed user profiles from chat history and match based on actual compa...
Cursor
AI-powered code editor; mentioned as example of successful company that uses AI as infrastructure, not branded as 'AI...
Perplexity
AI search tool; mentioned as example of successful company that uses AI as infrastructure
Vercel
Web platform company; mentioned as example of successful company that uses AI as infrastructure
People
Sam Lessin
Guest discussing etiquette as a business skill; former VP of Product at Facebook; published book on proper etiquette
Lenny Rachitsky
Host of the podcast; engaged in conversation about etiquette, AI investment, and business practices
Gary Tan
Reportedly expressed skepticism about Sam's etiquette class for YC founders, calling it a waste of time
Mark Zuckerberg
Referenced as example of famous person to approach with grace and without sycophancy at social events
Kevin Collard
Sam's partner at Slow Ventures; maniacal about respecting service staff and asking where to put coffee cups
Elon Musk
Referenced as example of narrative-driven founder whose storytelling allows companies to command high valuations
Dave Moran
Co-host of Sam's podcast 'More or Less' with Sam; contrarian by default, provides opposing perspective
Jessica Lessin
Sam's wife; co-hosts 'More or Less' podcast; runs The Information; optimistic contrarian to Sam's pessimism
Tyler Cowen
Referenced as having Alison Gopnik on his podcast discussing how children learn like scientists
Alison Gopnik
Researcher studying how children learn; discussed on Tyler Cowen's podcast; relevant to teaching etiquette to kids
Alan Durant
Author of 'Lessons from History'; recommended by Sam as one of his favorite books
Barack Obama
Referenced as example of famous person whose time is so valuable that scheduling flexibility is necessary
Donald Trump
Referenced as example of famous person whose time is so valuable that scheduling flexibility is necessary
Quotes
"Etiquette is a skill for how to show up in a room with a low heart rate."
Sam Lessin•Early in episode
"I just feel like no one's being honest and teaching founders this. Be early. Don't order the most expensive thing on the menu for a video call, an appropriate background. Don't smell like shit."
Sam Lessin•Opening
"This isn't your one shot. You'll have other opportunities. You kind of want to show up with the self-confidence and the calm of abundance."
Sam Lessin•Mid-episode
"The point about etiquette is that it gets you out of the way, right? It shouldn't be memorable."
Sam Lessin•Dining section
"I think 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."
Sam Lessin•Contrarian Corner
Full Transcript
I just feel like no one's being honest and teaching founder is this. Be early. Don't order the most expensive thing on the menu for a video call, an appropriate background. Don't smell like shit. Tell me why you decided to spend time teaching people proper etiquette. You have a lot of really young people. They've been holed up in a room, coding, and they show up encouraged by Silicon Valley to be somewhat 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. Etiquette is a skill for how to show up in a room with a low heart rate. You're at the Kleiner Perkins Holiday Party. You have all the venture capos in the world and all the CEOs. You're at your first company. You're like, oh my God, this is my shot. But I need to convince this person of that and make this connection that becomes very transactional. If you show up like a little energizer bunny, you're gonna scare them off. You're gonna project totally the wrong vibe. This isn't your one shot. You'll have other opportunities. You kind of want to show up with the self-confidence and the calm of abundance. This is part of the story. This is not the entire story. Today my guest is Sam Lesson, partner at 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 the stuff, but this is turning into a big thing for him. He's teaching classes around the world. He published a book on proper etiquette. I love his framing for why etiquette matters, that the goal of learning good etiquette is to show up in a room with a low heart rate. And we cover all kinds of social interactions like introductions, small talk, meals, meetings, and basically all of the most important things you need to know when it comes to etiquette. I personally found these tips really, really useful and I learned a lot from this conversation and from his book. Sam is also hilarious and so fun. And I hope you enjoy this very unique episode. If you enjoy this podcast, don't forget to subscribe and follow any of 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, replete, bold, gamma, innate, and linear, Devin, post-hoc, superhuman, descriptive, whisper, flow, perplexity, warp, granola, magic, pattern, jerry, cash, JPRD, mobbin, and Stripe Atlas. Head on over to lennysnewsletter.com and click product pass. With that, I bring you Sam lesson 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 VibeCoding platform. 10Web's VibeCoding platform is a powerful way to build websites. Think of it as lovable for WordPress, frontend, and backend. Users can build any website at any complexity, e-commerce, portfolios, information websites, blogs, and it comes with the 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 slash Lenny and use code Lenny for exclusive free credits and 30% off API or white-labeled solutions. That's the number 10web.io slash Lenny, VibeCoding 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, Adion, 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 slash Lenny. Let's getdx.com slash Lenny. Sam, thank you so much for being here and welcome to the podcast. It's a blast to be here. I'm excited to have the conversation. This is gonna be a very different kind of conversation. I suspect this is actually gonna be really, really useful and really, really interesting to a lot of people. Useful and interesting? That's so unlikely. That's the Venn diagram that we aim for. I also think it's gonna be a lot of fun. So I really appreciate you doing this. I wanna give you the opportunity to set the stage for why we're chatting through this. Just tell me why you decided to spend time on teaching people proper etiquette and why should people pay attention to this? Why is this important? I really enjoy things at the intersection of hilarious and useful, right? You kinda need both, right? And hilarious is just because you should have fun in life. We should be working on things that are fun and interesting. Also, candidly, if we're being more honest about it, it's very hard to cut through the noise these days. So kinda you need humor is a great way to cut through it. But humor just for the sake of being funny is not that useful. There has to be a deeper truth to it. And so 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 kinda believe that you should always, there you go, you got it with you. I've got my coffee too. You got the book. There's a rule, you always wanna just double down in life. And so I'd say like, why etiquette? Look, there's a serious real narrative to like why etiquette matters in 2025, for founders, almost 2026. Like one, we talk about software getting commoditized. We talk about all of this fear mongering and scared people feel about Silicon Valley and AI and like all the things that are going on. The net is if you wanna do business and you wanna do business and build great partnerships with team members, with companies you wanna do business with almost with anyone, the reality is etiquette ironically matters a lot. There is a deep truth to this. Especially when you ask people to trust you with their data, trust you with their business. And when technology is no longer some cute side show but it's like a major deal, like people are worried about losing their jobs. Understand how to meet people, where they're at, build trust, mirror kind of expected behaviors. These are all like tools. 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. Think, well, actually it does matter. And you, you know, I'm wearing a T-shirt. I'm not exactly noticing the most high etiquette personal but I do know the rules, right? And I think like that's kind of, there's some, it's fun and funny as well. I think those things are both important. I wanna get into the actual rules but just to follow that thread, you had a really great line somewhere that etiquette is almost a skill for how to show up in a room with a low heart rate. Yeah, this is the thing I think about a lot. It's like, again, I think about, again, you and I are now old people, right? But like, you're young. I feel that. You feel it in your bones. It's like you're young, right? You're in, you're at the Kleiner Perkins Holiday Party. You have all the venture capos 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 the people I need to talk to and I need to convince this person of that and make this connection that becomes very transactional. If you show up like a little energizer bunny, right? You're gonna scare one off. Like you're gonna project totally the wrong vibe but I can understand why you'd be like a high intensity moment in a lot of ways. I think understanding how to show up, take a beat, come in with a mindset, not a scarcity, but of abundance. Understand how to give more than you take. Understand how to build a relationship, not collect business cards. These are things that actually serve you massively well and I just feel like no one's being honest and teaching founders this, right? Instead they're saying, oh no, all that matters is your product. I'm like, the product does matter a lot but if understanding these rules can be the difference between doing really well and missing a business deal, if you show up with too high a heart rate and you burn a bunch of mild relationship opportunities, like I don't know why you wouldn't want these skills, right? Yeah, there is one way to think about it. You can be successful not doing any of this, not knowing any of this, you're hurting yourself, you're making it harder. Yeah, I think it's just an unnecessary, you're creating an unnecessary up-pill battle for yourself. I'd also say that, look, this goes back to technical differentiation where things are at. It is true that if you bring mana from heaven, right? 