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

Summary

Podcast Summary:

Lenny’s Podcast: Product | Career | Growth
Episode: How to Show Up in Any Room with a Low Heart Rate: Silicon Valley’s Missing Etiquette Playbook | Sam Lessin
Host: Lenny Rachitsky
Guest: Sam Lessin (Partner at Slow Ventures, ex-VP of Product at Facebook, two-time founder)
Date: January 15, 2026

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Episode Overview

Lenny sits down with Sam Lessin to discuss his unconventional crusade to bring etiquette back into Silicon Valley—and why it matters more than people think. Drawing on Sam’s new book and etiquette classes, the conversation dives deep into practical, concrete advice for showing up well in professional and social settings. Their guiding principle: etiquette isn’t about being stuffy, but about building trust, lowering your (and others’) heart rates, and signaling genuine confidence.

“The goal of learning good etiquette is to show up in a room with a low heart rate.”
— Lenny Rachitsky (01:24)

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Key Topics & Takeaways

1. Why Etiquette Matters in Silicon Valley

• The “move fast and break things” ethos has ignored core social graces; Sam argues this is now a weakness.
• Trust and relationships are more critical as software and technology commoditize.
• Etiquette is more than tradition: it’s a foundational skill for building partnerships, trust, and projecting calm confidence.

“There is a deep truth to this... understanding how to meet people where they're at, build trust, mirror kind of expected behaviors—these are all like tools.”
— Sam Lessin (05:00)

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2. Fundamental Principles: The ‘Low Heart Rate’ Mindset

• Etiquette is about making everyone (including yourself) comfortable—“show up with the self-confidence and the calm of abundance.”
• Avoid desperation or scarcity vibes; you’ll have more than one shot at opportunity.
• “Leave people wanting more” rather than unloading your entire life story or burning social capital in one go.

“If you show up like a little Energizer bunny, you're going to scare one off... understand how to build a relationship, not collect business cards.”
— Sam Lessin (07:10)

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3. Practical Playbook: 10 Core Etiquette Scenarios

a. Introductions & Entering a Room

• Be early (not too early or late; if late, apologize simply and move on).
• Give a strong, but not crushing handshake.
• Repeat names back to people to signal attention and help remember them.
• Make eye contact—signals you are present (give grace for neurodivergence, but effort matters).
• If someone you’re with forgets a name, use cues like, “I want to introduce you to…” to help prompt the other person.

“If you're with your partner, introduce them first… If you forget someone's name, let it hang so your partner can pick it up.”
— Sam Lessin (13:53)

b. Conversations & Small Talk

• Welcome people into the conversation (especially in group or power-dynamic situations).
• Ask questions, but don’t grill—conversation should feel like ping pong, not an interrogation.
• Match vocabulary and energy to the room.
• Leave them wanting more; don’t overstay your conversational welcome.
• Use “great to see you” instead of “nice to meet you” if you’re unsure about prior interactions.

“The conversation is a give and a get… It’s a game of ping pong.”
— Sam Lessin (18:21)

c. Hygiene

• Scent should not be noticeable—avoid overpowering cologne/perfume or body odor.
• Dress appropriately for the setting; look put together but not flashy.

“Your scent should not be noticeable, in any direction… There’s no advantage to that.”
— Sam Lessin (24:11)

d. Dress

• Dress one level up from the “room average” (not two or three).
• Fit matters more than brand or cost.
• Don’t be memorable for a flashy watch or misfit clothing—“you’re not going to trick anyone.”
• If unsure, ask about dress codes.

“A well fitting $20 shirt is way better than a misfitting $500 shirt.”
— Sam Lessin (30:16)

e. Dining Etiquette

• Don’t order the most expensive item, especially if someone else is paying.
• Offer to pay or to split, even if you expect to be declined.
• When in doubt, order after others to set the tone.
• Tip well (20%+), so that your tipping is never memorable for the wrong reasons—offer generosity, not stinginess.

“Tip to the level that no one is going to bat an eye... 20% feels like the minimum.”
— Sam Lessin (37:29)

f. Small Talk & Humor

• Humor is powerful but risky; use it sparingly and appropriately for the room.
• Self-deprecating humor is always safer than poking at others.
• Keep a few stories or “crowd-pleasers” in mind, but don’t monologue.
• Exit conversations gracefully—“I’m going to grab a drink” is a gentle signal to move on.

“The ultimate demonstration of comfort is to tell a joke that's a little over the line but not too over.”
— Sam Lessin (44:54)

g. Scheduling Etiquette

• Don’t default to sending a scheduling link (e.g., Calendly), especially when there’s a power hierarchy. Offer options, and let the senior/busy person choose.
• Respect time zones and the realities of the other person’s calendar.
• Always be respectful of EAs and gatekeepers.

“If you are the less senior person, you let the other person say when they’re free and then make it work on your end.”
— Sam Lessin (49:53)

h. Communication (Email/Text/DMs)

• No emojis in formal business email; match the recipient’s style.
• Keep emails short and to the point; proofread.
• Be mindful of recipient order in email threads—signal importance via order (To & CC fields).
• Always acknowledge receipt, even if briefly.

“Emojis feel like jokes to me—tell them at your own risk.”
— Sam Lessin (56:51)

i. Meeting Etiquette

• Arrive 10-15 minutes early, not much more.
• Offer small talk at the start.
• For virtual meetings: camera on, tidy background, appropriate dress.
• Clean up after yourself—don’t leave your coffee cup or trash behind.

“Close your closet... it's not a big deal, but, do you see your own self-picture here?”
— Sam Lessin (64:04)

j. Exiting & Leaving

• Stand when people leave the table or room.
• Don’t make a production out of leaving (Irish goodbye is often best at large gatherings).
• Send a simple thank-you afterward.

“There are lots of scenarios where I think an Irish goodbye is the best goodbye.”
— Sam Lessin (67:00)

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4. Broader Reflections & Notable Moments

• Teaching Etiquette: Sam describes teaching etiquette classes (sometimes tongue-in-cheek) to startup founders: “It started with a tweet, escalated to an event, and now it’s a book and classes.” (05:00)
• On Kids: Sam’s kids are now standing up at meals: “In our household, don’t judge me yet… judge me in a year on my children’s etiquette.” (25:09)
• YC Founders: “We’re making fun of the fact that YC founders do come out a little bit like animals... they’ve been holed up coding for months.” (27:46)
• Calendly Hot Takes: Sam’s viral diatribe against Calendly “personally drove most of their growth for a month” (49:26)
• Abundance Mindset: “Even if this is your one shot, show up with the calm of abundance.” (20:20)

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5. Bonus Segments

AI Corner (69:28)

• Sam uses AI to aggregate newsletters into daily cartoons via lettermeme.com: “It’s the best way I get an overview… all these smart newsletters, but I don’t have time to read any of them.” (70:07)

Contrarian Corner (71:25)

• Sam’s contrarian take: “Venture capitalists investing in branded AI companies are going to lose an impossibly large amount of money.” He distinguishes between using AI as a tool versus claiming “AI is the business.”
• “I invest in businesses that use AI, not AI businesses.” (75:02)

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6. Lightning Round Highlights

• Book Recommendations:

  • The Ancient City
  • Man’s Search for Meaning
  • Lessons from History by Will Durant (“most approachable, non-obvious book I love”) (76:35)
  • Area 51: An Uncensored History
  • The Fish That Ate the Whale, Last Kings of Shanghai

• TV/Film:

  • Landman (“I’m really into it... classic Texas/energy/Silicon Valley culture clash.”) (78:12)

• Product Recommendation:

  • June Date app – matches people based on their ChatGPT chat histories (“shockingly good description of who I actually am”) (80:12)

• Newsletter:

  • Sam’s newsletter: no sign up page, but you can email him or use his bot at wlesin.com (81:37)

• Motto:

  • “Carthage must burn.” (82:33)

• Podcasting Lessons:

  • “Weirdly useful, even without growth strategies... it’s not huge, but the people we care about listen. We’d do it if no one listened.” (83:40)

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TL;DR – Sam’s Core Etiquette Philosophy (Summed Up, 69:06):

“The goal of all etiquette is essentially building trust and projecting 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.”
— Lenny Rachitsky, reading Sam’s TLDR

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Timestamps for Key Segments

• 00:00 – “No one's being honest in teaching founders this… Don’t smell like shit.” (Sam)
• 07:10 – The Kleiner Perkins party and ‘Energizer bunny’ warning
• 09:41 – Etiquette rules: introductions & entering a room
• 13:53 – Technique: what to do when you forget someone’s name
• 18:21 – Conversation: ask, but don’t interrogate; ping pong principle
• 24:03 – Subtle fragrance and hygiene tips
• 30:16 – Dress: fit over brand
• 34:49 – Dining: don’t order the most expensive; tip policy
• 44:54 – Humor: use carefully and self-deprecate
• 49:26 – Calendly and scheduling etiquette rant
• 56:51 – Emojis in business emails
• 64:04 – Video call backgrounds and real-world meeting tips
• 67:00 – Irish goodbyes and low-key exits
• 69:06 – Etiquette TLDR/philosophy
• 70:07 – AI Corner: lettermeme.com
• 71:25 – Contrarian Corner: the risky future of ‘AI companies’

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Closing Reflection

This episode is packed with candid, concrete advice (delivered with the right mix of humor and humility) on a topic that is often ignored—but potentially career-defining. Sam’s etiquette playbook isn’t about being fancy, but about codifying how to build trust and meaningful partnerships in a world that too often encourages founders to act like the rules don’t matter.

