Sam Parr - Raising Normal Kids After a Major Exit

I'm incredibly nervous for my child growing up in a wealthy household. I've been reading books on like dynasty families and things like that and like, is it even worth it to give your kids money? Is it not worth it? My takeaway, by the way, is currently I think it's hard to live a fancy life. You will almost always have a spoiled kid, it seems.

Hello, fellow data nerds. My guest today, Sam Parr. Sam is the co-host of the My First Million podcast and the founder of Hampton, a community of entrepreneurs and founders. Sam previously founded The Hustle, which was a business and tech newsletter that was acquired by HubSpot for $27 million in 2021.

Reportedly.

Reportedly. I'm sorry, reportedly. Sam, welcome to World of Das.

What's going on, man?

How are you? Good. Great to see you. Uh, great to see you again. Now, um, I— one of the things I'm like, always troubles me is like, what advice do you give to a founder about branding? I feel like us founders, we just don't understand branding that well.

I think it's way more important than people realize. I think that I'm not particularly an expert on it, but I think the bar's low in the internet world. But I like to study the experts, and so I hopefully have learned a thing or two, but I'm definitely not the expert. I think that, I think that brand, you know, Peter Thiel has that book, what's his book called?

Uh, Zero to One. Zero to One books.

And he has this whole chapter on like competitive advantages, and one of the competitive advantages is brand, I think he says. And then I think he says something like, this chapter is going to be short because frankly, I don't understand it. Doesn't he say something like that?

Yeah.

And I maybe understand it a little bit, but I can't imagine more than Peter. But I think that it is hard to understand because it's not— it doesn't make a lot of sense in terms of like conversion rate or in terms of um, like direct ROI. It's about what it makes you feel. And I think that a lot of startups, particularly if you're a second-time founder where you, like, you know you're gonna follow through on something and you know you're gonna build a big business, I think they don't spend time on branding because they think that that is like a procrastination thing. They think that, like, and, and I agree, if you're like a new entrepreneur, and you spend too much time on branding, I'm like, dude, just make a product that people actually like. But if you are like proven that you can do that, or you're going to be attempting to do that, I think you should put more emphasis on the brand than you more— than you likely think you should. Does that— do you know what I mean?

Yeah, yeah. It's interesting because in the B2C world, when B2C companies buy other B2C companies, they never kill the brand. They always keep the brand going, you know. They always keep Instagram, keep YouTube. Procter Gamble doesn't have like Procter Gamble toothpaste. Paste or something like they have crust. Um, but in the B2B world, when they buy things, they sometimes kill the brand. They'll say now it's the Oracle Marketing Cloud email solution, or the Salesforce— they, they kind of kill this old brand that people loved. Um, you know, if you remember EchoSign, Jason Lemkin's company, like they, they, they, they rebranded Adobe Sign. Uh, but they somehow— there's something different in the B2B world than the B2C world.

Yeah, and I have a strong opinion on that, which is B2B people, they, they get silly. So a lot of B2B people think that a human being is one human from 9 to 5 and another human from 5 to midnight. Yeah, that's obviously false. I can be on this podcast, which is a B2B podcast, but I can make silly jokes and we could have a good time and we could talk about like silly fun stuff. A human being is a holistic person, but the nerds want to convince you that that's not the case. And I try to, I'm like, and that bothers me. Um, you know what I mean? Like, there's a reason why, like, the Joe Rogans of the world have excelled, which is like, you can have, um, very, you know, he has Bernie Sanders on his podcast or some other presidential candidate, and also he'll like make silly fart jokes. Like, you can, you can do all of it. And like, a B2B company doesn't have to like be crude. But they can be— if they want to be silly, they could be silly, you know what I mean? You could be a lot of different things. You don't have to be so uptight. And I think that's a struggle because no one wants to get fired. And yeah, I think that we should take a little bit more risk though. And I'm— and the risks I'm suggesting oftentimes aren't even that big.

Yeah, they don't sound that big at all. Now, you know, it's pretty easy to find out if someone's like a good engineering hire. I can figure out if someone's a good engineer very, very quickly. But it's much, much, much harder to figure out if someone's good at marketing. Like, how does one do a better job of evaluating that?

I ask them what content they consume and they'll, um, so I, I usually ask, I say, hey, every morning when you go on the internet, um, where do you go to and why and what's interesting about that? I then will ask them, like, if they say they go to Reddit, I say, what subreddits? And why.

Yeah.

Another thing that I tend to do is I call it the bottom fourth of the resume. And so I'll ask, let's say if they studied philosophy, I don't really know anything about philosophy, but I'll be like, all right, cool. What was the best class? And if they can't tell me an interesting story about a thing that they spent potentially hundreds of thousands of dollars and 4 years of their life on, if they can't tell me a good story or like convince me why it's like a good thing to study, then they're just not that interesting of a person. And if they're not that interesting of a person, then they're probably not gonna be good at that job.

So storytelling is kind of a key piece of— because that's a— that's something I think you could maybe interview for, is being able to tell stories.

Yeah, or the ability to have taste. And having taste is hard, but like, you don't always have to be the best storyteller, but you have to understand what the best story is. Do you know what I mean? So like, you don't always have to do the job the best, but you have to be at least pretty good. And you got to be able to say like, oh no, trust me, this is like this is a hit. Like you hear, you feel this emotion, you see how that makes people feel. That's a hit. That's what we want people to feel. I'm not always the best storyteller. I'm pretty good though at like seeing like, no, that's the thing. That's the angle. That's a pretty cool angle. And so I think that I ask people about the bottom fourth of the resume and I ask them about what they read or what they consume.

Is there a way of like, is kind of enthusiasm important? Like if they can make it somewhat contagious or something?

Yeah. Yeah, contagious. That's the whole thing. I'm on a Ralph Lauren kick right now.

I can tell. For those of you not watching on video, I can see it right here.

Yeah, and I've bought into it. So I'll tell you why I'm on a Ralph Lauren kick. So Ralph Lauren, the entrepreneur, I like the brand as well, but the entrepreneur Ralph, he grew up in the 1940s and 1950s in the Bronx as a Jewish kid, but he was obsessed with the American dream. He changed his name from Lef, Ralph Lifshitz to Ralph Lauren because he wanted like a very American name because he was fascinated with classic traditional America. And, um, he does such a great job— I'm reading his books— of selling me on the American dream and selling me on class and selling me on timeless. And it just so happens that the way he expresses that feeling is via clothing. And so I love these people that do a really good job of selling me a feeling or an idea, and it just so happens that our software, our product, or whatever, it's just one little piece of helping you get into that, uh, into that mindset. Do you understand what I'm saying?

Yeah, totally.

So, and so, like, let's say the American Dream, Ralph Lauren style, or Ralph Lauren's way of branding, that could be used for homes, it could be used for cars, it could be used for clothing, it could be used for a variety of products, but he's selling this lifestyle And I think that with a lot of B2B stuff, you aren't necessarily selling a lifestyle, or you don't have to be, I think, but you should be selling a feeling.