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 fully, that's it. It's literally like that happens. It happens very, very rarely, but it does happen. It is 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. Awesome. Okay. So let's get into it. There's kind of you divided this book into about 10 categories, 10 social situations is one way to describe it. So let's just go through each one and just give us some pieces of advice. Sure. And something I didn't mention, the reason I'm excited to do this, the reason I reached out to you to do this, this wasn't you like pitching me, hey, let's talk about this in your podcast. As I was like, wow, this is really interesting. I did not know these things. Cheers. I mean, again, like I think the thing for us is I'm kind of a ship early ship often guy. So V1, you should buy it now and study it because it's good and it's gonna be like a limited edition. There's a bunch of, the funny part about doing this is people come back with a bunch of other things we should cover. So I suspect that eventually this will evolve beyond it. But I think we're starting with some good stuff. Let's do it. Okay. So introductions and entering a room. Yeah. Be early. That's the first one. Like, again, I say this as someone who I'll be honest. Again, like hypocrisy, I live with hypocrisy. I'm frequently not early, right? But you should be early. 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 and racing in the room five minutes late, your heart rates up. If you come in, you had a second to beat and take a beat in the waiting room. They kept you waiting, right? That's the dynamic I think you wanna 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, one, four, we're gonna go back to this heart rate thing. You could just apologize simply and move on. I've seen people screw this up so many times, right? When they come in flustered and all over the place, you're like, it's okay, we understand, right? Like I think that's kind of another really kind of obvious one, but an important one. Something I've seen, I'll go for a few others that we talk a bunch about in kind of is, look, 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 what you're meeting. I'm gonna 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 for 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. One that I loved was if somebody else is late, do not make them feel bad. Yeah. Do the opposite of what you're doing. 100%. And I think this is like, I've seen this with entrepreneurs and like, I get like, I'm a VC, I do get scheduled in like 30 minute chunks back to back, like all the time, especially on Zoom. Guess what? I am frequently late. I don't feel good about it, but it happens, right? And a lot of times founders, most of the time I'd say, founders know that like, if I'm late, I will always apologize. I'll try to email them ahead, et cetera. But then it is what it is. And like, we kind of get right into it. Every once in a while, you'll have some founder who like is super indignant about it, right? They're like, oh, and they're like, 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, now I feel like I'm wasting the next 25 minutes of my meeting time, because 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? You had also some advice on eye contact, it's for that one. Yeah, it's really important. Again, I think the thing to keep in mind is, especially in the age where everyone's used to be in front of computer screens and looking at six different windows at the same time, again, people are taking their time to meet with you, or at a party, 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 in the room. Now look, there are some people, we all know this who are like literally neuro, quite neurodivergent, and that's very hard for them. Like that happens. And 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 it's a really big overarching theory. So it's like, look, if you have trouble with this, but you're really trying, that goes a long way versus just being like whatever. Maybe a final tip there is around partners, introducing the partner, saying hi to their partner, share that one. Yeah, so like look, this happens all the time. And again, in the spirit of I'm not permitted this either, if you're with your partner, introduce them first, right? They, 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 romantic partner, whoever you're with. You're gonna forget someone's name, right? And what you really should do is- All the time, all the time. You're gonna forget someone's name. And like that's what you're supposed to do. The etiquette is say, Lenny, please meet my wife, Jessica. You know, and like that's kind of thing. Now here's the thing. This is where you start betting rules. What if I don't remember your name, right? If you have your partner with you, you can flip it around and say, Jessica, I want to introduce you. And then you kind of like, you kind of figure out how to find it out. 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- You let it hang. You let it hang, which by the way- I love that. It's a great example of that. If you're really in tune socially, you kind of know what's going on. Right? Like, you know what I mean? You're not an idiot. Like, you know, oh, like what is proper, what this person is doing. There's a gap between it. There's a reason. The reason is, but it's at least enough plausible deniability of like semi-bad etiquette that leverages the social situation to be a better etiquette, right? That it's a useful thing to think about as a small cue. I'm so bad at remembering names. I think I have a medical issue. So I just can't remember names. So this tip alone is so good. And just to reinforce it. So there's almost like two ways to do this is what you're describing. Either it's like my wife's name is Michelle. So it's like, hey, Michelle, meet my wife, Michelle. And then they're like, oh, I'm Bob. Nice to meet you, Michelle. Or it's like make it a little more awkward of just like Michelle, meet, like, and then let it hang. Is that- Michelle, I want to introduce you, right? Or something like that. Or like something like that. Or I want to introduce you to Michelle. You look at them in the eye, right? And then your wife will be like, hi, I'm Michelle. Remind me your name or it's nice to meet you or whatever it ends up being. Look, I also, for this worth, I actually have such a clinical problem on name face recognition that's actually runs in our family. I have this whole backstory, which is part, you know, I worked at Facebook for a 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? And this was like a very valuable social thing for me. So I'm with you. I have the same problem. I think a lot of people do. Okay, let's move on to conversations. Give us some tips. So, I mean, on the conversations fronts, I mean, I think the key again is to welcome people into the conversation. Like consider it, you know, especially you see this happen sometimes, especially when there's weird power dynamics at play, you know, you'll see some famous VC or founder walk into the room. And then some young startup person will like waylay them, right? And like kind of almost like block them off, right? And they're like really excited to talk to this person. But you're like, there's a bunch of people around. And like the more you can be inclusive, 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 tome to think about in terms of like what a conversation is and like how to show up at a room and meet with people. You know, another really big one we harp on a lot in the book in kind of a bunch of the panels is like, ask questions, but there's a limit, right? So asking questions is great. You're coming in and it says, hey, it's nice to meet you. Let me give you my four minute startup spiel and everything I've been to, is like so self-centered. It kind of misses the point that a conversation is a given it yet and it should be of exchange. And so when you go in with a mindset of I should ask questions, that's great. There is doing it too much, right? Which is when it's done in a forced way, sometimes I feel this, you'll meet someone and you feel like it's the inquisition or like all they're trying to do is extract information 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 have. It's like a game of ping pong. Then you can kind of react to it. It goes back and forth