Lunch With A Billionaire, Fierce Nerds, And D2C IQ Tests
He goes, 7 of the 8 richest people in the world right now, or in America right now, are fierce nerds, right? So you have like Zuckerberg, Bill Gates, Elon Musk, like you have these, like these types, Jeff Bezos, these types of folks. But also he says intelligence is, you know, part of the thing, but fierce nerds are not, they're not winners because they're the smartest of the nerds. In fact, they're usually only moderately intelligent compared to other nerds, but they are way more competitive and impatient than, than the average nerd. And this is the difference between basically like who becomes a professor and who becomes like a founder or a great investor or something like this. All right. In this episode, we're talking about Sam's fight with a bunch of nannies.
Yeah, it's, that's a crazy story. That's in the beginning. Uh, Sean just had lunch with a billionaire. I had dinner with him that, at the, actually a few days before. Super fascinating guy. This, this, we, we're actually gonna share a couple stories that very few people get to see. I think that's the most interesting part.
We also do, uh, a couple ideas. We got an Apple-esque bath, uh, Apple-esque business for bathrooms and a business around the idea of an IQ test. So that's a little side hustle we got for you. So it's got everything. We got frameworks, we got stories, we got ideas, we got it all.
Have you ever seen this meme of like a black guy with a red shirt, like clasping hands with a white guy with a blue shirt. And it's like, we're in this together type of vibe.
The firm handshake meme.
Yeah, it's like us versus the world. Race, class, it doesn't matter. I just had a real life incident like that happen to me. So I was out. I'm in Brooklyn right now. I was out in this park in front of my house, like doing pushups and sit-ups and just like walking my dog, just hanging out. And I see this guy, I see like these 4 nannies like all skedaddle out of like an area where they're sitting. And then I see this like dude who's clearly harassing them, like coming after them. And I run over there and I'm like, hey, what's going on? And they're like, this guy just like spit on us. He's acting crazy. He's bothering us. And so I give him my dog's leash, uh, cause I had my dog with me and I go, hey, hold my dog for me. And we, I walked over and I start talking to the guy to get him to go away. And then like, it's like, oh, this is clearly going to become a fistfight. And then like 5 other guys who are all around the street. These guys just like basically sit on the block all day. I don't know what they do, but like one dude was like a Dominican dude. Another guy was a Black guy. We are all— and I'm sitting there shirtless in bright green running shorts with a fanny pack on with AirPods still in my ear. And we just like corral these women, these 4. It's like a Jamaican nanny. It was like an Asian nanny, an older white woman. It looks like— and it's like we were all just like corralling these guys or these, these nannies in this like circle. And we're just standing there like, an elephant guarding its herd, you know what I'm saying? And it was like the— it was like the real life meme of us coming together. And at the end, the crazy person, he walked away and we just look at each other like, job well done, you know, just like, who cares about our backgrounds? Who cares what we look like? We just— we're champions of the nannies. And I just got hyped over that.
First of all, the fanny and the nannies, that's an amazing combo. Don't mess with that. Secondly, what was that analogy? Like an elephant guarding its herd?
What is that? I don't know. I watched National Geographic. When the lions come, like the whole community of elephants, like get in a circle and they put like the babies in the middle and they're just saying like, you know, bring it on, dog. They're just ready to fight. And that's how it felt like we were just these—
you're like, you know, they call people like Renaissance man. Like you're not a Renaissance man, but you do have this strange set of influences that you watch and you consume and you play with to like We need like another word. You're like a redneck sans man or something like that. Yeah. I don't know what these things are. You're like, you know, like when you're swashbuckling over at the thing. It's like, no, I don't know that. Like, why do you know that?
Like, you know, I like, I'm watching Cops, but on commercial break, I'm reading Ernest Hemingway. You know what I'm saying?
Like, can't stop me.
Exactly. Can't stop me.
You know what I'm saying? How many episodes of Cops have you watched?
All of them. Jacksonville, Florida is my favorite part. How do you think I know so much about Florida?
What episode have I not watched?
All right, dude, by the way, Cops, I think, was the first reality TV, and that shit started in the '80s.
I love Cops. This happened this morning for you?
Yeah, like an hour and a half ago.
Isn't it amazing when you— when something amazing happens in the morning, the rest of your day you got a totally different pep in your step? Like, I remember once I went skydiving and I did it in the morning and skydiving was okay. I was cool, whatever. It's over in like 5 minutes, right? Like, it's like a lot of buildup that it's over in 5 minutes. It's like, you know, it's like your first time doing it. It's like, you know, a lot of buildup and then it's just over. And the one thing I remember was cool, like, it was 8:30 in the morning and then I like, yeah, exactly. I had to go on the rest of my day. Well, I also made the same joke. I said your first time doing it and you said the same joke.
So that's why I was like, okay, oh shit, but we could do it again.
We can do it 2 times.
Well, that's like when you make, when you, when you make a joke the second time and someone's like, you already said that one. I'm like, oh, I thought, I thought no one heard me.
I thought maybe you didn't hear it. Yeah. The, um, but the rest of your day is like, you feel like a champion who could do all things. That's how I felt the day after I sky, the morning after I skydived. And I feel like you're, you're in that mood now. Right? You fought off the crazy guy, the crazy spitting guy with a bunch of nannies. You saved a bunch of nannies and by proxy their babies. And so I don't know, you could kind of do anything. I could just tell you, hey Sam, you know, recite the, you know, tell me the next 5 companies that are gonna become trillion dollar companies and you could just tell me. I can ask you any question right now and you could answer.
Yeah, dude. Look, I, I created the UN of fighting off, you know, bad guys. It was just a bunch of us all looking different, different backgrounds. It was like, It was like the beginning of a '90s sitcom, you know what I'm saying? Like, you know, the blue collar guy, the doctor, you know, we all came together. Yeah, it was, it was right.
It was like a cross between, uh, you know, Golden Girls and like Power Rangers. Yeah.
So you, you, um, can we talk about Dharmesh? Because I have a, a lot of interesting things to talk about because I got to hang out with him. Can you talk about what, what y'all did?
Yeah, I think we both basically hung out with Dharmesh. So Dharmesh is the founder of HubSpot. HubSpot is the company that bought your company. He's a, billionaire. HubSpot is a— he's been there for, I don't even know how many years, 15+ years now.
In the beginning.
So kind of epic founder, built a, I don't know, $20 billion company or something like that. And, um, awesome guy, really fun guy to hang out with. He listens to the pod, so he's kind of like, like-minded and kind of knows our personalities. But we had never hung out in person, neither had you. So I think you hung out with him at the conference and then like a few days later I grabbed lunch with him cuz he flew to San Francisco. Um, give me your kind of initial take. Give me what you liked. Give me maybe something you didn't expect, and I'll do the same.
So he's lovely. Like, he's a sweetheart of a person. He's, um, easy to talk to. Like, he's incredibly— like, he seems emotionally, like, well-balanced and, like, knows what he is and what he isn't. So a lovely hang. And then the second thing, and I mean this with love, and I mean this as a compliment, He is so odd. He has done so many unique things in his life that he, like, you, you wouldn't even know, like he's odd in that he's like quirky, but he's also eclectic, uh, incredibly eclectic. So he's done so many interesting things. And when he tells you the stories about his interesting things, you realize, oh, you're like a lovely guy to be around and you have my back and we're friends, but you are, you're kind of a shark. You will, you'll, you win, you win at everything you do and you spot opportunities. For example, He just casually throws out these things and he's done this to me like 8 times. So I found out that when he was in his twenties, he was like, you know, I almost didn't even— and this reminds me of you. He goes, I almost didn't even want to start tech companies because I've, I, um, was going to become a professional poker player. I was like, what? He goes, yeah, basically like me and my brother, we, uh, we were up like, you know, mid to high 6 figures over our career, our short career of blackjack, because we learned how to play blackjack and we learned how to do well. And also we speak a language that isn't very common. I actually don't know what language it is, but a language where in India they don't even speak it that much. And he's like, we could talk at like the tables and like discuss strategy and no one would even know. And, uh, we just would win. We, I'm up and I know how to do it the right way. And I almost became a professional poker player. And so he like has like all of these little weird things that he'll tell stories about. And I'm like, oh, you're, you're a killer. And you're also so unique.
