All right, Sam Parr, been dying to talk to you on the show. I'm a huge fan of everything that you do and I love your work. Thanks for doing this.
I love your work. You came on my podcast as well, so I love your work.
You know what's the best? When I did your podcast and it's not a knock against you, I'm just like, I'm way behind on everything.
You didn't know anything.
I didn't know anything. And Rob was like, "You're going to do this show My First Million." I was like, "I'm not going to talk about making a million dollars on a podcast." He's like, "It's not even about that."
No, but I was like, "I'm not going to talk about money on a podcast." Which is funny when I listen to Moneywise and you are like, "Okay, so how much money? What's your liquid net worth?" And you interviewed my buddy Josh Payne.
And I could not believe all the things that he shared.
Me neither. I can't believe that people do it, but they do.
But it was awesome. But then you also interviewed my buddy Mark Hodick and he was like, "Dude, he was asking me how much money I had." I go, "That's the whole premise of the show. They tell them when they come on."
And he was like, "Yeah, but I wasn't doing that." And I go, "So I guess that your episode didn't air then." He's like, "No."
Yeah. So, we do it in a very non — I call it — can I curse here? I call it a non-douchy way.
We try to be very factual and not — it's not braggadocious at all.
No, for the record, I love it. I think that it's refreshing that someone will tell you like, listen, I had an exit. Everyone knows I sold my company for 50 million, so now I'm liquid for this. I live on this. Like, I find it to be incredibly informative and I think it's helpful when people just tell the truth. It's not a secret. If you sell your company for X million and it's public news, why should you dance around it? I mean, I get some people not wanting to, but I genuinely find it interesting and informative.
And a lot of the guests were anonymous and we changed their voices. So, there's some people who you won't even know who they are.
Oh, really? Oh, I didn't know that.
Like, for example, it could be a woman and we made her sound like a man or vice versa.
Early on, we hit a lot of voices.
It's really good. Like, that's what I was saying. Like, I love everything that you do. It's so like — I don't know if innovative is the right word, but it's just like...
I innovate in a very small field, I think.
No, it's very different. And you've called yourself — I've heard you call yourself a nerd before.
And I love it cuz I would say, yeah, he's a huge nerd, but I would call myself a nerd, too. But I don't say that as an insult. I'm like, Sam is my favorite nerd. He nerds out about...
Dude, when you nerd out about vintage jeans and vintage clothes, I'm like, I don't know why I love this.
I love it. I'm like, "Oh, Sam found a new pair of jeans." I said one night to my wife, "Oh, Sam Parr found a new pair of jeans." She goes, "What are you talking about?"
I love that stuff, man. I'm very passionate about certain things and I just love it.
So then I was describing you to her and she's like — and I was like, "Yeah, he's a nerd, but he's cool." And she goes, "It sounds like you're the nerd. You're watching him talk about his jeans." And I was like, "Exactly."
Yeah, I'm a loser, man. But I love it.
I'm just into what I'm into.
You're a winner. One of my biggest things is always telling people like whatever you think about yourself, it's true. So don't waste time thinking I'm a loser.
I don't think I'm a loser. I think I kick ass. But I think I've gotten really lucky.
That's a defense mechanism to say I'm a loser.
I think I kick ass. But I think that I've been incredibly lucky in life. And so sometimes you got to like, you know, bring yourself down a little bit. And I'm from the Midwest where you think you're horrible no matter what.
Well, yes to everything you said, but that's — I do that myself, where you do this self-deprecation thing as a way of protecting yourself because it's almost like if I tell you I'm a loser, you can't call me a loser. But the truth is you can't have the success you've had if you didn't believe in yourself. All the things that you've done have required exceptional conviction.
Yeah. I think people would be surprised at how like crappy something feels as you go, even if it looks like it's doing well though. But there is something in you that is like, this doesn't feel good, but I can't let it go.
Yeah. It's like a weird compulsive thing.
It's definitely — I don't know what it is, but there — I just think I'm a little autistic or something. I don't know. Like I just like — yeah, but there's like a weird OCD about these types of things.
I love it. So, let's start at the beginning cuz I think you had a hot dog stand. I remember at one point you had a freaking motorcycle in your living room or something. Just like all kinds of weird stuff where I'm like, "Wait a minute. What?"
So, let's start. Let's tell...
I've lived a few lives. I'm from Missouri, St. Louis, Missouri. Grew up there. Went to school in Nashville, Tennessee, where you are, to run track and field.
Oh. Oh, cool. They got a good track program, right?
Yeah. Yeah. I ran — it was a Division One — I was a Division One 400 meter runner.
Oh. Oh, I didn't know that.
Yeah. I ran — I was 400. I was like a 48 second 400 meter runner.
Anyone who has ever done any workout at the track, run one lap of the track. If you can get under a minute, you're a real runner.
I was good. In high school I ran high 21 seconds in the 200.
Um, and just until recently, I still do time trials and train. So, I could still run 23 seconds of the 200, which is good for a 36-year-old.
I can still dunk a basketball. I still got it.
