Episode · Apr 3, 2026 · 1 hr 30 min
Drunk and Directionless to Building an Empire
with Sam Parr
Sam Parr is an entrepreneur who built The Hustle, later sold it to HubSpot, and co-founded the Hampton network.
Summary
Ken opens by asking how Sam feels about money and why his own podcast asks guests to discuss net worth. Sam describes growing up in Missouri, running Division I track at Belmont, and leaving school. Before The Hustle, he worked for an antique picker in Nashville, ran a hot dog stand, and pursued Airbnb, where a lie cost him a job. He says he began hosting HustleCon to meet ambitious people; the event led into a newsletter and then the media business he sold to HubSpot. They discuss subscriber growth, revenue, the sale, and how luck affected the outcome.
Sam explains why he started Hampton and how its annual price and small founder groups are meant to help members make better decisions. He talks about arrests, alcohol use, and getting sober through a San Francisco clinic. Ken and Sam discuss fear, risk, and parenting. Near the end, Sam describes using entertaining email updates to win a meeting and argues that useful outreach can build relationships over time.
Show notes
Sam Parr built one of the most influential media companies of the last decade, but the path there was anything but clean.
Before selling The Hustle to HubSpot, Sam was getting arrested, struggling with alcohol abuse, and bouncing between odd jobs, from running a hot dog stand in Nashville to chasing a job at Airbnb that fell apart after a lie caught up to him.
This conversation traces the full arc. From Division I track athlete to dropout. From drunk and directionless to building a media empire. From rock bottom to getting sober through a San Francisco clinic that changed his life.
We get into:
The real math behind building and selling The Hustle
Why owning an email list beats chasing algorithms
The psychology of fear, networking, and taking swings
How Hampton became a $15K/year network for elite founders
What addiction actually looked like and how he got out
This story is about obsession, proximity, risk, and rebuilding, not just once, but multiple times.
Transcript
Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.
Ken Rideout
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.
Sam Parr
I love your work. You came on my podcast as well, so I love your work.
Ken Rideout
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.
Sam Parr
You didn't know anything.
Ken Rideout
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
Sam Parr
Like, "It's not even about that."
Ken Rideout
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? How what's your liquid net worth?" And you interviewed my buddy Josh Payne.
Sam Parr
Yeah.
Ken Rideout
And I could not believe all the things that he shared.
Sam Parr
Me neither. I can't believe that people do it, but they do.
Ken Rideout
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
Sam Parr
Tell them when they come on."
Ken Rideout
And he was like, "Yeah, but I wasn't do that." And I go, "So I guess that your episode didn't air then." He's like, "No."
Sam Parr
Yeah. So, we do it in a very non uh I call it Can I curse here? I call it a non- douchy way.
Ken Rideout
Yeah.
Sam Parr
We try to be very factual and not uh it's not braggadocious at all.
Ken Rideout
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 the I mean, I get some people not wanting to,
But I genuinely find it interesting and informative.
Sam Parr
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.
Ken Rideout
Oh, really? Oh, I didn't know that.
Sam Parr
Like, for example, it could be a woman and we made her sound like a man or vice versa. Like, that's awesome.
Early on, we hit a lot of voices.
Ken Rideout
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 light right word, but it's just like
Sam Parr
I innovate in a very small field, I think.
Ken Rideout
No, it's very different. And you've called you I've heard you call yourself a nerd before.
Sam Parr
Yeah.
Ken Rideout
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 one night to my wife, "Oh, Sam Parr got a new found a new pair of jeans." She goes, "What are you talking about?"
Sam Parr
I love that stuff, man. I I'm very passionate about certain things and I just love it.
Ken Rideout
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."
Sam Parr
Yeah, I'm a loser, man. But I love it.
Ken Rideout
You're not a loser.
Sam Parr
I'm just You're not a loser. I'm into what I'm into.
Ken Rideout
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. Even as
Sam Parr
I don't think I'm a loser. I think I kick ass. But
I do. You do.
But I think I've gotten really lucky.
Ken Rideout
That's a defense mechanism to say I'm a loser.
Sam Parr
I think I kick ass. But I think that I've been incredibly lucky in life. And so sometimes you got to like,
Ken Rideout
You know, bring yourself down a little bit.
Sam Parr
And I'm from the Midwest where you think you're horrible no matter what.
Ken Rideout
Well, yes to everything you said, but that's I 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.
Sam Parr
Yeah. I think people would be surprised that how like crappy something feels as you go, even if it looks like it's doing well though.
Ken Rideout
But there is something in you that is like this doesn't feel good, but I can't let it go.
Sam Parr
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.
Ken Rideout
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 [ __ ] where I'm like, "Wait a minute. What?"
So, let's start. Let's tell
Sam Parr
I've lived a few lives. I'm from Missouri, St. Missouri. Grew up there. Um went to school uh in Nashville, Tennessee, where you are. Um to run track and field
Where
Ken Rideout
Belmont.
Oh. Oh, cool. They got a good track program, right?
Sam Parr
Yeah. Yeah. I was I ran it was a division one I was a division one 400 meter runner.
Ken Rideout
Oh. Oh, I didn't know that.
Yeah. I ran I was 400.
Sam Parr
I was like a 48 second 400 meter runner.
Ken Rideout
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.
Sam Parr
I was good. I in high school I ran high 21 seconds in the 200. Oh my god.
Um, and just until recently, I still can I still do time trials and train. So, I could still run 23 seconds of the 200, which is good for a 36-y old.
Ken Rideout
Jesus.
Sam Parr
I can still dunk a basketball. I still got it.
Ken Rideout
I've seen you do some uh different fitness tests like a couple years ago. I remember you
Combine. Yes.
Sam Parr
Yeah. 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 um American Pickers?
Ken Rideout
Yes.
Sam Parr
I worked for that guy in Nashville. Uh,
Ken Rideout
This 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 uh pick like
Sam Parr
I saw them on the street outside of I'm a Gina Willie on 12 South
Ken Rideout
My favorite jean shop in the world.
Sam Parr
I love I 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 uh 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 in
Ken Rideout
Yeah.
Sam Parr
And then one outside of Deumbrean for the bar uh the bars at night. And I called it Southern Sam's Wiiers 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 internet, the internet.
Ken Rideout
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,
Sam Parr
"Yeah, but I was drunk, too, so it worked out."
Ken Rideout
Okay. Okay.
Sam Parr
One of the reasons why I did it was cuz I I I had like a drinky 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'd never 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 the college and stayed out there with my and got a job there. And the day before I was supposed to start, they called me. And at the time it was it was air 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. Uh and I had I spent uh 5 days in jail and
Ken Rideout
Five days
Sam Parr
Because um I didn't take the breathalyzer and you automatic. So I went to jail that day and then I got arrested a few weeks after for getting in a fight out outside Deumbrean and then I 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 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
Ken Rideout
One quick thing for a smart guy like how would you think that they're not going to know that you got arrested?
Sam Parr
I didn't know how background checks works. I was like they're not gonna know. And and I think I was still I hadn't been convicted yet. I think I was still in the
Ken Rideout
Oh, okay. So, technically you're innocent.
Sam Parr
Yeah. The way they asked the question, I thought like
Uh I can't remember but
Ken Rideout
There's some plausible deniability.
Sam Parr
Yeah. But I was 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 are right. And I was like yes sir. Uh and so I was out there in San Francisco with like nothing. And I eventually started a business called uh 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 like 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?
Ken Rideout
And what exactly did The Hustle do?
Sam Parr
Originally, it was a conference and so I um had just exited this roommate matching thing and I just made enough money that I had about six months and so I um 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 um like the founder of Casper or
I forget who else one of the co-founders of Wei Work before they had blown up.
Ken Rideout
Okay.
Sam Parr
And they gave like cool talks on how they're building their companies. Yeah.
And I made like 50 grand in six weeks.
Ken Rideout
Wow.
Sam Parr
And I was like, that was awesome. Uh and the way that I
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.
Ken Rideout
And you 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 [ __ ]
Sam Parr
I um 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 in like um I think it was 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 on like 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. Yeah.
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 antiBA is what it was called.
And so I kind of knew how to like organize some 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 and the way that it worked was um I created a newsletter where I would 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.
