I know this one guy who sold his company for $900 million and he made $3 million because he had raised so much and he had like four or five partners or something like that. And I was like, 'Was it awesome?' He's like, 'Yeah, it was amazing. It was worth it.' And I was like, 'Then you just care about different stuff.'
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Welcome back to the Further Faster podcast. I'm Jeff Becker, your host and general partner here in New York City. Today's guest, you know him, he's the co-host of My First Million. They have over 900 episodes, 100 million downloads. It's one of the most watched startup podcasts in history. Before that, he got a start in hot dog stands and in online liquor stores, and he sold The Hustle to HubSpot for over $20 million. He's back in the founder seat with Hampton, the CEO members club with over a thousand users, 18 cities across the world. You know him as Sam Parr. A lot of the content I've watched over the years seems anti-VC. That's more about building durable companies and profitability. Maybe I'm just...
I'm not anti-VC. I'm anti-VC for me.
Okay. My thought is if your main goal is freedom and like making money for yourself, bootstrapping is 100% the way to go. Yeah. If your main goal is to have like impact and buy a lottery ticket and go really big...
That's just not my... it doesn't meet my needs. So do you think that's wrong?
Well, no. I heard you say something like why sign up to own like less than 10% of something that has a 70% chance of failure.
Well, I don't know if I said why because I understand your why, but that doesn't satisfy my wants, right? So I get why people dig it. I'm just not like... I guess maybe I'm just selfish to be honest. I just care more about my own lifestyle and how I live.
Well, I think a lot of founders I meet, they don't realize there's this other path to building something that's bootstrapped. They think, oh, they see in the news, they see in the media, they see on LinkedIn, go raise money, get this valuation, this is success. That couldn't be further from the truth. That's actually like a bar to go hit, a hurdle to go climb over. And it's...
Yeah. And I think it's cool if you're into that. I just think like I know this one guy who sold his company for $900 million and he made $3 million because he had raised so much and he had like four or five partners or something like that. And I was like, 'Was it awesome?' He's like, 'Yeah, it was amazing. It was worth it.' And I was like, 'Then you just care about different stuff.'
What was the context? Like a pref stack that you couldn't overcome?
I don't even understand half those terms, but it was basically like a bunch of partners raised a bunch of money probably at low valuations. I mean, HubSpot, the company that bought my company, they raised their first round. The numbers are, I could be off by like 20%, but it was like a $5 million valuation and then they raised $2 million or something like that when they first started it. So it's like right away almost half a company goes away. Yeah. And they would say it was worth it because it got huge. They made a lot of money. But there's a lot of companies that don't make it, but that's just like the game you're playing. Yeah. I just don't want to play that game.
I think it's smart. You know, a lot of founders I meet because we don't invest up front at Antler, we get the chance to help people decide, do you go this route or that route? You know, like where do you sign up? Do you sign up for the treadmill? Do you sign up for the let's go build a trillion dollar company? Or do I increase the odds of, you know, some kind of outcome for myself, my family, and my employees?
Yeah. Well, I had all these people. I tried to raise... I tried to, by the way, I tried to raise money. I failed. Like no one wanted to invest in me. And...
I've heard you guys say that you don't want to raise money. You're never going to sell.
Well, I'm not raising money. No, I will never raise money for this thing. But for my first company, I tried raising money. I failed. Like no one... they were like this is...
Yeah. And they were like this is like a lifestyle business. And I was so bummed about it. And then I remember two things. I'm like, dog, you are a venture capitalist. That's a lifestyle business. And number two, that sounds awesome. Like when you think about it, like what is a lifestyle? Oh, I can make my lifestyle great and make... that sounds awesome. Yeah.
But like I invest in companies, so I'm not a venture capitalist, but I invest in venture companies. But so and like they're trying to get after and build something huge. So I support them. It just doesn't... it's just not what I... it just doesn't fit my need.
It is funny how VCs kind of talk down to the lifestyle business, but I read the wealth reveal report that Hampton did. That was cool, right?
It's awesome. It's incredible. And here you have all these people exiting for 10, 20, 50 million. People that have, you know, made billions of dollars and seeing the psychology behind it, seeing the types of businesses, I thought was very cool.