I love like that friend that is like super into something and then they take you on that journey with them. They're like, these are the best dumplings in the world, and they kind of describe it and then they bring you in and these— maybe the dumplings actually aren't that great, but like when you taste them with your friend there, you think they're the best dumplings in the world. Like you have this like incredible experience because you're seeing—

because that enthusiasm is contagious, correct?

Yeah.

And so I like being around those people.

Yeah, they're, they're amazing to be around. They're so— it is rare though. I feel like that is like people, oh yeah, you know, it's, it's that, that like it's this positivity that it's like maybe less cool when you're smart or something.

Well, I think to get really philosophical, but I think that the world wants you to be vanilla. They don't want you to stick out. And particularly at a company, oftentimes you don't want to stick out. You don't want to get fired.

Yeah.

So we do too bad of a job where you'll ask a coworker or an employee, hey, do you think that this thing that we're doing is good? And they'll say like, no, I think it like, maybe like it's not the right way to do it. And I'm like, well, why the hell didn't you speak up and like tell me? Because I will listen to you. I'll follow your feedback. And so like, it's a really hard thing to pull off, but you have to create a culture where like these like interesting ideas kind of surface.

Now you built kind of a mass media brand and now you're building a more kind of exclusive brand with Hampton. Um, maybe you went, you know, let's say like now you're kind of building like a new Ralph Lauren-ish thing. Like, how are they the same and kind of how they're— how are they different?

So my first company was called The Hustle. I don't know how many people read it a day, but maybe 3 million people a day, and we sold it to HubSpot. And I like to, I love news, I love Ted Turner. He's the guy who started CNN. I found him to be very romantic, like the idea of like a Southern guy from Georgia kind of taking over New York media. And I thought that that was really like novel and romantic. I really loved that idea. And I was from Missouri and Tennessee, and I moved up to San Francisco, and I was like, I wanna take over the news scene. And like, you know, I felt invigorated. And I wanted like this like edgy, cool, unique vibe. And we brought that to newsletters. And at the time everyone thought that newsletters were silly. I talked to one executive of a huge media company, an entrepreneur who you definitely know, and he was like, this is never going to make more than $1 million a year. And a lot of these businesses in my space, I sold too early, but a lot of the peers in my cohort, They are doing $80 or $90 million in revenue. And so like the bet was right, but I sold too early. But, and so what I learned with the hustle was it was awesome. I just wish that I could have monetized an audience differently than advertising ads because that's an exhausting way to make a living. I think that, you know, there's only, there's two ways to monetize an audience. You either sell your own stuff or you sell someone else's stuff. Stuff. And I would rather have done the first one. And so when I was thinking of which products and services I could make with Hampton, I had a friend who— he's now my business partner, but at the time he's my friend. And we used to like share everything with each other. We would share like our net worth, our income, our relationship issues with that. And it kind of changed my life. And I was like, let's just do this for all types of people. And that was the idea for Hampton.

Oh, that's so cool. And is it— but in, in something that's like more exclusive, like it's a little bit harder to join, or there's gates to join, etc., like building a brand is, is also— is different. Maybe it's a little bit more aspirational. Um, you know, I don't know that like Rolls-Royce is advertising on the Super Bowl or something. Um, like how, how does one kind of think about building the brand there?

That makes it really hard. So there's brands that have pulled it off, like a Louis Vuitton, or like somebody's luxury goods, like they're able to advertise a fair bit. But the, the, the crappy part about, so first of all, I will say with a community, I know that it looks like we are trading off of like cool and exclusive. That's not my goal because cool and exclusive, if you screw it up, it can go away. Yeah.

It's fickle.

It's fickle. I have to trade off of utility where like this actually makes your company or your life better. And so our, and so we remind our team all the time, don't trade off this cool nonsense. This will go away or it could go away. You trade off utility. Like, this is actually awesome.

Actually helpful.

Yeah. It actually has to be like a great product, not just a brand. And so the— but the crappy part is, is that like we've done just a very small amount of paid advertising, but like we don't want to do paid ads even though that would grow our company more. It kind of makes you look bad. Yeah, totally. So the bad part about a community business is that you can't grow it too fast, otherwise it gets ruined. And so we throw away so much revenue, people who have applied to join and we say no, and it breaks my heart because we'd probably have like $60 million in revenue right now and we don't. Um, but you just kind of have to do that in hopes that that will pay for, you know, pay dividends in the long run.

Now part of a community I imagine is you've got a cult a certain number of people. You essentially have to like fire a certain number of customers that are, um, not adding well, or maybe even negative add to the other people in the community. And if you're running like a software company, you'd never really like fire your customer, or maybe you would, but it would be a pretty extreme event to go do that. Like, how do you— that, that's obviously makes a bit building a community business a bit harder because you have this kind of like forced churn in it. How do you, how do you think about that?

It makes it awful, to be honest. Like, I mean, like a lot of people see the success of Hampton on the outside and they think like it's easy and stuff, or I don't know if they think that, but maybe, but like, these are the constant battles we have all day, which is like, how do you like grow the business without ruining the product? And, and so the number one metric that we care about is retention. And so, uh, if we nail retention, we'll eventually make a lot of money. But yeah, it's like that. It is a very hard part of the business. You just have to, yeah, you just gotta make the sacrifice of like, I, knock on wood, I hope this is gonna work where we're gonna lose all this money or not, we're not losing money, but like we're gonna turn away all this money on purpose that it's gonna pay off in the long run. And I hope it, I hope it does. And I'd be honest if I'd say that I'm certain that it will, but like I have to do a lot of work and a lot of faith to make sure that it We pull it off.

Now, you mentioned that you wish you didn't sell The Hustle. I have a kind of a similar thing where I didn't— I wish I didn't sell LiveRamp. Um, what—

how big— how big is LiveRamp now, by the way?

Uh, LiveRamp is maybe $600 million, like a $1.5 billion market cap company. Um, and, uh, and I think if we were still running it, hopefully it would be much bigger.

How big, uh, was it when you sold it?

It was almost 40 ARR. We sold it for 310. And so the, but yeah, I mean, in some ways, like, I wish we were, you know, I wish what I knew a year later I knew, 'cause then we wouldn't have sold it. But I didn't know that at the time.

Can I ask you one more question? And then, because this is context, were you wealthy before you sold it?

If you're enjoying this podcast, please sign up for our newsletter. Go to worldofdas. The link is in the description below. Now back to the video. No, um, so that was, so that was the big thing. Like, it, it changed my life. And I had kids, and those, now I could take care of my kids. So it was pretty, it was, it was, um, it's funny because my wife had a company that sold like 6 months later. One of my other friends that I was involved with had a company that sold 6 months later. If those had sold 6 months before, I would have never, also never sold, because then we would have had enough also to maybe take care of our kids.

Yeah, well, that's what I was gonna say. So I don't regret selling. I would've done the same thing over again.

What I regret was not being wealthy, was not being wealthy in advance. Like, totally.

Like, you know, like it, it's such a cool company and it was such a cool idea and it had legs to run and get big and, and, and it's exciting. But, you know, I didn't, I, I, for the first 2 years, I think I paid myself $50,000 a year and then the 3rd year, maybe $150,000. And then the 4th year I paid myself a lot. And so I started like making money in the 4th and 5th year, but I sold it in year 4 or 4, between 4 or 5. And I wish I had been wealthy. I wish I didn't have to sell it. And so I don't regret it, but I regret like it would've been nice to, like, for example, had I run the business differently, I would've paid myself a whole lot more money and not have acted. I sold it a little bit defensively. As opposed to being on the offense.