Ken Rideout
Ah,
Ken Rideout
What were you majoring in in college? Were you a writer?
Sam Parr
So, no. I No. Um, I studied um, music business, but I wanted to I eventually got my degree in um, 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 him to give me the any degree that I could have. So, I think I never got to graduate, but like business administration. I think
Ken Rideout
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 sound like you were doing things that were interesting and fun.
Sam Parr
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.
Ken Rideout
I can see that.
Sam Parr
And I was I desperately wanted a girlfriend. I wanted to be liked. I wanted to have someone
And I
Ken Rideout
I still feel like that
Sam Parr
Brother. Same. And I read all these books on how to meet girls.
Every book you could 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. The one of the first dates I took my wife, I was like, I'm really into like 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 that 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 like get excited. Once I learned that, I decided I'm going to share all my weird eccentricities with people and it was really effective.
Ken Rideout
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'm like 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 to you that's like, I love vintage.
Sam Parr
They they thought it was cool that I was passionate about something. And I think there's a correlation between passion and a mission.
Ken Rideout
100%.
Sam Parr
And so like I just learned that if you have like contagious, like energy can be contagious. So I have contagious energy.
Ken Rideout
Yeah. Well, that's what I that that this is one of the things like I'm I'm I'm [ __ ] loving this conversation. And I love how enthusiastic you are about everything. So, okay. So, you're out there. You you you you're going to have this conference. So, all these people sign up. You've got them all there. Are you [ __ ] yourself? Like, oh my god, I'm going to be putting on this convention. I'm having anxiety thinking about it.
Sam Parr
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 uh took a six week motorcycle trip cuz I was celebrating one year without drinking.
Ken Rideout
Oh, nice.
Sam Parr
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.
Ken Rideout
Jesus.
Sam Parr
And I was like, "All right, conferences aren't going to be my thing, but I love writing and I like um very nerdy stuff. I like emails. I like email. I like writing emails." Yeah,
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 interest 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.
Ken Rideout
When you say the business you need to know, like the business topics that are that are topical in the world.
Sam Parr
Yeah. So, I would find out all of the news that was going on and I would take give you my take on it. I would give you like so it was 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 um are like 10 cool blog posts I found this today I just curated the internet for the tech and business savvy person
Ken Rideout
So okay so geared towards tech people so you wouldn't write about like uh socioeconomic trends in Nigeria because it was something happened in you know
Sam Parr
Maybe that would be a small
Ken Rideout
Or oil prices are down because of the straight of hermu was like
Sam Parr
Only if it really it was the niche was like tech and business.
Ken Rideout
Okay. Okay.
Sam Parr
So, no.
Ken Rideout
So, there was no politics or anything controversial.
Sam Parr
No, typically. No. No. No. No. No. No. Um and the math was such that I could charge I forget exactly the numbers, but something like $75 per 10,000 cents. 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 64 is 24.
That would be something like, you know, uh 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.
Ken Rideout
Okay,
Sam Parr
I just did the math. It was all backwards back of the envelope math. And I sold the company a little bit early, but we were on track to do that.
Ken Rideout
And did you how many people were working for you?
Sam Parr
I think including freelancers when I sold maybe 35.
Ken Rideout
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 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
Sam Parr
I would 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. I was an okay business owner. And first of all, I want to be fair.
I got really lucky. I sold COVID was bad for a lot of people. It was really good for me. Yeah. Like things aligned. So, I don't want to like uh take like too much credit, but I think we did
I think the 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 was going to be we did 12. So from five to 12 and then that year we sold we were going to scare 18 million.
Ken Rideout
Do you talk about how much you sold it for?
Sam Parr
Yeah. So the headline said 27 million. It was more than that. So it was it was
Ken Rideout
Did you have investors?
Sam Parr
I took a little bit of angel money but I was the I was the majority owner.
Ken Rideout
What percentage did you sell of the company?
Sam Parr
100%. Basically.
Ken Rideout
No, no, no. Did investors own before you sold it? Like you took angel money on what? 15%.
So you own 85% of it.
Sam Parr
I have some employees got some I made north of $20 million.
Ken Rideout
[ __ ]
Sam Parr
Yeah. Um I made tens of millions of dollars.
Ken Rideout
Yeah. But just take a minute to think of what like I did it.
Sam Parr
Yeah. It was amazing. I was 31 years old. It was crazy.
Ken Rideout
So good. I love it.
Sam Parr
But that's why like luck is so like before the sale I thought I was the [ __ ] and then after the sale I'm like
Dude so many things outside of my control have just have just like aligned. Selling a business is so rare.
Yeah. And
Ken Rideout
Especially for that kind of money,
Sam Parr
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. I I 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.
Ken Rideout
Facebook didn't want anyone else to make anything.
Sam Parr
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 sales and I'm a pirate ship."
Ken Rideout
Yeah.
Sam Parr
And I'm like, I could I hit send because they 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 the little bit of time. So, why does it matter if it's a website or not? Because if I have I I we had a 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.
Ken Rideout
Yeah. Which is crazy.
Sam Parr
And I'm And they're going to be subscribed to me for like 10 years, 5 years, you know, something like years.
Ken Rideout
It would take a lot for them to unsubscribe if they went through the effort of subscribing. You'd have to be put out such [ __ ] content for someone to physically unsubscribe after they
Sam Parr
Get to know you. And I'm like, this could like this is a this can 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. Um, they started a company called Morning Brew, and they um only sold a portion of their company. So, they were still running up until recently, and they're scaring 100 million in revenue today. Wow.
So, the premise was correct. I just sold a little bit early, so I didn't get to see it through.
Ken Rideout
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 people 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 I like and and 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 I beat them. Like some of it was psychological. It was like but I had a hard time saying like no I'm the man. I did it. Anytime I've wanted anything I'm like I mean I got lucky that time but it but I think that that's the blessing and the curse.
The 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 like kind of like honesty with yourself and be like this only happened from like a win or die trying effort. Like I couldn't halfass it through this. You couldn't fake your way through that.
Sam Parr
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 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. I'm
Ken Rideout
When it's happening you have to wait. I say I always say
Sam Parr
Have you seen that thing with Mike Tyson where he goes like uh I'm David the Great. I'm the conqueror.
Ken Rideout
That's an awesome rant. Um but yeah, I always say train like you can't win, but race like you can't lose.
Sam Parr
That's pretty cool.
Ken Rideout
And then that is like I could go on forever with all these sayings and expressions, but I love them.
Sam Parr
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 um
Like have you ever if you ever talked to these guys? you've talked way more than I have, but I so I only see their interviews and like occasionally when they're retired they'll say like I was so afraid all the time like and you'll see guys like Mike Tyson like crazy guy and he was like every time I fought like I thought I was horrible. I was so afraid. I was fearful. But then he looks like a I think like a I think he would say he's like I'm a tiger, you know, like I'm going to like eat you.
I'm going to maul you. But inside he's like fearful. And it's been really cool to hear like my heroes or people who I think are tough guys like say they're fearful all the time. I got really lucky when we hosted this hustle cut event. You know, we 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.
Ken Rideout
Yeah.
Sam Parr
I just wanted to make sure they were there. I just want 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 like be talking about whatever and they were complaining about [ __ ] and being like fearful and stuff and I 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.
Ken Rideout
So I got lucky with that. 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." He like the 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."
Sam Parr
Have you talked, have you talked to any like uh you know, gangster like fighters like
Ken Rideout
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 Alice, we trained Alex Vosdic, the Ukrainian world champion. He was the WBC light heavyweight champion of the world. We trained him for eight weeks and I was and I worked the corner. We fought Ara betterv who was like then unified all the titles and was a killer. Never lost a Russian and um being in the locker room and seeing the emotions is like it is it's scary being in there.
Sam Parr
Never mind throwing up and stuff.
Ken Rideout
No, no, no, no. He put he had a brave face on. I'm just saying the like you could feel the nerves in the air and it was like everyone knows everyone is scared but the other guy 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 Terren Crawford has that kind of conviction he seems to like
Sam Parr
I don't think anyone does I don't even think even Conor McGregor who's like one of the most like bravado I wonder if uh Mayweather like
Ken Rideout
That's a that's a good one but I will tell you I've talked to Porier at length Dustin Porier is a good friend of mine and he has said he he he talks openly he's like yeah of course everyone is scared. He goes, "You just learn I 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 [ __ ] did I sign up for this? this 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 a 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.