Yeah. Have you ever read that Paul Graham blog post called Fierce Nerds?
No. What is it? I mean, uh, years ago, 10 years ago. It's old, right?
Um, no, not that old. Maybe like, uh, let's see, when did he publish this? He published this 2021.
So one year. Oh no.
Didn't know I had it. So it's an amazing post. I'm going to read you a couple pieces of it, but it is, it's one of those like Paul Graham, I think is somebody said this earlier. They go, uh,, what's that guy? Andrew Tate. They, some, some tweet that was really funny was Paul Graham was my Andrew Tate. Yeah. Like growing up with this, it's like so funny. So it's such a funny, it's such a deep cut joke, but if you get it, you're like, it just hits the spot. So, um, all right. So he wrote this post and he goes, most people think of nerds as quiet, you know, sort of like diffident people, right? Just sort of like, uh, you know, passive and in, or, and in most social situations they are, they're, they're quiet and you know, they're not the star quarterback in the middle of the gym, right? They're, um, They're kind of a fish outta water in a bunch of different things. He goes, um, but this is an illusion because when, that only happens when non-nerds observe them cuz they're observing them in non-nerdy situations. So you see a nerd at prom, you just see them as a quiet sort of passive nerd. There's no alpha in them. And he goes, but in fact, some nerds are quite fierce. Fierce nerds are a small but interesting group. They're extremely competitive, more competitive, I would say, than competitive non-nerds because the competition is more personal to them, partly because they're not emotionally mature and they, they distance themselves from it. Uh, but also because there's less randomness in the types of competition that they engage in. Therefore, they're justified in making it more personal. So this is like fierce nerds who get really into chess or a game that is less luck-based, more skill-based. Uh, this often happens with gaming or programming competitions or math competitions or spelling bees. Or is it way less about luck and way more about skill?
Dharmesh told me a story. He was like, when I was in grade school or high school, I, uh, like I got in trouble because I just like didn't go to school or like something like that. And I was like, why? He goes, well, I had never seen a ping pong table and they had one of those in the dorm. And I, right when I saw it, I decided I'm going to be the best at this. And so I dedicated my high school years to being the best ping pong player. Uh, but sorry, go ahead.
Really? Yes. That's amazing. Uh, I love how you get these gems out of people. Like what question do you ask that gets that answer?
I, uh, like, I'll just say like, like, wow, you're like really unique. Like, how are you so, why are you so different?
No, no. How did you really say it?
Wow.
You're so freaking weird, man.
Yeah.
I would say, dude, you're weird stuff your whole life.
I was like, you're a weirdo.
I'm like, I'm kind of a weirdo.
I'll say like, I'm kind of a weirdo too, but you're like extreme weird. Like, what were you like in high school?
Yeah. Yeah. Yeah. That's, that's, that's the Sam Parr question. I needed to get that out of you. That those are great. Cause I'll be honest with you. I had lunch with him and super nice guy.
Wait, by the way, keep, keep reading your article.
Okay. Yeah, yeah, yeah. Fair enough. Uh, so he go— so he goes on to talk about it. He's like, here's some other things about, about fierce nerds. One, they're independent-minded. They're willing to basically stand on what they believe even though it is socially awkward. You know, in school this becomes kind of a liability for them, but as soon as they graduate, they go into kind of the professional world, it becomes an extreme asset for them. Um, they're also impatient. They're annoyed by rules rather than being just like, you know, unaware of them or passively following them. And he goes, I'm not, he goes, I'm not, I'm not sure why fierce nerds are impatient, but they, most of them seem to be. You'll notice at first in conversation, they tend to interrupt you. At first it's merely annoying, but it's, uh, but the more promising fierce nerds, it's connected to a deeper impatience about solving the problem. They have this competitiveness and impatience, right? So those are two of the like characteristics. And, um, he goes, when you combine these qualities in sufficient quantity, the result is quite formidable.
And, uh, then he gives some examples and he goes, that's a beautiful sentence, by the way.
One more part.
If you combine these in sufficient— yeah, that's a really good sentence.
Yeah. He goes, 7 of the 8 richest people in the world right now on air in America right now are fierce nerds, right? So you have like Zuckerberg, Bill Gates, Elon Musk, like you have these, like these types Jeff Bezos, these types of folks. Um, he goes, the bad news, he goes, he goes, indeed, he basically, but also he says intelligence is part, you know, part of the thing, but fierce nerds are not, they're not winners because they're the smartest of the nerds. In fact, they're usually only moderately intelligent, uh, compared to other nerds, but they are way more competitive and impatient than, than the average nerd. And this is the difference between basically like who becomes a professor and who becomes like a founder or a great investor or something like this. And so, um, he goes, he goes, he goes, the idea of a fierce nerd is not a common one. So a lot of you might be reading this and might realize, hmm, that's me. And he goes, and now, and I love this writing. He goes, and it is to you, young fierce nerd, that I now turn. And he goes, and he starts talking directly to the fierce nerd. He goes, he goes, I got good, good news and bad news. The good news is your fierceness is gonna help you solve difficult problems. So, you know, scientific, technical problems, blah, blah, blah. You can get rich in business. Agreed, it is great for, you know, survival to be a fierce nerd. He goes, the bad news is that if not exercised, your fierceness will turn into bitterness and you'll become an intellectual playground bully, a grumpy sysadmin, the forum troll, the hater, and the shooter down of new ideas. He goes, how do you avoid this fate? And by the way, he created Hacker News, so I think he runs into a lot of fierce nerds, uh, on Hacker News. He goes, how do you avoid this fate? Work on ambitious projects, because if you succeed, it brings you the kind of satisfaction that will neutralize your bitterness. You don't have to succeed to feel this. Merely working on hard projects gives most fierce nerds a sense of satisfaction. Um, and it, and it, and even if you don't succeed, it'll keep you busy. So you're not so bitter. I thought this is an amazing blog post. Like one of his, you, you, you, you sent, literally I read this, I sent it to Emmett at Twitch. I was like, hey, it's you. Like, this is you. This is what I would describe you as, like a fierce nerd. And he went through Y Combinator. So, you know, he's like, you know, the archetype for it.
So you just pulled this up, by the way, without having any preparation. And you did a really good job, by the way, of like reading that. I was like enthralled. Uh, but dude, Paul Graham—
very hard, by the way, because I read this a year ago and I'm like skimming it, trying to cut the boring parts and also remember what the hell was this article about. That was actually quite difficult.
I know you did a really good job. I was like, tell me more, tell me more. Um, Paul Graham's a great writer. Uh, I love— I'm going to go back and reread that. Okay. And I interrupted you. To— I interrupted the interruption. So you met with Dharmesh and you said, to be honest, he was a nice guy. I forget what you said.