Yeah, but like, it's probably— you could have maybe done a secondary and sold 30% of it or something. And you know, there, there could have been other options, and I probably could have done that too, but I didn't really like think it all through.

I didn't think it all through either. I, I didn't think it all through. I had an offer and I liked the company.

Yeah, yeah, same.

Yeah, the offer ended up being like— I— we made a lot more money than like what the headlines As, uh, have said, um, because this, a bunch of things kind of worked out, but, um, I don't regret that. I just wish, I also wish I would've owned the company when I was older. So I started the business like roughly at age 25. Um, and I was pretty immature. I, I don't think I was a very mature 25-year-old. If I ran the business now, I think I would've like killed it. Uh, because, because, because media, dude, think about this. We had a daily email that went out 6 days a week. So I have a deliverable like every day and it's like, yeah, pretty hard. And each time we hit send on an email, it would be like $100,000.

Yeah.

Um, and so like it felt like very stressful, but it didn't have to feel that way.

Interesting. Now what advice would you give to founders about like preserving their own brand and also preserving their own identity post-exit, like kind of post-exit advice?

I didn't really have that. I know, I think some people have that issue where they're like, what am I without this thing? I didn't have that. The way that I saw it was, you know, people say like, this company is my baby. Um, I think my baby's my baby, and I think my company is my job. Um, and so like, I, I was fairly good at like being like— have you heard of negative visualization?

Uh, where you like kind of like specifically look at the negative to help you understand the positive or something?

Yeah, you like have these like you like sit down and meditate and you're like, my children has cancer, my mother just died in my arms, I just lost my leg and I can't ever run ever. Like, you like, you like picture all the worst things in the world and then you open your eyes and you think, well, that's not true, I'm okay. Like, I'm so grateful. Like, isn't life beautiful?

And like, oh, interesting. So it's like a, it's like a helpful way of like thinking of that life and stuff.

Yeah, it's basically like imagine all life is horrible and it makes you appreciate what you have. And I used to do that all the time with the company of like, just assume this is going to go out of business next week. And I kind of, because I did that, I was like, okay, if it goes away, I'm whatever.

Do you do that with your personal life too? Do you visualize like something, you know, a terrible plane accident or something or those types of things?

Yeah, yeah, I do it. And that's actually a lot harder. But yeah, but like I try to think, I just, I work my ass off at trying to be like grateful to what I have. I mean, I don't know what your background is, but like I didn't grow up around a lot of this stuff. And so I have to pinch myself and realize that the conversations that I'm having with a lot of people around how you had a company that you sold for $310 million and, but were bummed out about X, Y, and Z. I try to remind myself like, exactly. You know, like high class problems. And, and, and I don't like when people say, oh, that's a first world problem because first world problems are still problem. And, and it's okay to have a, And it's okay to have a problem when you're like wealthy and successful, and I don't wanna diminish that, but at the same time, I wanna remind myself like, uh, uh, you know, it, it, I could be worrying about many other things. Um, and, and exactly because particularly if you live in New York and Silicon Valley where you're only around like ballers and we're all complaining about like trivial shit. And I have to remind myself, I'm like, you know, like, um, there's some nurse, a single, single mother nurse who's like saving someone's life right now, you know, worry. And then while she's gotta worry about like, you know, taking care of her kid at home, like that's actually way more important than like these trivial things I'm worrying about.

How do you give it like wor— for people who are like kind of worried about keeping up with the Joneses and stuff like that? Like how do you help them think about those things?

I've been lucky that I have this podcast called MoneyWise and My First Million. Yeah. So I'm able to talk to all these really wealthy people and I have to remind myself that just because you have a lot of money doesn't mean you're gonna be happy. And that I think that when I see a lot of rich people with a lot of stuff, I think I definitely have to fight jealousy or like when I meet you and you sold your company for $310 million and that's more than mine. I'm like, well, I want to do that. But I have to remind myself that like, that's not what's important necessarily. What's important is like, are you happy and are you a good parent? And so I always have to remind myself that constantly. But yeah, I definitely fight urges of like—

and you have kids?

Yeah, I have a 1-year-old.

How do you think about that? Like, how do you think about that on the parenting side and stuff?

For one, I'm nervous. I'm incredibly nervous for my child.

You're nervous about what?

Growing up in a wealthy household.

Oh, okay.

Yeah, yeah, that freaks me out. Like, like, I, I stay up all night. Like, I've, I've been reading books on like dynasty families and things like that, and like wondering about like charity and like, is it even worth it to give your kids money? Is it not worth it?

Yeah. So I'm like, yeah, do you want to fly, you know, business class or not? Yeah.

Like, how do you want to fly? Like, and my takeaway, by the way, is currently I think it's hard to live a fancy life. And I'm not like, you will almost always have a spoiled kid, it seems. Uh, just, but, but all my learning has been academic, not realistic because my kid's brand new. Um, but, um, So with that, I'm nervous about that. I'm— I also, um, have come to the conclusion that, um, it's important for your child to see you work at least 30 hours a week.

Yes.

Um, they will get—

they will benefit a lot from that for sure.

Like a— like some type of— like however long a school day is, like you should be doing something like that long.

Yeah, potentially even more to see a little bit more.

Yeah, yeah, yeah. Whatever it is, like some amount of work I know, and having a kid makes you realize—

you have a girl or a boy?

A little girl.

Yeah.

Having a little girl has made me realize that the things that I thought important about, that were important about business and making money and chasing status, which I was all about, that's just way less important after you have some type of financial security. It's just not, it's just insignificant when it comes to like being a good parent. Um, do you know what I mean? Yeah. Um, and you know, like particularly seeing my wife pregnant and when she, we miscarried before we had my first kid and like no amount of money fixes that problem. And there's a whole bunch of like stuff with your kid that money and power and influence and likability, that shit doesn't matter. It doesn't matter at all. And so it kind of like is like a unique situation to feel helpless and I kind of enjoy it in a weird way. Like it's kind of nice to like be like, oh, I'm nothing.

On— I have these kind of couple theories on, on wealth and kids. The first one is, I think what you— the ideal situation is you want to get like super wealthy right before your kids are born and have all this wealth until they're like 5 or 6 years old, because it's super helpful when they're little.

Yeah, it's like the greatest thing on Earth.

You want to be able to afford that, right?

Exactly.

Then you want to like magically lose it all and go back to like just a normal middle-class lifestyle, um, until they're like 20, and then you want to like magically get it all back.

Is that what you're doing?

So like, do you know, like, it's impossible. That's the opposite, because most people like get wealthier over time, right?

So they're like, what age did you, uh, cross some type of threshold where you were like, I feel comfortable?

Well, how old are my kids? No, you, uh, let's say 4, you know, around 40.

And you're— so then your children were not babies?

No, I had kids— my first kid when I was 37.

Okay, so they were, you know, yeah, so they're still pretty young.

Yep.

Yeah, well, um, but I do think it's possible to dial it back a little bit, but maybe I'm being too naive.