“If nothing else, remember: show up with a low heart rate, project self-confidence, and be generous. The rest will follow.”
— Sam Lessin (69:11)

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Find Sam at:

• Venture firm: Slow Ventures
• Twitter/Instagram: @lessin
• Email: [e-mail]
• More or Less podcast

Find Lenny at:

• lennyspodcast.com
• Newsletter

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End of Summary

Transcript

[Sam Lessin]

I just feel like no one's being honest in teaching founders this. Be early. Don't order the most expensive thing on the menu for a video call. Have an appropriate background. Don't smell like shit.

[Lenny Rachitsky]

Tell me why you decided to spend time teaching people proper etiquette.

[Sam Lessin]

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

[Lenny Rachitsky]

Etiquette is a skill for how to show up in a room with a low heart rate.

[Sam Lessin]

You're at the Kleiner Perkins holiday party. You have all the venture capitalists in the world and all the CEOs. You're at your first company, you're like, oh my God, this is my shot. But I need to convince this person of that and make this connection. It becomes very transactional. If you show up like a little Energizer bunny, you're going to scareboard off. You're going to project totally the wrong vibe.

[Lenny Rachitsky]

This isn't your one shot. You'll have other opportunities.

[Sam Lessin]

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.

[Lenny Rachitsky]

Today my guest is Sam Lesson, partner at Slow Ventures, previous VP of Product.

[Podcast Producer]

At Facebook and two time founder.

[Lenny Rachitsky]

This is an unconventional episode that may surprise you in how interesting and useful.

[Podcast Producer]

It is to your life. I asked Sam to come on the pod and talk about proper etiquette.

[Lenny Rachitsky]

You'll hear the backstory of how Sam got into this stuff, but this is turning into a big thing for him. He's teaching classes around the world.

[Podcast Producer]

He published a book on proper etiquette.

[Lenny Rachitsky]

And I love his framing for why etiquette matters. That the goal of learning good etiquette is to show up in a room.

[Podcast Producer]

With a low heart rate.

[Lenny Rachitsky]

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 video. Very unique episode. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube.

[Podcast Producer]

It helps tremendously.

[Lenny Rachitsky]

And if you become an annual subscriber.

[Podcast Producer]

Of my newsletter, you get a year.

[Lenny Rachitsky]

Free of 19 incredible products including a year free of Lovable replit, bold, gamma N8 and linear Devin, Post Hoc Superhuman, Descript, Whisper Flow, Perplexity Warp, Granola, Magic Pattern, Jerry, Castprd, Mobin and Stripe Atlas. Head on over to Lenny's newsletter.com and click product Pass. With that I bring you Sam Lesson After a short word from our sponsors.

[Podcast Producer]

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[Lenny Rachitsky]

Sam, thank you so much for being here and welcome to the Podcast blast.

[Sam Lessin]

To be here, I'm excited to have the conversation.

[Lenny Rachitsky]

This is going to be a very different kind of conversation. I suspect this is actually going to be really really useful and really really interesting. So a lot of people useful and interesting.

[Sam Lessin]

That's so unlikely.

[Lenny Rachitsky]

That's the Venn diagram that we that we Aim for. I also think it's going to just be a lot of fun. So I really appreciate you doing this. I want to give you the opportunity to set the stage for, for why we're chatting through this. Just tell me why you decided to spend time on teaching people proper etiquette and why should people pay attention to this? Why is this important?

[Sam Lessin]

I really enjoy things at the intersection of hilarious and useful. Right? You kind of need both right and hilarious just because you should have fun in life. We should be working on things that are fun and interesting. Also, candidly, if we're being more honest about it, like, it's very hard to cut through the noise these days. So kind of you need. Humor is a great way to cut through it. But humor just for the sake of being funny is not that useful. Like, there has to be a deeper truth to it. And so, you know, with this etiquette thing that we've gotten into, it started as many things to do with a tweet that got escalated into an event. It's gotten escalated into a book and a bunch of other stuff. I kind of believe that, you know, you should always. There you go, you got it with you. I've got my copy too. It's like there's a, there's a rule like, you know, you always want to just double down in life, right? And so I'd say, like, why etiquette? Look, there's a serious real narrative to like why etiquette matters in 2025 for founders, almost 2026. Like one, you know, we talk about software getting commoditized, we talk about all of this fear mongering and scared people feel about Silicon Valley and AI and like all the things that are going on the net is if you want to do business and you want to do business and build great partnerships with team members, you know, with companies you want to do business with almost with anyone. The reality is etiquette ironically matters a lot, right? There is a deep truth to this, right? You, especially when you're asking people to trust you with their data, trust you with their business, you know this. And when technology is no longer some cute sideshow, but it's like a major deal, like people are worried about losing their jobs, like understand how to meet people where they're at, build trust, you know, mirror kind of expected behaviors. These are all like tools, right? And so that's the deep truth, the shallow truth is it's kind of funny to teach Silicon Valley people etiquette, right? Like the whole narrative for so long has been, none of this matters. Just focus on your product saying, well, actually, it does matter. And you, you know, I'm wearing a T shirt. I'm not exactly known as the most high etiquette personal, but I do know the rules. Right. And I think, like, that's kind of. There's some. There's some. It's fun and funny as well. And I think those things are both important.

[Lenny Rachitsky]

I'm going to get into the actual rules. But just to follow that thread, you had a really great line somewhere that etiquette is almost a skill for how to show up in a room with a low heart rate.

[Sam Lessin]

Yeah. This is the thing about. Obviously, again, I think about again, you and I are now old people, right? But like, yes, you're young. I feel that you feel it in your bones. It's like, you're young, right? You're in. You're at the Kleiner Perkins holiday party. You have all the venture capitalists in the world and all the CEOs. You're at your first company. You're young. Maybe you're from a different country. You're like, oh, my God, like, this is my shot, right? Like, I have all these people I need to talk to and I need to convince this person of that and make this connection. It becomes very transactional. If you show up like a little Energizer bunny, right? You're gonna scare one off. Like, you're gonna project totally the wrong vibe. And I. But I can understand why you'd be like a high intensity moment in a lot of ways. I think understanding how to show up, take a beat, come in with a mindset not of scarcity, but of abundance. Understand how to give more than you take. Understand how to build a relationship, not collect business cards. Like, these are things that actually serve you massively well. And I just feel like no one's being honest in teaching founders this, right? Instead they're saying, oh, no, all that matters is your product. I'm like, like, the product does matter a lot. But if understanding these rules can be the difference between doing really well and missing a business deal, you know, if you show up with too high a heart rate and you burn a bunch of mild relationship opportunities, like, I don't know why you wouldn't want these skills. Right.

[Lenny Rachitsky]

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

[Sam Lessin]

Yeah, I think it's just an unnecessary. You're creating an unnecessary uphill battle for yourself. I'd also say that, look, this goes back to, like, technical differentiation where things are at. It is true that if you bring mana from heaven, right? Like, you invent something that is literally the next Google or whatever out of pure thought that sometimes none of this stuff matters. Right. Like, if you just. If you fully. That's it. You know, it's like, it's literally like that happens. It happens very, very rarely, but it does happen. It is not what 99.9% of startups are doing. But if you have that, yeah, you basically can get away with anything. It is true. That doesn't mean you should. You shouldn't be a jerk. And like, candidly, over the course of history, you need to work with great people and, like, you'll be more successful if you show up with good etiquette and rules and context. But, like, there are ways in which that can trump all. It's just like, candidly, not the experience of 99.9% of startups.

[Lenny Rachitsky]

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

[Sam Lessin]

Sure.

[Lenny Rachitsky]

And something I didn't mention. The reason I'm excited to do this, the reason I reached out to you to do this, this wasn't you, like, pitching me, hey, let's talk about this in your podcast, is I was like, wow, this is really interesting. I did not know these things.

[Sam Lessin]

Cheers. I mean, again, like, I think the thing for us is I'm kind of a ship early ship often guy. So v1. You should buy it now and study it because it's good and it's going to be like a limited edition. You know, there's a bunch of. The funny part about doing this is people come back with a bunch of other things we should cover. Right. So I. I suspect that eventually this will evolve beyond it. But I think the good. You know, we're starting with some good stuff.

[Lenny Rachitsky]

Let's do it. Okay, so introductions and entering a room.