So, so he's a fierce nerd. That's the first thing. And I think you pulled out some good stories, the ping pong story, the poker story. This is classic fierce nerd hallmarks, right? All green flags, uh, going, going towards that. The second part was super nice guy and our lunch was totally fine, but there is a certain, uh, It's, he's this type of person. I actually, there's a bunch of people like this. I might be like this where you're almost better to talk to online. It's like you've spent more time talking to people online that your online social skill is better than your in-person social skill. I felt this myself cuz right, I left the house for the first time in many, you know, many days to go do a social hangout. Like, you know, he even texted, he was like, you know, totally understand by the way, if you don't wanna come, I'm like you, I don't like to leave the house and you know, I'm protective of my time. And I was like, no, no, no, I wanna do this. I'll, I'll drive an hour. Let's do this. Um, I felt rusty and I could feel almost that he was a little rusty or like, put differently, not rusty necessarily, but his main comfort zone, right? His pocket, his cockpit as a pilot is sitting at his desk in front of a computer. And I know a bunch of people like this. I have a, this guy we used to work with, Jake, if you met him, he's as quiet as a mouse. In Slack, he's like the class clown.. And I was like, what? Who is this guy? That's you, dude. You're like the most soft-spoken, like, you know, that foot pedal on a piano that makes all the keys like muted. He's like that for real life. Like somebody needs to like take the foot off the foot pedal for him. And, but then you get him in Slack and the guy's like, you know, the number one troll willing to cut the edgy jokes. And I was like, I can't believe this is the same guy. And it's like, he was 21 years old and he basically grew up in Malaysia. His only like English social interactions were online in like in chat rooms, games, Discord, that sort of thing. And so, you know, that's just his persona. And I've met so many people that are like this that I've now come to realize it's not something weird about them. It's actually a completely normal thing. And it's better to just figure out what's your, where are you the most you? Is it through text messaging? Is it on phone calls? Is it through written emails? Is it in person? Is it like long form in person? What is the version of you that's the most you? Uh, well, like what would you say it is for you?
Writing, like long-form writing. I think that's what I prefer. Like these podcasts, like I usually have to lay down for like 30 minutes because I'm like, I'm like dead after them. So no, I mean, I'm okay at this, but like writing I prefer. But listen to this. So I think Dharmesh would actually agree.
Like I have to elevate your legs to get the blood back to your brain. Yeah.
I'm just like, I'm so tired. I passed out. What happened? Dharmesh would probably agree with you, I would imagine. And so listen to this. So they, they asked you and me to like show up. So basically I was supposed to speak at this event and they were like, hey, uh, one of the main people had to cancel because something happened. Can you show up like in 12 hours the next morning and come and speak in front of 10,000 people? And I was like, I mean, I guess I could just like show up and riff in front of 10,000 people, but I don't prefer that. Does Dharmesh want to like do a thing? And they're like, no, he hates public speaking. I'm like, just let me ask him. He'll do it. So he ended up doing it. But backstage I asked him about that and he is like, yeah, I don't, I hate public speaking. I'm not good at it. And I go, well, you just did a keynote earlier today. Why'd you do that? And he goes, I'll tell you why. Basically for the 6 months or 5 months or whatever it was leading up to this event, I had this process where I read a bunch of comedy books and I realized that the laugh per minute was the most important thing for a talk. And so what I did was I got first, I made a presentation. I got, and I created a Zoom call and I got 10 HubSpot employees to do it and I recorded the whole thing. Then I got 20 to come and then 50 to come and then 100 to come. And what I did was I adapted each time and I built this Python, I built this Python script that analyzed the audio of the call to figure out what my laugh per minute was. And then each time I adapted it to get more laughs per minute. So for example, and he knew the exact numbers, he goes, I had 96 slides on this presentation and I had to click next 120 times and I know on which laugh and on which word to hit next because I practiced it so much because I'm optimizing for lap— my— he kept calling it the, the LPM.
Wow. And, uh, what the hell? This is amazing.
It's amazing.
These types of stories, it's amazing.
And he like— he— and I went back and watched his talk and he goes, in fact, So here's like another like side tangent. Have, if you've ever been to a big conference, have you noticed whether it's TED Talk or even Steve Jobs, all the big conferences that have more than 1,000 people, they all use the same slide clicker. Have you ever seen that clicker? It only has two buttons, a red, which means back and a right and a, and a green, which means next. So here's the secret, that clicker, it doesn't actually change the slide. It goes to a light, like a light that says red or green. And there's someone on the other end of the slide hitting left or right. Did you know that? No.
Yeah.
So that's like a, so it's so stupid because they do it because like the, the presenters or the organizer will be like, well, in case you can screw up, someone's here and, and we'll do a better job. But it's not automated. Like it, the, this is how it's, it works at all big conferences. So it, it is like this is a clicker or whatever. We have to do a talk on it actually. They have a, they've completely monopolized it. So every single big conference has this. And I told him that, he goes, dude, trust me. I know I've gotten in fights with these people for 8 years because I built a device and a program to make it so that clicker could actually work directly with the computer. Because in order to optimize my LPM, I need the click to happen faster than a human being can see the light and click next, because I've— that's how I've set it up. And every once in a while there'll be a slight delay, which decreases my LPM. And so This is how this guy looks at everything.
And he told me that— He thinks about his LPM like you think about your T levels.
Yeah. He just like spends months optimizing his LPM. And this is just like, when I hear stories like this, I think, A, you're unstoppable. Like, this is why you're successful. And B, I love you. Like, I just, you're my hero. And I, everything you're about, I'm into now. And I just, I love it, man. I love when these people are so extreme about shit. It's awesome.
That's amazing. Uh, that is amazing. What an amazing story. You've made my day. Um, that, that is really incredible. I can't even, uh, yeah, I can't even kind of wrap my head around the level of nerdery it takes to go that deep on something like, you know, Um, I feel like I live my life in this like 80/20 way where like good enough is as good as it gets. And like, I just kind of— good enough is as good as it gets for like almost everything in my life. Very rarely do I try to like take something to that like nth degree, that Olympic level of obsession. And part of me is very jealous of people who do that. Um, like we— another fierce nerd we had was this guy Quinn who used to work at, um, at our company. And Quinn, same thing. Most soft-spoken guy. You might have met him. He had the big crazy—
Yeah, I know.
Most soft-spoken guy. Gentle. Like if there was a fly that landed on his wrist, he'd be like, it's your wrist now, fly. Right? Like he just didn't want to harm a bug. Never said a bad word about anybody. And he was like a fierce nerd. Like we, we started playing like these little word games in the office. And I was like, oh, Quinn, you should play like this. Like, you know, like imagine like Wordle, but like 10 years ago. And he's like, oh, I can see him like getting like visibly stressed about it. And I was like, whoa, like, no problem, man. What's wrong? Like, you don't want to play? He goes, no, but if I play, then I'm just going to get super obsessed with it. Like, I'm just going to take it too far. And I was like, what do you mean? He's like, he's like, yeah, I just have to be careful with games like this. I just get like really into it. I just have to win. I was like, you, like, what do you mean? Like, you were this ruthless competitor? Get out of here. And he goes, did I ever show you, uh, the girlfriend thing? And I was like, what's the girlfriend thing? And he goes, you know that game that's like that word scramble game? Uh, like basically it's a bunch of letters, 9 letters on a grid. You're trying to like create as many words as you can, just like dragging your finger across the line. He's like, yeah, my girlfriend beat me in that game once. And then I went to Google's Headquarters, and I programmed the artificial robot arm to just make as many swipes as possible in like every, like per second. And, uh, like I just crushed her and I'd be like, I'm the world record holder now of this game. Like he basically created, he like programmed the robotic arm. He added a little like Nerf gun tip to it. So it'd be soft, like, uh, it could just scrape against the screen. And then he just programmed it to move in every direction, the optimal path to like create as many words as it can. And like, You know, a minute. And it's like his time is like unbelievably higher than everybody else. And his girlfriend's like, well, this game's not fun anymore. Like, I don't understand what's happened. Like, what happened here? And he's like, I happened.
Dude, let me tell you one more last, uh, Dharmesh story. So he owns like, uh, he has an 8-figure domain portfolio. So like random things, like he owns Cambridge.com, which he like just lets the government use. Um, you know how I, um, I have this copywriting thing. I was using trycopythat.com and he goes, hey, for your birthday, I bought you copythat.com. And I was like, what?
That's like, he's like, try not being a bitch.
He punched me in the stomach and walked away. Yeah.
He punched you in the stomach, but then gave you the credentials.