Sam Parr
Have you ever um have you had any like bouts? I I know you trained.
Ken Rideout
I had some amateur fights. Yeah. scar scared shitless.
Sam Parr
Boxing only. Boxing.
Ken Rideout
Yeah, just boxing.
Sam Parr
Oh my gosh. So, I like very casually trade 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.
Ken Rideout
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. That's nothing scarier than walking into the ring to have a fight with another guy.
Sam Parr
Yeah. I can't imagine that. I remember just like on sparring days, I would be 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.
Ken Rideout
That's it. Cuz when you're sparring, you like have respect for your opponent. Even if it's like a friendly like 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.
Sam Parr
Was he a nerd or good?
Ken Rideout
No, he was good. He was beating the [ __ ] out of me. At one point he was like cracked me. He's like, "You good?" And I'm like, "Yeah, I'm good." And
Sam Parr
Smoker, so you there was people there.
Ken Rideout
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
Sam Parr
I used to go to Church Street and there
Ken Rideout
With Martin Snow.
Sam Parr
Uh, no, a big Ukrainian guy. Um, what was his name? I forget his You know who trains down there now as a trainer is? Peter Quill and Kid Chocolate.
Ken Rideout
Really?
He was nasty. He was like a welterweight champion.
Sam Parr
It's fun going down there because they're not yuppies. And it's like kind of grimy and it's fun. And I and I whenever I would spar there, I would get scared. I was really scared.
Ken Rideout
That's funny. John Duddy is a trainer down there, too. Irish champ former Irish champion. Like a middleweight. Like
Sam Parr
It's cool walking in there. I love going in there.
Ken Rideout
Yeah.
Sam Parr
But it's it's scary.
Ken Rideout
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
Sam Parr
They're so big, too. Like I'm not a small guy. And I would The guy I sparred with was um well, he was my coach. So he it wasn't sparring. It was me hitting him and him laughing. And I I'm 2062 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.
Ken Rideout
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?"
Sam Parr
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, uh, it's super fun. It definitely makes you more courageous. Like I remember like complaining about like silly work stuff and I'm like, "I just got my ass kicked this morning and I was fine
Ken Rideout
So, you you build up the hustle and you sell it to who bought it?
Sam Parr
HubSpot.
Ken Rideout
Oh, cool.
All right. So, when they bought it, was there an earnout? Did you have to hang out?
Sam Parr
So, um 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.
Ken Rideout
Oh, that's that was part of the hustle. But it's not part of it anymore.
Sam Parr
No, it still is. Yeah. It's still HubSpot. Hubspot owns it.
Ken Rideout
Oh, really? Yeah. So, when you do the podcast, how is it earn How does the money get DVD?
Sam Parr
Yeah. So, they pay they pay us on performance. So, the bigger it gets, the more I get paid.
Ken Rideout
So, you get paid a percentage of the ad spend.
Sam Parr
No, what's crazy is so HubSpot was really cool. They um their whole premise was basically HubSpot is like a CRM. It's boring software, but they but it's like super necessary for small businesses. I still use it at my company.
Very awesome stuff. um I'm legitimately a customer and they um were like we have so many customers that we literally have to like own a media company to like reach more people. So instead of like sponsoring publications, what if we just owned you?
Ken Rideout
Yeah.
Sam Parr
And I was like that's pretty cool. So uh they they shut down all ads and we actually owned a handful of podcasts. And anyway, now my company is now 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. Okay. And all of it says like this is sponsored 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.
Ken Rideout
So does the So does my first million have no advertisers except HubSpot?
Sam Parr
Yeah.
Ken Rideout
Oh, okay. So So HubSpot is the advertiser. So they based on the CPMs or whatever the measurable is, that's how you get paid.
Sam Parr
Yep.
Ken Rideout
Oh, that's cool.
Sam Parr
Yeah. And so the reason the deal changed a lot was because the P podcast pas got huge.
Ken Rideout
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?
Sam Parr
Not anymore. No.
Ken Rideout
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.
Sam Parr
No. My company, I'm not the host of Moneywise, but um I I hosted the first handful to get it going.
Oh, okay. I didn't know that. No, I host the first handful just to get going and now we have a new host.
Ken Rideout
No, I've noticed that there's like a British guy, right?
Sam Parr
Yes. And now we have a different one. Um
Ken Rideout
I thought he worked for you.
Sam Parr
No, he was an agency who we hired and he did a great job.
Ken Rideout
Yeah, he did do a good job.
Sam Parr
Um 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 I we have I own other podcasts now. My my company Hampton, I liked what HubSpot has done that we were like, let's create our own little network. Oh,
Ken Rideout
Okay. So now you sell that. What was where did what did you I know you have Hampton now so I want to get to that but what did you do was Hampton the next move after HubSpot?
Sam Parr
Yeah probably I had a kid so I took like 6 months and I just chilled.
Ken Rideout
Where'd you meet your wife first?
Sam Parr
At a restaurant.
Ken Rideout
I I love your wife on your social media. She's she's beautiful. She's like
Sam Parr
She's like the best. I um I saw her at um I say restaurant. It was really a bar but I wasn't drinking and it's it was like a like a five o'clock like happy hour. So I didn't want I don't want to make it sound like weird. big club. But I saw her and I was with this um 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 I don't know.
Ken Rideout
Uh
I love denim.
Sam Parr
Maybe I'll say uh" And so she walks by and go, "Hey, um" My wife walked by. I said, "Uh, 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.
Ken Rideout
That was that's a pretty uh aggressive joke for someone who you're trying to court that you don't know.
Sam Parr
It was a litmus test. If she thought that a chick peed on my face was pretty funny, then she was the one for me and she thought it was hilarious.
Ken Rideout
Oh my god. And what was she What did she do for work?
Sam Parr
She worked at Facebook.
Ken Rideout
Oh wow.
Sam Parr
Yeah. My wife went to an Ivy League school.
Ken Rideout
Where'd she go?
Sam Parr
Pen.
Ken Rideout
And you?
Sam Parr
I didn't even know what that was, dude. I was such a hillbilly. When she said I went to pen, I was like with that rape rapist football coach. And she goes, "No, you [ __ ] It's called pen." 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?
Ken Rideout
Even the poor kids at Penn State, I feel so bad that the first reaction is like about Sand Dusky. Like uh
Sam Parr
Yeah, I didn't even know about like I didn't know about any of it. And she was like, "Look, like I'm not trying to brag, but like
It's kind of a big deal." And I was like, "That's awesome."
Ken Rideout
And she worked at Facebook.
Had you already had the exit from the hustle?
Sam Parr
No. No. No. No. No. No.
Ken Rideout
Oh, you met her while you were at
Sam Parr
I had 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 I was 24, she was 21 when I met her. 22, I forget. She was just out of college and uh that's probably why she liked me. She just we were in San Francisco and she didn't know anyone. And um I used to make her bring me dinner home every day cuz uh Facebook has free
Ken Rideout
Yeah. Yeah. Yeah. Free food.
Sam Parr
She was my sugar mama. And then she actually worked at Airbnb. We you know how I like I was like, "Dude, you should go work at Airbnb. I still think there's a lot it could be a great company." And she became a millionaire before me.
You're kidding. I swear to God.
Ken Rideout
Oh, when they went when they went public, she had equity.
Sam Parr
She killed it. And so, dude, she's awesome. And her She's from here. Her mom and dad started her father started a movie company.
Ken Rideout
What?
Sam Parr
Yeah. Just he was a He's a bluecollar like Italian Jewish guy from New York City. He's like this type of No way.
Yeah. He's like He's like the New York version of you. You're the Boston version of him, I guess. And he um 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.
Ken Rideout
Really?