[Sam Lessin]

Yeah. Be early. That's the first one. Right. Like, you know, again, I say this as someone who. I'll be honest, again, like, hypocrisy. You know, I. I live with hypocrisy. I'm frequently not early. Right, but you should be early. Right. And you don't need to be half an hour early. That's a little weird. But, you know, making sure that you have some buffer time. So that again, think about low heart rate. If you come in racing in the room, five minutes late, your heart rate's up. If you come in, you had a second to beat and take a beat in the waiting room, they kept you waiting, right? That's the dynamic I think you want to cultivate. Now. If you're not late, I'm sorry, if you're not early, just apologize. It doesn't need to be like a 511 flyer. Again, it goes 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, so I think that's kind of a. Another really kind of obvious one, but an important one, something I've seen. I'll go for a few others that we talk a bunch about in kind of it is, look, you want to have a strong handshake, firm, don't crush the person's hand. Again, this is not, you know, practice on your friends, right? You know, you want to repeat names back is a really, really valuable thing to think about. What you're meeting someone 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 going to be. So there's a bunch of things like that. I'm kind of curious. You know, we can go through a bunch more, but those are some of the ones I would think about.

[Lenny Rachitsky]

One that I loved was, if somebody else is late, do not make them feel bad.

[Sam Lessin]

Yeah.

[Lenny Rachitsky]

Do the opposite of what you're doing.

[Sam Lessin]

Of what you do, a hundred percent. 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, etc. 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, man. You're like, it's fine if you feel that way, but it's really not very productive to make a big deal out of it, right? Like, if this is a deal breaker for you that I was a few minutes late, then, like, I. Now I feel like I'm wasting the next 25 minutes of my meeting time because, like, I'm not, like, this is going to be the wrong dynamic, right? And so I just think there's like, don't, don't harp on it. It's okay.

[Lenny Rachitsky]

You know, you had also some advice on eye contact.

[Sam Lessin]

Share that one. It's really important. Again, I think the thing to keep in mind is, especially in an age where everyone's used to being in front of computer screens and looking at six different windows at the same time, again, people are taking their time to meet with you or at a party. They're, like, taking their time to, like, listen to you. And it's just a matter of respect to be like, I'm actually here in this conversation. I'm not off on my screen. I'm not like, glancing around the room. Now, look, there are some people, we all know this, who are, like, literally neuro. Quite neurodivergent. And that's very hard for them. Like, that happens. And a lot of founders have, like, neurodivergence in some ways. 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.

[Lenny Rachitsky]

Maybe a final tip there is around partners introducing the partner, saying hi to their partner. Share that. Yeah.

[Sam Lessin]

So, like, look, this happens all the time. And again, in the spirit of. I'm not perfect at this either. If you're with your partner, introduce them first. Right? 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 going to forget someone's name, right? And what you really should do is.

[Lenny Rachitsky]

All the time, all the time you're.

[Sam Lessin]

Going to find someone's name. And like, that's what you're supposed to do. The etiquette is you say, lenny, please meet my wife Jessica. You know, and like that's, you know, that's kind of thing. Now here's the thing. This is where you start bending rules. What if I don't remember your name, right? If you have your partner with you, you can flip it around and say, jessica, I want to introduce you. And then you kind of like can kind of figure out how to flame it up so that you then, lenny, extend your hand and say, it's really nice to meet you Jessica. And you get to pick up the name again, right? Or things like that. The way you put it there is.

[Lenny Rachitsky]

You let it hang.

[Sam Lessin]

That's you let it hang. Which by the way, I love it. It's a great example of that. Like, if you're really in tune socially, you kind of know what's going on, right? Like, you know what I mean? Like, you're not an idiot. Like, you know, oh, like what is proper what this person is doing. There's a gap between it, there's a reason. The reason is. But it's, it's at least enough plausible deniability of like semi bad etiquette that leverages the social situation to be a better etiquette, right? That it's, it's a useful thing to think about as a small cue. What.

[Lenny Rachitsky]

I am so bad at remembering names that like, I think I have a medical issue. Like 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, like and then let it hang.

[Sam Lessin]

Is that, is that Michelle I want to introduce you, right? Or something like that, you know, something like that. Or I want to introduce you to Michelle. You look at them in the eye, right? And then, and then your wife 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 it's 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. And like, oh my God, there's a resource I can study, right? Like, and this was like a very valuable social thing for me. So I'm with you. I have the same problem. I think a lot of people do.

[Lenny Rachitsky]

Okay, let's move on to conversations. Give us some tips.

[Sam Lessin]

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

[Lenny Rachitsky]

So the tip here, so it's basically index towards asking questions, but not like 100%.

[Sam Lessin]

Yeah, consider almost like, put it this way. Imagine you're playing ping pong, right? Or tennis or whatever you want. Like hit the ball back, right? That's the question, right? And they'll hit it back to you and then you hit it back to them, right? Like that's kind of what the flow should be. If you hit 10 balls at them in a row or like, you know what I mean? Or like, you know, that's kind of like not the vibe you want to go for. Yep.

[Lenny Rachitsky]

Awesome.

[Sam Lessin]

Look, we talk a lot about matching, matching vocabulary. You're going to meet a lot of different people. You know, you want to make people feel good and welcome. You know, I'm not saying that, you know, you should walk into a room and start talking in jibe. 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 words, like, again, the point is to meet people where they're at in a way that makes them feel relaxed and good. Not try to like mirror them, if that makes sense. But there is a subtlety that I think really matters to it.

[Lenny Rachitsky]

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.

[Sam Lessin]

Yes, this is important. I mean, I think in the end of the day, like most interactions, let's pretend you meet someone you're really interested in or whatever. If we're being transactional about it, what's the real goal? The real goal is to leave people in a position where they're like, wow, that was a really interesting person. I'd love to hear from them again. Or meet with them again. Or maybe even better, every once in a while this will happen. It's like, wow, that's a really interesting person or idea. The person walks across the room, hey, you really should talk to Lenny, shout to Sam. Like, that's kind of like you want to leave them being like, that's interesting. I like to continue this or expand it, not. I just heard this entire person's life story. I never need to talk to them again. Right. And so I do think there's, you know, again, like leave them wanting more. Right. I think is important. And that is partially about knowing when to excuse yourself gracefully as much as it is about when to enter.

[Lenny Rachitsky]

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.

[Sam Lessin]

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, I'll go so far to say that. Which is, look, we're used to, especially if you're young and these are big opportunities or big moments. People are kind of used to this like environment of scarcity. It like reminds me of the Eminem song when he talks about like a one shot, one opportunity.

[Lenny Rachitsky]

Oh, Eminem. Yeah, yeah.

[Sam Lessin]

It's a great song. It's a great song. Great beat. Every once in a while before a big presentation, you gotta listen to it and pump yourself up, right? But like, but actually again, in terms of putting people at ease and building relationships and etiquette, even if in your heart of hearts you're like, this really is my one shot, you kind of want to show up with the self confidence and the calm of abundance, right? Being like, this is not gonna be my only opportunity. This is an opportunity. I'm excited to be here. I'm engaged. Right? This is part of the story. This is not the entire story. And I think if you kind of remind yourself of that, you remind yourself that it's okay to not know everything. You keep focusing on low heart rate, engagement, eye contact, you get so much the way there.

[Lenny Rachitsky]

You also have a tip about how to handle famous people that you might meet.

[Sam Lessin]

I mean, there's so many ways. I mean, there's a bunch of tips about, I think, you know, generally famous people. But like, I think there's this thing which is like not being sycophantic is what I basically say. But also like you not being ridiculous is almost the way I would frame it in this conversation, right? Which the ridiculous is like, if you go up to Mark Zuckerberg and everyone knows what he looks like and who he is, and you're like, hi, I'm Sam and who are you? You're like, what are you doing? Like, it's like, ridiculous, right? On the other hand, going up and being like, you're the most important person I've ever met is wrong. Right? And so there's a way to. Again, it's about grace as much as anything else, right? And recognizing that there are people. And again, you're playing an iterative game and the best thing you can do is say, this is not my only. As much as it might actually be, this is not my only opportunity to meet Mark. And in an ideal world, when I walk away, I'm like, that was a pretty nice person. Like, maybe I want to talk to them again right now. Going up me like, I need your email address and phone number. It's like, no, let. Let him offer it. You know, like that. That type of stuff, I think matters.

[Lenny Rachitsky]

Maybe one last tip is that you actually start with this one of this line of great to see you when you meet someone versus, like, nice to see you.

[Sam Lessin]

Well, again, Lenny, you and I probably use this all the time, I bet, because I honestly, again, we go by name phase, 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. Hey, it's great to meet you, and you're like, we've met five times. It's like quite embarrassing, right? And for them, for you, for everyone. And so the more I, like, love. 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? Because. And I very clearly couldn't remember if we had met before. And we had, and she remembered. And so for me, this is an important one, right? To keep in mind.

[Lenny Rachitsky]

My wife is constantly making fun of me of saying, like, oh, like, not knowing if I've met someone before or not. She's like, how can you? Like, I don't. I don't know what to do with you. So that's a great one. So the line there is great to see you, because it works whether you meet them or not.

[Sam Lessin]

Yeah. And again, it's one of those things where. Here's the Thing. People aren't dumb. If you go around saying nice to see you to everyone, you're like, there's a small percentage chance this person doesn't remind me who I remember who I am. Right. And there are other ways or key. 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.