Yeah. Thanks, Dad. Uh, dude, that's hilarious. So he owns all these domain names and I was like, what? Okay, well you have this Wordle thing and you have all these domains. Any projects that interest you? He goes, I've been thinking really a lot about creating a Venn diagram community. I was like, what? What are you crazy? He goes, well, I own venn-diagram.com and I love communities and I'm into math. And I think there's a lot of other people who are also obsessed with Venn diagrams. I think I'm going to build a really cool community for Venn diagrams. And, uh, I don't know if he's gonna follow through with that.
You can just see them having like a tattoo on their arm of just a van. There's just a bunch of Vanners. Yeah. We're all just Vanners just getting in a room. I've been overlapped everywhere.
Yeah. Yeah. I don't know. Like what it's like, there's a circle. There's a circle. You see how this circle, like, what are they gonna do? Just talk about it all the time. I mean, I don't understand like what the, like, you know, this circle's bigger and this one's smaller.
I don't know. Vanner's gonna van, man. You can't help it.
But that's what he is gonna build is a Venn diagram community cuz he owns venn diagram.com.
Can I, can I tell you 5 random domains that I own? Uh, actually I'm gonna tell you 6 random domains that I own. I want you, I'm gonna say, let's play a little game. I'm gonna say a domain and you're gonna just pitch me a business off, off the domain, off top of your head. All right.
Okay. All right.
You froze.
All right.
There you go. Um, okay. Number 1, excelmonkeys.com. A domain I own, ExcelMonkeys.com. What does it do?
All right. ExcelMonkeys.com. That's where you buy smart chimpanzees.
That's your best idea with ExcelMonkeys?
ExcelMonkeys. It would be, um, that would be the name of a tax service.
Yeah, it could be a tax service. It could also be like selling amazing Excel templates for stuff. It's like, oh, you need like a cash flow statement? Here's a great one. You need like a P&L? Here's a great Excel.
Did you do that?
Oh yeah. Whenever I meet these finance nerds in reality, I was always jealous of them because they were making more money than me, like my friends. And I'd be like, dude, you're just an Excel monkey, man. Like they're just, All you do is play on Excel. You don't do anything. You don't create real value like me. Like, you know, I write a newsletter.
Dude, I have so many phrases like that. Like bakers who are always making PowerPoints. I'm like, ah, friggin slide jockey over here. I don't even know what it— I don't even know why, but I'm like, I want it to be derogatory. Or like the best one of all of them is the finance department that like watches the budget. You have to like get your expenses. It's like, oh yeah, I got to go talk to the bean counters. I like heard something, some guy say this, he was like in his 60s and I think it's a common phrase, but I was like, oh, that was like a racial slur as far as I was concerned. I was like, wow, calling someone a bean counter.
That sounds awful.
You were allowed to say that in the office? That's incredible. I'm going to use that.
When I was, uh, you know, younger and I was jealous of all these bankers, they'd be like, oh, you know, I work in banking. Like, oh, no shit. Which branch? You know, like, uh, I go to the one in Columbia. Is that where you are?
You ever been robbed? Has anybody come in with a ski mask? Have you guys ever heard about that?
Okay. ExcelMonkeys. That's a, uh, uh, that's a, it's a website for tax experts. What's the next one?
All right. Next one. Skillbad.com. I own skillbad.com. Skill bad. I don't know. It sounded good. It's two easy to spell, easy to say words. Put together.
Skill bad. Like you're bad at something.
I don't know what on earth, but it's ironic.
What, what would you, like, what would that be? What were you thinking?
It's like Skillshare, bro. It's so easy. That's easy. That's a layup right there. It's like Skillshare. It's, uh, you're bad at a skill, come to Skill Bad. We help you go from being bad at something to being good at something.
That's stupid. That is really stupid.
HubSpot is a CRM platform, so it shares its data across every application. Every team can stay aligned.
No out-of-sync spreadsheets or dueling databases.
I got, um, itstummytime.com. It's tummy time, baby. It's tummy time. What is it? What are we doing at tummy time?
Just, uh, what do you do on tummy time? Is that when the— what's the baby do? Just sit there and watch TV? What's tummy time? I don't even know.
Kind of. They just lay on their tummy and it helps them like, uh, you know, like develop their core strength or their neck strength to like look up so they don't just be face down. But they don't necessarily watch TV. But yeah, I guess you could do that.
Obviously you're going to be selling baby aerobics classes. I don't know.
For sure you'd go for like a 6-minute abs thing. It's tummy time, baby.
And it's all— I don't even know what that is. I, you know, I'm not, I don't, I'm not there yet. And what are the last two?
We're gonna have to work on your improv skills. You've been working on comedy, but not improv. I feel like, uh, I feel like the on-the-spot throw something at you. I'm gonna practice. I'm gonna keep doing this segment until you're good.
I'm, I'm still at the yes and part of the book.
What's the one thing everyone knows about improv? Yes and. It's like the number one tell that you've never done improv is that you say, you know, in improv, you know, in improv we have this thing called yes and. It means don't disagree with me in this meeting. Instead, say yes and then make my idea better because it's bad right now.
Have you ever gone out to dinner with a bunch of improv people?
Dude, I did improv for like, you know, 8 weeks of my life.
Dude, I've gone out to dinner. What time I went out to dinner.
Nothing more obnoxious than a bunch of improvers. I'd rather be with the Venners.
Yes, I'd rather be with the Venn diagram dorks than a bunch of improvers. Yuck. They go, it goes like in, in, in like places I don't want to be. Number 2 on top of that list is improvers. Number 1 is people who are part of a cappella groups.
Oh my God. I was about to say the same thing. A cappella where they're just like, hey.
Yeah.
Yeah.
Yeah.
Dude. Oh God, here we go. You know, shabuya. Shabuya.
Don't sing. Singing to me on the McDonald's line that you want a number one, bruh. Just tell me a Big Mac with no onions.
You know what makes any situation worse? Singing.
I cannot stand the a cappella people. I didn't realize that was a thing. Where I grew up in Missouri, if you were part of the a cappella, people would make fun of you. But then I started meeting people on the East Coast, like these people who go to Harvard and Cornell and shit, and they would brag about being part of like an a cappella.
They're so serious about it.
I'd be like, dude, why are you telling people that? What are you doing? Don't be talking about this in public. You don't talk about that. And they're like, why? It's awesome. I was always amazed at a cappella people.
Dude, on Duke's campus, like, who gets laid? Number 1, basketball players. Number 2, a cappella. And I was like, what the hell? What's going on? It was crazy. Yeah, I have these like dating rules, by the way. Uh, never date anybody who's into, who's an equi— what is it called? Equestrian? Somebody who likes to ride horses. Never date a horseback rider. Never date a dancer. Uh, never date an a cappella person. Uh, those are my 3. Those are the 3. Like, you just never wanna do it. Why? They're obsessed with something that's by all accounts useless. Number 2, they, all of their hobbies are extremely either expensive or time-consuming away from you. Number, uh, number 3, half of those hobbies basically are like really intimate with other people that are not you. They're just gonna be doing salsa with some, like, you know, some suave guy from Latin America who doesn't speak English, but is touching all over your person. You don't want to do that, right? So these hobbies and same, and then also you can't do the thing. So, oh, you're at a wedding, great. Isn't it awesome? You date a dancer. No, it's not awesome. You turn into a pole while they are doing like actual dancing or, oh, you date a singer. Great. Why don't you just sit there and nod and like tap your foot while they, who they actually know how to sing. So it's like, dude, do you do together?
I never dance at weddings. I just act like I have to go to the bathroom every song. I freaking hate it. I hate wedding dance floors. I watch the UFC.
You're like, I find two bathrooms on opposite poles. Yeah, I just make laps between them.
Dude, I don't ever dance. Like, I watched a UFC fight the toilet the other day, like, at a wedding. I don't— I hate dancing at weddings.
