Sam Parr - Raising Normal Kids After a Major Exit

Hello, data nerds. Welcome to World of Das. I'm your host, Oren Hoffman, CEO of Safegraph and GP of Flex Capital. Discover more episodes, get weekly data-as-a-service news at worldofdas.com. That's spelled worldofdas.com. 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 again. Now, one of the things that like always troubles me is 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 is 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 Peter Thiel has that book— what's his book called?

Zero to One, one of my favorite books.

And he has this whole chapter on 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. Does anybody say something like that?

Yep.

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 doesn't make a lot of sense in terms of conversion rate or in terms of 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 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. 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 gonna be attempting to do that, I think you should put more emphasis on the brand than you likely think You should, do you know what I mean?

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. They always keep Instagram, keep YouTube. Procter Gamble doesn't have like Procter Gamble toothpaste or something like that. They have Crest. 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 kill this old brand that people loved. If you remember EchoSign, Jason Lemkin's company, like, they rebranded Adobe Sign. But 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 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, and 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 that bothers me. There's a reason why the Joe Rogans of the world have excelled. He has Bernie Sanders on his podcast or some other presidential candidate and also makes silly fart jokes. You can do all of it. A B2B company doesn't have to like be crude. But if they want to be silly, they can be silly. You know what I mean? You can 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. I think that we should take a little bit more risks though. And the risks I'm suggesting oftentimes aren't even that big.

Yeah, they don't sound that big at all. 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. How does one do a better job of evaluating that?

I ask them what content they consume. I usually ask, I say, hey, every morning when you go on the internet, where do you go to and why? And what's interesting about that? I then will ask them, 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. 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 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 going to be good at that job.

So storytelling is kind of a key piece. That's something I think you could maybe interview for, is ability to tell stories. Yeah.

Or the ability to have taste. And having taste is hard. You don't always have to be the best storyteller, but you have to understand what the best story is. You don't always have to do the job the best, but you have to be at least pretty good. And you gotta be able to say, oh no, trust me, this is a hit. 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 seeing, no, that's the thing. That's the angle. That's a pretty cool angle. And so I think that I, I ask people about the bottom fourth of the resume and I ask 'em about what they read. Or what they consume.

Is enthusiasm important?

Hell yeah.

They can make it somewhat contagious or something.

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 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 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 Ralph Lifschitz to Ralph Lauren because he wanted like a very American name because he was fascinated with classic traditional America. 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 mindset. Do you understand what I'm saying?

Yeah, totally.

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 that friend that is 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 maybe the dumplings actually aren't that great, but when you taste them with your friend there, you think they're the best dumplings in the world. Like, you have this incredible experience because that enthusiasm is contagious. Correct. Yeah.

And so I like being around those people.

Yeah, they're amazing to be around. It is rare though. I feel like it's this positivity that it's 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. And 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, no, I think it's not the right way to do it. And I'm like, well, why the hell didn't you speak up and tell me? Because I will listen to you. I'll follow your feedback. It's a really hard thing to pull off, but you have to create a culture where like these interesting ideas surface.

Now you built kind of a mass media brand and now you're building a more exclusive brand with Hampton. Now you're building like a new Ralph Lauren-ish thing. How are they the same and 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. I love news. I love Ted Turner. He's the guy who started CNN. I found him to be very romantic. The idea of a Southern guy from Georgia taking over New York media, and I thought that that was really 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 want to take over the news scene. And I felt invigorated. And I wanted this edgy, cool, unique vibe. 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. The bet was right, but I sold too early. 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 because that's an exhausting way to make a living. I think that there's two ways to monetize an audience. You either sell your own stuff or you sell someone else's stuff. 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— he's now my business partner, by the time he's my friend, and we used to like share everything with each other. We would share our net worth, our income, our relationship issues, 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. In something that's more exclusive, like it's a little bit harder to join or there's gates to join, et cetera, building a brand is different. Maybe it's a little bit more aspirational. I don't know that like Rolls-Royce is advertising on the Super Bowl or something. How does one 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 some of these luxury goods. They're able to advertise a fair bit. So first of all, I will say with a community, I know that it looks like we are trading off of 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. This actually makes your company or your life better. 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 has to be a great product, not just a brand. But the crappy part is we've done a small amount of paid advertising. We don't want to do paid ads, even though that would grow our company more. It kind of makes you look bad. 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, but you just kind of have to do that in hopes that that will pay dividends in the long run.