[Lenny Rachitsky]

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.

[Sam Lessin]

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.

[Lenny Rachitsky]

Right.

[Sam Lessin]

Or cologne or whatever it is. But like, you also shouldn't smell bad. Right. And like, it's. Again, your scent should not be noticeable is almost the way I would put it, you know, in any direction. It's. It's not. You're not. There's, there's. There's no advantage to that is basically what I would say.

[Lenny Rachitsky]

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?

[Sam Lessin]

So it's an interesting question. I think broadly in this book, the answer is broad. Broadly, yes. I will say that there is probably in January or February going to be a what we internally been calling the femme etiquette course. Because my wife and other women have said this is good, but there's a bunch of other stuff that women need to know. And so I, I can't speak to that yet. I think the frag was one. I would say I don't think you want your fragrance to be memorable for anyone, no matter what your gender is.

[Lenny Rachitsky]

Awesome. This is a 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.

[Sam Lessin]

Well, 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 4 or 6 is not like stopping them. Well, in life I'm like you, I can't be the etiquette guy if you guys are reading like. So I. I've been putting it and some of them has been really cute, others have been really funny. Like my 6 year old has started standing whenever my wife comes to the table, which is kind of arcane from an etiquette perspective. You can argue about whether it's actually even really etiquette anymore or not. But if you're being really formal when a woman comes 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.

[Lenny Rachitsky]

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 as like a modern way of thinking.

[Sam Lessin]

That might be better is what I would say. I will say the. It's a. 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.

[Lenny Rachitsky]

I was just speaking that. I was just listening to. Tyler Cohen had Alex Allison Gopnik on podcast and she studies kids and she. Her whole thing is how kids learn like scientists. And she has a whole thing about how they figure out how to use a fork by just like experimenting until something works.

[Sam Lessin]

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?

[Lenny Rachitsky]

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.

[Sam Lessin]

Yeah, so, I mean, before the book, we did. We did a class specifically initially for YC founders. Right, right. Partially because YC Gary Tang got very mad about this. So I'm like, well, now I have to do it. Right? Because that, that's very funny. But, but, but yeah, we basically, you know, we gave him 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 irreverent. Like we had some very fancy wilk spasher people come in with models and show talk about Dress at different types of events and things like that, which was kind of tongue in cheek, but. But a lot of fun. We also did, like, caviar and wine tasting type stuff. But then we also spent a lot of time focusing on, like, the actual meat of the matter, right? Which is things like how to show up with a low heart rate, how to have an abundance, mindset, you know, basic skills, like looking for the eye, shaking hands, you know, how to eat. Like that shows that you're being respectful, Things like that.

[Lenny Rachitsky]

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.

[Sam Lessin]

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

[Lenny Rachitsky]

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

[Sam Lessin]

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

[Lenny Rachitsky]

This actually, you're getting to the next category, which is dress, which I'm excited about.

[Sam Lessin]

Yeah, I mean, dress like, look, I gotta say again, in terms of know the rules, but don't always follow them. When I, my first job out of college, I was an associate at baiting company, right? This is like a consulting firm and there was like a business casual. And I kind of came up with the snarky realization that there was a minimum dress code, but there wasn't a maximum dress code. So I started in the office as somewhat of a mini rebellion in the consulting firm, what we call tuxedo Tuesdays, where all the associates would wear tuxedos to work, which then meant we didn't have to go to the client meetings because they would never take us to client meetings and tuxedos. So it was like, 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 care, look like you made some effort, but you don't, don't overdo. It is basically the upshot of the most simple way to dress. Unless, unless you're trying to very intentionally break a right, which maybe you are, but I think you should do that with a lot of cultural understanding, let's put it that way.

[Lenny Rachitsky]

So here's a couple tips that I love. So one is just dress one level up as a really simple tip.

[Sam Lessin]

It's an easy way to win. Not two, not three, but one.

[Lenny Rachitsky]

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. Sure, less formal 100%. And then you talk about fit of the item versus the brand 100%.

[Sam Lessin]

Like, like at the end of the day, fit is everything, right? I say this is again, you guys, all your listeners have to understand. Part of my joy at doing this is there is some level of hypocrisy in it, right? Because like, which is great. Like you got to have a little bit of that in your life in terms of how I myself behave sometimes. But look, in the end of the day, like a well fitting $20 shirt is way better than a 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 to like show up as a startup founder with a Rolex. Right. It's just not. Again, it goes back to heart rates, trying too hard. You know, you're not going to trick anyone. Right? Is the upshot, right?

[Lenny Rachitsky]

Yeah. This bit of our brand and just expensiveness of the item is such a big one that I think is. I think people don't realize, just like it could be a pretty cheap thing that if you get tailored in some small way, it just looks so much better, even if it's not the highest quality item.

[Sam Lessin]

100 Again, I would put put differently, think about the average person. Not every person in the world, but the average person in the world can look at a suit and be like, intuitively that seems like it fits the person or doesn't.

[Lenny Rachitsky]

Yeah.

[Sam Lessin]

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

[Lenny Rachitsky]

One other tip you have is if you're not sure the level of dress, just ask.

[Sam Lessin]

Yeah, this is a big thing in general, which is I think people are afraid to ask in all sorts of situations, you know, down to like, which forks should I use? You know? You know, or what's the expect? Like, it is absolutely fine to ask. In fact, if anything, it shows a level of confidence and calm and humility to ask if you don't know. Right. So I actually think this is a great example. There's absolutely nothing wrong with asking about dress, about etiquette, about expectations. You know, I don't. Again, it goes back to this whole give to get. If you get someone on the phone and you ask them a hundred questions about etiquette, at a certain point you're like, there's no that's not a pig game of ping pong. Like you're not. But like, it's totally fine to call. Be like, hey, like, what's, you know, what's this going to look like? And by the way, it's important because in New York versus San Francisco, there's different expectations. Like, people do do things differently. And like, your job, you're not expected to know every nuance of every culture you might enter.

[Lenny Rachitsky]

So maybe as a final question, in dress, do you have any just, I don't know, tips for dressing? Well, I know this is a big question that a professional spend time teaching and charging for.

[Sam Lessin]

I really, you know, I think the answer is find someone in your universe who you think dresses well and again, ask them for help and like, what makes sense. If that makes, you know, from that perspective, again, the well tailored, great, though. That makes a lot of sense. The, like, basics I can say, yeah, like, have jeans that are clean. Right. And, like, fit you, things like that. But again, when my wife listens to this podcast episode and hears me being asked about specifics of dress, she's gonna, she's gonna be chuckling.

[Lenny Rachitsky]

Great, that's a win. Okay, let's talk about dining. Give us some advice for etiquette during dining.

[Sam Lessin]

Tip well, right? Don't, don't not tip. Don't tip badly. You know, don't be super stingy about, you know, okay, who ordered the flambe? You know, like, split bills evenly, make things easy for waiters in general. It's. Don't order the most expensive thing on the menu. Does it really matter? Especially like an investor, do they really care? No, they don't really care, but they do notice. And you're like, ah, you're the type of person that, like, is truly insensitive to what things cost, even if it doesn't actually matter. Right? And 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 what. How long is this meal going to be? Like, there's a lot of times in dining situations you don't know. And the more you let someone else set the tone and then match that tone, the better. Like, you kind of want to go middle of the pack to last, if that makes sense. So this, this. Yeah.

[Lenny Rachitsky]

So this isn't the situation. If someone takes you out to dinner, like, it's a vc, another found, like someone invites you a partner or whatever.

[Sam Lessin]

Whatever it.

[Lenny Rachitsky]

Yeah.

[Sam Lessin]

And look, I, I think in terms of this, which I always think is important, is like, look, within reason, always offer to pay. Now, you should be turned down, right? If you go out with a vc, right? And you're like, you know, you put a card down 99% of the time, they 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. There aren't 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 aren't on the hook for it. But that is, I think, the. The polite thing and the polite way to approach it.

[Lenny Rachitsky]

What if they're just like a. Like a billionaire? I just had dinner with, like, a very successful VC and I did not feel like offering to pay made sense. Would you?

[Sam Lessin]

Still depends. 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. With dinner to really fancy people, right? Or like, someone who's like, you're. You know, there are two interesting dynamics. One is it's actually, I think, especially nice to offer and even sometimes pay, because the reality is, if you think about it, they obviously don't care about the money, but no one does that, right? Like, they're like, well, clearly you should pay. And so the more you're like, oh, no, I like. 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 with 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 going to tip, like, 100% of the bill. Right. Because, like, it's just, like, the right thing to do. And so I do think, like, if you're going to do that, you really have to tip well.

[Lenny Rachitsky]

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.

[Sam Lessin]

Tip a lot.

[Lenny Rachitsky]

Okay?