I've seen you do some different fitness tests like a couple years ago. I remember you...
So, I could still move a little bit. Uh, and then I dropped out of school, but well, before I dropped out of school, I met this guy named Mike Wolf. Have you seen American Pickers?
I worked for that guy in Nashville.
This is what I mean about you. You're running Division One track. You're doing — you're like, I'm gonna drop out of school and work for a guy picking...
I saw them on the street outside of Imogene + Willie on 12 South.
My favorite jean shop in the world.
I love denim. It's a weird passion of mine. I love denim and I couldn't afford their denim cuz it was like 250 bucks when I was in college and I would just hang out there and they would let me take out the trash sometime. And then Mike Wolf, this guy on this TV show — at the time it was like the second most popular show on TV — was just hanging out and I go, "Mike, I love your shit." And he goes, "I'm opening up a store here." I was like, "Can I work there, please?" And so he let me work there. And then while I worked there, I started a hot dog stand because I learned about entrepreneurship. He was an entrepreneur. He was like the first entrepreneur that I met. He was making millions of dollars a year. We would sell like, you know, some days like $150,000 in t-shirts at his store.
And I was like, "This is awesome. I could do this, but I don't have any money." A hot dog stand. I don't know how I came up with it, but I had a stand one outside of Station Inn...
...and then one outside of Dan McGann's for the bars at night. And I called it Southern Sam's Wieners as big as a baby's arm. And I would kill it. And then I was like, "This is so hard to sell hot dogs at, you know, noon on a July day." Like, and so I got into the internet.
Well, one quick thing. I don't think selling the hot dogs at noon in July is nearly as hard as 4:00 a.m. to drunk people cuz I'm like, "Every person doesn't want to pay. They're drunk." I'm like...
"Yeah, but I was drunk, too, so it worked out."
One of the reasons why I did it was cuz I had like a drinking problem at the time, like seriously. And I wanted to drink all day. And it was like the perfect job. And so I found this company called Airbed and Breakfast. Cold emailed the founder and he was like, "Do you live in the Bay Area?" And I was like, "Yeah."
I didn't know what the Bay Area was. I thought that meant LA. I didn't know what it was, but he's like, "Okay, come to my office on Monday." And I was like, "Yes, sir." And so I flew out there. I'd never been west of Missouri really.
And he offered me a job. So I left college and stayed out there and got a job there. And the day before I was supposed to start, they called me. And at the time it was Airbnb. At the time it was only maybe a hundred people. I forget. It was a small startup. They're like, "We don't hire liars." Because at the time I had gotten a DUI driving out of the White Castle on West End. And I spent 5 days in jail and...
Because I didn't take the breathalyzer and you automatically — so I went to jail that day and then I got arrested a few weeks after for getting in a fight outside Dan McGann's and then I had to go back to jail for not taking the breathalyzer. So, I got Friday to Sunday in Davidson County Jail and it was horrible and I had a bunch of demons that I was working through and I lied about it on my resume to work at Airbnb and he caught me. They caught me. I told him I didn't...
One quick thing. For a smart guy like you, how would you think that they're not going to know that you got arrested?
I didn't know how background checks work. I was like, they're not gonna know. And I think I was still — I hadn't been convicted yet. I think I was still in the...
Oh, okay. So, technically you're innocent.
Yeah. The way they asked the question, I thought like...
There's some plausible deniability.
Yeah. But I was trying to pull a fast one. So I totally am on their side. They did the right thing. And I now have become a little bit friendly with the founder Joe and he was like, "I remember you." And I was like, "You were right to do that." He was like, "I know we were right." And I was like, "Yes, sir." And so I was out there in San Francisco with like nothing. And I eventually started a business called Bunk. It was like a roommate matching app. And that did okay. Okay. I made like 50,000 bucks in a year. Not like great, but I was paying bills and then I started my new company called The Hustle and that was like my big win.
But what prompted that? And what exactly did The Hustle do?
Originally, it was a conference. And so I had just exited this roommate matching thing and I just made enough money that I had about six months. And so I hosted a conference called HustleCon and I called it a TED talk for entrepreneurs and I convinced 15 or 10 people to come and speak and I charged $300 to attend and it was like the founder of Casper or...
I forget who else — one of the co-founders of WeWork before they had blown up.
And they gave like cool talks on how they're building their companies.
And I made like 50 grand in six weeks.
And I was like, that was awesome. And the reason I hosted that was I was like, I need to come up with an idea, but I don't know what idea I have. So, let me just host this event to like maybe I'll meet someone or something like I don't know. I'll just maybe serendipity will happen. I'm not sure what I'm going to do, but like I think I could pull off an event in 6 weeks and I think I can make a profit, but I don't know with the long-term vision, but let me just do this and see what happens.
And did you have any idea planning an event? Cuz to me, planning an event is like my kryptonite. I'm like, I don't want to deal with any of this.