where there's openness and they're playing with you, not playing single player. It's almost the way I would think about it in a conversation. So it's basically indexed towards asking questions but not like 100%. Yeah, consider almost like put it this way. Imagine you're playing ping pong, right? Or tennis, whatever you want. Like hit the ball back, right? That's the question, right? And they'll hit it back to you and then you hit it back to them, right? Like that's kind of what the flow should be. If you hit 10 balls at them in a row, or like, you know what I mean? Or like, that's kind of like not the vibe you want to go for. Yep, awesome. Look, we talk a lot about matching vocabulary. You're going to meet a lot of different people. You want to make people feel good and welcome. I'm not saying that 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. Cool. There's a few more I'll point out real quick. Connecting to this idea of asking questions, not trying to give your whole spiel constantly, this idea of leaving them wanting more. Yes. This is important. I mean, I think in the end of the day, like most interactions, let's say you meet someone you're really interested in or whatever, if we're being transactional about it, what's the real goal? The real goal is to leave people in a position where they're like, wow, that was a really interesting person. I'd love to hear from them again or meet with them again or maybe even better. Everyone's while this will happen. It's like, wow, that's a really interesting person or idea. The person who walks across the room, someone else is like, hey, you really should talk to Lenny. Shut the Sam. Like that's kind of like, you want to leave them being like, that's interesting and I like to continue this or expand it. Not, I just heard this entire person's life story. I never need to talk to them again. Right. And so I do think there's, you know, again, leaving them wanting more, right? I think is important. And that is partially about knowing when to excuse yourself gracefully as much as it is about when to enter. And again, this comes back to this idea of abundance. This isn't your one shot. You'll have other opportunities. People don't want to feel like you're just on them, just trying to. I've had this conversation with so many and I think it's a uniquely American and honestly a uniquely Silicon Valley thing, right? I'll go so far as to say that, which is, look, we're used to, especially if you're young and these are big opportunities or big moments, people are kind of used to this like environment of scarcity. It like reminds me of the Eminem song when he talks about like a one shot, one opportunity. I think it's, oh Eminem, yeah, yeah, yeah. It's a great song. It's a great song. Great beat. Everyone's 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 going to be my only opportunity. This is an opportunity. I'm excited to be here. I'm engaged, right? This is part of the story. This is not the entire story. And I think if you kind of remind yourself of that, you remind yourself that it's okay to not know everything. You keep focusing on low heart rate, engagement, eye contact. You get so much the way there. You also have a tip about how to handle famous people that you might meet. I mean, there's so many ways. I mean, there's a bunch of tips about, I think, generally famous people, but I think there's this thing which is not being sycophantic is what I basically say, but also you're not being ridiculous is almost the way I would frame it in this conversation, 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? So there's a way to just, again, it's about grace as much as anything else, right? And recognizing that they're people. And again, you're playing an iterative game. And the best thing you can do is say, this is not my only, as much as it might actually be, this is not my only opportunity to meet Mark. And in an ideal world, when I walk away, I'm like, that was a pretty nice person. Like maybe I wanna talk to them again, right? Now, going up and being like, I need your email address and phone number. It's like, no, let him offer it. You know, like that type of stuff, I think matters. Maybe one last tip is that you actually start with this line of great to see you. You meet someone versus like nice to see you. Again, Lenny, you and I probably use this all the time, I bet, because I honestly, like I'm gonna go in name phase or whatever, it's really difficult social situation to put someone in. It just think about from their perspective, if you go up to someone and say, hey, it's really great, it's great to meet you. You're like, we've met five times. It's like quite embarrassing, right? And for them, for you, for everyone. So the more I like love, in fact, my wife, my wife of many, many years I've dated since college has a really funny story about this, which is the first time right before we started dating, I went up to her and I basically did a nice to see you line, right, and I very clearly couldn't remember if we had met before and we had and she remembered. And so for me, this is an important one, right, to keep in mind. My wife is constantly making fun of me of saying like, oh, I like not knowing if I've met someone before or not. She's like, how can you, like, I don't know what to do with you. So that's a great one. So the line there is great to see you because it works whether you meet them or not. Yeah, and again, it's one of those things where here's the thing, people are dumb. If you go around saying nice to see you to everyone, you're like, there's a small percentage of people that doesn't remind me who I, remember who I am, right? And there are other ways are cute, but like that's okay. Like that's part of the etiquette dance to some degree is like, that's fine. What's not fine is it's so nice to meet you and like we've met six times, right? Yep, okay. Let's talk hygiene. There's a couple there that stood out to me. Tell me if I'm missing any that you think are really important. One is just like subtle fragrance. Yeah, don't smell like 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. As long as the way I would put it, you know, in any direction. It's not, you're not, there's no advantage to that. That's basically what I would say. By the way, this is a good question. Does this advice apply both equally to men and women? Is there anything that as maybe as we go through it? So today's another question. I think broadly in this book, the answer is broadly yes. I will say that there is probably in January or February are going to be a what we internally in calling the Fem etiquette course because my wife and other women have said, this is good, but there's a bunch of other stuff that women need to know. And so I can't speak to that yet. I think the fray was what I would say. I don't think you want your fray to be memorable for anyone no matter what your gender is. Awesome. This is good. Let me take two tangents here real quick. One is 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. Look, here's the funny thing. I literally have realized in doing this, I love my children. They have terrible manners, right? And like there's a certain things they're like not bad at, but broadly speaking, I have an eight year old, a six year old and a four year old. And like, I'm like, wow, you guys, you guys eat like animals. Like you just, you know, you don't know how to use a fork or knife properly. Again, it's not like at four or six, it's not like stopping them well in life. And like, I can't be the etiquette guy if you guys are reading like, so I've been putting it in 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 from an etiquette perspective. You can argue about whether it's actually even really etiquette anymore or not. But if you're being really formal when a woman comes to the table, you stand, right? It's very funny to have the six year old do that. So in our household, don't judge me yet, but in a year you can judge me on my children's etiquette. Then it might have to be a children's etiquette book. So good. I think actually at the end, you say that whenever anyone joins you for a meal, whether it's a man or woman, you stand up. That's like a modern way of thinking about that. That might be better is what I would say. I will say that it's an ongoing, somewhat hilarious debate at our dinner table. I'm just trying to get them to like, not use a fork and knife like animals right now, but we're working on it. We're working on it. I was just speaking that, I was just listening to Tyler Cohen had Alex, Allison Gopnik on his podcast and she studies kids. And her whole thing is how kids learn like scientists. And she has a whole thing about how they figure out how to use a fork by just like experimenting and sell something works. Right. Like to be clear, they're able to feed themselves. It works, but it's like, you look at it and it's like, what are you doing? Yeah. Yeah. Okay. The other tangent is you didn't share the class you actually taught to founders already. So maybe share a little bit about this class you taught. Yeah. So I mean, before the book, we did a class specifically initially for YC founders, right? Partially because YC, Gary Tang, I'm very mad about this. So I'm like, well, now I have to do it, right? Cause that's very funny. But yeah, we