[Sam Lessin]

Just tip a lot. Like, I think 10, 20%'s the minimum. Like, if you're out in, like, a situation, you know, I think you kind of want to tip in my mind, to the level of no one you're effectively paying for would bat an eye that you're being stingy is the way I would think about it. 20% feels like the minimum. 30%. Sometimes, like, more seems a little bit silly, but it's not. It is a squirrely topic. And I just. I don't. Again, let me put it this way. I don't think you want your tip to be memorable is almost way to put it. Like, this is not a thing to focus on when you think. When the person that you're out to dinner with thinks back on their dinner, on the dinner a month later, they want to think about the content of the conversation or what the ideas were or the business opportunity. They want to think about, oh, my God, that guy tipped an incredible amount.

[Lenny Rachitsky]

What was that?

[Sam Lessin]

And by the way, I. I have stories in my own life where, like, I've been out with people and they've tipped, like, so much that, like, a decade later, I remember it and I'm like, it's fine. They can afford it. It's like, it's, like, cool that they did that for the server. But honestly, the only thing I remember for the night is how much the person tips.

[Lenny Rachitsky]

So you're okay. But I think if you're, like, extremely rich, you do it. Don't even tell anyone, basically. But feel free to do it, obviously.

[Sam Lessin]

Sure, yeah.

[Lenny Rachitsky]

I mean, you know what I mean?

[Sam Lessin]

The tip is not a point. The tip is, like, everyone should feel good about it, right? Like, and, like, again, there's about. It's about, again putting people in a sense of ease and comfort. And you might not like it, and it might not be fair in the world, but people are like, everyone's being taken care of. I can be relaxed about this. Is kind of what you're going for.

[Lenny Rachitsky]

I recommend your next book after this. Femic Fem. Fem Femicit Edition is a tipping guide.

[Sam Lessin]

A tipping guide. Well, you know what 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.

[Lenny Rachitsky]

I love Seinfeld. I don't remember.

[Sam Lessin]

There's a great tipping. It's a great tipping episode. I feel like you could honestly like have a very funny like modern LLM app that is only about tipping. Like imagine like a tipping app where it's like, it's like instead of a tipping calculator, you take a picture of the bill. It geolocates where you are. You kind of give it. You're like, this is the situation. And it's like it just tells you what's a tip.

[Lenny Rachitsky]

Well, like the tip. Like a restaurant's one thing, but then it's like the garbage person. A gardener. The especially.

[Sam Lessin]

Especially this end of year. Like what at the end of year? Like I, I think no one knows how to tip anymore.

[Lenny Rachitsky]

I soak it like. Yeah. Some guy that like installs the shades in our house. Do I, do you?

[Sam Lessin]

I don't think you tip that person. I actually. Do you tip that person?

[Lenny Rachitsky]

No, I, I did not. Because that. Just because I already paid a bunch of money for this thing.

[Sam Lessin]

Yeah, no, I feel like that is weird. I wouldn't tip people like that.

[Lenny Rachitsky]

That's, that's why we need this book. This is. You're going to make. It's going to be a huge hit.

[Sam Lessin]

Why we could fund it. You want to fund it with me? We should fund an app, talk about Y 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 the all the things and it's like this is how much to tip. That is hilarious.

[Lenny Rachitsky]

And probably quite useful and probably not venture scale, but I don't care. I.

[Sam Lessin]

You know what 2026 it might be. You know, everyone has the problem. Everyone globally has the same problem, which is tipping.

[Lenny Rachitsky]

Yeah. Just the tokens cost of that.

[Sam Lessin]

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.

[Lenny Rachitsky]

Yes.

[Sam Lessin]

Do you remember about that? What's up? Bristomatics, Mathics. So basically the Idea is that after the Improbability Drive, the way they're able to move across the unit very quickly is the most complicated math in the universe, which is the math of your bill at a restaurant. So I think we're on to something. It's in science fiction.

[Lenny Rachitsky]

Oh, man. One other tip that I just thought of as around dining is you had this tip about Somalia is give them a sip of your wine if you order something. Yeah.

[Sam Lessin]

If you. If you order something nice, I'll be on. Be very clear again, in terms of I don't order a very nice wine.

[Lenny Rachitsky]

Yeah.

[Sam Lessin]

No sommelier really cares what I'm drinking. But if you are doing that or you're into it, which is great. Again, like, think about being generous, right? If they're like, oh, I would love to taste that. Like, taste. It's great.

[Lenny Rachitsky]

I love that. I would love to do that. That sounds really nice. Yeah. Okay. And one other tip here. I wrote down B for bread, D for drinks. Tell. Explain.

[Sam Lessin]

Oh, bd. You just gotta look at your hands, right? D's and D's for. Which was your bread plate. Right? Is a kind of the way to think about it. And look, people get this wrong all the time. You sit down at a big table, right? And you're like, ah, which is mine. You're kind of waiting for someone to pick it up and kind of do the math. I'm like, okay, that's my bread. But that's the B. And D is useful also. Like, look, forks and knives, like, just knowing what side they go on. Knowing one thing, I always drives 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 play goes in because, you know, like, you don't want to, like, stab your partner next to you. But, like, it was really funny. I had an entrepreneur. This is not yet a product that people started sending me videos of them, like, dining or situations and asked for feedback. Right? And I recently had to give feedback to an entrepreneur who was like, you did a very nice job eating your soup. Good job. Your napkin should have been in your lap. And your knife is pointed the wrong way.

[Lenny Rachitsky]

Okay. Napkin, actually. Okay, so napkin and lap.

[Sam Lessin]

Napkin and lap. Not in your neck, not off to the side. You know, napkin and lap.

[Lenny Rachitsky]

I saw someone once had a napkin on just one leg versus both legs. Any opinion there?

[Sam Lessin]

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.

[Lenny Rachitsky]

It's like the Kindle. You don't want to think about the technology.

[Sam Lessin]

No. You just let the conversation flow.

[Lenny Rachitsky]

Yeah. Okay. Amazing. Okay. Speaking of conversation, small talk and humor, give us some tips.

[Sam Lessin]

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, to the audience. So, like, in the. The room you're in dirty jokes, right? You tell a dirty. You don't want to tell a dirty joke in the wrong room. You. But I think the thing to think about humor is it kind of. There's this interesting subtlety to why it's so useful in social settings, which is one. It kind of shows the ultimate mastery of a social situation if you're able to tell a joke which is right up to the line or even pushes it one degree to show your own comfort in the space. Right. It's the ultimate demonstration of comfort in a space is to tell a joke that's a little over the line or a little off color, but not too off color. It's like the ultimate thing. So if you're really in it and like, feeling good, using humor is great. Should not be remembered as only the comedian. And again, like, the level of jokes that you're playing with is like a very subtle thing, right? So you don't want to tell a knock knock joke, right. When, like with adults. Right. But the off color sex joke, that is hilarious. You, you, you gotta be pretty confident before you tell it. Right? In space. The last thing you want, like, a thing that. A joke that everyone laughs at is great. A joke that no one laughs at is a huge. It's like a huge risk maneuver. You failed. Right. And, like, it's not the point. So it's a great tool. I love it. Like, I think everyone should have their file of jokes. I do. I don't know about you. Like, I have like a Evernote. It's not Evernote anymore. It's like a bear of, like, my favorite jokes. And I. They're loosely ranked and from least offensive to most offensive because, like, I forget the jokes. But, like, you know, you kind of want to use humor sparingly and smartly.

[Lenny Rachitsky]

This was your next book. This list of jokes.

[Sam Lessin]

List of jokes ranked by, like, social situation and, like, level of extremeness.

[Lenny Rachitsky]

Everyone's gonna be telling you same jokes. Oh, man.

[Sam Lessin]

Well, there's a There is a funny joke about that, right? Which is the whole the prisoners. I won't even tell it. It's a funny. There's a funny joke about people who know all the jokes. I'll leave that. I'll leave you hanging and wanting more for our next podcast conversation Abundance.

[Lenny Rachitsky]

Okay. You also recommend self deprecating as a.

[Sam Lessin]

Make fun of yourself, not other people.

[Lenny Rachitsky]

Yeah, I mean that's.

[Sam Lessin]

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 or people aren't on the same wavelength, it's a very high risk maneuver. Making fun of yourself is always fine.

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[Lenny Rachitsky]

So you said you had this kind of list of jokes that you. Because I. I can't remember. I have zero jokes in my head that I'm like okay, here, I'm going to get one. So I should make a list.

[Sam Lessin]

Make a list. I. I got some good ones for you.

[Lenny Rachitsky]

Okay. I'll have to borrow some. You also recommend having some stories some crowd please read kind of stories to tell.

[Sam Lessin]

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

[Lenny Rachitsky]

Your last tip in that section was how to wind down a conversation. Just the importance of realizing it's time to wind down. Any tips for how to do that?

[Sam Lessin]

Yeah, just like when the conversation is over gracefully leave the upshot, you know, people, the worst is like the conversation ends and the person just stands there and you're like, I'm going to go get a drink, you know, or do you want it? And then once in a while the person will be like. You're like, if someone says to you in a conversation to wind it down, it's like, I'm going to go grab a drink. Most of the time that is not an invitation saying, I'd love one too, and follow them to the bar, right? Like that. That is not so, Like, I just think you have to kind of recognize the signs effectively when the moment is passing or it's time to move on, et cetera, and then like, respect it.