Sam Parr
Yeah. He was like a blueco collar guy who just creamed him. And then his wife, my mother-in-law, Smithy, when when I was uh when Sarah and I had been dating for 5 years, she had been a stay at home stay at home mom forever. And she was like, "I have I want to start a business." And I was like, "Okay." And she like told me her idea. I was like, "All right, cool. That sounds great. Let me know you need anything." Well, she two weeks later starts a Shopify store and she sends it to me.
I'm like, "Is this yours?" She's like, "Yeah, you I did what you told me to do. I created this thing and and so now she has a business. She was a retired she was a stay at home mom. Now now she has a warehouse and um a bunch of workers and she has a business doing millions of dollars a year and they sell
Fancy throw pillows.
Ken Rideout
Decorative pillows.
Sam Parr
Decorative pillows.
Ken Rideout
Yeah, I remember you showed me that. I remember you told me about that. That's funny.
Sam Parr
And so my wife came from her mother's Haitian, a Haitian immigrant, and her dad's this like New York like kind of hard guy. And so I was like that right.
Ken Rideout
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
Sam Parr
Yeah interracial couple
Ken Rideout
You it just wasn't as casual as 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 like Indian friends black friends that grew up in the places where I where I grew up it was racist like
Sam Parr
Well where would you go in Boston
Ken Rideout
Yeah well in likeville like a blue collar part of Boston
Sam Parr
Boston's like notoriously
Ken Rideout
Notorious that's where they had forced busing where in the 70s they basically said, "Okay, black kids over here in like Roxberry 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 It was a disaster. It was
Sam Parr
I thought it was cool. Like I love immigrants. Like I I do too. I love immigr I love English as a second lang like when people like I take so much pride that I live in a place where someone's willing to risk so much to like come here.
Ken Rideout
I completely agree. It's when 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?
Sam Parr
No.
Ken Rideout
No. All we do is we we 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.
Sam Parr
Yeah. It's a very um strange thing, but like I just love like this idea that um like the reason I like entrepreneurship is like a loser can become a somebody.
Ken Rideout
Yes.
Sam Parr
And like with immigrants, obviously they're not losers, but like to start from the bottom and like there's like a world where like 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, um his his his father's sister was like living in like uh in Kenya without electricity and she came into 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 my mother-in-law is a black woman. Her mother is a was is an older black Haitian and my kid looks kind of white and she's like a yepy now because we're really successful. Imagine like her holding like growing up in like a Haitian like you know 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 like thing together and I just
Ken Rideout
Listen I have an Ethiopian daughter and she like definitely does not look white. I mean she's Ethiopian and
Sam Parr
And like your offspring is going to be potentially like oh you're going to have a whole black line.
Ken Rideout
It's 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 I first thing I always do is see, is there other black kids there? But when when we're together, I never like for my for the longest time, my kids would be like, "Oh, Dad, there's another kid in our in our school with the dark tan like Tensei." I'm like, "Oh, there's another tan lit literally another dark tan." and 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 the 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 may maybe my black friends would say, "You're crazy. You don't you don't see it." But I don't notice it the way I did when I was a kid.
Of course not.
Sam Parr
It's it's
Like Yeah. I 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 I that's not good.
No, of course. But in general, like if if someone was going to say something on the street like there would be 10 people that would say like
Ken Rideout
What the hell?
Sam Parr
How dare you know what I mean? So, you know, I'm I'm you know, one incident is too many, but I still think it's America's pretty awesome.
Ken Rideout
I dude I was I did a show in um promoting my book in London and it was a 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 they the headlines come from this show it's called the Jeremy Vine channel 5 show and it was a daytime TV show so the guys one the woman was one anti-Trump hated Trump would never come to America while Trump was the president so I'm just listening like whatever he goes oh can at the risk of uh being controversial do what do you think of your President Donald Trump?
I 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 is in, I respect the office. I 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 [ __ ] 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 [ __ ] on my president. He was obviously anti-Trump. I'm like, don't ask me to talk [ __ ] about my president. You think I'm Gavin Newsome. I'm going to go to a foreign country, trash, if you're in another place,
Trash my own country. We can fight amongst ourselves. It's like Boston people. We beat the [ __ ] out of each other when we're in Boston. But if two Boston people are at a Patriot 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 [ __ ] about my own country.
Get out of here. I would never. I love this country.
Sam Parr
I like One of my my passion is uh history, like American history from uh like 1880 to like 1930. That's like my sweet spot.
Ken Rideout
With your Levis's denims,
Sam Parr
Dude. That the reason I love denim so much is it's a quintessential American invention.
Ken Rideout
Yes.
Sam Parr
And it represents the gold rush, you know? That's where Levis's, you know, it's where it got popularized. And so, that's why I love denim. And also denim ages beautifully. It mines nicely. Like it's good. And like I love old stuff because I love things that can last a long time. Yeah. And I love American history because I 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.
Ken Rideout
Yeah.
Sam Parr
Um like the the phrase um 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 are like Madison and Jefferson were like 29 when
Ken Rideout
I know that's the crazy thing. And they
But also the lifespan was like 30, you know.
Sam Parr
Well, it's the reason it was so young, by the way, is because infant mortality rates were super high. So, of the 486 presidents,
Like 75% of them have lost a kid before they became in office. Like the the you like the reason they had eight kids is like three of them would die of like dysentery and like these silly things. And uh I just I I'm obsessed with the Constitution right now. I love this idea that you can create like a self- amending document and like somehow we all buy into it.
Ken Rideout
Yeah.
Sam Parr
I just think it's magic. So anyway, that's why I like Denim so much. It's like it's a very like historical thing.
Ken Rideout
All right. So after you sell to HubSpot and now you're doing your podcast, when do you get the idea for Hampton and what is it? Give me the whole like give me all the details.
Sam Parr
So at the hustle, we made money through advertising in the newsletter. And then we started this thing called Trends and it was like a paid newsletter and it had a community component. It was $300 a year and our first year I think we did six million in revenue from it and it was like and I only had three employees on it. It would like made stupid money and um it was like a newsletter where we would like deconstruct different businesses but then also tell you like cool trends that were pop getting popular and we had a Facebook group for our customers and we got like 20,000 people to sign up.
It was pretty crazy and this Facebook group was popping off. People loved it. Yeah.
And that's when I was like paid communities are pretty cool.
Ken Rideout
Yeah. Yeah,
Sam Parr
But I messed it up by only making it $300 a year because on $300 I can't provide that amazing service to a customer. There's not enough profit.
Ken Rideout
And in your mind, what's the service that you think was missing with the revenue that you were generating?
Sam Parr
Well, for one, more exclusive like keeping like uh like if like if sometimes the price can like keep a certain type of person out and makes people who are only really serious about it.
Ken Rideout
Yeah.
Sam Parr
But then also I wanted like in real life events and things like that. And so I wanted um the idea for Hampton was I wanted to build a business that could last a long time that I could probably or I could attempt to bootstrap to a billion in revenue. That was what I wanted. Like and so I researched a ton of companies and there was all these cool communities like have you heard of YPO?
Ken Rideout
Of course.
Sam Parr
That was launched in like 1963. Um or like Vistage uh this is this other company that does close to a building a year in revenue. It's a community for entrepreneurs. Um that was launched in like 1958 or something crazy. And I was like, what can I I'll just [ __ ] do that for like my generation. That sounds good. Yeah.
But I made a huge mistake at first. It was the idea was like, I'm going to create these like core groups of eight people, eight founders and CEOs of companies and put them in groups of eight and they can meet um online to discuss all their issues because it was like COVID era, COVID time. And I was like, yeah, online is cool. Which obviously that was a huge mistake. And so we've switched since pivoted to in real life. So we have thousands of members paying 15 grand a year.
And what you get is you're put into a core group of eight people and you meet with them once a month in real life and we have like 90 executive coaches on staff and they lead every single meeting and it's the only group of people who you have in your life that have full context and like your daddy issues or your spousal issues but also your business.
Ken Rideout
Oh, so people get there and talk about it's almost like an AA meeting for entrepreneurs.
Sam Parr
Well, we don't call it that but it is that because like we sell it as like don't make $50 million decisions alone. So our average member does like 25 million a year in revenue and it's like come and talk with other people. So like when I was selling my company, I distinctly remember there was this phone call that I did with HubSpot and they had like 16 lawyers on staff or 16 or they had 16 people on the call, eight lawyers, eight accountants and they're asking me all these questions and I distinctly remember thinking like I don't know what the [ __ ] I'm doing.