That's so true, 'cause UFC's always Saturday nights. I watched UFC at like three weddings already.
Yeah, I hate going to weddings and going to the dance floor. I just tell Sarah, like, don't even ask me. And they're like, well, it's fun. I'm like, uh, no, this is the worst. I don't want to do this. I don't know what to do. I don't like it. It just— It ain't for me.
There's a great little Chris D'Elia clip on YouTube. I dunno if you've seen it. He goes, there's no bigger dick move than inviting your friend to your wedding. He goes, if you're doing an out-of-state wedding and you invite me, like, you know what you just did to me. You know what you just did. You cost me money, time. I don't want to be at a wedding. And, and I thought it was like very, very true. Um, all right. New, uh, new segment. So, or new idea. So I got two ideas for you. Would you like to hear about— I'll give you options. Would you like to hear about the next Apple, or would you like to hear about, um, the next, the next little side hustle that I think could kind of work? The next Apple or the next side hustle that might kind of work?
Well, the second one.
All right, just as I expected. Um, Do you know your IQ?
No, of course not.
Ben, do you know your IQ?
Of course he does. I, I've done only unofficial IQ tests.
What does that mean? Yeah.
Like a banner ad on a website. Yeah. So there's some online that are supposed to be better than others, but basically in order to get your actual IQ, it's supposed to be like proctored and they have someone administer it. But you can go take tests online. I took one of the better ones. Um, and, but it's still not like a totally accurate IQ.
Okay.
Yeah.
I ate at one of the better Arby's the other day.
So what did you get? Yeah. What, what did you get?
Yeah. What's your IQ?
It said 132.
Oh, that's genius level, right?
No, no, but it's, it's, it's smart, but not genius.
So, um, I think you could create a DTC IQ brand. Uh, so I think you could basically take the same playbook that everybody's using for DTC brands, right? Uh, we were just joking about banner ads, but yes, banner ads, uh, Facebook ads, Taboola ads everywhere. I think you could optimize a funnel that basically buys clicks for less than a dollar and then converts, you know, let's call it I don't know, whatever, 10% of people, you need to convert 10% of people to pay you the $25 that it's gonna take, or the, you know, maybe it's the, maybe it's, maybe it's $99 or something like that. You have to figure out some version of the economics that's gonna make sense to make this, the math work on the CAC versus the, the value. But I feel like somebody could create a funnel that will get you in. Why do I think that this will work? It's not really economics driven, it's just work backwards from what's an ad that I think would work. And I think an ad that's like, only geniuses can solve this puzzle. Um, like, I don't know if you've seen these ads on TikTok that are like, people say this puzzle is impossible, or this number game is impossible. You can't draw a line through these 4 things without lifting your finger. And you're like, I bet I could do that. That looks doable. And you like click it. And then now it tells you to download some game. But instead of a game, I think it could be basically like an IQ game. And I think you can basically make a monthly subscription that's like, these are IQ games or IQ tests to get your score., for either you or maybe, maybe it's, maybe we're going after the baby Einsteins. Maybe it's for your kids. 'Cause I think people wanna know if their kid's a genius more than as an adult, it's less, less important. And so I think somebody can build a D2C IQ test that like, I don't know exactly how well it'll do, but would it surprise you if I told you, dude, I met this guy and he runs this like Facebook funnel that basically takes you down an IQ test and then you pay for your results. And, and like half the people forget to cancel their subscription. And the guy makes, you know, $50,000, $50,000 a month or the guy makes $100,000 a month doing this. Would you be shocked if I told you that?
No. In fact, I think you could build a company that could actually make 9 figures, like $100 million plus. And here's why. I think I've told you about this, but have you heard of Gallup? You've definitely heard of Gallup. Like they're cited in the news. Yeah, their surveys. Well, they own this company called CliftonStrengths. Have you heard of CliftonStrengths? I think CliftonStrengths—
we've talked about Wait, wait, we talked about it way back in the day, but we should do it again because the pod was way smaller back then. But yeah, I've done this test, the StrengthsFinder test.
I don't have all my research, so I'm going off memory, but basically StrengthsFinders, I think it was a test and then a book, or a book then a test, something like that.
It's a book that has a link to the test inside. So basically the book is like, you don't even need to read the book. The book just has like a code, says go to this website, type in this thing, now you take the test, and then it gives you at the end, like your 6 or 7 strengths is like, oh, you're a futurist. It's just like literally tarot card reading to me. Like, it's like you're a futurist, you're a determined leader, you're a, uh, you know, problem solver or whatever. I don't know what they are, but like I took the test and I was like, oh, they just gave me 7 like generically positive words. Like, oh, for sure. I could identify with some of these and like, great. What does this do?
It's a horoscope, but basically Gallup, the company Gallup is a survey business. They own StrengthsFinders. And Gallup is privately owned. But if I remember correctly, 4 years ago, maybe it's 2 years ago when I did research on them, I think they're north of $1 billion in revenue. And CliftonStrengthsFinder, I think what it is, is, um, so they charge like $40 to $50 for one of these simple things. And, but then they do like more heavy duty consulting where they'll like put your whole company through it. And during my research, I'm pretty sure that that test was making hundreds of millions of dollars a year in revenue because they have thousands of employees and like, I don't know where they're based, like Minnesota or like something. They're just like one of these— I guess they're the main thing. Gallup is based in D.C., but it's one of these companies that you like totally forget about that exists and you just don't even think about it. But if you look at the traffic of their website and you look at some of the numbers based off of news articles, it's like a pretty wildly huge company, right?
Is it private or is it public?
It's, it's private. It might have been public at one point, but it's like they have on Wikipedia, it says they've got 50 offices and I know they have thousands and thousands of employees. And it's privately owned by, uh, I think still, uh, just the, the family.
Wow. Uh, yeah, that's amazing. Yeah. So I think you could do like the, this is like the enterprise personality test. That's what I call it. Uh, you could do the personality test, you could do the love language, uh, test, you could do IQ. Uh, I think you could do a D2C funnel that would work with these things. Um, so I, I don't know, I, I'm kind of interested in this. I think this is like, if you're a good internet marketer, like actually not good. I think you kind of need to be an amazing internet marketer. Yeah. If you're an amazing internet marketer, the world is your oyster. But like one fun one that I think somebody could spin up would be, um, these like sort of, uh, take a test, get a score type things, whether it's personality or it's IQ. Okay. So that's, that's that one. Now let me tell you my Apple idea.
All right.
I'm taking a shower today and that's nice. You're welcome. The, my fa— one of my favorite feelings of the day. I'll, I'll give you a list of my favorite feelings. Most people don't have this list, but I got a, I got a list of favorite feelings throughout the day. In my top 5, 2 of them, maybe 3, come in the bathroom. Showers, wash my hands, taking a poop. Love all 3 of them. My trainer says this thing, by the way.
Do you do it in that order? That'd be, you'd be a freak if you did it in that order. It's not a routine in that order.
No, I We go the other way, right? There's a method to the madness. By the way, my trainer has this thing he says, which is like, he's like, yeah, of all my clients, he's like, the number one thing people actually struggle with is stress. And he goes, what's the opposite of stress? And it's like, I don't know, relief. He's like, yeah, relief, satisfaction. He goes, think about how many things a day stress you out. I was like, oh, that's a lot. There's a bunch of things that can stress somebody out. He goes, think about how many things give you relief in a day. He goes, I, I was like kind of struggling to think of anything. He's like, he's like, people usually have relief once a day. It's right when they're pooping. And he's like, that's the only time they experience this emotion. That's why they're bad at it. They don't practice that emotion very much. And I was like, wow, that's, that's interesting. So anyways, back to my story. I love having clean hands after washing my hands. I love taking a shower and I love the relief. All right, great. So, but when I'm in those situations right now, if I go to my shower, Nothing that special. I, I don't know. I got standard shower head, shampoo, body wash, got a loofah in there cuz you know, my wife hooks me up. Yeah. So this is, this is like, that's what I'm working with. And for something that I do every day, something that's like, you know, kind of an important part of my day. Why are, I, I think somebody could make an Apple for the bathroom and what, what is the company that's Apple for the bathroom gonna do? So I don't know. Have you ever tried to like hack your shower experience to make it more awesome?