basically, you know, we gave them all certificates of completion, but we did a class. We hosted it was at the four seasons. We did some stuff that was fun and a little bit of reverent. Like we had some very fancy Wilkes Bachelors 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 a lot of fun. We also did like caviar and wine tasting type stuff. But then we also spent a lot of time focusing on like the actual meat of the matter, right? Which is things like how to show up in the low heart rate, how to have an abundance mindset, you know, basic skills, like what people with the eyes shaking hands, you know, how to eat like the shows that you're being respectful, things like that. Why do you think Gary Tan was so mad at it? Is it because he's like, this is a waste of time, not worth it versus like just build a thing that's successful? I don't know. I mean, I don't really understand what makes Gary Tan mad and it's fine, but like from my perspective, I think, yeah, I think he's just like, in some ways, again, to be clear, it's a little tongue in cheek or a little bit making fun of the fact that YC founders do come out a little bit like animals, right? There's like having met with many of them. I guess that they're 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, but you may or may not know, but like, I think it's valuable. Maybe they're like, this is the wrong thing to focus on. I just think it's funny as much as anything else. I love it. Okay, so on the hygiene thing, is there anything else? I think the hygiene stuff, I mean, you should get the book. I think it's like fairly obvious hygiene stuff, like don't be covered in schmutz, you know what I mean? Like show respect, try to anticipate how the room is gonna be dressed and like don't massively over dress or under dress. It's like, if you show up to a business casual thing in a tuxedo, you know, you're like, you're kind of trying to stand out, don't be memorable from that perspective, but you also don't wanna be memorable in the other direction as like, wow, that person like really has no respect for the room. This actually, you're getting to the next category, which is dress, which I'm excited about. Yeah, I mean, dress, like look, I gotta say, again, in terms of know the rules, but don't always follow them. When I, my first job at a college, I was an associated bathing 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, that there wasn't a maximum dress code. So I started in the office as somewhat of a mini rebellion of the consulting firm, what we call tuxedo Tuesdays, where all the associates would wear tuxedos to work, which then we didn't have to go to the client meetings because they would never take us to client meetings and tuxedos. So it was like, 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 overdo it is basically the upshot of the most simple way to dress. Unless you're trying to very intentionally break a rule, right? Which maybe you are, but I think you should do that with a lot of cultural understanding. Let's put it that way. So here's a couple of tips that I love. So one is just dress one level up as a really simple tip. It's an easy way to win, not two, not three, but one. And oftentimes you can like reduce that. Like if you have a suit on, you could like take off the jacket and you're less formal. 100%. And then you talk about fit of the item versus the brand. 100%. Like, like in the end of the day, fit is everything, right? I say this 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 got to have a little bit of that in your life in terms of how I myself behave sometimes. But look, in the end of the day, like a well fitting $20 shirt is way better than a misfitting $500 shirt, right? And candidly, like it's the same thing. It's like, if you're a startup founder, you do want to kind of dress to the level of the room, but you kind of shouldn't show up in like, like you shouldn't have a Rolex, right? It's like very classless, if that makes sense. So like show up as a startup founder with a Rolex, right? It's just not, again, it goes back to heart rates, trying to hard, you know, you're not going to trick anyone, right? Is the upshot, right? Yeah, this bit of a brand and just expensive-ness 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%, I mean, again, I would 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? Like 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? Like what are we talking about? One other tip you have is if you're not sure, the level of dress, just ask. Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations, you know, down to like, which forks should I use? 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 big game of ping pong. But like it's totally fine to call me like, hey, like what's this gonna look like? And by the way, it's important because in New York versus San Francisco, there is different expectations. Like people do things differently. And like your job, you're not expected to know every nuance of every culture you might enter. So maybe as a final question in dress, do you have any just, I don't know, tips for dressing well? I know this is a big question that a professional will spend time teaching and charging for. I really, I think the answer is, find someone in your universe who you think dress as well. And again, ask them for help. And like what makes sense if that makes, from that perspective. Again, the well-tailored, great. That makes a lot of sense. The like basics I can say, yeah, like I 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 be chuckling. That's a win. Okay, let's talk about dining. Give us some advice for etiquette during dining. Tip well, right? Don't not tip, don't tip badly. Don't be super stingy about, okay, who ordered the flambé? Like split bills evenly, make things easy for waiters. In general, it's don't order the most expensive thing on the menu. 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 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, 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 kind of wanna go middle of the pack to last, if that makes sense. So this, yeah, so this is the situation if someone takes you out to dinner, like it's a VCE, another family, like someone invites you to dinner or a partner or whatever it is. Yeah, awesome. And look, I think the way it is, like in terms of this, which I always think is important is like, look, within reason, always offered to pay. Now, you should be turned down, right? If you go out with a VCE, 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 $10,000 dinner, if they've ordered a super expensive bottle of wine, like there are limits to this, right? But if you go out to a normal dinner, in a normal situation, you don't offer to split it, you just offer to pay for it, right? And then, you know, you should be declined on that, but there is a little bit of a risk there, because someone might not decline you, and then you kind of are on the hook for it. But that is, I think, the polite thing and the polite way to approach it. What if they're just like a billionaire? I just had dinner with like a very successful VC, and I did not feel like offering to pay made sense, would you still? Yeah, I actually would, I think it depends what the dynamic is. If the billionaire ordered a $10,000 bottle of wine, you don't need to offer, right? If you had a normal meal, right, I actually think it's great to offer, and they'll almost certainly be like, of course not, right? But I will say, you know, I'll tell you a funny story, which is like, when you go out to a dinner to really fancy people, right? Or like someone who's like, you know, there are two interesting dynamics. One is, it's actually, I think, especially nice to offer, or even sometimes pay, because the reality is if you think about it, they obviously don't care about the money, but no one does that, right? Like they're like, well, clearly you should pay. And so the more you're like, oh no, like I'm treating us like this is a conversation in equals, and like I'd love to offer or just pay as 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 relatively known, and you're making the gesture of buying it, not because they obviously don't care about the money, it's more like the gesture that's nice that you would offer that, you kind of have to tip the way they would tip, and they're 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 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. It's a tip a lot. Okay. Just tip a lot. Like I think 20% is the minimum, like if you're out in like a situation, I think you kind of want to tip in my mind to the level of no one you're effectively paying for, would bat an eye that you're being stingy is the way I would think about it. 20% feels like the minimum, 30% sometimes, like more seems a little bit silly, but it's not, it is a squirrely topic, and I just, I don't, again, let me go this way. I don't think you want your tip to be memorable, is almost way to put it. Like this is not a thing to focus on. Well, you think when the person who has dinner with thinks back on their dinner, on the dinner, a month later, they want to think about the content of the conversation or what the ideas were, or the business opportunity, they want to think about, oh my God, that guy tipped an incredible amount, what was that? And by the way, I have stories in my own life where like I've been out with people and they've tipped like so much that, like a decade later, I remember it, and I'm like, that's fine, they can afford it. 