Yeah. When we sold, when I sold my last company, I know a lot of venture-funded companies and some of my friends sold for hundreds of millions of dollars and I know what they earned. And my deal was like a rounding error. It was like a little fart and I think I made more money than a lot of these guys made. Now they have... they could potentially feel a lot of pride because what they built was huge and it employed all these people and it was probably awesome and everything like that and they probably have more like street cred and all that stuff, but it's just different.
What do you see from the members? Are they this thoughtful about the lifestyle they're trying to create and how does it work?
My opinion is a lot of people who start businesses aren't that... like the first one and the second and third one are way different. The first one you get into it, you're kind of a dummy and you're just like, 'Whatever happens, I'll do.' Like, 'Whoever says yes, I'm into.' And then the second one you're like, 'I screwed up here, here, and here. I'm going to avoid that mistake.' No. First company founders usually are kind of like morons. I mean, I was a [__] and I still am, but they... but it was like just whoever says yes, I'm into it. Or like... or this... I remember like there was a time where someone like a venture capital guy told me like, you know, instead of doing this, I was pitching him, 'You should do this other thing.' And I was like, 'I'm in, you're right, whatever you said, I'm in.' Yeah, it's like the fear of God in these founders and if someone tells them, 'Hey, you'll be more successful doing this or go do that,' they'll say yes.
But counterintuitively for the VC, it's more attractive if they're very opinionated. If they know what they're doing, what they're saying no to. If they understand like how to build culture, where the customer problem is, spend time.
Yeah. I think now it's like this is what I'm doing. And by the way, this is like... I met... when I was a kid, I used to read all these books on how to like meet girls cuz I was like a nerd and I like desperately wanted to grow. How to Win Friends and Influence People. It started there and then it was like pickup artist books. I was like, I need a girlfriend. I want to meet a girl.
Did you watch the show, The Pickup Artist?
Hell yeah. Dude, like read the game. Like I could cite all the lore because...
What's your peacocking? Is it the belt buckle? The hat?
It... I don't... back then I had this like huge afro and I thought that was cool and it was the worst. [laughter] And like one of the... what I kind of realized was like the best way to like meet an awesome woman is to basically just say like, 'I am here and that's where I'm going. I would love to have you come with me, but if you say no, God bless you. Have a good one. I'm getting after it.' Yeah. And like if you have that energy, like you tend to like attract more people. And that's the same way I think with raising money. You know, treat them mean, keep them keen a little bit. It's like this is where I'm going. You in or out. And so that I found it to be very beneficial.
It is an attractive thing when someone is going to do it come hell or high water. Like this is my life's purpose. This is what I'm doing. Similarly at Hampton, you guys are pretty unapologetic about the bar to get in and...
Yeah. Which sucks because we turn down a lot of like money. Yeah. But yeah, my business partner Joe, he is like adamant that like you will never break any rules and so he refuses to do that.
Yeah. But it's a respect for like the culture. It seems like it's a tension with the stated goals, the 50 million, 100 million revenue. How do you balance...
My stated goals? Did I say that publicly?
I don't know. I thought that's what I heard you say.
Yeah, I do a big business. I did say that. I don't know... I don't remember if I said that publicly, but I say that all the time. Yeah. I'm trying to build a really big business. Yeah. My co-founder Joe is just so anal though about requirements. So, for example, we'll have... I don't know the exact numbers, but we'll have like two or three thousand people apply a month and tons of them are below 3 million in revenue and not one person I don't think ever has gotten in who doesn't at least cross that. But then he turned down... well, he watches 100% of the people who interview to join and he'll go ahead and just turn down half right off the bat. Wow. And it kind of sucks because like our revenue would be so much higher. But the hope is that if we keep it tight, that's going to help retention and it will make us grow a lot better over the next like 20 years.
Yeah. You have to like respect the product, like the culture. It's almost like Clubhouse. It was like this amazing thing in COVID. You could listen to the most amazing interviews and then once they got the pressure of all the capital, they opened the doors and that thing was just not exciting.