I — when I first moved to San Francisco, I was really envious of a lot of these kids who went to Stanford and Berkeley and all these like fancy colleges, and I desperately wanted that network. And so I started a book club called the AntiMBA and I posted an ad on Craigslist and on Facebook and I said, "My name is Sam Parr. I'm hosting a weekly business book club. You can apply to join my book club." And I got like over the course of a year like 2,000 people following me online giving me their email. And like I invited like a hundred of them over the course of a year and we would read one book per month and talk about a quarter of the book every week.
And I would have a speaker come in to talk about that book's chapter or you know what I'm saying.
And it was just a way to like meet people and like I would read like a week in advance and no one else would read but I would like kind of teach what I'm reading but it was just like a fun way to network because I didn't know anything hence the AntiMBA is what it was called.
And so I kind of knew how to organize in some capacity but I was like, how hard can it be? I'm just going to get 300 people, put them in this theater, and I don't know, I'll figure it out. And so it worked, but the way that it worked was I created a newsletter where the website was just like enter your email if you want to come to this event and I'll invite you if you get invited or something like that. And I got a lot of people to sign up because I would create these cool blog posts about each speaker.
And people loved my emails.
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What were you majoring in in college? Were you a writer?
So, no. I studied music business, but I eventually got my degree in just like some generic business degree because when I left school, I finished online. My mom was like, "Please finish." So, I finished online while I was in San Francisco and I just asked them to give me any degree that I could have. So, I think I never got to graduate, but like business administration, I think.
This episode is going to be a must-listen for any high school, college entrepreneur, any kid who feels like he's like a little bit different and doesn't feel like I want to go to New York and work and to go the banking route or do something that you don't have to follow the crowd. Like this is such an awesome inspirational story for someone who's just like, I just want to hustle. I don't even know what I want to do. I just want to have fun. Cuz it sounds like you were doing things that were interesting and fun.
No. When I was a kid, when I was 14, I wanted a girlfriend so bad and I was so ugly and goofy looking.
By the way, you're very handsome.
Not bad. Thank you. But not bad. I looked like Napoleon Dynamite. And I was goofy and I had braces.
And I desperately wanted a girlfriend. I wanted to be liked. I wanted to have someone.
Brother. Same. And I read all these books on how to meet girls.
Every book you could have about how to meet a girl, I read about it. And one of the rules of meeting a girl is you have to be passionate about something and bring her along with you. So like if you're like enthusiastic about a passion that you have, I swear to God, this sounds super nerdy, but I've always been into denim. One of the first dates I took my wife on, I was like, I'm really into vintage clothing. There's this amazing thing and they sell this very particular type of thing and it's made in Japan. It's really cool. Do you want to come with me and I'll show you about it? She didn't care about any of that stuff. She thought it was cool that I was passionate about it. And so once I learned that you can kind of let your freak flag fly a little bit and if you are excited about it and earnest about it, people get excited. Once I learned that, I decided I'm going to share all my weird eccentricities with people and it was really effective.
The one thing that people should take from that is that if you are trying to pretend to be something you're not, you're going to get revealed. You're much better off like not putting on an act cuz if someone likes you for the character you're playing, that is unsustainable. Whereas you just leaned into like, hey, I have these weird quirky interests in vintage denim, which I mean, she didn't like it, but you never know. You could find like one sexy woman who's like, I love vintage.
They thought it was cool that I was passionate about something. And I think there's a correlation between passion and a mission.
And so like I just learned that if you have like contagious — energy can be contagious. So I have contagious energy.
Yeah. Well, that's what I — this is one of the things like I'm loving this conversation. And I love how enthusiastic you are about everything. So, okay. So, you're out there. You're going to have this conference. So, all these people sign up. You've got them all there. Are you shitting yourself? Like, oh my god, I'm going to be putting on this convention. I'm having anxiety thinking about it.
It was very stressful. It was very stressful, but it made like — I forget exactly how much — 40 or 50 grand in profit.
And I was like, that was cool. So, I took the money and I took a six-week motorcycle trip cuz I was celebrating one year without drinking.
Yeah. So, I was celebrating one year and I just made a little bit of money and I came back and I was like, "Let's do it again." And this next time I did it again six months later and I made 150 grand.
And I was like, "All right, something's here." And so through that and a couple other stuff like my past work, I had like $350,000 saved up.
And I was like, "All right, conferences aren't going to be my thing, but I love writing and I like very nerdy stuff. I like emails. I like email. I like writing emails."
Let's see if I can start a media company. And that's when I pivoted my conference to this thing called The Hustle, which doesn't sound interesting — a year with just an email newsletter that tells you about the business that you need to know every single morning.
That was like the premise. I was like, I think I can do this.
When you say the business you need to know, like the business topics that are topical in the world.
Yeah. So, I would find out all of the news that was going on and I would give you my take on it. So it was only 1500 words and it would be like here's everything you need to know, like here's the top story, here's a bunch of small ones, here's a funny thing, here's a cool book to read, here are like 10 cool blog posts I found this today. I just curated the internet for the tech and business savvy person.
So okay, so geared towards tech people. So you wouldn't write about like socioeconomic trends in Nigeria because something happened in, you know...
Maybe that would be a small...
...or oil prices are down because of the Strait of Hormuz, like...