Now, part of a community I imagine is you've got to cull a certain number of people. You essentially have to like fire a certain number of customers that are not adding well, or maybe even negative 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. That obviously makes building a community business a bit harder because you have this forced churn in it. How do you think about that?

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

Now, you mentioned that you wish you didn't sell The Hustle. I wish I didn't sell LiveRamp.

How big is LiveRamp now, by the way?

LimeRamp is maybe $600 million, like a $1.5 billion market cap company. And I think if we were still running it, hopefully it would be much bigger.

How big was it when you sold it?

It was almost $40 ARR. We sold it for $310. But yeah, I mean, in some ways, like, I wish what I knew a year later, I knew, because 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, sure, because this is context, were you wealthy? Before you sold it?

No, that was the big thing. It changed my life and I had kids. Now I could take care of my kids. It's funny because my wife had a company that sold 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've also never sold because then we would've had enough also to maybe take care of our kids.

Yeah. Well, that's what I was going to say. 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.

Totally. Yeah, it's such a cool company and it was such a cool idea and it had like run and get big and it's exciting. But for the first 2 years, I think I paid myself $50,000 a year, and then the third year maybe $150,000, and then the fourth year I paid myself a lot. And so I started making money in the fourth and fifth year, but I sold it in year 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 it would've been nice to, for example, had I run the business differently, I would've paid myself a whole lot more money. I sold it a little bit defensively as opposed to being on the offense.

Yeah. You could have maybe done a secondary and sold 30% of it or something, and there could have been other options and I probably could have done that too, but I didn't really like think it all through at the time.

I didn't think it all through either.

Yeah.

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

Yeah.

Yeah.

Same.

The offer ended up being, we made a lot more money than what the headlines have said. A bunch of things kind of worked out, but I don't regret that. I also wish I would have owned the company when I was older. So I started the business roughly at age 25 and I was pretty immature. I don't think I was a very mature 25-year-old. If I ran the business now, I think I would have Killed it because dude, think about this. We had a daily email that went out 6 days a week. So I have a deliverable every day and each time we hit send on an email, it would be like $100,000. And so it felt very stressful, but it didn't have to feel that way.

Interesting. Now, what advice would you give to founders about preserving their own brand identity, but also preserving their own identity post-exit? Post-exit advice.

I didn't really have that. 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. People say like, this company is my baby. I think my baby's my baby. And I think my company is my job. I was fairly good at being like, have you ever heard of negative visualization?

Where you like specifically look at the negative to help you understand the positive or something?

Yeah. 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. 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. I'm so grateful. Like, isn't life beautiful?

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

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

Do you do that with your personal life? Do you visualize? A terrible plane accident or something or those types of things.

Yeah, I do it. That's actually a lot harder. 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 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 but were bummed out about X, Y, and Z. I try to remind myself like—

High class problems.

And I don't like when people say, oh, that's a first world problem, because first world problems are still problems. And it's okay to have a problem when you're wealthy and successful, and I don't want to diminish that. But at the same time, I want to remind myself I could be worrying about many other things. Because particularly if you live in New York and Silicon Valley where you're only around ballers and we're all complaining about trivial shit, and I have to remind myself, I'm like, there's a single mother nurse who's saving someone's life right now. She's got to worry about taking care of her kid at home. That's actually way more important than these trivial things I'm worrying about.

For people who are like worried about keeping up with the Joneses and stuff like that, how do you help them think about those things?

I've been lucky that I have this podcast called MoneyWise and My First Million, so I'm able to talk to all these really wealthy people. I have to remind myself that just because you have a lot of money doesn't mean you're going to be happy. I think that when I see a lot of rich people with a lot of stuff, I definitely have to fight jealousy. 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'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.

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.

About what?

Growing up in a wealthy household.

Oh, okay. Yeah.

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

Yeah. Do you want to fly business class or not? Yeah.

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

They will benefit a lot from that for sure.

However long a school day is, you should be doing something that long.

Yeah, potentially even more to see you.

Potentially more.

Yeah, yeah, yeah.

Whatever it is, some amount of work.

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 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 insignificant when it comes to like being a good parent. And particularly seeing my wife pregnant, we miscarried before we had my first kid. No amount of money fixes that problem. And there's a whole bunch of stuff with your kid that money and power and influence and likability, that shit doesn't matter. It doesn't matter at all. It's a unique situation to feel helpless and I kind of enjoy it in a weird way. It's kind of nice to like be like, oh, I'm nothing.