That like I think VC would destroy our company. Like there's this company called Chief that is a network or like we are like them. I guess they were first. And they raised I think $100 million. A lot of money. And it was a really cool idea. Their idea was great. Their branding was cool. I think the lady who runs it, Caroline, I think she's real smart, but because they kind of like made the... there's basically like only maybe one or two mistakes in business that you can't undo and your cap table's one of them because when you sign up to that, you're signing up... you're saying it's my duty now to like get a return. And that unfortunately is not good for every type of business. There's a bunch of them where growth can really mess you up. And frankly, that kind of sucks because I want to grow, grow, grow. But you definitely have to be more careful.
Yeah, I have a lot of respect for it because people don't know this about LinkedIn, I don't think, but when I was there, we treated every decision with this idea of members first because the idea was that if you lose the members, you lose the whole thing.
LinkedIn is now... I don't know. When I left, we were, you know, over a billion members. Now I think it's 1.4 billion.
You called people members?
Well, the idea of members first was make no decision that impacts the member negatively. And so when you think about like an advertising business, nobody wanted to show up to, you know, MySpace or Friendster or BranchOut and just see a bunch of ads. And so we deprioritized the ads business for 10, 15 years. We didn't really launch sponsored content till 2013. We really focused on the recruiting business because if you showed up to LinkedIn and got a better job offer, you got recruited, you got, you know, the opportunity to improve your life, you were more than happy to get that email even if you weren't looking for a job.
How much did it sell for?
That's crazy. And now it's doing, you know, probably 15 billion in revenue. So this is the acquisition for Microsoft. Dude, what do the people... I love LinkedIn by the way, but what do the people who work there do? Because it has not changed ever. There's still so many errors that like you click buttons and it like...
Well, I'm not a spokesperson now, so I can't speak on it too closely, but I just do appreciate this idea of understanding who your customer is. Like the story you told about SoFi at The Hustle. Yeah. Where you have this ad revenue which is if you were a venture-backed business, I got to respect the revenue like Chief, but you shipped that article anyway and I don't know if you lost the revenue.
Yeah, basically it was the founder of SoFi. I forget what he did, but it was some like sexual thing. It wasn't like... I think he like said something smart or, you know, smartass and our headline was 'SoFi more like so [__]' and it sucked because like they're an advertiser, but it's like who are you going to appease? And it was definitely unfortunate, but I mean we said it anyway, but like I'm not... I don't want to act like I'm like everything for the audience. Like it hurt. Like I was like, 'Ah, this sucks, but I guess you got to do it.' Like...
But you prioritized the audience over the advertiser.
Yeah. And that ultimately makes more money by the way. Like so it's not like I'm some altruistic person, but yeah.
Can you explain that a bit more because it sounds the same with Hampton. It's like if we prioritize the quality of the members, even though it feels slower on a day-to-day from the rejection rate, you guys are only letting in like 2 or 3%.
Yeah. A lot less. But basically...
You think that'll grow faster?
The bad thing about... so advertising-based businesses, there's a lot of really great things about it. You're basically creating money from thin air, right? You're creating an audience and just like this podcast and it's really exciting and then you're like, 'I'm going to sell this fake... this thing that isn't... just like attention.' Yeah. Right. You have no like cost of goods sold. It's like pretty amazing. But the downside is that you start having... it depends like if your CEO is like a suit or something like that versus a creator, you start basically saying like, 'What can we do to sell more ads?' And what you can do to sell more ads is be safe, not say anything wrong. And it's very tempting to do that because that makes a lot more money earlier on. And or if you have big deals like we would have... I think LinkedIn was a big advertiser of ours. I don't know if they were like a seven-figure, but we had like seven-figure contracts and there was often times where I would be like, 'I want to say this' and in the back of my head I'm like, 'Well, that's going to cost us this other stuff.' Like we had Goldman as an advertiser and I said something and I'm not like that offensive of a guy by the way. Like I don't think I'm a very offensive person. I try to default to kindness, but like it was just like a joke that had the F-word or something like that, right? And they like were like, you know, 'I don't think this is safe.' And so you start having two customers and it's challenging to know who to appeal to, right? And that's really hard, right? But I think you ultimately do make more in the end if you are like appeal to a very particular type of person. Like I don't... I'm not like... I don't follow Barstool like crazy, but I know that what they've done is interesting where it was unapologetically appealing to this one person and they probably made shitty money for a long time and then once the audience got so big it was like, okay, we have to advertise here.