Only if it really — the niche was like tech and business.
So, there was no politics or anything controversial.
No, typically. No. No. No. No. No. No. And the math was such that I could charge — I forget exactly the numbers, but something like $75 per 10,000 subs. And so, I was like, I think I can get a million people to subscribe to this. I think I can get probably two or three million people actually. I was just doing the math. And if I can get a million people to subscribe to this, I can make 70 grand every time I hit the send button. And if I send every single day, so like 26 days. So we actually sent six days a week. So 6 times 24...
That would be something like, you know, I can't even do the math now, but that's like $2 million a month in revenue that I can make.
And then if I had another newsletter, that gets me to this. And then if I keep doing events, that's how I get to 100 million.
I just did the math. It was all back-of-the-envelope math. And I sold the company a little bit early, but we were on track to do that.
And did you — how many people were working for you?
I think including freelancers when I sold maybe 35.
When you started hiring people, this is one thing I think about like with my own agency is like just the thought of having multiple employees gives me anxiety. It's like right now I have like contractors. They're like my friends. Like I trust them implicitly. The idea of having employees and HR and stuff, I'm like, "Oh, this is getting away from me." It's like I don't want to manage people, but I like the business.
How did you handle that? Because I always find it interesting and it's what separates like the wheat from the chaff, right? Oh, you have a good idea and you can make a little money, but that's a far cry from you have a scalable business that's sellable.
How did you master those qualities? Because obviously you did. You had a great idea, but not only did you...
I wouldn't say master them, but I was effective.
You were effective, but you did. You took a good idea and then you became a good CEO.
I was an okay CEO. I was a good business owner. And first of all, I want to be fair. I got really lucky. COVID was bad for a lot of people. It was really good for me. Yeah. Like things aligned. So, I don't want to take too much credit, but I think we did — I think that first year I think I said I did three or 400,000 in revenue from mostly events. The second year was 2.2 million. Then I think it went to 5.5.
Then maybe it went to like roughly 10. No, the year we sold it we did 12. So from five to 12 and then that year we sold we were going to scare 18 million.
Do you talk about how much you sold it for?
Yeah. So the headline said 27 million. It was more than that. So it was...
I took a little bit of angel money but I was the majority owner.
What percentage did you sell of the company?
No, no, no. Did investors own before you sold it? Like you took angel money on what? 15%.
So you own 85% of it.
I had some employees got some. I made north of $20 million.
Yeah. I made tens of millions of dollars.
Yeah. But just take a minute to think of what like you did.
Yeah. It was amazing. I was 31 years old. It was crazy.
But that's why like luck is so — like before the sale I thought I was the shit and then after the sale I'm like...
Dude, so many things outside of my control have just aligned. Selling a business is so rare.
Yeah. And especially for that kind of money.
I think that there's a lot of people, maybe there are such things as these dealmakers who know how to just sell a company, but it was luck to be honest. It was probably 70% luck. I think I built a good business. What wasn't luck was I had a good insight. My insight was that, and this is really nerdy stuff, but media stuff. Basically, Facebook, if you had a million people who liked your BuzzFeed Facebook page, they would post an article and it would get traffic to their article. Over the years, it was going down. Facebook was pulling back reach.
Facebook didn't want anyone else to make anything.
And I was like, "This is so obvious." And I think a lot of people thought it was obvious, but I was like, "If we create an email list, every newsletter subscriber I get, it's like a little bit of wind in my sails and I'm a pirate ship."
And I'm like, I could hit send because people would make fun of me, but I'm like, "Guys, pull up your phone, click email."
Okay. What's the difference if you're looking in your email app or on Chrome? It doesn't matter. You're looking at a screen and I own that screen for a little bit of time. So, why does it matter if it's a website or not? Because if I have — we had a 55% open rate. I forget. Let's say 50% open rate. So, if I send to 1 million people that day, I'm getting half a million views.
And they're going to be subscribed to me for like 10 years, 5 years, you know, something like years.
It would take a lot for them to unsubscribe if they went through the effort of subscribing. You'd have to put out such shitty content for someone to physically unsubscribe after they...
Get to know you. And I'm like, this could be a huge thing if you do this right. Nobody, very few people believed me. And coincidentally, this guy named Austin and Alex, who I'm dear best friends with, they live out here. They started a company called Morning Brew, and they only sold a portion of their company. So, they were still running up until recently, and they're scaring 100 million in revenue today.
So, the premise was correct. I just sold a little bit early, so I didn't get to see it through.
The funny thing is, I think that all people that have any level of success have a hard time relishing in the victory. Like when I won the age group world championships in Chicago, I called my wife and she's like, "Oh my god, you did it." She didn't even realize what the significance of that race was. It was like, you know, the age group World Championships was inside of the Chicago Marathon. And she's like, "Oh my god, how happy are you?" when she realized what it was. I was like, I just feel so relieved that it's over. But like you, I'd be like, "Man, I just got lucky. The two guys that were second and third have both run minutes faster than me in the same year. They just made some mistakes and I got them. Like I just beat them. Like some of it was psychological." But I had a hard time saying like, no, I'm the man. I did it. Anytime I've won anything I'm like, I mean I got lucky that time. But I think that that's the blessing and the curse. The blessing is that you won these things. The curse is that if you take a minute to think you're great at it, you're probably not going to get it again. Like you have to have that honesty with yourself and be like this only happened from a win or die trying effort. Like I couldn't half-ass it through this. You couldn't fake your way through that.