It's definitely possible. Um, one of the other things I've seen is that, you know, as you— we, we know a lot of people who are also very fortunate people, and their kids are amazing. And, and some of them are teenagers, some are in college, and you meet them. And so there are ways to— there are ways to— I'm much— when I was younger, I was much more worried about it like you are now. And I constantly— my wife and I constantly talked about it. What are we going to do better? How are we going to do this? How are we going to make sure our kids aren't spoiled? We talked about it like all the time. Like, it was, it was like a topic of conversation like almost every dinner. It was like that kind of, that kind of acute, like, what are we gonna do? And nowadays we're just like much less worried about it because we see so many other people who have been able to make it happen. Doesn't mean we'll make it happen, um, but there's just like so much evidence that it's possible to do it.

Yeah, well, I think that's rooted in— did you grow up in a wealthy family or— no. Neither did I. And so I just assumed that every rich kid was unhealthy. And my wife grew up around wealthy people in a, in a, in a very successful family. And she was like, no, that's not true. Like all of, like most of, like you, she was like, you love all of my friends, right? I was like, yeah, there's like 8 of your friends that I think are like some of the best women I've ever met in my life. And she was like, you know, they're all rich, right? And I was like, you're right. Like, what am I?

I just like, and so this is like a, this is a story we like, there are screwed up people who are wealthy, or screwed up people who are poor, there's screwed up people middle class, there's screwed up people everywhere. And then there are non-screwed up people everywhere too. Like, it's just, it's, it, it's— I don't know where the correlation is, but I don't know either.

Yeah, it should be like, Sam, you know that like 8, you know, like 6 of your friends are like drug addicts? I'm like, oh yeah, that's right. Like, like, there's like no— there's no— I, I don't think there's a correlation, but we make up this story, correct? I think it's okay to be paranoid.

Now, you are a student of communities, um, and you studied a lot of communities before starting Hampton. What did you— what are the types of communities that you studied?

So when I started The Hustle, I like did this math. I'm like, you know, I think if you have this many subscribers and you charge this much money for ads, I think you could get to $100 million in revenue. And people laughed at me and I'm like, guys, like, do you believe that? Is this the going rate for advertising? And they're like, yeah. I'm like, all right. Are there this many people in the world who'd wanna subscribe to this? Yeah. But still that number doesn't work out. It's the same way with community where there's a lot of, there's a lot of my goal with the community. I wanted to build a multi-billion dollar company and there was a lot of like people who are like, this can't be possible. And so I actually found a bunch of them. So I'll give you, um, uh, maybe two examples. Um, so there's one company called World 50.

Have you heard of World 50? Oh my God, I love that company.

Amazing. I have—

so it's a successful company.

They recently sold, so I was like the second or third time, right? Or yeah, or yeah. And they sold for $2 billion, or what, between $1.5 and $2. I forget the exact number, something like that. It's a company where if you are basically a Fortune 5000 executive, World50 stands for, well, 50-person communities. So they have a CFO community, a CMO community, a CIO. And if you're a Fortune 5000 executive, you join this community and you get access to an online community. And then you also go to a variety of events and maybe you get one or two perks, but something like that. It costs ranges between $50,000 to $80,000 a year, and they're doing well over $100 million a year of EBITDA. So we're talking like maybe at this point 150, it could be 150 million and probably more.

Yeah.

I mean, yeah. Or more. I just, the data that I saw was 3 years old. Um, and that company sold for roughly 15 times that, uh, $100 million plus profit.

EBITDA.

Yeah. Uh, there's another company called Vistage. Vistage. Um, what Hampton is doing is very similar to Vistage. They have something like 40,000 small business owners who are members. They do meetings once a month with your, uh, core group, and they charge around, uh, $1,000 to $2,000 a month depending on your company size. They are doing like $200 million a year in EBITDA. So Vistage— the Vistage is, uh, Vistage and World 50 are two communities, but there's like maybe 3 or 4 or 5 more communities that I know of that are multi-billion dollar companies. So it's shockingly big. It's just that, um, when a lot of people think of communities, they think of like small business, like, um, like free communities. And they don't realize that like some of these things could be substantial. That now the downside, all those companies that I just, uh, mentioned are— Vistage is, um, 70 years old or '60s, I think, uh, it was launched. Uh, World 50 was launched in '05. So like they, they, they're 20 years old. Yeah. They're, they're not new. And so it takes a while to grow.

But you can grow it effectively, you can grow it profitably. You don't have to raise money oftentimes, right? In fact, maybe raising money will maybe even like make it worse.

I think it's bad. I think I spoke to Chief, uh, Chief is, uh, chief.com. It's a community, uh, mostly for female executives. And, um, I think that the CEO there, I think she's a really good leader. Um, I've talked to her a bit. I think she's fantastic. But the problem was, is that they raised $100 million. Wow. And VC funding. And when you do that, you have an obligation to grow really fast. And I think that she could have built it.

Then you're going to make, then you're going to make these quality decisions like we talked about earlier, and you're going to go for the revenue as opposed to the quality, make some short-term decisions.

Yeah. And I think that she could have built that huge business. Without taking any of that money. But she lived in New York and maybe was like inspired by people who I frankly think that was a bad decision.

Uh, yeah.

And so it sucks.

Yeah. In fact, I think— I feel like I'm seeing so many businesses recently where you meet these founders, they've got— they've got a great idea, and so they're— but their default is still like raising money. In so many cases, it seems like the wrong decision.

It seems like the wrong decision because When you ask them, I'm like, hey, have you done the math? Do you realize that, like, like, you know, this is crude to talk about, but it's the truth. It's like, you know, you're going to get richer if you don't raise money, and your lifestyle is going to be better. Yeah. And also the third point, which is more important to the customer, the product will probably be a little bit better.

Yeah.

Uh, and so it's like a win-win-win. It's just, um, it was easy for me because I had an audience, so, uh, it's easy for me to talk about, uh, and criticize But I don't know, I feel like a company like Chief, they would have took off no matter what. Um, and I wish they would have not raised funding because I think the world needs their product.

Now we kind of— we live in this time now where it's the bowling alone time. We're less likely to know our neighbor, we're less likely to do— have a religious attendance. You know, people are kind of like in some ways like starving for a community. Um, is that just part of being human? Like, is community just something that we all humans want?

Yeah. And remote made it more challenging. And so we're pivoting our company. Um, we're actually, uh, uh, so the way Hampton works is you join and you have access to an online community where you can talk to like thousands of members. But we have, you have a monthly meeting where you meet with 8 people who have a similar size. Well, it used to be digital. Now we switched it all. So where it's happening in person, which is a logistical nightmare, but I think it's a way better moat. And so we're actually switching. Um, and so we actually already have groups meeting in real life right now. Um, and people are begging for it. They're like, I'll drive an hour to go, uh, once a month. Like, I, I like— and I'm one of those people, by the way. I'm like, uh, I— we built Hampton remotely with remote— a remote team all over the country. I regret it. Uh, I'm like, oh man, we should have all done it in New York.

Uh, interesting.

Yeah, it was a huge error.