[Lenny Rachitsky]

That's what I would say. I use that one all the time. Is there, is there any other ways you find useful to wind down a conversation? Just get out of a conversation.

[Sam Lessin]

Well, I think, I think the other thing people do frequently, which again is totally fine, respectfully, is bring someone else into the conversation, right? Like in some ways, like, give them their next partner, you know, like, oh, like, I've enjoyed this conversation. It's super cool, you know? 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. Okay, I'm gonna go say hi to my wife. You know, like, there's ways to handle it. Again, like, the key though is subtlety on these things, right? Like, I think in all things, like, you want to basically let people feel respected as much as anything else. So if you, if you're too overt about it, right, you don't give them. Even if everyone kind of knows what's going on. The key is to give them like plausible deniability to themselves in the community. Effectively. That like we've wound down this conversation means you have to kind of look for the signs.

[Lenny Rachitsky]

Awesome. Okay, there's four more sections. The next one is scheduling etiquette. Give us some advice.

[Sam Lessin]

Oh, well, like, I think I'd like to say that I'm fairly famous for hating calendly. There is a. I actually I. I think I am not overstating it when saying there was a period where calendar where I personally had driven most of their growth for the month. I got messages from the board because I went on this diatribe about how much I hate Cali and how disrespectful it is. And apparently this was such an Internet fervor, I got like millions of engagements that it meaningfully drove their month.

[Lenny Rachitsky]

So I thank them for it.

[Sam Lessin]

No.

[Lenny Rachitsky]

No bad press.

[Sam Lessin]

No bad press. No bad tweets. Yeah. So I think like, look, there's a few obvious ones when you're. 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 going to use a scheduling agent or something. It just needs to actually have real options. Is basically. I think that comes up all the time. Look, rescheduling happens when you do it. Give notice as much as possible. Once you are asking for rescheduling, you need to be even more accepting of what the other person can do. Right. I think is really important. Like if you're asking to reschedule, you basically within reason need to make it work for them. Right. Is what I would say. And then, look, I think 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, especially at like reasonable times, like sometimes people like, I want to 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, which you make in the book, is like, you really need to respect EAs and PAs and the whole. People. Like, this is the, the number one look. Way to look extremely classless is to not respect people who are helping the other person. Right? Like, this is like the number one thing. Now, you don't need to be so over the top exuberant. Like you don't want to overdo it, but there should be this deep well of like, respect for anyone who's helping you, whether that's a server or a PA or an EA or whatever. This needs to come with an extra gesture of respect. That means saying thank you when they schedule and like following up with them and things like that.

[Lenny Rachitsky]

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

[Sam Lessin]

It helps the general story of, like, make the gatekeepers happy and like you is true. But I, I do think there are ways to overdo that. For what it's worth. It becomes almost too transactional if you show up with flowers for the ea. You know, like, you better be damn confident, like, in what you're doing, if that makes sense. But yeah, just like the small things go a long way. Like, you just, you know, make eye contact with them, thank them, respect them. You know, ask, you know, if, if they bring you a coffee cup, ask them where to put it when you're done. Like, don't treat people who you might who feel like the team or the staff feel that way. Make them feel like part of the team at equals.

[Lenny Rachitsky]

The calendly stuff, I feel like that's its own separate book of calendar etiquette.

[Sam Lessin]

Yeah, the calendly look. Calendly is one of my favorite, my favorite episodes of going hyperviral on something hilarious.

[Lenny Rachitsky]

So One thing that Cal 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 look.

[Sam Lessin]

I'll be honest. I go the other way. Like, I. 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 won't say Donald Trump. Someone wants to meet with me, and it's like, four in the morning, my time, right? Or, like, I'm totally putting. You know what, I'm gonna make it work, right? And, like, so I do think, like, I'm actually kind of against the, like, flat hierarchy. All meetings are the same. Da, da, da. That does mean. Honestly, I think that you probably knock me is like, my bet is that my calendar moves more than most people's. And I'm sure that feels disrespectful to some. And it is. Like, I want to be really clear, but it's also the reality of trying to balance these things.

[Lenny Rachitsky]

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.

[Sam Lessin]

I'm like, the funny one I've had is there are people whose names are very similar to other people I know. And every once in a while, I've ended up, like, accepting a cold meeting and showing up 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.

[Lenny Rachitsky]

Oh, man. Okay. Well, one last question. With calendly, something I try to do, I'm curious to get your take is like, okay, someone went like a founder. I'm meeting with a founder. And the way I approach it is like, okay, do you have a calendly or. 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.

[Sam Lessin]

And that's perfectly fine. Right. In terms of the way to do it, I just think the key is to make it easy for the person you're trying to do business with. Right?

[Lenny Rachitsky]

And not make.

[Sam Lessin]

Yeah.

[Lenny Rachitsky]

And not make them feel like they have to do the work if they don't want to.

[Sam Lessin]

No, you do the work. Like basically you're asking for something. You do the work is a shot.

[Lenny Rachitsky]

Okay, sweet. Moving on to the next topic, communication.

[Sam Lessin]

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 is I feel like from an etiquette perspective, like I don't owe you a 12 page essay, but I do owe at least an acknowledgement quickly, right. Of what you've sent. Like, you don't want to leave people hanging. But again, I don't. I 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 going to find time? Like, this is like, you're asking a lot. It's kind of like a monologue in a conversation. You've just said, I'm going to spend 10 minutes talking at you. Right. And so I do think, keeping it short and to the point, you know, not being silly, not using emoji, trying to make it readable. Like, these are all.

[Lenny Rachitsky]

Say more about the emoji piece. Like, is your advice just no emojis if it's a business.

[Sam Lessin]

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?

[Lenny Rachitsky]

Awesome. Okay. I do use emojis. I use like the thank you hands one a lot.

[Sam Lessin]

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

[Lenny Rachitsky]

An emoji sometimes kind of implies use AI to generate this thing. Because ChatGPT loves emojis.

[Sam Lessin]

Totally. And also, like, look, I mean, there's a whole. We want to get. You want to get spicy for a second?

[Lenny Rachitsky]

Yes.

[Sam Lessin]

I don't know how I feel about people who have, like, invested too much in their emojis. Right. So you get people who have, like, changed the colors of their emojis from the default or whatever. I'm not saying not to do it. I'm just saying it's quite a statement. Is my view that you've invested in your emoji pack or like using special emojis people haven't seen before? Or like, it's like, again, it's a subtlety and you got to understand the room and like the culture and like, what you're responding to. But I, I do think that people read more into that than people want to be read into it.

[Lenny Rachitsky]

You know, it's crazy now, I don't know if you've seen this. You can like create your own emojis now in iOS and emojis or so it's like a whole new world. Just.

[Sam Lessin]

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.

[Lenny Rachitsky]

They should be finding product market fit.

[Sam Lessin]

Yeah. Or learning etiquette.

[Lenny Rachitsky]

The other tip you had that I love, which is think about the order of the emails when you're emailing somebody.

[Sam Lessin]

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

[Lenny Rachitsky]

And because the implication there is you, who you think is most important comes first, like who's first to put.

[Sam Lessin]

Who are you really sending this to? You know what I mean? Is almost the way I think and like, who's kind of included. So like if I look at an email and I'm the first person in the two, right. Candidly, I, I mildly pay more attention to it than when I'm the fifth, right? Because in my head I'm like, okay, well like, this is really to Kevin. And like, I'm on it. Like, if you see an email sent to many, many, many people, almost by definition it's not that important, right? Is almost the way I would put it. And so you have to be really careful with manager 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 subtlety 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 5th CC on an email, you're not expected to be the first response. Again, you can break this rule. Like there are times to break it. There's a subtlety to it, but it wasn't really sent to you, right? Like, and so there is 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.

[Lenny Rachitsky]

So true, 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.

[Sam Lessin]

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? Because what we're basically saying is like, these are unknown things, but intuitively you should just know them. And that is actually what you're signaling is like, you can trust me because intuitively there's this well of knowledge and cultural connection and whatever that we can, we can share effectively.

[Lenny Rachitsky]

And if you're bcc, definitely do not reply all.

[Sam Lessin]

Yeah, I mean, I. I have some unbelievably funny faux pas from my history with ccbcc. 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 proofreading thing. Proofread, proofread. And don't send emails to people about them that they're not supposed to see.

[Lenny Rachitsky]

And it's like Gmail makes it too easy to do that because it adds them automatically if you, like, talk.

[Sam Lessin]

If you add their name. No, for me, it was more just like the way to check the spelling of someone's name is not to put them in the two field ever.

[Lenny Rachitsky]

Yeah. Okay.

[Sam Lessin]

Oh, man.

[Lenny Rachitsky]

Well, you're still kicking so bad.

[Sam Lessin]

I'm still kicking.

[Lenny Rachitsky]

Okay, two more meeting etiquette.