Yeah.
Ken Rideout
What the I know exactly what you're talking about.
Sam Parr
I was like I'm 30 I'm 30ome. I'm still young but I built this business up to be 12 million in revenue. I'm about to sell it for tens of millions of dollars. I should know what the hell I'm talking about. I don't and I don't have anyone to talk to.
Ken Rideout
You didn't think to hire like an attorney or a banker?
Sam Parr
I had a great attorney. Okay.
But I didn't but they didn't they hadn't been through it.
Ken Rideout
Why'd you hire an attorney that didn't haven't gone through some of these?
What I mean is they had stolen the company, but they hadn't like been a young person who was about to like have their life.
Talking about the emotional aspects.
Sam Parr
They did deals like this every week, but like they didn't know like I'm like [ __ ] insane right now, dude. Like this is like my life, you know? Like they didn't, you know? They kind of understood, but they weren't like, "We got you. We're with you. Like, let's do a call where we can like walk you anyway."
And so,
Ken Rideout
So, do Hampton members do things like that? Like, if someone's selling the business, could they be like, "Hey, I want to bring in six of my peers on the call and just listen."
Sam Parr
Well, they could, but what what it is is like, so like there's a group there's a guy in my group who's who's in the he's about to um get the get the wire, but he just sold his company for $450 million.
Ken Rideout
Oh my god.
Sam Parr
And so during the eight-month process of doing it,
He's brought his deck to us. He was like, "Hey, I got an email from this one company that wants to buy us. What should I do?" And we would like give him feedback. He's like, "All right, you know, this guy's interested. Like, all right, let's make a deck. Like, who's got a good lawyer who I should hire? Who's got a good banker? Okay, guys." And then next month, like,
"Okay, the buyer went cold. Like, what should I do?" And we're like, "That's normal." This anyway, we were like advising him now.
Ken Rideout
That's pretty cool.
Sam Parr
Yeah. And so, like, that happens for thousands of times every, you know, thousands of people every single month. But it could be also like, you know, I'm working hard, my wife's complaining, or like for me, I just had children. Yeah.
How do I like set boundaries between work and like what do you do? Like should I just not be around? I don't know. Like you have these conversations that you can't literally have with anyone else.
Ken Rideout
Yeah. Yeah. Yeah. Oh, that's interesting.
Sam Parr
Um and so that's what it is.
Ken Rideout
So when you started it like so you had it you had it initially it was 300 bucks and then how'd you sell?
Sam Parr
No, no, no, no. My early community.
Ken Rideout
I mean the early community but when you
Sam Parr
The first community and then I I sold that community and then I started Hampton and we charged like five grand at first and we were like that's stupid. Let's charge more and we charged then 9500. We're like that's stupid. do more. 1250 stupid, do more. And now we're at 15,000 because we kept upping the price because we wanted to hire the best executive coaches to lead these meetings
And also have enough profit to host events and things like that.
Ken Rideout
But I would also think that someone who would pay 10 would pay 15. Like someone who pay 15 probably pay 20.
Sam Parr
Yeah, maybe
Ken Rideout
To a certain extent because what you're being a [ __ ]
Cuz what you're describing sounds incredibly valuable but on the surface you're like 20 grand to be friends. It's like one of these private dogs. It's 50 grand to be with this doctor.
Sam Parr
But we don't say you're with friends. We say
Ken Rideout
I mean with with peers, you know what I mean?
Sam Parr
We call it a peer network where you say like you're so you do become friends. Your families do meet but you're coming because you have big decisions to make. And if you make when you're running a company, you don't want to like come off you don't want to tell your employees that things aren't going well. You don't want to fear make them fearful. You don't want to tell your investors
Everything. And you're like, "Dude, I'm literally making these massive decisions in this vacuum. I need like a sounding board because when you actually do like state your problem out loud, that's like a huge way to solve your problem. And then you get like
Uh seven other people advising you and then they're going to be like, "Dude, you complained about the same [ __ ] last month. What the [ __ ] man?" Like you got to figure this [ __ ] out. Here's how like you get like accountability, too. We So like it it it's like ROI driven. And so we don't actually tell people it's for like business therapy, but it does like it is a lot of like spousal stuff or like you know like a lot of guys in my group are Jewish and when October 7th happened they like
Wanted to express how they felt and like make sense of things. You know what I mean? So like it became like all types of conversations.
Ken Rideout
But you may not want to describe it as AA but it sounds exactly like an AA
Sam Parr
types of stuff from them. Yeah. Like the cult building stuff like is awesome.
Ken Rideout
Yeah. No, no. I've been That's the other thing I wanted to come back to. When you stopped drinking, you were drink How bad was your drinking and how did you stop?
Sam Parr
I was intoxicated probably 24 hours a day for at least a year, but
Ken Rideout
24 hours a day. So, you'd wake up and stop drinking again?
Sam Parr
Yeah. I love beer.
Ken Rideout
Oh my god. And then Okay. So, how did you stop?
Sam Parr
So, I went to like a homeless clinic in San Francisco.
Ken Rideout
A homeless clinic?
Sam Parr
Like a Soma, South of Market mental health clinic for homeless people.
Ken Rideout
Okay.
Sam Parr
And uh it was awesome. Tell me, it changed my life. I met this woman named Jocelyn. She was a doctor and I was like,
Ken Rideout
"Where'd you find the courage to go in and ask for help when you're that deep in your addiction?"
Sam Parr
I met a guy who was like a ladies man and he was sober and I was like, "Oh, you can be." And he told me, he was like, "I'm an alcoholic so I don't drink." And I was like, "You're willing to admit that to me, huh? And you still are the life of the party and you can get a girl? Like, I don't need this to like fit in?" Like, what? That's crazy. In fact, girls like you even more when you tell them this. Like, and I needed that encouragement.
Uh that I could like still be I was fearful. I was like, "Can I tell someone I'm [ __ ] up and still like they or are they going to think, "Oh, you're a freak. I can't talk to you." Like, I thought that's the way it was.
And I didn't realize how bad it was for a long time. And then I got arrested, you know, those three time. I got in trouble three times and I lost this and I was like, "Oh my god." And then I started making these decisions around my life. I was like, "Well, I have to live here so I could ride my bike all the time because I don't want to drive because I know I'm going to be drunk." And I was like making all these I'm like, "What the [ __ ] is going on?"
And then I like I was like, "I'm going to be like a homeless person or like a billionaire by the time I'm 50. Like, which one is it going to be?
I got to get my [ __ ] together." And so I went cold turkey and I got um
That's bad for your health sometimes to go cold turkey. I didn't realize that.
I felt miserable and then I relapsed after 3 months or something like that. And then when I went to San Francisco, I got my act together and I met this amazing doctor who worked with me and it and it worked out really nicely and I was with her until after I sold my business.
Ken Rideout
So you walked into Soma Clinic?
Sam Parr
Yeah. And I was around a bunch of crazy people and I was like, "This is where I belong." So it's good that I'm here.
Ken Rideout
That's amazing. The fact that you had the wherewithal to know that you needed help and then have the guts to walk in there, it's like walking into a boxing gym. It's like takes takes courage to go in and say, "I need help."
Sam Parr
Yeah. It takes courage to probably not do it in the first place, but yeah, it it worked out. But it was not fun. I thought it was Yeah, it was really bad. I liked beer and I love whiskey and occasionally I would like some pills.
Ken Rideout
Oh my god.
Sam Parr
Yeah, I had to work through a bunch of stuff. I didn't realize I didn't realize it, but it worked out.
Ken Rideout
That's great.
Sam Parr
Yeah, it took a long time, but it's like the greatest thing that's ever happened.
Ken Rideout
Yeah. But that is um an incredible story of resilience to be able to pull yourself together like that and continue hustling on all these like oddball things that all worked out that on the surface.
Sam Parr
For the record, not everything worked out. I've tried a lot more than I've even mentioned.
Ken Rideout
Tell me what's your what's give me a couple of the big flops.