I have these couple of theories on wealth and kids. The first one is 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, like a night nurse is like the greatest thing on earth.

Yeah, you want to be able to afford that, right? Exactly. Then you want to magically lose it all and go back to like just a normal middle-class lifestyle until they're like 20, and then you want to like magically get it all back. It's impossible. That's the opposite, because most people like get wealthier over time.

What age did you cross some type of threshold where you were like, I feel comfortable?

Let's say 40.

So then your children were not babies?

I had my first kid when I was 37.

Okay, so they were toddler age.

Yeah, so they're still pretty young. Yep.

Yeah, well, 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. One of the other things I've seen is that We know a lot of people who are also very fortunate people, and their kids are amazing. And some of them are teenagers, some are in college, and you meet them. 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 all the time. It was like a topic of conversation, like almost every dinner. It was like that kind of acute. What are we going to do? And nowadays we're just 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, but there's just so much evidence that it's possible.

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 and a very successful family, and she was like, no, that's not true. 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. This is a story we like make up.

There are screwed up people who are wealthy or screwed up people who are poor. There's screwed up people in middle class. There's screwed up people everywhere. And there are non-screwed up people everywhere too. Like, I don't know where the correlation is.

I don't know either. It should be like, Sam, you know that like 6 of your friends are like drug addicts. I'm like, oh yeah, that's right. I don't think there's a correlation, but we make up the story. I think it's okay to be paranoid.

Now you are a student of communities and you studied a lot of communities before starting Hampton. What are the types of communities that you studied?

So when I started the hustle, I like did this math. 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, do you believe, 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 want to subscribe to this? Yeah, but still, that number doesn't work out. It's the same way with community. My goal with the community, I wanted to build a multi-billion dollar company, and there was a lot of people who are like, this can't be possible. And so I actually found a bunch of them. So I'll give you maybe two examples. So there's one company called World50.

Oh my God, love that company. Amazing. Such a successful company.

They recently sold for like the second or third time, right? Yeah, and they sold for 2 billion or 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 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, profit, 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 maybe at this point $150 million, it could be $150 million, probably more. Yeah, or more. The data that I saw was 3 years old. That company sold for roughly 15 times that $100 million plus profit. There's another company called Vistage. Vistage, 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 core group. They charge around $1,000 to $2,000 a month depending on your company size. They are doing $200 million a year in EBITDA. So Vistage and World50 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 when a lot of people think of communities, they think of small free communities and they don't realize some of these things could be substantial. Now the downside, those companies that I just mentioned, Vistage is 70 years old or 60s. I think it was launched. World 50 was launched in '05.

20 years old. Yeah.

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, maybe raising money, maybe even like make it worse.

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

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. I frankly think that was a bad decision. And so it sucks.

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

It seems like the wrong decision because When you ask 'em, I'm like, hey, have you done the math? You realize this is crude to talk about, but it's the truth. It's like, you know, you're gonna get richer if you don't raise money and your lifestyle's gonna be better. And also the third point, which is more important to the customer, the product will probably be a little bit better. So it's like a win-win-win. It was easy for me because I had an audience, so it's easy for me to talk about and criticize. I don't know, I feel like a company like Chief, they would've took off no matter what. I wish they would've not raised funding 'cause I think the world needs their product.

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 have a religious attendance. People are starving for community. 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. 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. You have a monthly meeting where you meet with 8 people who have a similar size. It used to be digital. Now we switched it all. So where it's happening in person, which is a logistical nightmare, I think it's a way better moat. And so we're actually switching. So we actually already have groups meeting in real life right now and people are begging for it. They're like, I'll drive an hour to go once a month. And I'm one of those people, by the way, we built Hampton remotely with a remote team all over the country. I regret it. I'm like, oh man, we should have all done it in New York. It was a huge error.

Now, because of Hustle and stuff, you're kind of a student of media. What are the independent media companies you really admire the most today?

In which category?

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 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. At The Hustle, SoFi was an advertiser, but their CEO, don't quote me on this, but I'd 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. 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. 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. And so I was like, oh man, this sucks. I'm like, I will make you happy before the audience because I care about you. So anyway, I care about companies that are paid for by their customers. So I like the information. I love Flash and Flames. Do you know flashandflames.com?

No, I've never heard of them.