Now, you, you're also kind of a— you just— because of Hustle and stuff. You're kind of a student of media. What are some of like— what are, what, what are the like the independent media companies you really admire the most today?

Um, let's think, in which category?

Um, like, I mean, you've studied all— just like you study communities, you've studied so many media companies over the years.

So I like companies that take money from their customer and not from the just the advertiser. I think that makes a huge difference.

So there's maybe an event that's involved or there's some other type of thing, or—

Yeah, like I'll give you an example. The Hustle, um, we— SoFi was an advertiser. Yeah, but, but their CEO— don't quote me on this, but yeah, I mean, I have to Google it. Something happened with their CEO where he did something Not cool. I forget exactly what he did, so I don't even want to say it, but something that was in the headlines where it was like lame, like where you read it and you're like, oh, you're not a good person if you did what you're accused of. And I remember our team was like, you can't talk about that. And I'm like, no, I'm talking about this. And I don't give a shit about their revenue. Like, you know, they can go fuck themselves. Who cares? We're talking about this. And then I remember one of my coworkers was like, but I sold them the ad and I'm not going to get paid my commission. And my heart broke because I cared about her, but I don't give a shit about SoFi. Yeah. And so I was like, oh man, this sucks. Like, this is like— I'm like, I will make you happy before the audience because I, because I care about you. So anyway, I care about companies that, uh, they are paid for by their, by their, by their customers. So I like the information. Um, I love, um, I love Flash and Flames. Do you know Flash and Flames?

No, I've never heard of them.

So Flash and Flames is my absolute favorite blog on media and B2B media companies. Oh, okay. It's run by one guy and it charges, he charges $400 a year and he produces 3 or 4 articles a week and I pay him money and I get a great service that I look forward to. He makes probably just barely enough money to make a, make an income. Yeah. And I love that. So I love Flash and Flames.

Oh my gosh, that sounds so cool.

Uh, that's probably my— that's for sure my favorite one.

So it's kind of this like artisanal, like, media in a way.

Yeah, but the goal is not to be artisanal. The goal is probably like a 65-year-old or 60-year-old that he's like, I just love this stuff, I'm just gonna write about it. Yeah. And so I love the idea where the editorial team is like pirates and they don't owe anyone anything. Um, I subscribe to The Wall Street Journal, so I like, uh, The Wall Street Journal. I pay, I pay money for that. And do you know who I shockingly love? I love Business Insider.

Uh, oh, interesting.

I really like—

surprised. Okay.

I love fashion.

You pay for it?

Yeah, I pay $100 a year for it. Okay. Um, I try my hardest to pay for things that I like. I think that— I think that we have to incentivize that type of behavior. So I actually like Business Insider, um, and I read Reddit like crazy, but I don't really read, by the way, any political news. I'm like fairly not up to date on politics.

Yeah.

It makes me—

that's a very healthy— that makes you happier.

It makes me very stressed. What I hear— I'll give you kind of like my media journal or my media way of living is I read probably 1 to 2 books a week, not because I'm trying to read fast, but like at night when we put the baby down at 7:30, I just, we just don't turn the TV on and I just like to sit there and read. And then what I do is I buy the book and I buy it for Kindle and I read it on my Kindle and then I download it illegally as a PDF and I upload the PDF to ChatGPT and then I ask it questions as I'm reading. Like, uh, oh, oh, that's cool. Where I'll be like, um, I'm reading this.

You make it, you make kind of an inter— you're almost having like interactive conversation with the author while you're reading it.

Yeah. And I, and the reason I always say it this way is like I do download it illegally because I need it in PDF format. But I always pay for the book, so I'm not stealing. She pay for it.

It's interesting. So have you used like NotebookLM at all?

Yeah. So I just, I've been using ChatGPT, but yeah, everyone said NotebookLM is better. And so I, and it is totally better. So what I do is I download the PDF, I upload it to NotebookLM or ChatGPT previously, and I'll be like, um, I'm reading this great book by David Nassaw about Andrew Carnegie. Andrew Carnegie lived in the 1800s. And so the dollar signs or the dollar figures are kind of hard for me to understand. So I'll be like, hey, Uh, he built the Keystone Bridge. Um, you know, how much, how much money did he use in today's money to like, yeah, yeah, yeah. You know what I mean? Or, uh, you know, he referenced his mother, but I forget what did his mother say to him when he was a kid? Like, like I use it for that reason. That's cool.

And have you tried, tried to like up, like, okay, you have the book that you put in PDF, but like that, that author probably has like 50 podcasts that they've done on the book and a whole bunch of other types of like nuance and maybe a few other articles around that. And maybe a few other like Andrew Carnegie, like Wikipedia things you could, Could you like, have you ever decided to like throw all that into NotebookLM?

Yeah, so if you particularly, if you read history, um, a lot of the books that you can find for free on Google Scholar because they're out of copyright, and so I'll upload those. And you could also upload YouTube videos, you just type in the YouTube video in there. And so I'll have like an— so like for example, I'm obsessed, I go through like obsessions. Um, I, uh, just finished like an obsession with the Kennedy family, and so I actually read 7 books on different Kennedy members.

I upload all of them and I'll be like, um, you know, and Ethel Kennedy just died. So, which is, uh, uh, very—

when did she die?

Uh, I mean, we're, we're, we're taping this October 14th. It was first week of October 2024. Oh wow.

RIP. I didn't know that. Um, and so I, um, like Joe Kennedy, JFK's father, he set up these amazing trusts and I'm reading about JFK Jr. So he's the, the grandson of the patriarch.

Yeah.

And I'm like, damn, he still had money. That's crazy that the money went to the grandkids. Tell me about the trust that Joe Kennedy said he set up. And how much was it that JFK Jr. had? Do you know what I mean?

Like, I get like, you know what's cool is like, yeah, because if you're reading, like sometimes I'll do that in a theme as well. I start reading a theme, as you mentioned, like all the Kennedys. And if you're reading all the cases, like you may also even have like a World War II piece of the theme and a Cold War theme and like a— and you know, you could put it all in a book because they all kind of feed off one another.

Yeah. And the World War II stuff is actually another great example. I've done that before where like I'll be like, dude, I still don't understand this. Why was Hitler angry at this group of people? Like, I, like, what's the— you have to tell me the background of like World War I, not World War II. Like, I don't understand all this. Like, yeah, like, you know, like give me context here. Like, what, what was the angry— like, I don't know where this hate come from. And they'll have to explain these complicated topics, but they use my sources and books.

Uh, interesting. That's cool. I'm going to start doing that too. I'm going to start like, you know, this is a great idea because I read a lot as well. And just like having a chat with the author. When I was younger, I sold my first company for not that much. I decided I was going to go like create my own master's on foreign policy. So I would read a book every week. I'd read a book and then I would email and it was usually some obscure book. And then I would email the author who is like some, you know, like professor at like, you know, Florida State or something. And I would say, hey, I just read your book. Um, would you mind, like, if I— could I take you out to lunch? I'll come and take you out to lunch. And they were always so flattered because, like, the only one who read their book were, like, the people they assigned it on class. Um, and I would just, like, quiz them. And but obviously it was, like, took a lot of time. I'd, like, fly to Florida. I was like, you know, I just look at massive amount of time and money to go do that. Like, now I could just, like, have a conversation with their— with them on, on, uh, ChatGPT or NotebookLM, and it's, like, way more effective.