Sam Parr
I mean, I started a poison ivy business, a poison ivan treat me treatment business called itch juice.
I did uh
Ken Rideout
What happened?
Sam Parr
It was It did work. No one bought it. I mean, it was just the dumbest thing ever. It was just I've done like everyone who makes money on the internet has probably done like 10 things. I started an online liquor store called Moonshine Online where we sold popcorn Sutton's whiskey out of Tennessee. Uh what else? I mean just like all a billion things like Hampton started as um we were going to try and go after VPs of marketing and like no one bought it. I mean like there's been like a billion different things that I've tried that haven't worked.
Ken Rideout
So
But I think that's important for people to hear because if we don't talk about those things it just sounds like Sam's got the mightest touch. He just shows up and throws up a flag and he's winning.
Sam Parr
Like most days that I was running the hustle like I told you our growth looking back it grew fast but I I wanted to quit every day. Like I my wife would have to like tell me like dude don't be a [ __ ] You could do it. Like I remember like laying on the kitchen floor like all the time like I can't do this. Uh so no I felt miserable during the whole time. But yeah getting clean was like the greatest thing ever.
Yeah. And now like no one drinks.
Ken Rideout
I know. Now it's cool not to drink. Andrew Huberman single-handedly destroyed the liquor industry.
Sam Parr
Did he really? Yeah, I did.
Did he drink at all?
Ken Rideout
No.
What a nerd. Did he do anything?
Sam Parr
No.
[ __ ]
Ken Rideout
My youngest son My youngest son got a concussion on um Sunday playing flag football when I got to the city. Dude,
That's the one thing about having kids that is difficult, man. You're only as happy as the saddest kid. If one kid has an issue, you have an issue. So, he gets a he gets a concussion. I'm not there. and my wife drives over to pick up my daughter who's coming back from a high school like weekend uh Christian trip like a weekend away with her friends to do some Christian things. So my wife drives over to pick him up, comes back and she gets a phone call from a number she doesn't recognize.
I mean who answers a phone call from an unrecognized number
Sam Parr
Like the someone with your kid.
Ken Rideout
So she answers it and it's like the coach from the flag football team says, "Hey Cameron banged his head. I don't know. I might have a concussion." Well, obviously had a concussion. She goes back and he's like, he's completely out of it. He and he's like a little superstar. He's awesome at everything. He's just one of those kids where he's just at this age and hopefully he doesn't burn out. He's just better at everything. And my wife goes to get him and he's like, you know, he looks a little foggy and his pupils were like the size of pins.
And he says, "Uh, mom, what happened?" And she's like, "You banged your head." Oh, where? How? You were playing football. I I was playing football. What What position do I play? You a quarterback. I'm the quarterback. Who were we playing? Cowboys. Huh? Mom, what happened? This is all as fast as I'm telling you is how he's asking questions. My oldest son's in a serious one.
Serious. My wife my oldest son is in the car with him and says, "Mom," he's kidding. He's He's joking. And she's like, "No, no, he's really hurt." And dude, it was it was scary. It was scary cuz I'm talking to him and he's like, "What's up, Dad?" And I'm like, "How you feeling?" He's like, "I'm feeling good. What's up?" I'm like, "Did you bang your head?" He's like, "Mom, what happened to my head?" I'm like,
Sam Parr
"Have you been knocked out?"
Ken Rideout
Have I been? Yes.
Sam Parr
And it feels like that?
Ken Rideout
No. I You just don't remember anything, but I don't remember.
Sam Parr
Wait, when you get knocked out, where do you think you were when you sleeping?
It feels like sleeping.
Ken Rideout
Anyone who's been knocked out will tell you when you wake up, you feel like you're sleeping. You're like, "Whoa, where am I?" Like first thing you say, "Where am I?
Sam Parr
Does it hurt?"
Ken Rideout
No, it's like you're just confused. It's like waking up and you're on the floor like
Sam Parr
What about when you get those guys in UFC get knocked out and they still get about three more punches in? Oh.
Does it still So that doesn't hurt?
Ken Rideout
I don't think any of it hurts. Like I don't even getting into a fight. I don't remember getting punched in the face. Like I talk about in the book going to jail in Jacksonville in a fight and the cops beat the crap out of me. I don't remember any of that hurting. I just remember they sprayed
Sam Parr
But it hurts like 3 hours later.
Ken Rideout
Of course. They sprayed me in the face with mace while I was handcuffed behind my back and bleeding from my face. So every the pepper juices in my eyes, my cut. And I was like, "Guys, please take these handcuffs off. I need to like get this out of my eyes." They were like, "No, no, you're all right. Don't worry about it." and like kept me like that for a long time. It was horrible,
Sam Parr
Dude. That's crazy.
Ken Rideout
Crazy.
Sam Parr
Yeah. Like some of the UFC guys whenever I see those sometimes they won't know where they are for like three hours.
Ken Rideout
Yeah. Well, and a lot of times they don't remember anything. They'll be like riding to the am hospital in the ambulance be like where am I? Like what the hell? And they're like, "Oh, YOU GOT KNOCKED OUT." NO, I DID.
Sam Parr
OH, HORRIBLE.
Ken Rideout
But this my poor son. So I called Andrew right away. I'm like, "Dude, what do I do?" Like cuz it's a Sunday night. And I'm like, "Do I take him right to the emergency room?" He's like, "Nah." He's like, "Keep an eye on him as long as he's not vomiting, passing out, or anything.
He's got a bruise on his brain." And so then she took him to the pediatric neurological pediatric doctor and he was like telling my son, he basically said, "Look, you have a bruise on your brain. It'll go away. If you go out and play again in the next like month and bang your head again, that will become a scar that the things you feel now will feel like this forever."
Sam Parr
Dude, I when I was a kid, I fell off a bunk bed when I was sleeping it and I got a concussion. And I was throwing up all the next day.
Ken Rideout
Yep.
Sam Parr
And I I think it had permanent damage.
Ken Rideout
The CT is a real thing.
Sam Parr
Yeah. Like I I think that like there was issues later on.
Ken Rideout
Yeah, man. When you get a bruise on your brain, it's a serious thing. But it was, man, again to have the point of having kids, it's so scary to see your kids hurt and and think like, oh my god, now he can't play. He's in the fourth grade. He plays on the middle school lacrosse team, sixth to eighth grade, and he plays a lot. And it's like guy buddy you can't play for you gota we gota probably take a month off and he's like you know to him he's not yeah Andrew said it might be take six months off but I'm like I don't know like trying to find the like right this you know it's hard he's like the kid loves sports but it's scary when they get hurt like that
Sam Parr
Dude I've gotten more hurt running though than any other sport
Ken Rideout
Really
Sam Parr
I know I've got I broke my novicular bone stress fracture
Oh
Two stress fractures that require one required surgery
Ken Rideout
Oh my god, I got more hurt riding my bike, crashing my bike. Oh my god, I had a hip surgery. I freaking I I almost broke my neck riding my mountain bike in I was in in LA in the Palisades. So like in the mountains between Malibu and Calabasas and I'm coming down a thing on my mountain bike on a trail and the littlest like little rut in the road and I didn't kind of pull up on the handlebars fast enough and my wheel hit that rut and launched me head first like a lawn dart into the ground and it was I wasn't going super fast and I came like I was dazed and I come to my glasses smashed onto my nose, sliced my nose open and I'm covered in dust, dirt and blood and the seat on my the saddle busted right off the the the the the carbon post snapped right off and the
Guy comes by. He's like, "Oh my god, let me call 911." And all I could think is like, "Dude, are you [ __ ] crazy? They're going to have to bring a chopper in here. We're in the middle of nowhere." And I was like, "Don't call an ambulance." And I get up, put the saddle in my back pocket on my shirt, stand up on the bike, and ride like five miles home, like a a mess. And I was late to meet my wife to do something.
And I come rolling up and she's like, "Oh my god." She gets so angry every time I come back busted up and crashed cuz like a month before I called her from an ambulance and I'm like, "Hey, I'm on I'm in an ambulance. I'm on my way from um I crashed coming down to Panga Canyon on my road bike and like at like 35 miles an hour, skidded down the highway. My back's all burned up. I was with my buddy Jack McDall and I jump up with all adrenaline.