Flash and Flames is my absolute favorite blog on media and B2B media companies. Oh, it's run by one guy and it 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 an income and I love that.

Oh my gosh, that sounds so cool.

That's for sure my favorite one.

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

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

Oh, interesting. I'm surprised you pay for it.

Yeah, I pay $100 a year for it. I try my hardest to pay for things that I like. I think that we have to incentivize that type of behavior. So I actually like Business Insider 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.

That makes you happier.

It makes me very stressed. I'll give you 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 at night when we put the baby down at 7:30, 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.

Oh, that's cool. You're almost having an interactive conversation with the author while you're reading it.

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

Have you used NotebookLM at all?

I've been using ChatGPT, but everyone said NotebookLM is better. 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 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, he built the Keystone Bridge. How much money did he use in today's money? Or he referenced his mother, but I forget, what did his mother say to him when he was a kid?

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

Yeah, particularly if you read history, 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. So like, for example, I'm obsessed. I go through like obsessions. Just finished an obsession with the Kennedy family. And so I actually read 7 books on different Kennedy members. I upload all of them.

And Ethel Kennedy just died.

Oh, when did she die?

We're taping this October 14th. It was first week of October 2024.

Oh wow, RIP. I didn't know that. Joe Kennedy, JFK's father, he set up these amazing trusts. And I'm reading about JFK Jr., so he's the grandson of the patriarch, and I'm like, damn, he still had money. That's crazy that 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.

Yeah, because if you're reading, sometimes I'll do that on a theme as well where I start reading a theme, as you mentioned, like all the Kennedys and if you're reading all the Kings, you may also even have a World War II piece of the theme and a Cold War theme, and 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 good example. I've done that before where I'll be like, dude, I still don't understand this. Why was Hitler angry at this group of people? You have to tell me the background of World War I, not World War II. Like, I don't understand all this. Give me context here. Where'd this hate come from? And they'll have to explain these complicated topics. But they use my sources and books.

Oh, interesting. I'm going to start doing that. This is a great idea because I read a lot as well. 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. Every week I'd read a book and it was usually some obscure book. And then I would email the author who is some professor at Florida State or something. And I would say, hey, I just read your book. Could I take you out to lunch? I'll come and take you out to lunch. And they were always so flattered because the only one who read their book were like the people they assigned it on class. And I would just quiz them, but it obviously took a lot of time. I'd like fly to Florida.

Dude, that's so funny.

Massive amount of time and money to go do that. Now I could just have a conversation with them on ChatGPT or NotebookLM, and it's way more effective.

You and I are very similar. So 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. Was it a business or was it just for fun?

Business.

Okay. Oh, got it. People like got their anti-MBA with you.

Yeah. Where it was, we're going to do the same thing, but it's going to be free. The education is part of it, but the network's the other part. Come here and we'll network.

If you read a book a week, which isn't crazy, it's a lot of work, but it's crazy.

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

Yeah. If you read a book a week in whatever, in something you're interested in, you will learn way more than someone getting their master's. Way more. So if someone's getting your master's in like ancient European history, if you cared about ancient European history in that year, you would learn 2, 3, 4 times more than that person because you could kind of move around in the way you want to know, or this book seems interesting, or you could stop the book in the middle because you're like, this book sucks. 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.

One of the problems I have with reading so much, I forget 90+% of what I read within like 2 months. Sometimes I don't even remember reading the book.

Yeah. So quiz is helpful. Yeah.

That's a great idea.

What I like to do is I use NotebookLM. 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. When I read Warren Buffett, I was like, Starting at the age of 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. One little story like that, but 5 of them.

Oh, okay. Because I feel like even if no one reads it, I feel like that would help me 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, here's 20 good quotes from the book.

Kind of simple.

Yeah, it could be simple.

Things you maybe highlighted along the way.

Exactly.

And are you reading the physical book or are you reading Kindle or are you listening or?

I do 3 at a time. When I go for walks, I do audio and that's usually something that's entertainment. So a lot of fiction.

You do fiction audio. Interesting.

Yeah, because if there's a good voice actor, it's kind of like you're listening to a movie and I love that. And then for my book between 7:30 and 10 o'clock at night, that's usually physical. And so right now I'm obsessed with like Ralph Lauren's as my wife will be sitting there. 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 back and forth. So that's a physical book. In bed, that's a Kindle.