But sort of like running, like when you get in between the lines and you're going to race, you're like, I'm the best. I'm going to kill everyone.
But then like before and after you're like, I'm horrible. I need to work harder this or that. So like there's definitely moments of like I'm going to — I'm the best.
When it's happening you have to believe. I always say...
Have you seen that thing with Mike Tyson where he goes like, I'm David the Great. I'm the conqueror.
That's an awesome rant. But yeah, I always say train like you can't win, but race like you can't lose.
And then that is like I could go on forever with all these sayings and expressions, but I love them.
The reason I love boxing, which that's what you and I have bonded over a little bit, but I particularly love UFC, is because — have you ever talked to these guys? You've talked way more than I have, but I only see their interviews and like occasionally when they're retired they'll say like I was so afraid all the time. And you'll see guys like Mike Tyson, like crazy guy, and he was like every time I fought I thought I was horrible. I was so afraid. I was fearful. But then he looks like a — I think he would say he's like I'm a tiger, you know, like I'm going to eat you. I'm going to maul you. But inside he's fearful. And it's been really cool to hear like my heroes or people who I think are tough guys say they're fearful all the time.
I got really lucky when we hosted this HustleCon event. You know, I kept doing that event for like five or six years or something like that. And I would have billionaires come and talk and so many of them backstage — I would tell them to come up, you know, they would talk at 3:00 and I was like, "You got to be at soundcheck at noon." But there was no soundcheck.
I just wanted to make sure they were there. I just wanted to hang out with them backstage and we had this like green room and so I would get all these ballers who were all like 100 times more successful than me and they would be talking about whatever and they were complaining about stuff and being fearful and stuff and I found that was awesome. I was like, "Oh man, dude, this is like my version of Mike Tyson who I admire and he's telling me he's fearful. That makes me feel so good cuz I'm fearful too." So that's pretty cool. So I got lucky with that.
That's one thing that I emphasize with my kids all the time and I've told this story before, but my middle son is very timid and my younger son is a savage. He's like — he wrestles, he does jiu-jitsu, but he's also not afraid to say — I'm like, "You nervous?" He's like, "Yeah, I'm nervous." And I'm like, "It's all right. I promise you the other guy's nervous, too." But my middle guy is very timid. So, he's playing baseball because there's no contact. And every time the guy throws the pitch, he kind of steps out of the batting box. And I say, "Buddy, it looks like you're scared every time he throws the pitch." And he goes, "I am." And I said, "All right, but you need to know like everyone is scared and that ball, even if it hits you in the head at the way he's throwing it, you are not going to get hurt. It might hurt a little bit, but not a lot. As soon as you stop being afraid and learn to do things scared — you can be scared, but you got to learn to push through that."
Have you talked to any like, you know, gangster fighters like...
Oh, yes. That's what I was going to tell you. One of the nice things that happened when I was hosting the show with Teddy Atlas, we trained Alex Gvozdyk, the Ukrainian world champion. He was the WBC light heavyweight champion of the world. We trained him for eight weeks and I worked the corner. We fought Artur Beterbiev who then unified all the titles and was a killer. Never lost, a Russian. And being in the locker room and seeing the emotions is scary being in there. Never mind throwing up and stuff.
No, no, no, no. He had a brave face on.
I'm just saying you could feel the nerves in the air and it was like everyone knows everyone is scared but the other guy in the other locker room is the same thing. Like you'll never hear someone be like, oh, we're in the locker room, we knew we were going to win. Maybe Terence Crawford has that kind of conviction. He seems to like...
I don't think anyone does. I don't even think Conor McGregor who's like one of the most like bravado — I wonder if Mayweather like...
That's a good one, but I will tell you I've talked to Poirier at length. Dustin Poirier is a good friend of mine and he talks openly. He's like, yeah, of course everyone is scared. He goes, "You just learn — I was telling someone this the other day. You got to be comfortable with being uncomfortable." And they're like, "I don't think so. I don't think you ever be comfortable with that." I said, "It's not that you're comfortable being uncomfortable. You're comfortable being in uncomfortable positions." Meaning, you know how you're going to react. You trust yourself enough to be like, "Okay, I'm scared shitless, but I know once I get in there, I'm going to be able to execute." It's like being at a race. I've never woken up for a race and been like, "I'm so psyched. It's race day." I'm like, "Why the fuck did I sign up for this? This is shit. I'm going to embarrass myself. I'm in the worst shape." And then I've won the race and I'm so happy when it's over because I'm relieved that it didn't go badly.
But Dustin told me that he's been in the locker room for an MMA fight in big promotions and the guy he was cornering from his team like multiple times would cry and be like, I don't want to go. I don't want to do it. I don't want to do this. And he'd be like, I know. I know. No one does.