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 tipped. So you're, okay, but I think if you're like extremely rich, do you do it? Don't even tell anyone basically, but feel free to do it, obviously. Sure, yeah, I mean, you know what, the tip is not a point. The tip is like, everyone should feel good about it, right? Like, and like, again, it's about, it's about putting people in a sense of ease and comfort, and you might not like it, and it might not be fair in the world, but if you were 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 Femmikit, Femmikit. Edition is a tipping guide. A tipping guide. What you know would be funny is like, there's a great episode of Seinfeld, it's all about the tipping calculator. I don't know if you're a Seinfeld guy. I love Seinfeld, I don't remember that. There's a great tipping episode. I feel like you can honestly like, have a very funny, like modern LLM app. It is only about tipping. Like imagine like a tipping app. Pay money for that. It's like, instead of a tipping calculator, you take a picture of the bill, if you locate where you are, you kind of give it, you're like, this is the situation, and it just tells you what's the tip. Well, like a restaurant's one thing, but then it's like the garbage person, a gardener, the person that stalls it. Especially this end of year, like what's the end of year? Like I think no one knows how to tip anymore. I'd soak it, like yeah, some guy that installs us shades in our house, do I? Do you tip him? I don't think you tip that person. Do you tip that person? No, I did not, because that just, I feel like- Because we already paid a bunch of money for this thing. Yeah, I know, I feel like that is weird. I wouldn't tip people like that. That's why we need this book. This is, you're gonna make, you're just gonna be a huge hit. Well, you can fund it. You wanna fund it with me? We should fund an app. Talking 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. I really just love the stitches. You know what, it's 2026, it might be. Everyone has the problem. Everyone globally has the same problem, which is tipping. Yeah, just the tokens cost of that. It actually reminds me, I'm reading one of my sons right now, the third book of Hitchhiker's Guide to the Galaxy. And I don't know if you've read this series. Yes, yes. Do you remember about what's a 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 have this tip about Somalia, is give them a sip of your wine if you order something. Yeah, if you order something like that, I'll be very clear again in terms of, I don't order a very nice wine. No Somalia really cares what I'm drinking. But if you are doing that or you're into it, which is great, again, think about being generous. If they're like, I would love to taste that, like I love a taste, it's great. I love that, I would love to do that. That sounds really nice. Yeah. Okay, and one other tip here I wrote down, be for bread, be for drinks, tell them, explain. Oh, BD, you just gotta look at your hands, Bs and Ds, which was your bread plate, is kind of the way to think about it. Look, people get this wrong all the time. You sit down at a big table, right? And you're like, ah, which is mine, you're kind of waiting for someone to pick it up and kind of do the math. I'm like, okay, that's my bread. But the B and D is useful. Also, like, look, forks and knives, like just knowing what side they go on, knowing one thing I always drive is me nuts, that kind of goes, is related, is the knife blade goes in, right? People, when they put their knives down, right? The knife blade goes in, because you don't want to like stab your partner next to you. But like, it was really funny, I had an entrepreneur, this is not yet a product, and people started sending me videos of them like dining or in situations and asked for feedback, right? And I recently had a 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 pointing 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. Someone once had a napkin on just one leg versus both legs, any opinion there? I mean, I don't think you want your napkin placement to be memorable. That's kind of, my biggest thing is like, these are not, the point about etiquette is that it gets you out of the way, right? It shouldn't be memorable, you know? It's like the Kindle, you don't want to think about the technology. No, just let the conversation flow. Yeah, okay, amazing. Okay, speaking of conversation, small talk and humor, give us some tips. Here's the thing, humor's 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, right? It's the ultimate demonstration of comfort in a space. It's to tell a joke, it'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 gotta be pretty confident before you tell it, right? In space. The last thing you want, like a joke that ever laughs at is great. A joke that no one laughs at is 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 they're loosely ranked and from least offensive to most offensive. Cause like I forget the jokes, but like, you know, you kind of want to use humor sparingly and smartly. This is your next book, this list of jokes. List of jokes ranked by like social situation and like level of extremeness. Never is going to be telling the same jokes. Oh man. Well, there is a funny joke about that, right? Which is the whole, the prisoners, I won't even tell it. It's a funny joke about people who know all the jokes. I'll leave it at that. I'll leave you hanging and wanting more for our next podcast conversation. Abundance. Okay. You also recommend self deprecating as a joke. Make fun of yourself and not other people. Yeah. I mean, it's just like, you can make fun of yourself as much as you want, right? Again, making fun of other people shows an incredible level of familiarity, 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 where people aren't on the same wavelength, it's a very high risk maneuver, making fun of yourself is always fine. Here's a puzzle for you. What do open AI, cursor, perplexity, versell, 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, skim, 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 strike 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, cause 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. Make a list, I got some good ones for you. Okay, I'll have to borrow some. You also recommend having some stories crowd, please read kind of stories to tell. 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 in the same way of life. And in some ways think about it as like, who's carrying the conversation? It shouldn't be your monologue. You shouldn't force them to monologue either, right? That's where questions come in and back and forth. Having a fun build on story. They tell a story, you have a story to tell. 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 wanna have a few of those in your arsenal. Your last tip in that section was how to wind down a conversation, just the importance of realizing it's time to wind down any tips for how to do that. Yeah, just like when the conversation is over, gracefully leave, the upshot, you know, the people. The worst is like the conversation ends and the person just stands there and you're like, I'm gonna go get a drink, you know, or do you want it? And then whatever it's a while, the person will be like, you're like, if someone says to you in a conversation, they're wind it down, it's like, I'm gonna 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 all in all time. Is there any other ways you find useful to wind down a conversation? Just say and get out of a conversation. Well, 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, 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 they're like, 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. You wanna basically let people feel respected as much as anything else. So if you're too overt about it, right? You don't give that, 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. I actually, I think I'm not overstating it when saying there was a period where Calendly where I personally had driven most of their growth for the month. I got messages from the board because I went on as 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. They immediately drove their month. Wow, no bad press. No bad press, no bad tweets. Yeah, so I think like, look, there's a few obvious ones. When you're just, 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 default, 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, is what I would say. And it's fine if the first slot doesn't work, but one of the first three really needs to, right? So I think that like in some ways that it's important to kind of respect that. It's better to ask what they can do and then move your schedule. If you really can't and you're gonna use a scheduling agent or something, it just needs to actually have real options. Is basically, I think it comes up all the time. Look, rescheduling happens when you do it, give notice as much as possible. Once you're asking for rescheduling, you need to be even more accepting of what the other person can do. I think it's really important. Like if you're asking to reschedule, you basically within a reason need to make it work for them, is what I would say. And then look, I think like there's obvious stuff that people should know, but sometimes forget. 