It's really hard to do things. Yeah, things I bought. I was really interested in like different shower heads and I remember researching them on Wirecutter and I bought the fanciest one and then I— it wasn't even that fancy, but the best one. And I remember like it took forever to call a handyman to install it.
It was a pain in the ass. Where did you fall into the trap? Installing it. It's always the install that's like, you know, who's going to do that?
And same thing with toilets. It's like you, we've probably all heard that there's these Japanese toilets that are amazing that will like, you know, give you a butt massage or whatever. You know, they're, they're like incredible toilets, but who's gonna rip out their toilet and replace it with this fancy one? That's a, that's a big, big overhaul. And washing your hands, nobody even touches the mirror. Nobody touches like there's, so I think you could build a product that simply says, I'm gonna give people relaxation and relief. I'm gonna give them, motivation and inspiration through products just for the bathroom. And you could just nerd out about how to make the bathroom experience amazing. Like I bought these little eucalyptus like pods that you put in the shower and basically when hot water hits the, the pod, it like releases like this eucalyptus, like kind of like, uh, aroma. Awesome, right? Like the, the thing itself is kind of janky. Like it's not the best product. Like it's, uh, you know, in between it gets all soggy. It's not great. It's like, it's only good the first time. But the concept is amazing and it's like, why isn't there just a better diffuser that's gonna add this like eucalyptus steam into my shower while I'm doing this? Why isn't there an add-on attachment that doesn't require me to replace my shower head but just makes the shower head better? Um, why isn't there something that's on my mirror that is motivational and inspirational that's like, that looks nice? Why isn't there a product that's like washing your hands but it's not washing your hands? It's like some heat UV bullshit. I don't know, something that's gonna like, Make my hands feel clean and toasty. Um, why isn't there, uh, Eight Sleep for the toilet? That's a device that sits inside the toilet and measures your pee and your poo and tells you when you need to go see a doctor or, you know, the quality of your hydration or whatever else. I think that somebody should build a company. I want some, somebody who is like that Venn diagram between quantified self. They like, they wanna like optimize, they, you know, the Rob Dyrdek, I am human optimization. They're that guy, but they're also a hardware nerd and somebody who has that overlap. I just wish that they would create Apple for the bathroom. So it's, I think it's something I wish somebody made because I would buy hundreds of dollars worth of products from a brand that could actually do that well. What do you think of this idea, dude?
So, uh, I, I, I haven't researched a, a ton of this, but, um, there's two interesting players in this space right now. So interestingly, both of them have come from like, Tier 1 VC-backed businesses that they previously started in traditional, like, cool kid areas. So the first one, I think, is it called Revolution Bathrooms?
Uh, Maid Revolution.
Maid Revolution. Maid Renovation. Maid Renovation. I believe it started by, I think it's Roger Dickey, I think his name is. His company was called Gigster. Successful tech guy who started, like, businesses I think that have sold for hundreds of millions of dollars and he, like, up and quit, like, this one, like, company that he had, Gigster, that was killing it. And he's like, I'm going to get into the bathroom business. And so a little bit different than what you're talking about, but interesting. But another one that's actually really cool. Have you heard of Block Renovation?
They do the same thing, right?
Ish. Yeah. I believe they do the same thing. But basically the coolest thing about this is if you go to the website, it looks slick and cool and everything. And it's almost fits your Venn diagram once because the guy who started it, his name is Luke Sherwin. He's the former founder of Casper. Uh, so he like took Casper public and left, and then he started this thing for bathrooms. And I think at this point, I think they've brought in $90 million in funding or $50 million in funding. I forget, but it's like close to $100 million. And I think it's like doing really, really well.
Yeah. Both of these are basically how do you renovate your bathroom so that you get a like super nice looking bathroom or in their case, kitchen also. Um, like just like pick from the menu. It's like, here's, you know, here's 5 amazing bathroom designs, pick one. And then we have people that can install that bathroom in your bathroom turnkey versus today, the way you do a renovation is like, all right, what do you guys think of for tile? It's like, I don't know. I never thought about tile. Uh, what are the options and how much does each one of these cost? And like, okay, then what about sinks? And you just sort of have to piecemeal it. Whereas this was like a turnkey bathroom in a box, which is a great idea. This was one of the first ideas we brought up on, on this show, by the way, was I saw this ad and I was like, this Maid renovation idea is amazing. And I should have just invested in it because back then it was like in a seed stage. Like it was very early. And, um, yeah, both of these have done really well.
Have you ever tried to buy a bidet? So like what you can do is buy these like bidet, uh, covers where basically it's like this, like it's basically just a sophisticated toilet seat and dude, they are so janky. Like you have like an electrical cord.
I have one right here, never installed it. And in fact broke my toilet trying to install it.
Dude, they're so janky, and you have like a cord going from like where your like electric razor goes, and you're like, what the frick? Why is this cord like going like across the room?
Yeah, it's like running from the kitchen into my bathroom.
Yeah, and then you've got this like stupid hose that goes up to the top of the toilet. It just looks like a, like a science experiment, like that's duct taped together. It sucks, right? But I've always wanted one, you know, like whenever, you know, you use one, you're like, I want a real bidet. Yeah, that's sick. That's dope. So yeah, I'm on board. I, I, I think this is, uh, the next Apple. That's ambitious. Maybe the next company that gets bought by Apple.
I didn't say it's the next Apple. I said it's Apple for the bathroom, meaning it's a company that just cares about the design, the simplicity of use, and, um, just making a really high quality product. And people are willing to pay a premium way more than you think. They're willing to pay 3 times more if you can actually pull that level of quality off. And I think that, You have this place where people go all the time. You have the shower, you have toilet, you have a sink, you have a mirror, you have these things to work with, and then you have all the accessories. Oh, maybe this scale that I have in my bathroom is like, I don't know, it's just like some random weight scale. Maybe there's like a really good version of that that, that can go with it. And you could just cross-sell into all these different categories, but you just say, we're gonna own the bathroom. We're gonna make the goddamn best products ever for the bathroom. And I think if somebody just simply took that idea and then just decided to execute on that for like 10 years, you could have a billion-dollar company in the same way that like, you know, the Nest thermostat was able to sell for a billion dollars, right? Like I think if you can, if you can actually pull off this thing that's in every home and in with a bathroom, you got like 3 or 4 in every home. So it's like you have this like, um, this thing that today everybody kind of ignores and just treats in this, uh, sort of like it's an afterthought type of way.
No, I think that's dope. I'm in. You want to do one more or what?
I want to talk about one other concept, which is actually, do you have one? We could do one of yours if you want. No. If you want to do one.
All right. No.
I gave a talk at HustleCon with this phrase, and in my mind I was like, oh yeah, we've already talked about that. But I'm like, wait a minute. No, that was just at HustleCon. I don't know. There was like a couple hundred people in the room at my breakout talk. So most people have not heard this concept.
The one on selling a company?
It was the one on how to sell your company. And in general, it's really about like, you know, how to do a part of business that you don't do often and maybe you don't have the reps in. So like most people who become like business owners, CEOs, you're great at product, you may be great at marketing, you might be good at finance and making money, but what you're not good at is stuff that you only do once in a while, like fundraising or, um, M&A or, um, you know, things like that. The sort of like these large one-off transactions that are very important, very expensive. You don't wanna get them wrong, but you also don't have reps doing it. And, um, and the other side, like when you're fundraising, the investor, they talk to hundreds of people like you every month. They're getting tons of reps. So you, it's a, it's a very asymmetric skillset. You don't really know how to negotiate like them. You don't know what clauses are standard and what are not standard. Um, so you don't have that same level of reps that the other party has. Same thing with M&A. You're going and talking to somebody who does M&A for a living and, um, and they've done hundreds of deals and you don't know the first thing about the first thing. And so here's the solution that most people have, right? Like if you're really big, you can afford a banker. Like, uh, did you guys use a banker? I don't think so. When you, when you sold, right?