Have you ever had any like bouts? I know you trained.
I had some amateur fights. Yeah. Scared shitless.
Oh my gosh. So, I very casually train boxing and I'm like, I can't. I thought running was hard. Imagine getting equally tired, but then you get your ass kicked. This is way worse.
Well, the worst is when you're tired and the other guy senses it and he's gaining momentum and you're like, I'm getting more tired and this guy's — it's giving this guy fuel to attack me. So, that's when you learn to fake your way through it. Like, you do not want to show that you're breaking down. But yeah, man. There's nothing scarier than walking into the ring to have a fight with another guy.
Yeah. I can't imagine that. I remember just like on sparring days, I would feel nervous and I'm like, I can't imagine doing this where he's actually trying to hurt me and I'm in front of everyone.
That's it. Cuz when you're sparring, you have respect for your opponent. Even if it's like a friendly smoker, like the amateur fights, like I fought Wallace Matthews one time, who's like the boxing writer for the New York Post or the Daily News or something.
No, he was good. He was beating the shit out of me. At one point he cracked me. He's like, "You good?" And I'm like, "Yeah, I'm good."
Smoker, so there was people there.
Yeah. Oh, yeah. It was like I was fighting for the New York Athletic Club and I think he was fighting for like Long Island Athletic Club and it was the last fight of the night.
We were like the main event. I was like, "How am I in the main event?" But he was like one of the organizers. I think it was him. It might have been the owner of...
I used to go to Church Street and...
No, a big Ukrainian guy. What was his name? I forget. You know who trains down there now as a trainer is Peter Quillin, Kid Chocolate.
He was nasty. He was like a welterweight champion.
It's fun going down there because they're not yuppies. And it's like kind of grimy and it's fun. And whenever I would spar there, I would get scared. I was really scared.
That's funny. John Duddy is a trainer down there, too. Irish champ, former Irish champion. Like a middleweight.
It's cool walking in there. I love going in there.
I trained at the Somerville Boxing Club. And when I went in there, John Ruiz, who was the heavyweight champion of the world, was training there. So like that tells you like...
They're so big, too. Like I'm not a small guy. And the guy I sparred...
With was, well, he was my coach. So it wasn't sparring. It was me hitting him and him laughing. And I'm 206, 210, and I would hit him as hard as I could and he would be like, 'That's it.' And I remember feeling so emasculated. It's just the difference between the big guys. It is incredible how big they are.
But the fact that you even went down there and showed up, like how many people would never have the guts to walk into a boxing gym, period. It takes a lot of courage to even show up in there and be like, 'Hi, I'd like to learn how to fight.' No one's in there like, 'Hey, come on in, buddy. Thanks for showing up.' They're like, 'What do you want?'
I quit doing it. I got hit in the head a few times and I had headaches for like a few days and I was like, 'This is foolish. I'm not doing this anymore. I got what I needed.' But it's super fun. It definitely makes you more courageous. Like I remember complaining about like silly work stuff and I'm like, 'I just got my ass kicked this morning and I was fine.'
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So you build up The Hustle and you sell it to who bought it?
Oh, cool. All right. So when they bought it, was there an earnout? Did you have to hang out?
So when I sold it, I had a really good executive team. So I didn't run the company anymore, but part of the deal was me continuing to host this podcast that we owned, My First Million.
Oh, that was part of The Hustle. But it's not part of it anymore?
No, it still is. Yeah. It's still HubSpot. HubSpot owns it.
Oh, really? So when you do the podcast, how does the money get divvied?
Yeah. So they pay us on performance. So the bigger it gets, the more I get paid.
So you get paid a percentage of the ad spend.
No, what's crazy is, so HubSpot was really cool. Their whole premise was basically HubSpot is like a CRM. It's boring software, but it's like super necessary for small businesses. I still use it at my company. Very awesome stuff. I'm legitimately a customer. And they were like, we have so many customers that we literally have to like own a media company to reach more people. So instead of sponsoring publications, what if we just owned you? And I was like, that's pretty cool. So they shut down all ads and we actually owned a handful of podcasts. And anyway, now my company is called HubSpot Media and they own a ton of podcasts, a ton of newsletters, and they own a ton of YouTube channels. So it's basically a whole media network. And all of it says like, this is brought to you by HubSpot. So imagine this podcast being owned by HubSpot and they would just pay you. They'd be like, assume that you have advertisers, but we're the only advertiser.
So does My First Million have no advertisers except HubSpot?
Oh, okay. So HubSpot is the advertiser. So based on the CPMs or whatever the measurable is, that's how you get paid.
Yep. Yeah. And so the reason the deal changed a lot was because the podcast got huge.
So what's the deal now? Like hypothetically, if you were like, I don't want to do this anymore. I want to start my own podcast. Do you have some kind of non-compete with them?
So you could theoretically just be like, you know what? I'm going to do my own podcast. Like Moneywise, that's not a HubSpot product.