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, you're getting the numbers right, but then also really importantly, it's usually at like reasonable times. Like sometimes people are like, I wanna meet at this time, you're like, you're on EST, you're, 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, what you make in the book is like, you really need to respect EAs and PAs and the whole people. This is the number one way to look extremely classless is to not respect people who are helping the other person, right? Like this is like the number one thing. Now you don't need to be so over the top, exuberantly, you don't wanna 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 say, thank you when they schedule and like follow up with them and things like that. There's a, I'll tell a story. When we were selling our company to Airbnb, 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. It helps lubricate the thing. The general story of like make the gatekeepers happy and like you is true, but I do think there are ways to overdo that for what it's worth. It becomes almost too transactional. You show up with flowers for the EA, you know, like you better be damn confident like in what you're doing, if that makes sense. But just like the small things go a long way. Like you just make eye contact with them, thank them, respect them, you know, ask, you know, if they bring you a coffee cup, ask them where to put it when you're done, like don't treat people who you might, who feel like the team or the staff feel that way, make them feel like part of the team and equals. The Calendly stuff, I feel like that's its own separate book of Calendly etiquette. Yeah, the Calendly, look Calendly, Calendly is one of my favorite episodes of going hyper viral on something hilarious. 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. Look, I'll be honest, I go the other way, like I really, I don't use any of that stuff. Like, and look, I think scheduling is like very complicated. This is part of it, is, you know, I always think of these animals, like when are you free? It totally depends on who's asking. If Barack Obama, or I don't know, I will 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 of the same that are not, that does mean honestly, I think you probably knock these like my bet is that my calendar moves more than most people's and I'm sure that feels disrespectful to some and it is like, I'm gonna 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, I'm just like. The funny one I've had is there are people whose names are very similar to other people I know. And every once in a while, I've ended up like accepting a cold meeting and showing up and be like, you were not the person I expected because it's like, I was like, oh, your name is off by one letter. That's cool. That's not a thing to call out, by the way, from an 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 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 Calendly in case that might make it easier. Yeah, and that's perfectly fine, right, in terms of the way to do it. I just think that he has 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 a good shot. Okay, sweet. Move it 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. You know, I do think people have different things on this. I personally do think that on things like email, you kind of do have an SLA to respond. There's some people I know who are like, email does not mean I have to respond. You send me an email, you may or may not get a response, it's completely up to me. I have no contract to respond to your email. I personally go the other way, which I feel like from an etiquette perspective, I don't owe you a 12 page essay, but I do owe at least an acknowledgement quickly, of what you've sent. Like you don't want to leave people hanging. But again, I just think it's like, if you read an email, I'm sorry, if you write an email, imagine you're receiving it. How does it feel, right? Does it feel like you're asking a ton of the person you send it to, if you send them 10 paragraphs, it's annoying, right? You're like, okay, I have to read all this. What am I gonna find time? Like this is like, you're asking a lot. It's kind of like a monologue in a conversation. You've just said, I'm gonna spend 10 minutes talking at you. Right? And so I do think keeping it short and to the point, not these silly, not using emoji, trying to make it readable, like these are all important things. Say more about the emoji piece. Like is your advice just no emojis if it's a business? I think emojis, emoji from my perspective is very, it's like a, it's like quite a step of familiarity, if that makes sense. If you, 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 taxes 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 use their 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. And I think you just want to come across as like a literate to the point, simple, clear person. And emoji sometimes kind of implies use AI to generate this thing, because JGPD loves emojis. Totally. And I'll say like, look, I mean, there's a whole, 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 emoji people haven't seen before. Or like, it's like, again, it's a subtlety. And you got to understand the room and like the culture and like what you're responding to. But I do think that people read more into that than people want to be read into it. You know what's crazy now? I don't know if you've seen this. You can like create your own emojis now in iOS and emojis or so. It's like a whole new world. You just internet emojis. And again, it's like, if you choose to use those, you are going way out on a limb, right? That people are going to be receptive to that and not be like, this is a person who spent a lot of their time customizing their emoji pack when they probably should be doing something more interesting. They should be finding product market fit. Yeah, or learning etiquette. The other tip you had that I love, which is think about the order of the emails when you're emailing somebody. Yeah, I do think you kind of want to think about, you know, there is a connotation to who you send it to and who you CC and the order in which people know. Now, 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, who you think is most important comes first? Like who's first to put to mind? Well, who are you really sending this to? You know what I mean? It's 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 the Kevin and like I'm on it. Like if you see an email sent to many, many, many people, almost by definition, it's not that important, right? It's almost the way I put it. And so you have to be really careful with managing that. I think even 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 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 sell to like who responds then. 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? And so there was a whole language to who you send to and who you CC in the order that like, again, it's very subtle, but it's worth understanding. So true. Oh man. And 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 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? 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 cause intuitively there's well of knowledge and cultural connection and whatever that we can share effectively. And if your BCC definitely do not reply all. Yeah. I mean, I have some unbelievably funny faux pas from my history with CC BCC two lines. 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 two line to check the spelling of their name and then hit send. That's a bad idea, right? So whatever you're doing, that's not even an etiquette thing. That's just like a being smart. Poof reading thing. Fruf read, fruf read and don't send emails to people about them that they're not supposed to see. And it's like, do you know makes it too easy to do that? Cause it adds them automatically if you like talk to them. No, for me it was more just like the way to check to the spelling of someone's name not to put them in the two fields ever. Yeah. Oh, yeah. I thought that. Okay. Oh man. Well, you're still, you're still kicking. Still kicking. I'm still kicking. Okay. Okay. Two more. 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 someone's off. Cause then all of a sudden it feels like this person's been here a long time. Like this people's feels like even though we're not scheduled like we're leaving them hanging, your six coffees deep with the receptionist, like you don't want that, right? Like, so I think you want to be like 10 to 15 minutes early. You do not want to be much earlier than that. We talked about meeting other convenience. I do think it's fine to start with a little bit of small talk. Right. You know, there are times it's not or times people are running behind, but like the pleasantry of like the weather is nice or how is your weekend or like something that kind of cuts, cuts the air a little bit. And then you kind of flip into business is like a good thing. Even though it like feels transparent is still useful. Right. Is what I would say to kind of like, and again, 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 TCP IP hack handshake. I love it. It was a great description. I would always, I was described as like, imagine the modem crash from when we were kids on a 14-4. We were like, doodoo, doodoo, doodoo, doodoo, doodoo. 