You may have had some advisors, but I had hired one and then I disliked them, so I fired them. So I ended up being the banker.
Right. And same thing when we sold, I was the banker, but I had a, uh, I talked to a banker who could kind of like give me some free advice from time to time. It's amazing.
I had a really good lawyer. That was like a huge thing. Although I do see the value in a banker. I do think that a good banker totally is worth the fee. A good lawyer is 100% needed, right?
This guy, Dick Filippini, he, he, he was amazing actually. He was a banker that helped me, but I, we were too small for like his normal deals, right? He does $100 million plus deals and we were way under that. So, um, so basically I was like, okay, well I don't have, I could maybe do a boutique banker, but again, which one? I don't know who's good, who's not., you, you said you had a great lawyer. Cool. I got a lawyer. Is my lawyer great? Are they okay? Are they good? Like, how am I supposed to assess this? And by the time you, you figure out if your lawyer was good or not in a transaction, it's too late. It's too late. It's done. Same thing with tax strategy or negotiation, all these different components. And so I had talked about like, um, doing this process is like a very— fundraising is usually like an intense sprint. Uh, M&A is like an intense sprint. It's this couple month process that you work on really hard. It becomes your main focus. At the end of the day, you're trying to like get to this amazing endpoint. And I was like, I made the comparison. I was like, it's like birthing a baby and you go through this labor process and then by the end you like, you have the thing you wanted at the end. And so just like when you're having a baby, you, you, you might have a doula. A doula is somebody that kind of like, they're not your doctor, right? This, the doctor would be like your lawyer, right? Uh, they're not your nurse, which would be like maybe your, your CPA. Um, they're just somebody who's there to coach you, guide you, and they've been, they've seen the births of hundreds of babies, whereas this might be your first. And I talked about you need a deal doula. I was like, if you're gonna do a deal, if you're gonna do a transaction, you're gonna do a fundraising, you need a deal doula.
A deal doula.
It's different than a mentor. A mentor is this like general thing in life that's like gonna be your kind of like your, you know, the better version of your dad. And a deal doula specific, it's for this period of time. It's around one specific problem or process that you're going through. And I talked about how when I, when I sold my last company, I had these 5 deal doulas I started with, and eventually it ended up being these 2 that I was working with the most.
But like, I talked to— and, uh, who else?
Yeah, uh, there was this guy Fouad who I talked to who gave me great advice. Like, he told me one thing, like, each one of them told me like one thing that was really important. So that guy Dick was one of them. Uh, but like, for example, Fouad told me, he's like, You need to— he's like, oh cool. I was like so excited. I was like, look, we got this. Like, these guys are interested. They're about to give us a term sheet tomorrow. And he was like, you know, just sort of chuckling. And he's like, sure. I was like, oh, you don't think they'll do it? He's like, it'll happen. It's just every timeline you think of is wrong. Everything they say is gonna fall through and then come back and then half fall through again. He's like, this is the normal M&A process. So you might have an outlier where it just all goes smoothly, but like, If you're gonna have a normal M&A process, you should expect these bumps and bruises. And it's like, you know, going through these contractions, basically there's like painful ups and downs during the process. He also said, he's like, you need to turn your company into a giant buy button. I was like, what do you mean? He's like, you know when you go to Amazon, it's like one-click checkout. He's like, you think because these guys are giving you a term sheet, you're at the end. It's like, this is when you're gonna have to sprint the hardest. He's like, let me see your data room. I was like, oh, uh, yeah, we're, we're working on it. He's like, Wrong answer, bucko. Like, you know, you know, that's what you sh— you shouldn't be at lunch with me. You should be turning your company into a buy button. You need everything so organized, so precise, uh, ready for them, answer all of their questions.
Dude, did, did I show you my data room?
You did.
Yeah. I had a fire data room. Me and this woman named Edie, this woman named Edie who works with me, Edie's probably, I think she's in her sixties. And when I hired her, she was great, but she didn't like know how to use technology really. And I would, it would be like me and her on the phone with HubSpot and HubSpot would have like 5 representatives. Then they would have like 6 lawyers who are probably $2,000 an hour apiece. Then they would have like 6 accountants. And so like this meeting cost them $50,000 and it'd be Edie and I, and they would be asking us questions about different documents and we're like, oh yeah, we'll get it for you. And I remember them like having a list and Edie didn't know how to take a screenshot on a computer. And I just hear her constantly with her phone and every once in a while she would bring it up and their phone just taking, Taking pictures of the screen, and I just, and I would have to message her, Edie, put your phone on silent. I know what you're doing. And she was just taking pictures.
And we would, you know, we talked about fierce nerds. Edie is like a fierce grandmother. Like, I would go to your office and you'd be like, oh, how's, you know, how's your daughter? Like, she knows her name. She's like, remember my daughter's name. It's like, show me pictures. She was like so kind and cuddly. She'd be like, you submitted your invoice wrong, bitch. Like, you know what you're doing? Keep this shit organized. We're running a tight ship around here. And I was like, Yeah, well, this is— how did you find this woman? Because I was like, she's like the polar opposite of you. But she was so needed for what you guys had.
She was so needed. I've always been really good at finding those people because she was— she worked in banking for a long time, actually. And she was like really successful banking person. And she comes off as this like really nice, naive woman. It's like not even a little bit. She's like pretty— not sharky, but like she's— she'll get you because she worked in banking in Japan. Where she was like helping companies go public, I think at Morgan Stanley. So it's like, she's like a shark.
Say no more.
Yeah. And then she like raised her daughter. She had a daughter and decided not to work and raised her. And she came to me and she was like, uh, I don't really need the money, but I want a job to prove to my young daughter who just graduated college that, uh, I'm a badass and that women can be badasses. And I was like, oh yeah, cool. You're hired, Ed. Like, I love that. And, uh, she ended up being amazing. And I remember her during the due diligence process, I had to teach her how to use Dropbox and I had to teach her like some like pretty like basic computer stuff, like how to like copy and paste. And then she like bought a course on Udemy and stayed up all night and mastered it. And she's like, all right, I know how to do it now. But like, if I didn't show her how to do something, I would see her taking a screenshot. Like she would have her phone just up and you hear a click. And I'm like, Edie, they could see this. Anyway, sorry, go ahead.
She's amazing. I don't know what she's doing now, but like, uh, I need to hire her. Is she still working with you guys? Yeah, she's still there. Amazing. I would have thought like, you know, normally in like these acquisitions, they don't like bring on the finance team or whatever, but that's, that's amazing. I would never let her go. She's, she's so good. She was the most impressive. Honestly, I, I like you, but she was the most impressive person at the Hustle. She was wonderful, man. People know you, they know Troy, they know Steph. She was the most impressive person there.
Yeah, she was wonderful.
I don't even know what we're talking about this.
Oh, Deal Doola.