Ah, okay. Got it. Cool. Yeah, that's really interesting. Yeah. So many people have so many interesting habits. Now I think at some point I read like an interview with you a while ago where you said in the past your goal was to retire with $20 million. You made your $20 million, which is a lot of money. Now you're still working super hard, you're still working crazy hours. What changed your mind?

It wasn't necessarily the retire in the typical sense. It was basically, 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 something like 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 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 the stress of money, then I won't be nervous anymore and I'll only focus on doing good in the world. Now that premise, it's not fully true because then your tastes move up. Your tastes move up and the goalposts always move. But that brings us to a whole different discussion, which is basically the answer is it's never enough. Humans always want more. That said, it definitely helps. It definitely made me worry a lot less. And the reason I'm working is because I went from working to make more money to working for fulfillment. This feels good for my soul. And warriors can't just sit around all day. Men have to go and contribute. We're all built to do something. And like, I think most men women maybe as well. I don't know, I'm only speaking from a man's perspective. I feel like we are obligated to, like, produce for the world, and I feel like I have that deep sense of obligation.

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

I think I only know one person like that. 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 have enough. I don't want to do business ever again. 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. Most of the people I know who made money, they might quote-unquote angel invest and they dabble in 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.

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 Some of them maybe made more than they would have ever expected. And a lot of people are very young and they just want to spend more time with their family and they all seem very happy. And then other people, I don't think there is any number that they would ever stop. They're going to keep working until they die. Like in this one day they'll die. There seems to be 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.

I don't know too many people like that. Like I said, one, I know people who did it, failed, like quit.

There's another thing I think that is common. So here's what's common that I see. 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.

Of course, at this point they had a family, they had a lot of other reasons. It's like they couldn't take on another failure in their head. Because of course start doing something again, risking something again means there's some decent high likelihood of failure. And when 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, ended up with a great success. And then inevitably we all have failures in life, in business, et cetera.

Andrew Carnegie, who I brought up, he's a person 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 I'm going to devote my life to non-money-making things because the making of money is like an evil task. And 2 things happened. 2 years later, he started Carnegie Steel, which went on to make him the second richest person to ever live in the history of the world. And the second thing was 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 after you get your first hit or you're one of these people who bounce, you realize kind of what I was saying earlier, that like business, it's definitely more than just dollars and profit. It has to do something for the soul.

And he eventually sold to U.S. Steel. He didn't have to do that. He sold to U.S. Steel. And I believe then he mostly focused on philanthropy after that.

Yeah. Well, he was very philanthropic the entire way, all the way before. Okay. Yeah. He was really good about that.

All the libraries he's so famous for.

He was a very contradictory person because he was very giving and yet he was like a slumlord for his company. If you worked for him, you were getting shit wages.

And if you had a union, 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 going to give all away, all this money, which he did, by the way.

He was like an early EA guy or something.

Yeah, he was like intense. And anyway, my point with that is I do think that 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 realize 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's not the answer. In which case I say, yes, go experience it yourself. But there's gotta be more to it than just profit.

I think it's funny, we live in DC and 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.

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

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

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 your job offer.

Yeah. And I was like, well, technically I haven't been convicted yet. I lied. I thought I wasn't lying, but they accused me of, and I'll accept their answer. They are more right than I was. And they were like, dude, we don't hire liars. Don't show up.

Now, 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 starting the next day in 12 hours.

And if you actually said I had a—

they would have let me, they would have hired me.

They still would have hired you.

I think.

Yeah. So you weren't confident in yourself.

I was a fool. I lost that in a variety of ways. I was a fool. 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 prisons and they teach prisoners how to code and they get jobs when they get out of prison. So I'm pretty on board with that, of hiring people who maybe aren't traditional people.

Giving people a second chance.

Yeah, because that's kind of a win-win-win. Even if you don't want to have sympathy for these people, which I don't think you should, If you commit the crime, you do the time. It's good for all of society that they get a job because they'll do less bad stuff 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, even at Hampton, I did a good job of hiring people. I used to say like, we want you to let your freak flag fly at our company. I did a good job of hiring non-traditional oddballs and giving them a place to like be wacky. And that was the fun part of running a media company.

If you were like Sam Parr, the hedge fund, and you got to invest in these 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 out there. What are the moneyball signals that you're going to find that I wouldn't find that you would invest in?

The traditional things are like, are they good? At poker, video games, puzzles, anything that's quote worthless or weird or whatever, they're like amazing at. I look for those things.