Yeah. No, that's so interesting because I think that the respect for your current members, like who else you let in their circles, is super important and if they appreciated the referrals and the word of mouth, probably outweigh anything.
Yeah. So the biggest way that we get customers at Hampton, there... it's two. The top one is the stuff I make. So...
Great, hopefully we'll contribute.
Yeah, thank you. Apply. And then so like My First Million, our podcast, Moneywise, and then the second... so media, and then the second one is referrals. That's the biggest one. And then we just started buying ads online and that's like a distant... like way down in the order, the pecking order of like where we get customers. So it's not through advertising, it's referrals and media.
Yeah, I've seen recently this huge shift in spend to creators when it comes to advertising. So, instead of the traditional channels, the email newsletters, the, you know, the ads online, we're seeing folks kind of buy time on podcast ad reads and influencers on TikTok. Are you seeing that similar shift?
We haven't done that yet. We will because we kind of are the creators. I'm the creator and then we have Moneywise, which is another podcast.
I've listened. It's awesome. If it's a cool podcast, if you haven't seen Moneywise, go watch. It's a ridiculous concept. Basically, high net worth people like open up their finances and say, 'Here's my monthly income. Here's my expenses. Here's my portfolio.' I was... it was crazy to see some people worth so much spend so little and like the way they treat money.
Dude, I am shocked that people say all these things. There's like this small niche of person and they're really cool and like Anne Mahlum is one of them. She started Solidcore and her thing is like, 'I had the help of so many people leading up to this and it was so hard to understand finances when I was building my company that I'm just going to be an open book so I can help everyone else.' And she's sort of sacrificing her own privacy in order to help other people. And I think that's amazing. And so someone like her will come on and be like, 'Here's all the numbers.' Yeah. It's nuts. I can't believe that there's people that are crazy enough to do that. And I love that there are. Awesome. And so we've had billionaires. We had this one guy who he appeared anonymously and he's worth $3 billion and he's like, 'Yeah, here's everything.' Wow. And it's just pretty awesome that people do that.
I found in our portfolio as the companies get more mature, they get lonelier. Like there's less people at those levels to talk to and to learn from. And not just how do I run my business, but how do I manage my personal finances? How do I manage my family? How do I do the things? And I imagine being in Hampton or being in one of those circles, you get exposure to not just like the Moneywise content, but also like even more behind the scenes.
Yeah, for sure. Because for one, talking about that stuff can be lame, right? Like it doesn't feel comfortable talking about finances, particularly if you're doing well. Like there's... it's a thing where you can get called a douchebag very easily and people be like, 'Oh, that's champagne problems.' And I'm like, 'Yeah, but that champagne problems are still problems, right?' And for a small subset of people and even ambitious people who want to like are up and coming like I was for the longest time, I would need to know this stuff because it's sort of like when you see that someone just ran a sub-four mile, you're like, 'Oh, now I know what's possible. I feel encouraged.' And so when I was younger, when I was in my 20s, I had this spreadsheet where I would read all these biographies and I would map out like I would read like four biographies on a person. And I would create a spreadsheet where I'd map out their timeline and like how much money they were making at each time and what was the different inflection points and why things happened because then it was like, okay, now I have a little bit of confidence. I kind of know what's possible that this move can create this outcome and then this move will create this other outcome and it was really enjoyable and very helpful for me. That's awesome. And so I... and I still do that by the way.
You have the spreadsheet?
Yeah, I still have all of this and I use it all the time.
Do you share with anyone or is this like a...
Yeah, there's some places if you Google it, you could probably find it, but I have other ones that are more private that I thought about making public, but I'll do it with like modern people as well. So like when I was trying to figure out the newsletter business, I would read like 50 interviews. Then I would go and interview the early employees and I would get their... they would tell me the numbers and I'm like, 'Okay, now I understand like the physics of this business and like how wealth is created and all that stuff.' And I would like map it out and it's like, okay, so here are my constraints. It was like, I can get, let's say, $50... I think it was $25 at the time. I can get $50 per 1,000 sends in my email. Therefore, in order to build a business that hits my goal of achieving this much money by this age, I need to send an email... I need to come up with a concept that I can send an email six days a week and it needs to be for a niche that I can get a $25 CPM and there's enough of them that exist out there. Then I was like, what's my skill set and what do I love? And it was like, well, I like news. I like business. I like writing. Okay, how about a daily business news for like higher earning or aspirational younger people? I can send that every single day. Yeah. And then like I created these like constraints, you know what I mean? And if I get 100,000 in year one, if I get 500,000 in year two and a million in year three, I could actually be at 10 million in revenue at that point. And so it was like all that.