[Sam Lessin]

Yeah. I mean, again, we've talked about arriving a little bit early. You should do that. Don't arrive up too, too early. Like, you shouldn't. Again, like, if you're an hour early, walk around the block. It's fine to walk around the block. You don't want to sit in someone's office because then all of a sudden it feels like this person has been here a long time. Like, this feels. Feels like even though they're not scheduled, like we're leaving them hanging. You're six coffees deep with the receptionist. Like, you don't want that. Right? Like, so I think you want to be like 10 to 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 was your weekend? Or like something that kind of cuts. Cuts the air a little bit and then you kind of flip into business is like a good thing, even though it, like feels transparent, is still useful. Right? Is what I would say to kind of like. And again, it's. It's almost a signal of like, I am here for business, but I am like a normal person. And like, I'm willing to have like a nor. You're like signaling like, oh, I know that we should start with a normal conversation, if that makes sense. Right.

[Lenny Rachitsky]

I don't know if you saw this on Twitter. Someone described small talk as like the TCPIP act handshake.

[Sam Lessin]

I love it. It's a great description. I would always. I always describe it as like, imagine the modem crash from when we were kids on a 42 4, you know, like that old modem crash. Like, that's. That's what small talk is. It's a modem crash. We're trying to hit the wavelengths, you know, et cetera.

[Lenny Rachitsky]

Is like, so that you're ready to talk, so that you really communicate.

[Sam Lessin]

Yeah. For meetings, virtual ones, camera on, like, and again, I say this as someone who sometimes violates this, right? I violate it knowingly. I violate it knowing what it costs me. But 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, 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. That type of stuff I think goes further than people realize.

[Lenny Rachitsky]

Awesome. One other tip you had was clean up after yourself. If you're in a real meeting, this.

[Sam Lessin]

Is actually the easiest way. And this is, by the way, is for my partner, Kevin Collard. But the easiest way to come off badly is to not offer to put your coffee cup in the kitchen, right? And like, honestly, we do this like we. Because like, if you think about it, we work for LPs limited partners, right? Like, that's who we raise money from and then deployed from. And my partner Kevin, even more than me, has this thing which is, he is maniacal about this, which is no matter who's in the room, if we're with an lp, you take the coffee, you take the Diet Coke. Even if you know full well someone's going to come in and clean up after you. And you make a point of asking where we can put it or putting on the side table, et cetera, and acknowledging that there is a mess.

[Lenny Rachitsky]

I feel that final topic is exiting and leaving. What are some tips?

[Sam Lessin]

You should stand when people leave the table, right? Not ridiculously, by the way. You should go stand with 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 they shouldn't be long. They shouldn't be ridiculous. But like, we met, I got something out of it. Like, thank you for taking your time is like always appreciated is what I would say. Obviously there's stuff like don't take calls, et cetera. Like, this is kind of like the kind of obvious stuff in terms of exiting and how you think about it. Like even if someone, if someone rings you, right, and you're like, and the meeting's over and you're over time, you're like, I got to pick up this call. You hit the button, says I'm calling you right back and then walk away. Don't just pick up the phone and like wave, you know, is what I would say. Yeah, and I, I think like, there's stuff like that that I would just keep in mind.

[Lenny Rachitsky]

They also had like, don't make a production of your exiting, just like, just.

[Sam Lessin]

Yeah, yeah. I mean, again, I don't like, you know. Yes, I think that's really true. It's. I mean, there, 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 thank one person on the way out of the host, right? But like, you know, the, the I am leaving now, right? Like, let me kind of say goodbye to everyone and hug everyone. It's too much. It's too much. I love that.

[Lenny Rachitsky]

Okay, we got through everything. Is there anything else that you think might be important?

[Sam Lessin]

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. Because, like, there'll be a second version of the book and then a third. And like, I actually really want to, like, cite the people who contribute to it. Like, the book is what, like 50, 60 pages? It will be a few hundred eventually. And I think there's a lot more to come. And we're going to be doing classes next year all over the country and actually world we'll be, we got, we invited to do, we're going to do one in Tel Aviv. We're going to do one, we're certainly doing one in New York and a few other places. And, you know, it'll be fun.

[Lenny Rachitsky]

This is, oh my God, you got a whole new life forming here.

[Sam Lessin]

I, I, you know, the funny thing is this stuff, the etiquette story is obviously pretty fun. And so, like, people like Morning Brew just like, keep making videos about this. And like, there's this whole etiquette thing going on. And I'm like, oh my God, I've done some pretty good investments in my life, built some cool products. Am I going to be ultimately remembered as like the etiquette guy? That's kind of hilarious.

[Lenny Rachitsky]

That's what we're doing here.

[Sam Lessin]

I'm into it. I'm fine with that.

[Lenny Rachitsky]

So I'll read, you have the TLDR at the beginning. I'll just read this real quick and add anything that we're missing. So this is just like what to do if you do nothing else. Remember, the goal of all etiquette is essentially building trust and project genuine confidence. Always maintain an abundance mindset. Remember that you are worthy and have nothing to prove and that it's okay to ask questions and keep your heart rate low.

[Sam Lessin]

That's the point. If nothing else, if you remember those points, you will be served well.

[Lenny Rachitsky]

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.

[Sam Lessin]

Lay it on me. I love Contrarian Corner. An AI Corner. Depends what you mean by that.

[Lenny Rachitsky]

So the question in AI Corner is just, what's one way you found AI useful in your work or life that might be helpful for people to hear?

[Sam Lessin]

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

[Lenny Rachitsky]

Except Lenny's newsletter, but keep going.

[Sam Lessin]

And what. Except Lenny's newsletter? Sure. Of course, that one I don't put in the aggregator, although of course I don't do that. But it's great. So I'm super into into it.

[Lenny Rachitsky]

And that's lettermeme.com. check it out.

[Sam Lessin]

Lettermeme.

[Lenny Rachitsky]

I love this. So this is AI generated, aggregates all the important newsletters and creates a little summary and a cartoon.

[Sam Lessin]

Yeah. And you can make your own. So, like, for me, I actually. I'm looking at this now. There's actually one thing that got messed up on this. We need to change. But the, yeah, the, the. The idea is you basically get an email digest once a day and it's continuously updated to, like, what's going on in the world. And you pipe your own newsletters into it. So it's like whatever. You actually trust and pay attention to genius.

[Lenny Rachitsky]

And how did you build this? Was the vibe coded? Did you have an engineer help you?

[Sam Lessin]

Well, both actually, like, I actually. The vibe coding thing, this is exactly what vibe coding is good for, is like, this is like, you know, cursor and digital ocean and cloudflare will get you a long way in terms of just like building this stuff on the fly. And so I built the first version of this myself, end to end. But then vibe coding also doesn't really scale. And so the reality is after, at 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.

[Lenny Rachitsky]

Well, let's go to Contrarian Corner. This could be an entire podcast conversation with you, I suspect. But just like, what's something you want to share that you believe that most other people don't believe?

[Sam Lessin]

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 would be insane. Like, of course we're going to use these tools, but there's a difference between a great business that you're using AI to supercharge or make better or just as a piece of infrastructure. That's not an AI business. This is a business. Right? And I'm very into those versus, like all of these companies that come out, whether that say we are the AI blank. I just, I think they're all going to zero even. You know, my, my kind of argument is from a seed perspective is like, look, is OpenAI a good investment or not? It's a terrible seed investment, right? The way the numbers baked out, even at a $500 billion market cap, when all is said and done, the seed investors have made something like 25 times their money. That's insane, right? If you think about it like, that's basically the worst. It's like a middling at best seed investment for like the company that is defining the moment. And the reason is because these things are so capital consumptive. So if you're trying to employ a hundred billion dollars, 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. You know what if the storytelling of Elon Musk allows SpaceX, which, by the way, I love, I think SpaceX is an awesome company. But if all of a sudden that actually can be worth $1.4 trillion to the public market. Guess what? The money powers are 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. Because even if you look smart for the moment, you're playing a dangerous game of get out before the narrative collapses.

[Lenny Rachitsky]

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 so many reasons.

[Sam Lessin]

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 or value is on any of these things. Right. And so it's just like the whole dynamic is off. And the thing is people are desperate right now for things to believe in. Like if you think about the history, you know, we've done so well as a country with Terra Nova, like the US was amazing for so many years because we had the west and if you were going to work hard, you would like go west and you'd do great. And like there was all this opportunity, land of opportunity we've had reverberated like, you know, my generation, your generation, we were blessed because we had the Internet. The Internet was digital Terra Nova and like we got to build fortunes and do amazing stuff and new work, be in this like new world that was created. But it was effectively the same thing as the west all over again. Right. And ever since then, whether it's mobile, which again, if you look at the math on it, everyone wants it to be disruptive. And terranova, 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.

[Lenny Rachitsky]

So what is it you look for? Do you. Yeah, what do you look for when you're investing in AI startup?

[Sam Lessin]

Well, again, I won't invest in things that I would consider an AI startup. I'll invest in things that use AI. Right. For me, I think I'm really interested in the cultural implications of AI or the new businesses that need to exist because it is a force 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 Conf test from great Blade Runner, which was the test they basically ran to the are you a real or are you a bot? Right. Like, that's a huge problem.