God, they're the best Call of Duty player or something.

Something that you would laugh at if you were their peer, or like, oh, our friend Dave, he's so nerdy, he times himself how fast he puts together puzzles. If you're like one of those guys, I really love that.

Oh, that's a good one.

I love reading people's blogs or their Twitter seeing like the written word.

It's so rare that people write today, or ever. It's interesting because 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 22-year-old woman named Steph Smith. 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. She works at Andreessen Horowitz, and it was all because she just had a blog that no one was reading, but It was really thoughtful. 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, like enthusiast places on Reddit where there's 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. 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, and Kennedy things.

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

Yeah.

Secrets are really hard to keep, particularly when you're dealing with a $50,000 a year soldier who like wants to get paid for a ton of secret. What conspiracy theories do I believe?

The Jack Ruby thing, like, that's just so weird.

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

Yeah. Like R.J.R. Nabisco type of thing.

And yeah, they were owned by like Philip Morris. 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 make this food addictive. And so I think that there is I'm fairly interested in like, I do think there's a corruptness around food and getting people addicted to certain foods. And I think that it's insane that a large percentage of medical degrees don't require any nutrition classes. And I think that there is evil big food that's controlling the strings behind the curtains. I believe that to be true. Which one do you believe?

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

Yeah. Yeah, for sure.

It could be very micro conspiracy. There could be lots of different things that are out there, but almost always that's the case. If they're benefiting from it somehow, there's a good chance, maybe not, but there's a good chance that they're involved.

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

We didn't fake the moon landing. Yeah, yeah, yeah. The earth is not flat.

I generally believe that really big conspiracies are quite challenging to keep secrets.

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 other ones where you have kind of a group getting together and 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, it's like one of their competitors is the one funding it. So even when you see in the Wall Street Journal, there's like a very high likelihood that they got the material from one of the competitors.

The whole media thing is interesting. I tried to recruit, but I was a lowbrow publication compared to them. A lot of like New York Times people in that caliber. The New York Times, Washington Post, Vox, BuzzFeed, it's all the same 1,500 like journalists. It's very circular. Even though New York Times, many people regard it as like highly reputable. I think most all of it is really hard to trust. It's 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. They all live in like the same area. This is weird. So I tend not to like trust a lot of those news sources.

Yeah. Last question we ask all of our guests. What conventional wisdom or advice do you think is generally bad advice?

What do people say about winning? Fail fast.

Yeah.

I kind of think that's stupid. Just succeed. I think that fail fast, 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. You can brush yourself off and do better and get after it again. But don't dismiss this as being okay. This is not okay. And you better make up for it. I remember I've angel invested a bunch of times and people are like, I failed, but I learned. So it's okay. I'm like, no, it's not okay, man. That was my money. You should tell me I failed and this is really horrible. I'm so sorry, but don't tell me it's okay that you learned.

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

Yeah, but some things are not okay.

If you're a venture investor, you could have 3 hits that drive massive returns to your fund and everybody else could go under. But it's like those 3 hits really hit.

But that's not a failure. It's like this: if you're a good baseball player— I don't pay attention to baseball— but 3 out of 10 you get hits, quite good. That's good. And so that's not failing. But what I mean is, I think far too often we get stuck in this idea of failure being like acceptable. And I'm like, dude, it's not okay if LeBron James misses the game-winning shot more often. LeBron James has talent and he comes through when it counts. 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, okay? But you have to be right more than you're wrong. And so I hate when people Sometimes like my employees will do this, employees I've worked with or coworkers or just people in general will be like, I fail fast. It's okay. I'm like, that's not fucking okay. It's not okay to fail.

Okay.

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.

If you're a super data nerd, go to worldofdaas.com. That's D-A-A-S, worldofdaas.com, and sign up for our weekly data-as-a-service roundup newsletter. Thanks for listening. If you enjoyed the show, consider rating this podcast and leaving a review. For more World of Daas, and Daas is D-A-A-S, You can subscribe on Spotify or Apple Podcasts or anywhere you get your podcasts and also check out YouTube for videos. You can find me at Twitter @Auren. That's A-U-R-E-N, Auron. And we'd love to hear from you. World of Das is brought to you by SafeGraph. SafeGraph is geospatial data for physical places. Check it out at safegraph.com and by Flex Capital. Flex Capital invests in data companies like those we talk about at World of Das. Check it out at flexcapital.com.