It sounds a little like Ikigai. Like what am I good at? What does the world need?
Well, it is Ikigai. I stole it. Yeah. So it's what does the world want? What does the world want to pay for? What am I good at? What do I love doing? And you get something right in the middle. And so I took like months thinking about that, doing that exercise. And I was like, okay, daily newsletter. That's it.
It's like an obsession for you. I've seen the... I didn't know about this one. This I got to find the spreadsheet now. But you've done this with like companies to work for and...
I did that for... Yeah. Yeah. I love doing that stuff. Like we... Yeah. We had this thing. I was thinking about... we almost launched this product called... well, we didn't have a name for it. I just called it Jobs. But it was like the idea was like there are companies that exist out there where you can join them at Series B or C, where meaning they pay well, they have good maternity and paternity leave, you can probably have a normalish life, meaning you're with startups, you're grinding and stuff. Some of these companies are a little bit more established and so you can have more balance and yet the stock can 10x. Meaning if you got $100,000 in stock over the next six years, that could 10x to a million dollars. Yeah. If you went to Anthropic five years ago, right? But there's tons of these. Like for example... maybe $10 billion and now it's worth 80 or 90 or 100 or something like that. And it was like what are these companies that are established, they're not going to zero, but they definitely can 10x potential... they potentially could 10x. And so we like would do all these interviews and like these and we would editorialize it and figure out what those are and we made a list and people would pay money to access it. No one wanted it.
Maybe we executed poorly.
Maybe timing. Maybe now they... I think that could exist by the way. I think it should. If it doesn't...
I think it's harder now. Between 2016 and 2022 it was easier. Now just because they grow so fast and like Lovable was like nothing and then all of a sudden it was a billion dollar company. Yeah. So it's a little bit more challenging. Yeah. But it definitely should exist.
How do you think this process... I'm like fascinated by it. You're like unpacking things very methodically. It almost seems like David Senra. Have you listened to his podcast?
He's like this biographer and he's just going so deep on these founders. It seems similar to the way you're describing the obsession.
So, you've said we did 900 episodes on MFM. That's crazy. I didn't know it was that high. Is it really that high?
I think I researched and saw 899. Wow. I think I've heard someone say 850. It's over eight, but that's crazy. Yeah. And I was telling someone the other day, I went to this thing last night and they were like, 'What have you learned talking to all these cool people?' And I was like, 'I've learned a lot.' But the one... one of the very few rules that I would say that I can create for myself or for anyone else after talking to all these people is there's an infinite number of ways to get to the end destination. And so in Silicon Valley, people will say all these rules. They'll say focus. They'll say make an MVP. They'll say you have to work a certain amount of hours or get whatever the rules are. Those rules could work. And also, I can show you dozens of examples of people who ignored and broke all those rules and they ended up in an awesome place as well. Sometimes a better place, sometimes a little bit worse, but like they achieved the end goal, right? And I forgot what you had asked. We...
We were just talking about obsessing over biographies.
Obsessing. And so it's the same thing with biographies. And so like for example, Andrew Carnegie. Yeah. I love reading about Andrew Carnegie. I think he wasn't like the greatest human being, but I love learning about him because he had this quote where he was like, 'I work from like 8 to 11 and if you can't get a day's amount of work done in those three hours, then you're doing it wrong.' Wow. Okay. And that like why is that interesting? Because...
8:00 a.m. to 11:00 a.m. Okay. Three hours in the morning. Yeah. He was like, I get it all done in three hours a day. And like that was mind-blowing to me because he's so successful. Andrew Carnegie is one of the richest people to ever live in the history of America if you adjust for inflation. He created a steel company that he sold for billions and billions of dollars in like 1930 or something. So it was a lot of... I mean it's a ton of money. Yeah. [snorts] And so okay, so I read that and I'm like, oh, I'm not going to work hard. Okay. But...