You and I are very similar. So Google, Google, Google this. Google The Anti-MBA Book Club. Okay, so that's my website. I used to own a book club called The Anti-MBA because I wanted to get my MBA but I didn't want to go to school. And so I read a book a week and then I would have an expert on the book's topic come in and talk to me and 20 of my friends.

Oh my gosh, you'll love it.

We did the exact same thing.

Oh, that's so hilarious. And was it, was it a business or was it just like for fun?

The business.

Okay. Oh, got it. So like people like also like they got their anti-MBA with you.

Yeah. Where it was like, we're gonna do the same thing, but it's gonna be free.

Uh, yeah.

Because, and I was like, the education is part of it, but like the network's the other part. So like, come here and we'll network. And, uh, yeah.

It's, if you read a book a week, which isn't like crazy, it's a lot of work, but it's not crazy.

It's actually, a lot of people think it's harder than it is. Yeah. For me it's like an hour a day. I, I can get one a week.

Yeah, if you read a book a week, you will, you will like, and you're in whatever, in something you're interested in, you will learn way more than someone getting their master's, like way more. So if someone's getting their master's in like ancient European history, if you cared about ancient European history in that year, you would learn like 2, 3, 4 times more, um, than that person because they're just like, they're just, they're just not, they're just kind of getting, because you could kind of move around in the way you want to know, or this, this book seems interesting, or you could stop the book in the middle because you're like, yeah, This book sucks, right? So you just have way more leeway into like actually getting smart.

And NotebookLM will give you quizzes too.

Oh, that's cool.

That's pretty awesome.

So that's what really helped you, because that's one of the problems I have with reading so much is like I forget like 90+% of what I read, um, like within like, within like 2 months. I like, I like, sometimes I don't even remember reading the book.

Yeah, so quiz is helpful.

Yeah. That's a great idea.

Yeah. So what I like to do is, um, I use NotebookLM, uh, and then I also, I, I usually will write a blog post. I call it an essay. It's not really an essay. It could be like a 500-word thing and just says, here's what I just learned from this book.

Just to force you to remember it.

Yeah. Just like, here's 5 interesting antidotes. Like if, when I read Warren Buffett, I was like, uh, starting at the age of, uh, 50, he started investing a lot more in a brand. And so he actually bought Coca-Cola and Coca-Cola made him more money than anything he'd ever done. Like, like one little story like that, uh, but 5 of them.

Oh, okay. All right, I, I should— because I feel like even if no one reads it, I feel like that would help me, uh, like retain some of the knowledge.

Yeah. And actually, if you go to The Anti-MBA right now, my blog, I wrote one on Ralph Lauren, and I just said like, here's 20 good quotes from the book.

Like, yeah, okay, it's not kind of simple.

Yeah, yeah, it could be simple things you maybe highlighted along the way. Exactly.

And are you reading the physical book, or are you reading like the Kindle, or are you listening, or I, I do 3 at a time.

So I do, uh, when I go for walks, I do audio. Yeah. Um, and that's usually something that's entertainment. Um, so a lot of fiction.

Um, fiction audio. Interesting.

Yeah, because if there's a good voice actor, it's kind of like you're listening to a movie. And like, I, I love that. Um, and then for my book, between like 7:30 and 10 o'clock at night, that's usually physical. And so right now I'm obsessed with like Ralph Lauren. So like, as my wife will be sitting there, she'll be like— she likes to put together Legos. She'll be putting together Legos and I'll just sit there with my book just like reading, and we'll like talk occasionally, uh, like back and forth. So that's a physical book. And then in bed, that's a Kindle.

Ah, okay, got it. Okay, cool. Yeah, that's really interesting. Yeah, so many people have so many interesting habits. Um, now I think at some point I read this— I read like an interview with you a while ago where You said in the past your goal was to retire with $20 million. Okay, now you made your $20 million, which is a lot of money, right? But now you're still working super hard. You're still working crazy hours. Like what changed your mind?

It wasn't necessarily the retire in the typical sense. It was basically like I grew up with not a lot and I wanted to feel this sense of security. And I asked a whole bunch of wealthy people how much money they spent per month. The richest person told me that he spent like $80,000 per month or something like that. And I was like, all right, so 3% of that equals like something like, or, you know, if I only spent 3% of a lump sum, that would be like $20 or $25 million and you could still live like a really lavish lifestyle. At that point, I'll feel like secure. I think that was my hypothesis. And so I was like, all right, that's the number I'm going to try and hit. By 30, because if I can just remove like the stress of money, then I won't be nervous anymore and I'll only focus on like doing good in the world. Now that premise was— it's not fully true because like for some reason your tastes move up, your tastes move up, and the goalposts always move. So, and, and so, but that brings us to a whole different discussion, which is like basically the answer is it's never enough. Like humans always want more.

Correct.

That said, it definitely helps. Like it definitely made me worry a lot less. Yeah, but, and the reason I'm working is because, um, I went from working to make more money to working for fulfillment, to where like this feels good for my soul. And like, war— warriors can't just like sit around all day. Like, men have to go and contribute. And like, you know, we're all built to do something. And like, I think most men— I mean, women maybe as well, I don't know, I'm only speaking from a man's perspective— I feel like we are we are obligated to like produce for the world. And I feel like I have that deep sense of like obligation.

Now, um, there are some people who are like content with a certain amount of success and then they, they, they kind of cap out on their ambition. They don't need anymore. They're very happy. Um, and they go get a winery or something like that. Um, and then there's others who just like kind of keep going and, or, or would never stop. Like there's no level that would ever kind of stop. Like Is there a way of like identifying those people early on or?

I only know, I think I only know one person like that who, I have a friend named Jack Smith. He sold his company called Vungle. You maybe know Vungle.

Yeah.

He sold it for $800 million when he was 29 or 30.

Amazing.

And he was like, I've, I have enough. I don't want to do business ever again. And he's happy. And he's the only person I've ever met who made money and walked away successfully.

Interesting. I know tons of people. Well, maybe more, more, almost most of the people I know who made money, kind of like they, they, you know, they might quote unquote angel invest and they dabble in, you know, real estate or something like that. But they like go have their little winery, they go do these other things.

What's their average number of net worth that they made?

I think it's very dependent.

So like, what's the low end and what's the high end?

It would be as low as you can imagine you can sustain that life to, you know, um, and you know, someone maybe made more than they would have ever expected. But I think a lot, and a lot of people are very young and they just want to spend more time in their family, and they all seem very happy. Um, and, and then, you know, other people I know, like, I don't think there is any number that they would ever stop. They were probably just, they're just, they're gonna, they're gonna keep working until they die. Like, and this one day they'll die. Um, like there's just no— there seems to be like just people who are very different wired or in some sort of way.

The people who retired, were they entirely self-made?

I think so, yes.

Yeah, I, I think that, um, I don't know too many people like that. Uh, like I said, one. Um, I know people who did it, like bailed, like quit, but they're not happy.

I think what happens— there's another thing I think that is common So here's what's common that I see. So you, you, you, you had a success and it was fairly successful. Then you did something else and that failed and then they stopped.