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 the way over there. So that you're ready to talk. So they're ready to really communicate. Yeah. For meetings, virtual ones, camera on. Like, and again, I say this to someone who sometimes violates this, right? I violated it knowingly. I violated 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 ways, and I go a step further. I actually, this is, this is less a hard rule. I actually really don't love virtual backgrounds for the same reason. I'm like, look, I'm not going to judge you if you're in your bedroom, if you're a startup founder. It's fine, but I would like to see that your bed is made. Or like, I'll give you another one that's classic that I see with founders all the time. Close your closet. Like people will get on Zoom calls and level, 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 picture here? Like, can you just close your closet? I don't want to see your shirts, you know? Like that type of stuff I think goes further than people realize. Awesome. One other tip you had was clean up after yourself if you're in a real meeting. This is actually the easiest way. 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, 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 coffee, even if you know full well someone's going to come and clean it up after you, you make a point of asking where we can put it, or putting it on the side table, et cetera, and acknowledging that there is a mess. I feel that. Final topic is exiting and leaving. What are some tips? You should stand where people leave the table, right? Not ridiculously, by the way, you should go stand with them at the table. Stand to shake hands. Don't be sitting when you're shaking hands. It's just what you do, right? And like it shows that you're aware of it. Follow up with gratitude. Like you should send people thank you notes. Even if it shouldn't be long, it shouldn't be ridiculous. But like we met, I got something out of it. Like thank you for taking your time. It's like always appreciated is what I would say. Obviously there's stuff like don't take calls, et cetera. Like this is kind of like the kind of obvious stuff in terms of exiting and how you think about it. If someone rings you, right? And you're like, and the meeting's over, and you're over telling, you're like, I gotta pick up this call. You hit the buttons as I'm calling you right back, and then walk away. Don't just pick up the phone and wave, is what I would say. Yeah, and I think there's stuff like that that I would just keep in mind. They'll say like, don't make a production of your exiting. Just exit. Just leave. Yeah, yeah, I mean, again, I don't like, you know, yes. I think that's really true. I mean, there's even a point to like, there are lots of scenarios where I think an Irish goodbye is the best goodbye, but you just kind of disappear. Like any large group setting, I think is great. Maybe you take one person on the way out of the host, right? But like, you know, the, I am leaving now, right? Like let me kind of say goodbye to everyone, and hug everyone. It's too much. It's too much. I love that. Okay, we got through everything. Is there anything else they think might be important? 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 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 want to like site 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. We're going to be doing classes next year all over the country and actually world. We invited to do, we're going to do it in Tel Aviv. We're going to do one, we're going to do one in New York and a few other places and you know, it'll be fun. This is a, 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, it just like keep making videos about this. And like, this is a 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. I'm into it. I'm fine with that. So I'll read, you have a TLDR at the beginning. I'll just read this real quick and add anything that you're missing. So this is just like, what to do if you do nothing else? Remember the goal of all etiquette is essentially building trust and project genuine confidence. Always maintain an abundance mindset. Remember that you are worthy and have nothing to prove and that it's okay to ask questions and keep your heart rate low. That's the points. If nothing else, if you remember those points, you will be served well. There we go. Okay, I'm going to take us to close out, make this more of a regular episode. I'm going to take us to two recurring segments on the 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 depends what you mean by that. So the question in AI Corner is just, what's one way you've found AI useful in your worker life that might be helpful for people to hear? So look, I'm by default pretty skeptical of most AI applications. I will say the thing that I've had the most fun with AI and I find great is actually it's 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. 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 because there's all these smart newsletters. You don't have time to read any of them. So I pipe them all in. Except letting you do it. But keep going. And what? Except letting you do it. 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 letter meme.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 for me, I actually, I'm looking at this now. There's actually one thing that got messed up on this week and changed. But the idea is you basically get an email digest once a day. And it's continuously updated. Like what's going on in the world. And you pipe your own newsletters into it. So it's like whatever you actually trust and pay attention to. Genius. And how did you build this? Was it VibeCoded? Do you have an engineer help you? Well, both actually. Like I actually, the VibeCoding thing, this is exactly what VibeCoding is good for. Is like this is like cursor and digital ocean. And Cloudflare will get you a long way in terms of just like building this stuff on the fly. And so I built the first version of this myself and the end. But then VibeCoding also doesn't really scale. And so the reality is after a certain point, I had some friends who are great engineers, just take it and like up level it in a few ways that I honestly ran out of time to work on. Well, let's go to a contributing corner. This could be an entire podcast conversation with you, I suspect. But just like what's something you wanna share that you believe that most other people don't believe? 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. It'd be insane. Like of course we're gonna use these tools. But there's a difference between a great business that you're using AI to supercharge or make better or just as a piece of infrastructure. That's not an AI business, this is the business. And I'm very into those versus like all of these companies that come out whether they didn't say we are the AI blank. I just, I think they're all going to zero. Even my kind of argument from a seed perspective is like look, is open AI a good investment or not? To terrible seed investment. The way the numbers baked out, even at a $500 billion market cap when all 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 cause these things are so capital consumption. So if you're trying to pull out $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 space is an awesome company, but if all of a sudden that actually can be worth 1.4 trillion dollars to the public market, guess what? The money plowers are going to do great with all this narrative driven religion is what I would put it. But if you're a disciplined seed investor, I guess my contrary intake would be run away from things that are AI companies. Cause 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 story a little bit. So is the, you're saying because of the dilution that goes along with these companies? It's like they're too capital. If they work, they're too capital intensive. Like seed investing does not work in highly capital intensive businesses. So like that's not going to happen. Two, they're fundamentally commoditizing in all sorts of ways. It's very unclear what the lock in her 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. Cause we had the West and if you were going to work hard, you could like go West and you do great. And like there was all this opportunity, they had an opportunity. We've had reverberating, 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, being 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 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. 