[Lenny Rachitsky]

Turtle on their back.

[Sam Lessin]

Yeah. There's a whole, like, set of companies that are, like, implications of AI. And how do you manage it and handle it as a society? There's a lot to do there. I use a lot to do in cultural shifts from AI. Right. You know, there's all sorts of interesting trends to follow there. Like, there's. There's all sorts of businesses that will be disrupted. They're like non AI businesses. They're businesses that'll be disrupted in interesting ways. So I think there's a lot of opportunity. But again, I think there's a. I at least draw a distinction between if you're trying to be. I mean, certainly a foundation model company. But like, any of these things that are like, we're going to win because AI, I'm like, yeah, you're going to win because of something else. Right. And AI is going to be a propellant to it.

[Lenny Rachitsky]

Sam, you're a fascinating human. I feel like we could talk for hours. Is there anything before we get to our very exciting lightning round? Anything else you wanted to.

[Sam Lessin]

Look, I'm happy to be here. Like, I love your work. It's good to be on your podcast. Happy to bullshit whenever. No, we're good.

[Lenny Rachitsky]

Okay. Well, with that, we've reached a very exciting lightning round. I've got five questions for you.

[Sam Lessin]

Five questions. I'm ready.

[Lenny Rachitsky]

Five questions.

[Podcast Producer]

What are two or three books that.

[Lenny Rachitsky]

You find yourself recommending most to other people?

[Sam Lessin]

Ooh, okay, so let me pull up my list, because I got to pull up my Kindle for this one is I'm reading right now. I gotta admit, I like to make fun of Marc Andreessen a lot, but he recommended a book called the Ancient City, which is fascinating. And so I'm in the middle of that right now. I'm really enjoying it. Man's search for meaning is great. I'm just going through. What have I read recently? You know, it's great. Area 51, an uncensored history. 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.

[Lenny Rachitsky]

I did that one on Audible and it's. You just listen to it all like, not like in a.

[Sam Lessin]

It's a short read, it's not a long book. I honestly think for me, hours of investment to intellectual return. My one real answer right now would be that I could give you a thousand others from. I, you know, there are things like the Banana King. Have you heard this one? Have you seen this one? Oh my God, this is so good. What's it called? It's the Fish that Ate the Whale. Incredible book. So is the Last Kings of Shanghai, if you know that one. Like, these are all like amazing books, but they're longer and there are more stories. Just everyone on the podcast should go read Will Durant. Okay.

[Lenny Rachitsky]

I love it. Favorite recent movie or TV show that you've really enjoyed.

[Sam Lessin]

Oh, I gotta say, I mean, recent. I think Landman is fabulous. Have you watched Landman?

[Lenny Rachitsky]

Yeah, yeah, I think it's great.

[Sam Lessin]

I. I'm like really into it. That would be my most recent take.

[Lenny Rachitsky]

What's interesting about that show is now tech companies are all super into energy. And you know, I talked to it.

[Sam Lessin]

I talked to. Well, I'll tell you a funny story, which is 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 Silicon Valley people and now think they understand the energy industry because they watched Landman. He's like. So there's all. He's like. I'm like, it's like wild. But I totally believe it because I know too many venture capitalists. Like, oh, I now understand this because I watch Landman and he's like, this is totally a thing.

[Lenny Rachitsky]

Yeah, I would feel that. Okay, favorite product that you recently discovered that you love could be like a gadget, could be an app, could be clothing.

[Sam Lessin]

Okay, 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. Okay. I actually don't use this product because I'm happily married, but this is cool. And here's the basic idea is if you think about so much of AI right now, this goes back to, like, what businesses do you overhaul that are interesting, that have AI implications, but are not AI? So everyone's got this, like, old virtual girlfriend loneliness. You're going to chat with your friend, da, da, da. Like, whatever, Fine. These guys came out and what they do is they're like, look, if we're really trying to match up humans, like, call it Tinder 2.0, one of the best sources of information to do that is their ChatGPT histories. So this app is kind of built around the premise of distilling. You ask ChatGPT a structured prompt that they've designed. It pulls out an unbelievably good profile of who you are, and. And then you basically match with people based on, like, what you're actually asking ChatGPT about and the implications of who you are? And the fun part is I haven't obviously done dates on it. Not for me, but I have pulled my profile from, like, wow, this is, like, shockingly good description of who I actually am. And so I think that's, like, a really fun business.

[Lenny Rachitsky]

That's. It's like that prompt that the ChatGPT folks once had of just like, draw, visualize my space based on everything you know about me. And it was like, holy moly. You know, a lot.

[Sam Lessin]

It's pretty good.

[Lenny Rachitsky]

And so. So in this dating app, I love this idea. That's so good. So do people read that? Are they able to see that as your profile or, you know, it's.

[Sam Lessin]

It's a little abstracted from that and, like, but it's like the matching and the core thing is, like, based on it. And it's like, again, I'm like. I was like, wow, like, this is good.

[Lenny Rachitsky]

Like, and it goes on dates for you. Okay, so it's like, it simulates what the date might be like between you.

[Sam Lessin]

Two, potentially, I guess.

[Lenny Rachitsky]

I mean, yeah, your AI goes on dates for you, receives one high match, each one carefully sight. Wow. So fun.

[Sam Lessin]

It's good. I get if you're single. I tried with my newsletter at one point. I was like, oh, you know, honestly, the people who read my newsletter are pretty weird and specific. And so, hey, why don't I just, like, offer a matchmaking service where I'm like, okay, if you read my newsletter, really, you're here. Tell me who you are. I will, like, build a little LLM and try to match these people didn't work for me because candidly, you know what happened? Way too many qualified women and not enough men. I just don't know the liquidity, like, I have hundred great women who wrote in me like, hey, this is what I'm looking for. This who I am. You're like, you were an amazing person. And then like the four guys you write in are like, I want a 25 year old hot girlfriend. You're like, ah, this is not going to work. But June day might have the liquidity to make it work.

[Lenny Rachitsky]

By the way, your newsletter is awesome. Tell people where to find it.

[Sam Lessin]

While we're on that topic, you actually can't. Like I just kind of like there's no way to sign up for it. If you send me an email perfect. If you send me an email lesson at Gmail, I'm fine. Like then I. You get. If I respond, you get automatically added. I basically just like that's how I like people I'm interacting with. Get added or I'll just add you. But I. It's actually funny. There's not. I. Oh well, you know you can do actually that will get you on it is if you go to wleson.com l e s w l e s I n.com I have my little like bot app up 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.

[Lenny Rachitsky]

I love, I love this contrarian growth strategy. Now, now you can't really sign up. Okay, that's great. Okay. Two more questions. Do you have a favorite life motto that you find yourself coming back to often in work or in life?

[Sam Lessin]

No, but I will say that I have hanging in my gym which I love from the Facebook hackathon. After the launch of Google, this is going way back in history. They made great posters which was Carthage must Burn. And it was just like this great moment in work time when it was like okay, game on, like Google's coming for us. Like let's. And I had some of the most fun work experiences. We were working literally 24 hours a day, like past midnight. Every night was in that period. And I love that poster. So Carthage must burn. How about that?

[Lenny Rachitsky]

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 the mores.

[Sam Lessin]

We love our lesson. We also like my wife and I are contrarians and hate everything by default. And the Morins like think everything's amazing. So it kind of works from a dynamic perspective.

[Lenny Rachitsky]

I'd Love it. It's Dave Morin, Brit Morin, just to be clear. And your wife, she runs the information.

[Sam Lessin]

So she's good at prompting us with. It's actually going on the world. And then we just bullshit about it.

[Lenny Rachitsky]

So what's. What's something you've learned from that experience? I don't know any surprises about podcasting?

[Sam Lessin]

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 more. We don't live that close to them, so it's kind of fun to just like, have that time set aside and then cut it up and post on the. 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 the 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. It's. I actually think the thing that's been most surprising to me about it is that even though, like, we don't really have growth strategies and, like, we're not trying to blow it up and, like, we don't get paid for it, it's, like, weirdly useful is what I would say. You know, even the fact that it's like, you know, I don't know. I'm not sure if that's your experience too, but, like. And I think your podcast is probably much larger than ours, but it's, like, weirdly listened to and useful by the people that, like, we care about and is 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 bullshit about something and then some entrepreneur shows up as like, hey, by the way, here's a better idea. You're like, that's great, Sam.

[Lenny Rachitsky]

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. Two final questions. Where can folks find you online if they want to reach out? Check out.

[Sam Lessin]

Look, our venture firm is 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. Email is my last name is my email address and I do read it. So I don't know. I appreciate you having me on. It's always fun to see you. It's been too long and I don't know, come hang out in the pool house sometime.

[Lenny Rachitsky]

Okay.

[Sam Lessin]

I love this.

[Lenny Rachitsky]

This is an excuse to hang out. Sam, thank you so much for being here.

[Sam Lessin]

Hey, great to see you.

[Lenny Rachitsky]

Bye, everyone.

[Podcast Producer]

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 [e-mail] See you in the next episode.