That's not the truth. The truth is, you have to read the biography and be like, okay, but it said he also had this much success when he said that. Therefore, put the work in at a certain time. Once you get to this threshold, now I have an example of someone who then took his foot off the gas and it still grew and still got huge. Same with John Rockefeller. When John Rockefeller was 36 years old, he went into semi-retirement. He became the richest American in the history of America at the age of like 60 or something like that.
I was going to say because in Titan, it's like the guy's like a maniac.
He was a maniac. He was ruthless.
He chilled when he was 36. And if you read his biography, Titan. But then there's a few others. There's another one that I really like, written in the 1970s, about more of his business tactics, and it's like a case study.
And he wrote a letter to John Archbold, and he said, just so you know, you might dislike this, but my kids are around and I'm going to start working from home and you're not going to hear from me a lot. And he was 36 years old. He goes, I'm going to go, this is his quote, he goes, I'm going to go into a period of semi-retirement.
So what is it leading up to that? Is it different leading up to that moment?
Yeah. He was, he was, he was...
Seven days a week. Like, is this nine months?
Yeah. No, he was a hardcore Baptist. So he always took Sundays. I mean, Sunday was a day of rest. But then he also had all, like both actually, him and Andrew Carnegie. John Rockefeller has this famous line where he's like, I pity the man who only thinks about business and doesn't have like a rich life outside of business, you know, doesn't worry about, have hobbies or children or whatever.
Andrew Carnegie actually wrote a thing similarly at the age of 36, and he goes, I make this much money per year at the time, I think he said $50,000. I don't need to make any more money. I don't want to focus on money, and pursuing money for money's sake is an empty search, and I'm not going to do it. And of course it's easy for him to say because he was very rich at the time.
So I think that's a little shallow, but like, the point I'm getting at is if you like read all these interesting stories...
That is one way to do something, right.
And then I could tell you 10 other ways of like someone who like grinds, like Sam Zell was like grinded until he died, like work 100 hours a week. There are some people I feel like they make it look easy, but they are thinking about business all day, every day. It's like part of their life. Maybe they're in the office 20 hours or 40 hours, but like they're emailing instantly, nights and weekends. So like I don't know where they draw that line, but there are some people where it appears there is more balance, where it appears there's more...
That's true. I fall in that category where it appears as though I'm balanced, but I'm thinking about things, I'm thinking about it.
But like there's just a billion different ways to like get the same thing done.
Is there a through line on that? To sort of like do the thing that you think is right and...
No, because I don't think so. I think it's just having an open mind, but I also think like listen to yourself and like try to figure out. I sort of believe that like weaknesses mostly can't be fixed, and strengths, you should like create systems that allow you to show your strengths more often.
Okay. Create systems that...
Weaknesses can't be fixed, strengths can be improved. I don't want to say they can't be fixed. It's just like it's really hard to change.
And it's much easier to change the environment to optimize for your strengths.
So hire for your weaknesses and lean into them.
Yeah. And like create things that you don't have to do the things that you suck at, or live the life that you think you hate. I think that's a more practical way to go about it.
It does seem a lot like almost like life design, like what kind of business you build, who you surround yourself with.
Yeah. I believe in this concept of a rich life, and my friend, I don't know if he invented it, but he told me about it, and it's just this idea of like being very specific about what your ideal day is, and like your finances, what you want them to be, and like when you die, like what would you look back and say this was a fulfilling, full life.
Yeah. And we did, I did this with my wife, by the way, when we were dating for six months. We sat down and I was like, look, this is going to sound like a business meeting, but I think it's important. I want us each to answer these questions, which is like in very specific detail in five years and in ten years. It's okay if all this changes as we grow, but what is your ideal setup? What is your ideal routine? Where do you want to live? All of that. Like get as specific as possible.
Is it the Z on the ABC? Okay.
Yes. And then let's talk about what are you willing to give up to get there, and what are you unwilling to give up, and let's come back to the table and let's look at where are we both willing to compromise and not compromise, and do our values align on where we want to go? And if it does, that's a really good sign. If it doesn't, then that's good that we know now.