Here's the, here's the, I don't know if it's a business idea, but I hear, I know that if you're gonna do a transaction, you need somebody like this, which is every time I've done one of these things, I need this person. And here's what they teach me how to do. They teach me how to use the lawyers. They teach me how to use the accountants. They teach me how to do the negotiation because they've been through hundreds of these. So they know what to expect. So they can emotionally coach you when you're like going through ups and downs. Yeah. They're your therapist. They're your advisor on the business side of things and the negotiation. But that's honestly the least Usually that's pretty obvious about what you should do there. They're your, your speechwriter and your copywriter as you, you know, prepare to like, you know, write a pitch deck or, you know, a follow-up email or whatever it is. And the most important thing is they teach you how to use expensive lawyers and accountants. Because if you just go to a lawyer and you say, what should I do? You're going to end up with a document that's basically the Constitution. And it's like, oh great, you lawyered the shit out of this. But like, that wasn't what we needed in our business case. Like, you didn't. A lawyer, if you defer too much to the lawyer, they're gonna overlawyer things. If you don't, if you don't listen to the lawyer, you're gonna have too much liability. How do you find that line? That judgment is the most important thing. And judgment is something you can't really hack. There's no shortcuts to judgment. The closest thing you can get to it is partner up or borrow somebody else's judgment, one of these deal doula. So same thing on the fundraising side. You see a term sheet, you don't know all these terms. What do they mean? Should I agree to this liquidation preference? They, oh, they have this, you know, clawback thing. What, what is this? Should I agree? A, a deal doula is the one who can kind of teach you how to do that.
Or I love that.
You know, my tax person's suggesting this and they're gonna say, don't do that. It's gonna over— yes, that saves you in taxes, but it's gonna add deal risk over here because it's going to introduce delays and, and complexity that you don't want to have.
That's a really good, uh, it's been a really good idea.
It's been so indispensable to me. I'm like, I don't think there's a business cuz that normally these are successful business people. That's the only person you can get to do this and they don't want money for this. They're just doing it cuz they want to help you typically. Um, maybe somebody could make a business outta this, but even if they don't, my advice to any founder out there is if you're going through either a fundraising or an M&A process, make sure you have your deal duelist to keep you sane and keep you smart about how you're gonna go through the process.
Dude, there are so many things that I didn't even know, like I didn't even know to ask. For example, when people talk to me about selling their companies, they'll be like, well, you know, you really want to optimize for, time to close. So you want to like close as quickly as possible. Because in my head I was like, why does it matter? They gave you a thing. I'm like, well, just shit happens. For example, Brian Halligan, the CEO of HubSpot, got into a near-death accident 5 days after the deal closed. I'm like, if that happened at any other point, or if the economy changed, like just shit happens, or like the person leading the deal quits, like stuff changes all the time. And another thing that I didn't even notice, look for is like I would get these offers from these PE firms, from small businesses, from, And then HubSpot has a board, a board of directors. They're a huge company and they're like, well, we, we present the LOI before we gave it to you to our board of directors. And I was like, this isn't gonna go through, yada, yada, yada. Well, once the board approves it, the likelihood that it's gonna get done is quite high because the employees have to look good to the board and they already like, you know, they can't. Whereas you have another guy who's just like a, a, a smaller business and it's just the founder leading the deal. It's like, oh, he, he don't give a fuck. He'll bail at any point. Like he just, he's like, he, you know, it's their money. They're the, he, you know what I'm saying? Like the dynamics are different. And so there's all these things that I didn't quite understand that now I know that you really, it's hard to learn unless you've been there. Cause you don't even know what to ask.
With our last deal, one of the, we took the low, we took the second highest offer. Like, uh, we turned down the top offer and we took the second offer. And why was that? Well, there was like a bunch of intangible reasons. Maybe we preferred one over the other. But it was like, I personally left, I don't know, $1.5 million to $2 million total on the table, just me, on taking the second deal over the first deal, which is like, that was a lot of money to me. That wasn't small. That was meaningful. And the reason I did it, one of the reasons, there was a few, one was our team. We wanted our team to our whole team to go with the deal, then, and that was only gonna happen with the second one. That was probably the biggest reason, but there was some small reason like commute and stuff like that. Then the, but the other one was likelihood to close. Uh, yeah, they had told me, they go, look, yes, we've been a pain in the ass in negotiation. Like we're sticklers about this stuff. Like we, we don't move super fast, but the good news is that means we've thought it through and we've got our approvals already. Once we sign this thing, we will close and we will close on time. And he's like, that's the good news. The bad news is leading up to it, we're not the quickest, fastest dealmakers who are gonna promise you everything. It's like, we're only gonna promise you what we can deliver.
That's the ideal. We're gonna do it slow. That's the, that's the ideal setup, by the way.
And I didn't really know how to value it at the time. Like he was pitching it to me as a value and I was like, yeah, whatever. The other guys are offering more. Like, what do I care? Um, but in retrospect, that actually was quite an important thing because it's very important. 100% of the second best deal is better than no deal from the, from the best offer, right? Or, somebody who's going to try to retrade the deal in the last minute. Like, that's one of the worst signs you can have is somebody who comes back in, in the 11th hour trying to retrade the deal. And they told us that these guys were like, we're not going to retrade the deal. We are going to close. And so that's the good news. The bad news is it takes us longer to get to the term sheet and we're not necessarily going to be the top offer. We're going to offer you the best we can. And now I've learned that that's actually quite important in this process. But as a first time, first time going through it, I didn't know how to weight that. You also gave me some good advice, which was you were like, tell them everything. Tell them upfront all the reasons that they shouldn't buy you, all the skeletons in the closet, drag 'em out once. Okay. Not the very first meeting, but like once they're interested and it's getting to where like, hey, we're gonna make an offer, um, or we're making an offer, say, before we do that, I'm gonna literally brainstorm and try to figure out every reason why I think you maybe shouldn't do this deal. And, um, you know, hey, we don't have our ducks in a row on this. Um, this is an unknown. This is like a contract dispute we're in, but whatever they may be, right? You, you have to drag those out and basically let somebody run away then because it is far less painful and less wasteful to let them run away then. They're gonna find it out. No deal closes without the final. So they're gonna find it out no matter what your instinct is. Ooh, don't tell 'em. That's a, that's always the first-time entrepreneur's instinct.. It was my instinct the first time. And then somebody gave me this advice. You gave it to me also, which was, no, no, no, don't do that. Just tell them what's great, what's bad about your business. You're going to get in bed together. They need to know both sides of it.
And if you lie, you're getting sued anyway.
You're on the hook. You definitely can't lie. You definitely can't lie. That's obvious. But you can't even just hope they don't see it or don't find it because they're going to see it or find it.
And then they're going to say, and they'll say, What the fuck?
You did close this? Yeah. Yeah.
What else are you telling me?
And so it was actually a mega trust builder to do that. Um, you know, when we sold the, the first company. So those are some of the things that you kind of only learned through these deal. You don't, you don't learn that except through either experience or talking with people who are experienced. So anyways, that's my rant on Deal Duel. It's, it's a, I, I think a very underrated thing.
We went, we've covered it all. We've, we, this has been a, this has been a rollercoaster of an episode.
Dude, there was a comment on YouTube about a guy unsubscribing. He goes, ah, I'm unsubscribing. Last few episodes haven't been great.
I replied, I said, good.
Yeah, you said good. Some other guy was like, man, what are you talking about? These guys are trying to hurt— I said, over my dead body. I now work for you. You know, Big Booty 357 on YouTube. I now work for you. I am motivated beyond belief to come with the fire every time.
One guy wrote, these guys are great, comma, overall. And I was like, oh, that's a good dig.
You got me. That's great. That's an amazing one. The, um, it's, remember Petty Court? It's Petty Court and court is in session. Uh, that's how I feel when I read the YouTube comments.
Yeah, that, that, that was a good one. The comments are actually quite good.
You had such a funny, um, Such a funny joke in a group chat where it was the, the no offense thing. And then the, uh, with all due respect.
With all due respect.
You're an ugly dude with all due respect.
It's like when people start sentences saying, I'm not racist, but, uh, it's like, oh, okay. The other thing that I hate when people say is Well, at least he's honest. I'm like, what? But his honest opinion sucks. I don't care if he's honest. Like, I don't—
he's a straight shooter. So you shooting bullshit though? Yeah.
Yeah. Like, you straight shooter.
Yeah.
But what you say is stupid. And I just— you know what I mean? It's like dumb. I hate it. I've always hated that excuse.
Oh, man. Good times. All right, we're out.