Yeah. And they probably had a family.

Yeah, they, of course at this point they had a family, they had a lot of other reasons, but they had, it's like, it's like they didn't, they, they couldn't, they didn't want another, they couldn't take on another failure in their head. Uh, because of course, start doing something again, risking something again means there's some decent high likelihood of failure. Um, and, um, and when that, that failure hit them— and maybe these are people, I can't go back in time and understand their psyche, but maybe there's people who didn't have a lot of failure when they were younger, had just tons of success after success, end up with a great success, and then, you know, inevitably we all have failures in life, in business, etc.

Andrew Carnegie, who I brought up because I went— he's a person I, I read a lot about. He fascinates me. He wrote at the age of 33, he was like, I earn this much money per year, which is like the equivalent of $5 million today, so a lot of money. And by the age of 38, which is in 3 years, I'm going to retire and to do— and I'm going to devote my life to non-money-making things because the making of money is like an evil task. And two things happened, uh, two years later he started, uh, Carnegie Steel, which went on to make him the second richest person to ever live in the history of the world. Um, and the second thing was like, obviously he went and made money, but he did dedicate a lot of time to like doing good in the world, even though he's a contradictory person. He did a lot of bad stuff, but he also like wrote and read a lot and like hung out with literary men, that he called it. And so I think that like after you get like your first hit or you're one of these people who bounce, you realize that like kind of what I was saying earlier, that like business, it's definitely more than just dollars and yeah, profit. It's, it has to do something for the soul.

And he eventually sold to US Steel. He didn't have to do that. He sold to US Steel, and I believe then he was— didn't he mostly focus on philanthropy after that?

Yeah, well, he was very philanthropic the entire way, all the way before Okay, yeah, he was really good at all the libraries he's so famous for. He was a very contradictory person because he was very giving, and yet he was like, uh, a slumlord for his company. Like, he was like, yeah, yeah, if you worked for him, like, you were getting shit wages. And if you had all—

yeah, I mean, he, he like went with troops against his own workers a couple times, right?

He's a contradictory person where he justified some of those actions because he's gonna like give all the way away all this money, which he did.

He was like an early EA guy or something.

Yeah, he was like intense. And, and so, um Anyway, my point with that is like, I do think that like what Andrew Carnegie said is what a lot of business people feel, which is like, oh my God, I was in this just to get profits. And once I got the profits, I realized this, like, something else, like it's, there's gotta be more than this. And unfortunately this makes me sound like a silly for talking about this because you kind of have to experience this to actually appreciate it. And you're like, I don't believe you. So let me go experience this myself. Let me get rich and realize that like, that's not the answer. Uh, in which case I say yes, go experience it yourself. But, but there's a, there's, there's got to be more to it than just, uh, profit.

I think it's funny, we live in DC and, you know, it's like there's so many public servants who eventually like, I gotta go make money. And then there's so many people we know who made money who want to go into public service. It's like everyone thinks the grass is greener going the other way.

For the record, I think the right way is to make a living and then go and do the other thing.

That, yeah, but it's harder because like there's just things you don't learn when you're younger and stuff like that. And You know, it just is— everything is— everything's different, and there's less spots to go do it in the later life. Um, now you, you mentioned, I think, I think one time I saw an interview, you said you lost a job at Airbnb because you had like a criminal record. Like, how do you think about hiring like today with maybe people have some non-traditional background?

I think that I, um, so I got fired because I lied. So basically, I'm, I'm completely sober now, but I had an alcohol issue And I got a DUI and I lied about it, uh, when I was going through the Airbnb process.

You lied about— they asked you about what, or what was the lie?

So basically I was still going through the system, the court system, where I hadn't exactly had my court date yet, and they're like, have you been accused? I forget the words, but do you have like a misdemeanor?

There was like a questionnaire to fill out after you get a job offer.

Well, technically I haven't been convicted yet, but like, whatever, it was like That was not within the— the— the— I lie. I, I didn't— I thought I wasn't lying, but like, they accused me of, and I'll accept their, their answer. They're, they're more right than I was. And they were like, dude, we don't hire liars. Like, you don't show up. Yeah, yeah.

And so do you think they would have hired you if you told the truth?

Well, I did. I had a job and I moved out to San Francisco, and I was gonna— I was starting the next day in 12 hours.

But they didn't, they didn't know about the—

I mean, if you actually said I had a you know, they would have hired me.

They still would have hired you. So you just were like, yeah, so you, you weren't confident in yourself to—

I was a fool. I was— I, I lost that in a variety of ways. I was a fool. Um, now when it comes to like other— now for traditional backgrounds, I work with this thing called The Last Mile, which is started by my friend Chris, where they go to different, uh, prisons and they teach prisoners how to code, and they get jobs when they get out of prison. Um, so I'm pretty like on board with that, of hiring people who, who maybe aren't traditional people, giving people a second chance. Yeah, because that's kind of a win-win-win, which is like, even if you don't want to have sympathy for these people, which I don't think you should, you know, if you commit the crime, you do the time, it's good for the, the all of society that they get a job. Like, yeah, because they'll, they'll do less bad stuff more like statistically. So I'm like on board with employing people like that as long as they're qualified and can help me get the job done. At The Hustle, my old company, and even at Hampton, I did a good job of hiring people that I, I used to say like, we want you to let your freak flag fly at our company. Like we were, I did a good job of hiring non-traditional kind of oddballs and giving them a place to like kind of be wacky. And that was kind of the fun part of running a media company.

If you were like, if you were like a Sam Parr, the hedge fund, and you got to invest in these like 20-year-olds or something, and you could get a percentage of the goodness they give to society, a percentage of their earnings, and it's competitive— me and you are competing against each other and trying to invest, um, out there— what are the signals that, you know, kind of the Moneyball signals that you're gonna find that I wouldn't find that you would invest in?

Well, the traditional— that's a good question. The traditional things are like, are they good at like poker, video games, puzzles. Like, is there anything that they're like— anything that's quote like worthless or weird or whatever that they're like amazing at? So I usually look— I look for those things.

Kind of the best Call of Duty player or something.

Yeah, like whatever. Like something that like you would laugh at like if you were their peer, or like, oh, our friend Dave, he's so nerdy. He does the— he, he's— he times himself how fast he puts together puzzles. Yeah, if you're like one of those guys, uh, I, I, I, I really love that.

Oh, that's a good one.

I also, um, I read— I love reading people's blogs or their Twitter or, uh, yeah, seeing like the written word. And so I've actually—

so rare to find— it's so rare that people write today, you know, or ever, you know. It's, it's, it's interesting because it's so, it's so easy to differentiate yourself, yet so few people do it.

Yeah, one of my best hires at the time, she was a 23-year-old, 22-year-old woman named Steph Smith. Uh, she was a product manager somewhere and she had a blog and I read her blog and it was great. It was a good-ass blog. It was so good. And I hired her. Now she's a big shot at, uh, her name's Steph Smith. She, uh, works at Andreessen Horowitz. And it was all because she just had a blog that no one was reading, but like it was really like thoughtful. And so I love seeking out people who are just really thoughtful online. And so I find those people in forums. I used to find them in like chat rooms. This sounds weird, finding young people in chat rooms, but you know what I mean? Like in like anything that I like, enthusiast places, like on Reddit where there's like fun topics and you're like, this person's talking and they're like 18 years old. You're like, dude, you're a freak. What the hell? What's your story? Like, how are you so knowledgeable about this topic? So I like people like that.