No. My company, I'm not the host of Moneywise, but I hosted the first handful to get it going.
Oh, okay. I didn't know that.
No, I hosted the first handful just to get it going and now we have a new host.
No, I've noticed that there's like a British guy, right?
Yes. And now we have a different one.
I thought he worked for you.
No, he was an agency who we hired and he did a great job.
Yeah, he did do a good job.
He, it's called Lower Street. Shout out to them. They did great. But we just wanted to bring it in house because I just got a new office and I wanted to have him here with me. So yeah, I own other podcasts now. My company Hampton, I liked what HubSpot has done that we were like, let's create our own little network.
Oh, okay. So now you sell that. What did you do? Was Hampton the next move after HubSpot?
Yeah, probably. I had a kid so I took like six months and I just chilled.
Where'd you meet your wife first?
I love your wife on your social media. She's beautiful.
She's like the best. I saw her at, I say restaurant. It was really a bar but I wasn't drinking and it was like a five o'clock happy hour. So I didn't want to make it sound weird, like a big club. But I saw her and I was with this really nice girl, Lily, who was just my buddy. I go, 'Lily, that girl is so pretty. That girl who just walked in. I got to talk to her.' And she was like, 'All right, what are you going to say?' I was like, 'I don't know. Maybe I'll say...' And so she walks by and I go, 'Hey, um...' My wife walked by. I said, 'What's the difference between a chickpea and a lentil?' And she goes, 'What?' And I say, 'I don't pay $500 to have a lentil on my face.' Get it? A chickpea.
That's a pretty aggressive joke for someone who you're trying to court that you don't know.
It was a litmus test. If she thought that a chickpea on my face was pretty funny, then she was the one for me and she thought it was hilarious.
Oh my god. And what did she do for work?
Yeah. My wife went to an Ivy League school.
I didn't even know what that was, dude. I was such a hillbilly. When she said I went to Penn, I was like, with that rapist football coach? And she goes, 'No, you idiot. It's called Penn.' And it's like part of the Ivy League. I was like, the Ivy League? Is that Hogwarts? I don't know what that is. Like what is Ivy League?
Even the poor kids at Penn State, I feel so bad that the first reaction is like about Sandusky.
Yeah, I didn't even know about any of it. And she was like, 'Look, I'm not trying to brag, but like it's kind of a big deal.' And I was like, 'That's awesome.'
And she worked at Facebook. Had you already had the exit from The Hustle?
Oh, you met her while you were at...
I hadn't even started it yet. I had just only done my first event where I made like 40 grand and she was making like 120 grand. I was 24, she was 21 when I met her. 22, I forget. She was just out of college and that's probably why she liked me. We were in San Francisco and she didn't know anyone. And I used to make her bring me dinner home every day because Facebook has free...
Yeah. Yeah. Yeah. Free food.
She was my sugar mama. And then she actually worked at Airbnb. You know how I was like, 'Dude, you should go work at Airbnb. I still think it could be a great company.' And she became a millionaire before me.
I swear to God. When they went public, she had equity. She killed it. And so, dude, she's awesome. Her mom and dad started... her father started a movie company.
Yeah. He was a blue-collar Italian Jewish guy from New York City. He's like this type of...
Yeah. He's like the New York version of you. You're the Boston version of him, I guess. And he started this movie company and just murdered it. He killed it. They got a big old house in the Hamptons and this fancy apartment overlooking Central Park.
Yeah. He was like a blue-collar guy who just creamed it. And then his wife, my mother-in-law, Smithy, when Sarah and I had been dating for five years, she had been a stay-at-home mom forever. And she was like, 'I want to start a business.' And I was like, 'Okay.' And she told me her idea. I was like, 'All right, cool. That sounds great. Let me know if you need anything.' Well, two weeks later she starts a Shopify store and she sends it to me. I'm like, 'Is this yours?' She's like, 'Yeah, I did what you told me to do. I created this thing.' And so now she has a business. She was a stay-at-home mom. Now she has a warehouse and a bunch of workers and she has a business doing millions of dollars a year and they sell...
Decorative pillows.
Yeah, I remember you showed me that. I remember you told me about that. That's funny.
And so my wife came from... her mother's Haitian, a Haitian immigrant, and her dad's this like New York kind of hard guy. And so I was like, that right...
Interesting combination that a hardcore Italian New Yorker marries a Haitian immigrant. Even that must have been like...
Like back in the day, like it wasn't just like...
Yeah, interracial couple.
It just wasn't as casual as it is now. It's like you don't look twice. But I mean, when I was growing up, I always have huge respect for my Indian friends, black friends that grew up in the places where I grew up. It was racist like...
Well, where would you go in Boston?
Yeah, well, in like a blue-collar part of Boston.
Boston's like notoriously... notorious. That's where they had forced busing where in the '70s they basically said, 'Okay, black kids over here in Roxbury and Dorchester, you're going to school in South Boston. White kids, you're going to school over here. We're desegregating all these schools.' How do you think that went over? Poor kids are coming in on school buses and getting pelted with rocks in both directions. It was a disaster.