My ankle bone is completely exposed. All the skin's rubbed off it cuz I went down so hard. I jump up. I'm like, "Oh, Jack, my back." I'm like, "How bad is my back?" And he he goes, he he goes, "IT'S SO BAD." AND I'M LIKE, I TURNED around and I go, "Dude, what the [ __ ] Lie to me." And it was it was terrible, dude. Fire trucks, ambulance. And I was in so much pain. I'm like, "Buddy, give me some morphine or something." And the guy's like, "I can only give you morphine if you're going to the hospital." I'm like, "I'm going to the hospital." Cuz I was like in so much pain.
Sam Parr
Dude, I've gotten six kidney stones. Whenever they give me the morphine, whenever they give me the morphine, I'm like, I understand why why I should dedicate my life to consuming this this drug.
Ken Rideout
Dude, six kidney stones. How bad did that hurt?
Sam Parr
Oh, the worst. The second one, I distinctly remember saying, "If I could kill myself, I would right now." Is the worst. But like whenever they give you the that the morphine, I'm like, I like this.
Ken Rideout
Yeah.
Sam Parr
Yeah. You feel it go through your veins. I'm like, I get why San Francisco has all these guys on the street doing it.
Ken Rideout
Dude, when I had it so shoulder surgery, they gave me something. And they gave me they gave me the IV in the um prep room and I was like they were going to give me a um a guided uh what the hell the camera guided needle nerve blocker into my shoulder and I had had a PRP injection with this sonar guided needle thing and it hurt so bad. I was like no I don't want it. I I I can't handle the pain of that needle. So they're like hey here we'll give you something to calm you down.
And so a few seconds later I'm like whoa I have and my wife is recording me. I'm like, "Whoa, I am so effed up."
Sam Parr
You feel it go in your in your arm here. And you're like, "Oh yeah, dude. My shoulder, mouth, my
Ken Rideout
I was high in a way. I never been." I said, "Oh my god, I'm okay. I'm ready for that needle." And they're like, "We're done." And I'm like, "You already did it." I'm like, "Oh my god, what did you give me? I'm so high."
Sam Parr
Like fentanyl.
Ken Rideout
Yeah. They were like, "Fentinel." I go, "Leave me here for an hour. Don't even do the surgery yet. Just leave me here for a few minutes."
Sam Parr
Yeah. It's awesome.
Ken Rideout
And then they were like, "All right, let's go, junkie."
Sam Parr
Yeah.
Ken Rideout
They went whenever I go through that, I'm like, "This is crazy." So, I get the surgery done during the day, go home, I'm, you know, I'm like on nerve a nerve locker. I'm all whacked out on the anesthesia still. I'm like in a fog. When I woke up at like in the middle of the night with that post surgery, the pain was like nothing I've ever experienced. It was like my shoulder was in a vice grip and it wouldn't stop and no amount of medicine was helping it.
I was like almost crying. I was saying to my wife like, "What am I going to do?" Like, "This is something must be wrong." And then I called the doctor in the morning. He's like, "No, no, that's part for the course." I'm like, I'm such a baby.
Sam Parr
You know, like all these tough guys. Who's like the toughest dude you know?
Ken Rideout
I say the toughest people are like the quiet tough guys. They don't Usually tough guys don't have to tell you who they are. It's like these military guys that like my friend Mitch Hall is a Navy Seal. He's like won a Silver Star. He's told me stories about how he won that Silver Star. It is so terrifying. He was with another Navy Seal. The guy gets shot through the eyeball with an AK-47. So he's like, "Oh [ __ ] my buddy's dead." Okay, so they're fighting it out.
They now got to get him off the roof and bring the body back. They they like basically get him off the roof. Kind of like I I assume they lowered him down, but I mean, if you think the guy's dead, you're like, just throw him down there and let's like they get him out of there. They put him on a helicopter. The guy survives. He's like a cop somewhere with missing an eyeball. Like Mitch saved his life and like by by getting him out of there was just
Sam Parr
Dude, I've got a couple SEAL buddies and they have the craziest stories. One time I was doing a tough mutter with one of them and we were like crawling under barb wire. I'm like this sucks. I never crawl. He's I was like, "Do you ever like work on this? You're going fast." He's like, "Yeah, yeah, once." I was like, "What are you talking about?" He's like, "Well, one time we were like in the bottom of a valley and Taliban had us surrounded, so I had to hide under a truck for 48 hours and we basically had to like plank and like piss there." And I was like, "Okay." Or he'll tell stories of how he's like um one time I got into um the first ice bath I took was with him and I was like, "Dude, I'm getting a little panicky.
Like this is I'm not I didn't I didn't know what to do." And he was like, "Well," and he was telling me the story. He's like, "Well, one time in training, they put us in like a coffin and they put a hole in the coffin where I could put my mouth in and they filled the coffin with water and then put it into a hole into a ground and I just kind of had to like breathe out of this small little hole while I was in this coffin filled with water and uh so I got really comfortable with like, you know, like knowing that like I'll be okay and like I'm really claustrophobic." And he just would throw all throw out all these stories just like on a regular basis.
And I just think that like I'm happy tough guys exist and I know I'm not one of them. Like there's like a difference between some of these like real actual hard guys. And you know what I've noticed about the real tough guys? They're hilarious.
Ken Rideout
Yeah.
Sam Parr
And my friend um I was like why are you I've noticed that you and your seal guys have like the runchiest humor ever. Have you ever noticed that?
Ken Rideout
Yeah. Of course.
Sam Parr
Like they like do the the craziest things and like their like practical jokes on on one another are like over the top.
Yeah. And he's like, I've noticed that all the he would say he's like all of us SEAL guys were really funny because like when we're in these situations, we just laugh all the time because that's like one of the best ways to like make ourselves happy. So they would like tell the runchiest [ __ ] ever about like you know mooning each other and [ __ ] like when they're like doing in these like crazy stories.
Ken Rideout
But that to me is like real toughness when you have to have mental fortitude. I mean you imagine you're in a gunfight with someone and the guy next to you gets shot through the eye and you're like, "Oh my god, I'm going to die." But still having the mental fortitude to be like, "All right, let me get this guy out of here. I mean, how much do you want to just be like, "Guys, we're overrun. Run for it."
Sam Parr
And they like signed up for it.
Ken Rideout
Yes. Yes. And they're like excited when they get the next mission. Yeah.
Those are like real tough guys.
Sam Parr
And a lot of my buddies who were in the SEALs, they um suffer from a lot of PTSD and all types of issues. And one of the issues where my friend would tell me that he feels down all the time or he was like, "I just lived such an exciting life. like I had so much like adrenaline all the time and now I just feel like everything is kind of the volume's turned down and it it kind of makes me sad sometimes and like he he fights through that a little bit and I just remember hearing these like that and I'm like that's just incredible.
Can you imagine like we just talked about like sparring and like now imagine like you know amping that up times a thousand. It's pretty I love hearing those stories.
Ken Rideout
I do too. I definitely missed my calling. It's like my biggest regret in life was not joining the military when I was convinced I had to go make money to pay off these student loans and then I had a job at a
Sam Parr
Pharmacy loans.
Ken Rideout
No, no. I had I I wanted to go start making money so I could pay all this stuff.
Sam Parr
I know. But if you join the military, if you had
Ken Rideout
I'm sure they probably had some incentive programs, but I was like and I went down and did all the strength test. I was like so close to signing up and then I'd like have second thoughts and I kept going back and forth and eventually I got a job in finance, started making a lot of money. Even when I was there, I'd check back in with this guy all the time and I just I missed it. I'm pissed. I wish I did it because I might have avoided my whole like addiction thing.
Sam Parr
Yeah. Yeah. The I think there's pros and cons to it. Like I read a lot of the books by the SEALs and like the rules are you're not supposed to talk about it.
Ken Rideout
Yeah.
Sam Parr
And then the guys who write the books are kind of like disliked amongst the community.
But they all consistently say, and I totally understand this perspective, they're like, "Dude, I was making 80 grand a year. I have a family to support." Like you're telling me if I write this one book like I'm taken care of. Like I served my country. I risked my life. Like let me get paid.