Yeah. Now a couple of personal questions that we ask everybody. What is a conspiracy theory that you believe?

I'm passionate about conspiracy theories because I think most of them are nonsense.

Okay, and you've read all these JFK things too?

Yeah, that's one where I'm 99% sure Lee Harvey Oswald acted alone. There is some— a bunch of weird stuff that's hard to explain, but conspiracies are hard to be— uh, see, the reason I think most aren't real is secrets are hard to keep.

Yeah.

Uh, secrets are really hard to keep, particularly when you're dealing with like a $50,000 a year soldier who like wants to pay money, uh, or wants to get paid for telling a secret. Uh, so what secrets do I— or what conspiracy theories do I believe?

Like, you mean the Jack Ruby thing? Like, that's just so weird, right? Like, how did this guy—

I think it's weird, but the JFK one in particular, I think I'm 99% sure that Lee Harvey Oswald acted alone and he did it. Um, the reason I think that is because like JFK Jr. and a bunch of other people have like read a bunch about it, like because that was his father, and they're like, yeah dude, he acted alone. Um, so that's my opinion on that one. Yeah. Which conspiracy do I believe to be true? This is such a fun question. Um, One thing that I'm reading about now, I'm newly interested in this, so I haven't read too much. A lot of the cigarette companies, they bought the major food companies.

And so, yeah, like R.J.R. Nabisco type of thing.

And yeah, they were owned by like Philip Morris. They were like, they owned the majority or a large percentage of their stock because they're like, hey, we know how to make cigarettes addicting. Let's, let's make this food addictive. And so I think that there is— I'm fairly interested in like the idea of like, I do think there's like a corruptness around like food and getting people addicted to, to certain foods. So like, and I think that it's insane that like, you know, a large percentage of medical degrees don't require any nutrition classes. Yeah, and I think that like there is like some like evil, you know, like evil big food, uh, that's like controlling the, the, the strings behind, uh, behind, you know, behind the curtains. So I do believe that's a pretty good one. I believe that to be true.

All right, last question we ask all—

wait, which one do you believe?

Uh, I believe so many. Um, and, uh, I, I generally think like if there's a scenario where people are, um, are advocating for something, and yet there's a— but there's another party that would directly benefit from it that is not advocating for it, um, that there's a good chance that that party is involved in maybe funding the people who are advocating for it.

Yeah, yeah.

And so it's kind of like— and it goes like, it could be very micro-conspiracy, um, it could be, um, you know, it could be— there could be lots of different things that are out there but almost always, like, there's almost always— there's— that's the case. Um, like, if they're benefiting from it somehow, then they're probably— there's a good chance, maybe not, but there's a good chance that they were involved.

And you're in DC where all that happens. I, I generally think, uh, usually the simplest answer is best. I think Epstein did kill himself. I think that, um, 9/11 was not an inside job. I think, uh, we did—

we didn't fake the moon landing. Yeah, yeah, the Earth is not flat.

It's definitely like— I generally believe that just Conspiracy— the really big conspiracies are quite challenging to keep secret.

Yeah, yeah, I think I agree. But there's a point where these conspiracies aren't so big and they actually can make things happen. The government ones are less believable, but the, the other ones where you have kind of a group getting together and kind of directing it in certain ways— there's a lot of PR things. Almost always when you see an article that's like negative about a company, um, it's like one of their competitors is the one funding it. Um, so even when you see in the Wall Street Journal, there's like a very high likelihood that they got it, they got like the material from one of the competitors.

Um, and the whole media thing is interesting. Um, like I know a bunch, or I know I tried to recruit, but like I was a lowbrow publication compared to them. Like a lot of like New York Times people are like, you know, in that caliber. And like they, like the New York Times, the Wall Street Journal, uh, or sorry, New York Times, Washington Post, and like 5 other, like Vox, BuzzFeed, it's all the same, like 800 or like, you know, 1,500 like journalists.

Yeah.

And it's very circular. And, and so like, I, even though New York Times, uh, many people regard it as like highly reputable, um, I think most all of it is like really hard to trust. And, and, and it's all like similar people who are all friends with each other and they are read by the majority of the country and they all live in lower Manhattan. You know, like they all live in like the same area. Like this is weird. So I tend not to like trust a lot of those news sources.

Yeah. Now last question, we're gonna ask all of our guests. What conventional wisdom or advice do you think is generally bad advice?

What's like, what do people say about winning? They say like, like fail fast or sorry, fail fast. Yeah. I kind of think that's stupid. Like, it's a lot better just like, just succeed. Like, whenever— like, I think that fail fast is— they justify it for like, I missed my shot on goal, it's okay. And I'm like, no, it's not okay. It's not okay to fail. Like, you can brush yourself off and, um, do better and get after it again, but like, uh, don't dismiss this as being okay. This is not okay, uh, and you better make up for it, uh, you know, like I remember I've angel invested a bunch of times and people are like, you know, like, I failed, but I learned, so it's okay. I'm like, no, it's not okay, man. That was my money. Like, you should tell me, like, I failed and this is really horrible. I'm so sorry. But don't tell me it's okay that you learned. Okay.

But you like, just to, just to push back, like in your company in Hampton or something like that, like there's things that you're doing all the time where you're failing, like you're trying things out, it doesn't work. Maybe the company itself isn't failing, but there's like many micro things that you're doing.

Yeah.

And that's the same thing with a fund. Like, if you're in a— if you're a— if you're a venture investor, you know, you, you could have 3 hits that drive like massive returns to your fund, and everybody else could go under. But it's like, those 3 hits—

like, but that's not a failure. Because it's— for example, it's like this, um, if you're a good baseball player, you know, I don't pay attention to baseball, but like 300— 300, uh, 3 out of 10, right, you get hits.

Quite good.

That's good. And so that's not failing. But what I mean is, is like, I think far too often we get stuck in this idea of failure being like acceptable. And I'm like, dude, like it's not okay if LeBron James misses the game-winning shot like more often than he— than he— you know what I mean? Like LeBron James has talent and he comes through when it counts.

Yes.

So you are not coming through when it counts. And don't tell me it's okay, that failing is okay. Messing up on small things every once in a while is good. Yeah, okay. But you have to be right more than you're wrong.

Yeah.

And so I hate when people— sometimes like my employees will do this, or like employees I've worked with, or coworkers, or just like people in general be like, well, I, you know, I fail fast, it's okay. I'm like, that's not fucking okay. It's not okay to fail. Okay, don't— it's— don't dismiss this. That is really bad. If you want to be a winner, you got to win more than you lose.

Yeah, yeah, I love that. I love that attitude. That's awesome. Well, thank you, Sam Parr, for joining us on World of Das Podcast. I follow you @TheSamParr on X or Twitter, whatever it's called. And I definitely encourage our listeners to engage with you there. This has been a ton of fun.

Thank you. I appreciate you.

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