I thought it was cool. Like I love immigrants. I love English as a second language. Like when people... I take so much pride that I live in a place where someone's willing to risk so much to come here.
I completely agree. This is my problem with politics. If you and I are on a hockey team together and you get voted captain and the majority of the team says Sam's the captain. I hate Sam but we're on the same team but the election has happened. You're the captain. Would I go out on the ice and shoot the puck in my own net?
No. All we do is half the country votes for one president and then the other half spends four years trying to destroy him at their own demise. It drives me crazy.
Yeah. It's a very strange thing, but like I just love this idea that the reason I like entrepreneurship is like a loser can become a somebody. And like with immigrants, obviously they're not losers, but like to start from the bottom and like there's a world where you can get to the top. Like I always think about this. I read Barack Obama's biography and there was one part that stood out for me. Basically at his inauguration, when did he get elected? In '08. His father's sister was like living in Kenya without electricity and she came to the inauguration. And I always think about that. Imagine being like this guy in Kenya, this black guy in Kenya being like, this kid I'm holding is going to be an American. He's going to be the president and the most powerful person on earth.
Yes. We live in such a special place that allows anything like that to become... or like for example, my mother-in-law is a black woman. Her mother was an older black Haitian and my kid looks kind of white and she's like a yuppie now because we're really successful. Imagine like her holding, like growing up in a Haitian town and being like, this little, my offspring is a white...
And I always think that's like insane. Like how cool is that that like we all are this thing together and I just...
Listen, I have an Ethiopian daughter and she definitely does not look white. I mean she's Ethiopian and...
And like your offspring is going to be potentially like, oh, you're going to have a whole black line. It's crazy like you don't know where it's going to go, but I never... It sounds crazy, like I'm not trying to sound corny, but like I never see her as like the black kid. Like, you know, if I see pictures and the first thing I always do is see, is there other black kids there? But when we're together, I never like...
For the longest time, my kids would be like, 'Oh, Dad, there's another kid in our school with a dark tan like Tensie.' I'm like, 'Oh, there's another tan, literally another dark tan.' And they didn't know that there were black people. They were just like, 'Oh, there's other people with darker skin.' But I think that we're moving towards that just as a society that it's like race is almost like... obviously there's still very much racist pockets, but in the more advanced pockets of our society, there's like... I just, maybe my black friends would say, 'You're crazy. You don't see it.' But I don't notice it the way I did when I was a kid.
Yeah. I agree. Like I've seen some incidents because of my wife where people every once in a while and it's mostly subtle and that's not good.
No, of course. But in general, like if someone was going to say something on the street, there would be ten people that would say like, what the hell? How dare you, you know what I mean? So, you know, one incident is too many, but I still think America's pretty awesome.
Dude, I did a show promoting my book in London and it was a political show and there was a liberal and a conservative and then I'm on there talking about my book and my publicist said don't take... if they talk about politics, don't engage. The headlines come from this show, it's called the Jeremy Vine Channel 5 show and it was a daytime TV show. So the woman was anti-Trump, hated Trump, would never come to America while Trump was the president. So I'm just listening like whatever. He goes, 'Oh, at the risk of being controversial, what do you think of your President Donald Trump?' You know what I said to him? I said, 'Brother, I'm a proud American. I would die for my country. I love America. I love all Americans. And when we have a democracy and majority rules, once we vote for the person who's in, I respect the office. If it's Joe Biden, Obama, Clinton, or Trump, I support the president. I don't agree with everything that he does and I don't disagree with everything he does.' The guy didn't know whether to shit or go blind. He was in a pretzel. He was like, 'All right, cool. Next.' Well, what are you going to say to that? And the truth was, I'm American. Like, don't ask me to shit on my president. He was obviously anti-Trump. I'm like, don't ask me to talk shit about my president. You think I'm Gavin Newsom? I'm going to go to a foreign country and trash... if you're in another place, trash my own country. We can fight amongst ourselves. It's like Boston people. We beat the shit out of each other when we're in Boston. But if two Boston people are at a Patriots Super Bowl in Dallas and there's a fight, those Boston people are going to fight to the death for each other. And that's how I feel about Americans overseas. Like, yo, there's an American over there. Someone's starting trouble with him. Let's go. He needs help. So the last thing I'm going to do is talk shit about my own country. Get out of here. I would never. I love this country.
One of my passions is history, like American history from like 1880 to like 1930. That's like my sweet spot.
Dude, the reason I love denim so much is it's a quintessential American invention.
And it represents the gold rush, you know? That's where Levi's, you know, it's where it got popularized. And so that's why I love denim. And also denim ages beautifully. It fades nicely. Like it's good. And like I love old stuff because I love things that can last a long time. And I love American history because I'm just so passionate about America. Like right now I'm obsessed. This is going to be really nerdy. I'm obsessed with like the Constitution. Like the phrase, 'We hold these truths to be self-evident.' I just think that's like the greatest sentence of all time. I love that. And I love the fact that like the founding fathers were like, some of them were like, Madison and Jefferson were like 29 when...
I know, that's the crazy thing. And they...