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. So what does it you look for? Do you do? Yeah. What do you look for when you're investing in a startup? Well, again, I won't invest in the 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-Kampf test from Great Blade Runner, which was the test they basically ran. And are you a real or are you a bot? Right. Like the turtle, huge problem on their back. Yeah. It's like this is 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. With, you know, there's all sorts of interesting trends to follow there. Like there's all sorts of businesses that will be disrupted. They're like not AI businesses. Their businesses will 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 distinctions between if you're trying to be, I mean, certainly a foundation model company, but like any of these things that are like, we're going to win because AI. I'm like, you know, we're going to win because of something else. Right. And AI is going to be a propellant to it. Sam, you're a fascinating human. I feel like we could talk for hours. Is there anything before we get to a very exciting lightning round? Anything else you wanted to share? Like I love your work. It's good to be on your podcast. Happy to bullshit whenever. But no, we're good. OK, well, with that, we've reached a very exciting lightning round. OK, 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 other people? Oh, OK. So let me pull up my list because I got to pull my kindle for this. One is I'm reading right now. I 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, 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 Lessons from History is like one of my favorite books ever. I would really, really, really recommend it. It's a short read, but I would Lessons from History by Alan Durant is like probably the most approachable, non-obvious book I love. I did that one on Audible and it's you just listen to it all like not like in a couple of hours. It's not a long book. I honestly think for me, few hours, hours of investments to intellectual return. My one real answer right now would be that I could give you a thousand others from, you know, there are things like The Banana King. Have you heard of this one? Have you seen this one? Oh, my God, this is so good. What's it called? It's The Fish to Date the Whale. Incredible book. So is The Last Kings of Shanghai. 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 Wilderant. OK, I love it. Favorite recent movie or TV show that you've really enjoyed? I got to say, I mean, recent I think Landman is fabulous. Have you watched Landman? Yeah, yeah. I think it's great. I think it's great. I'm like really into it. That would be my most recent take. What's interesting about that show is now tech companies are all super into energy and I talked to it. I talked to it. Well, I'll tell you a funny story, which I talked to a founder who's in Midland, Texas, and it was just kind of part of the show. And it's so classic and typical. He's like all these people and now think they understand the energy industry because they watched Landman. He's like, so there's all these like I'm like it's like wild. But I totally believe it 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 feel that. OK, favorite product that you recently discovered that you love could be like a gadget, could be an app, could be clothing. OK, I'll pitch, you know, I'll pitch people on. This is a little self serving, but I will pitch people on June date. So, OK, 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? So everyone's got this like old virtual girlfriend, loneliness. You're going to chat with your friend that I like whatever. Fine. These guys came out and what they do is 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 there chat GPT histories? So this app is kind of built around the premise of distilling. You ask to be 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 to be about and the implications of who you are. And then the fun part is I haven't obviously done dates on it, 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. 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 was like, holy moly. It's pretty good. It's pretty good. And so so in this dating app, I love this idea. It's so good. So the people read that. Are they able to see that as your profile? You know, it's a little abstracted from that. And like this, but it's like the matching and the core thing is like based on it. And it's like, yeah, I'm like, I was like, wow, like this is good. Like and it goes on dates for you. OK, 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 site. Wow. So fun. It's good. I get it. If you're single, I tried with my newsletter at one point. I was like, oh, you know, honestly, the people who read my newsletter are pretty weird and specific. And so, hey, why don't I just like offer a matchmaking service where I'm like, OK, if you read my newsletter really, you're here. Tell me where you are. I will like build a little LLM and try to match with people. Didn't work for me because candidly, you know, it happened way too many qualified women. And not enough men. I just don't have the liquidity. Like I have hundred great women who murdered me. Like, hey, this is what I'm looking for. So I am like, you were an amazing person. And then like the four guys who write in are like, I want a 25 year old hot girl. You're like, this is not going to work. But you and Dave 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 the topic. You actually can't. Like I just kind of like there's no way to sign up for it. If you send me an email, perfect. If you send me an email, lessen it. 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 interacting with get added. Or I'll just add you. But I it's actually funny. There's not I. Oh, what do you know you can do? Actually, they'll get you on it. Is if you go to W lesson dot com. LES W LES as I am.com. I have my little like bond at 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. But no, there's not like a sign up page. OK, I love I love this contrarian growth strategy. No, no, I can't really sign up. OK, that's great. OK, two more questions. You have a favorite life motto that you find yourself coming back to often in work or in life? No, but I will say that I have hanging in my gym, which I love from the Facebook hackathon after the launch of Google Plus. This is going way back in history. They made great posters, which was Carthage Must Burn. And it was just like this great moment in work time when it was like, OK, 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. It's very cleverly named because of Lesson and with the more. We love our lessons. We also like my wife and I are contraries and hate everything by default. And the more and like think everything is amazing. So it kind of works from a dynamic perspective. I'd love it. And it's Dave Moran, but Moran just to be clear and your wife, she runs the information. So she's going to prompt us with it's actually going out of the world. And then we just bullshit about it. So what's what's something you've learned from that experience? I don't know. Any surprises about podcasting? So here's the thing. I think people like it's kind of a weird podcast in some ways because. Honestly, I don't think any of us are highly filtered and it's kind of just like talking to your friends for an hour a week, which I want to do. Like I love them or we don't live that close to them. So it's kind of fun to just like have that time set aside and then cut it up and post on the internet pretty raw. Here's the funny thing about it. It's fun. 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 pieces they like from it and like talk to us about it. So it's like a great conversation starter. So it's like weird. It's like, I don't like it's not a huge podcast. It's big enough, but it's, I actually think the thing that's been most surprising to you about it is that even though like we don't really have growth strategies and like we're not trying to blow it up and like we don't get paid for it. It's like weirdly useful is what I would say. You know, even the fact that it's like, you know, is I don't know. I'm not sure that's your experience too, but like, and I think your podcast is probably much larger than ours, but it's like weirdly listened to and useful by the people that like we care about. And it's fun, despite the fact that, you know, it's not like a, I don't know, it's not all in or something yet. I don't think it ever will be. It's like way too niche, you know, like, but we have fun. I mean, I would, I would happily do it with my friends if no one was listening. 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 bolstered about something and then some entrepreneurs is up and like, Hey, by the way, here's a better idea. You're like, that's great. Sam, you're awesome. This was such a fun chat. Very different from my regular podcast. I think people will find this extremely interesting and useful as I thought. And also fun to find out questions, working folks find you online if they want to reach out for a check out. I'm basically just, well, that's my look are venture firms called slow ventures, slow.co. I'm Sam lesson. I'm kind of lesson everywhere, whether it's like Twitter or Instagram or whatever you used, or just lesson at Gmail is my last name is my email address. And I do read it. So I don't know. I appreciate you having me on. It's always fun to see you. It's been too long. Uh, and I don't know, come hang out in the pool house sometime. Okay. I love, I love this. Like this is an excuse to hang out. Sam, thank you so much for being here. Hey, great to see you. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lennies podcast.com. See you in the next episode.