Ken Rideout
Yeah.
Sam Parr
And they all complain about being broke and like this idea of like I just did everything and now I'm like coaching cross country in a high school to make ends meet. Like this is [ __ ] [ __ ] And I totally empathize with that situation.
Ken Rideout
Yeah, I do too. If for someone who's starting out, like when you look back on your journey, your career as an entrepreneur, like what advice would you give to a young person now who's thinking like I was describing like I have to go follow this protocol. I'm going to go to New York. I'm going to work in the investment banking program. What would you advise like kids today?
Sam Parr
I would still advise someone to move to New York or San Francisco. Um I think that proximity is power. I think that you should go and just be around the action and go to meetups and meet all the nerds and infiltrate the community. And I think that like um for me like a lot of my the friends that I have now are like people who have started like really big companies and they were my my poor homies like we were just trying to make it happen and that that's pretty magical.
So I would say still move there.
I think that like when I was starting my businesses I was still I was envious. I was like, "Oh, my friend's an accountant making 100 grand a year. Oh my god, I wish I had that." Uh, so like that's normal, but I think that like there's a whole lot of people that are like some nobody dentist who is worth like $18 million in Ohio.
Ken Rideout
Yep.
Sam Parr
And I just think that like people need to realize that like in the small small business space, it's so much
More likely to create like substantial wealth.
Ken Rideout
Yeah.
Sam Parr
The odds are in your favor. You just got to look like a kind of like a loser for about 10 or 15 years.
Ken Rideout
Yeah. Well, the next question is, how do you advise people on building their network? And I asked that, let me tell you why I'm asking first. It drives me crazy when people are like, Ken, how'd you build your network of people? I'm like I I didn't try to like you consciously were like building a network. I am the that that's like the antithesis of what I do. I don't want to build a network. It's almost like I'm almost reluctant to meet new people because I don't want to be disappointed.
So, there's a part of me that's like starts out disliking people in general. And the people that are in my circle are like they're like my genuine friends. I never think of it as networking. Like I didn't meet you because I was like, I got to meet Sam. But when I met you, I'm like, I love Sam. He's the coolest guy. And it's like through that then like I know John Bear. I I don't know if I met him through you or or if we just coincidentally both know, but it's like I just know people and they've become my friends, but I never consciously did it.
You took the opposite approach. How do you
Sam Parr
When I was a kid, I did. Now I have a rule, no new friends. I'm like, I don't
Ken Rideout
Roster's full. I'm having cuts. No, no new applications.
Sam Parr
I don't want new friends anymore. Um, when I was um um 21, I had this rule called stalk and talk, which is I would stalk someone on the internet who I really wanted to meet and I would find like serendipitous ways to like meet them and I knew all about them and I would like say things that they were interested in, but basically like I cold emailed people like crazy. I had a rule that like I will follow up until they tell me to [ __ ] off.
And so what I learned was that, but this is only good if you're young, but for if you're under 30 years old and you're ambitious, other su really really successful people will take a liking to you as long as you don't piss them off too much. Yeah. And if you're like consistently emailing them showing progress and if they give you advice and you take that advice and so like I became friends with this guy named Tim Westeren who I'm not I don't talk to him anymore, but back then he founded a company called Pandora.
Ken Rideout
Yeah.
Sam Parr
And I cold emailed him 32 times. Another guy was this guy named Kevin Ryan. Kevin Ryan started um MongoDB, which is like a $40 billion publicly traded company, Business Insider, Guild Group, and a bunch of other companies like that. I emailed him 20 times, and I would just send him updates once a month. And then finally on like the 20th one, he was like, "All right, we can talk." And and he let me talk to him. And
Ken Rideout
That's interesting because when someone emails me too many times, if it's like, "Ken, just following up to see if you saw my last email." No, don't say that.
Hold on. There's no I want to emphas emphasize this to people. when you send that effing email to me after the third or fourth time, I go, "Not only did I see every I've done this and my wife's like, "Why are you wasting your time? Why don't you go, not only have I seen them all, but do you know that there is a fine line between persistence and harassment?" I said, "This is [ __ ] harassment." And now, now you've got my attention for all the wrong reasons.
You and whatever [ __ ] company you work for, all you've done is wasted my time. Look how much time I've just spent responding to you for what? You You added no value. You've offered me nothing except trying to tell me why you can do something for me. But there was like the worst sales pitch ever. And all of your follow-ups were dog [ __ ]
Sam Parr
I would send updates. I would say, "Hey, Kevin, since I last talked to you, uh, my company now we're doing $160,000 per month. I'm really nervous because we're only doing like, you know, 20 grand in profit because I hired these other people." But um I remember you one time said in one of your talks like this this and this and that really inspired me and so I made this change and anyway talk soon.
Ken Rideout
Now that I like that that's like you're delivering some form of value.
Sam Parr
It was an entertainment to be honest. I was just entertaining him and then eventually he was like all right [ __ ] it. Like you're at 3 million in revenue. Like it's kind of get serious. I'll talk to you.
Ken Rideout
That like that's that that's what I that's why I wanted to emphasize like if you're just telling me like hey Ken we help companies like yours scale. We can help you find capital. Here's a great one. Guy today [ __ ] sends me an email and he's like, "Ken, I love what you've done with Ride Out Sports and Entertainment. Have you ever considered writing a book? We help authors write books." I wrote back, "Dude, do you do a [ __ ] ounce of research? This is the laziest email I've ever received with a link to my book."
Sam Parr
Yeah. It's insane.
Ken Rideout
No response.
Sam Parr
Like I would like get like crazy. I was basically like writing a newsletter.
Ken Rideout
Yeah. Like
I love it.
But it was like it was entertaining. But to the young people out there, if you just think you're going to like harass your way into it, it has to be like have some ounce of creativity. There has to be a value ad. Like
Sam Parr
I heard someone say um they're like um um like if I see you pulled over on the side of the road with a broken down car, I don't think I'm going to help you. But if I say you push your own car, I'm probably going to like get out and help you push.
Ken Rideout
That's perfect.
Sam Parr
And I heard that analogy and I was like, "All right, I'm going to make sure all these people see me pushing the car." that I love that because some people do break through and they get my attention and I'm like, "Okay, what do you what's up?"
Dude, I know people who have like cold emailed like Jeff Bezos, like Mark Zuckerberg. Like the cool thing about email is like um you can pretty much reach anyone. Um you're you're maybe it's going to take you 10 years or five years and a whole bunch of outbound, but like you can kind of reach anyone.
Ken Rideout
Cold email pisses me off. DMs, I respond to everything.
Sam Parr
Twitter is where a lot of like crazy [ __ ] happens. Like Twitter
Ken Rideout
Twitter is like a sore for
I hate Twitter now. Yeah, I I I I like it for news and entertainment, but I've never the messaging part and like or if I post something on Instagram and someone leaves a really shitty comment, I'm like, "Dude, take this [ __ ] to Twitter, man. You're on my page. Like, you come to my page to tell me I suck. Like, get out of here."
Sam Parr
People tell you you suck.
Ken Rideout
Guy sent me an email, a DM yesterday. Obviously, it's an anonymous handle cuz he's a [ __ ] cuz only no real man would call would tell you like mean things to your face. Guy wrote a thing. I hate you. You You have nothing on David Gogggin. So, I thought it was a goof or something. I go, "Just a question. You hate me?" He's like, "I hate you more than anyone on Instagram. [ __ ] David Gogggins, blah blah blah." I have no problem with David Gogggins.
I just simply wrote back, "If I ever saw you, I'd kick the [ __ ] out of you and David Gardens. Go [ __ ] yourself." And the guy wrote all these nasty [ __ ] back. I just blocked him. But I was like I was kind of laughing when I did it, but I was like, "Who has the energy to hate?"
Sam Parr
Dude, I get sensitive to all these things. Like when I see mean comments about me.
Ken Rideout
Oh, I I get I get sensitive to them. But that was a crazy one. But yeah, when people write mean comments, that's why I'm like, "Dude, go to Twitter. Like, why are you coming to my page to like talk [ __ ] to me?" Like, no, it bothers
It says more about you than me.
Sam Parr
I'll like uh but sometimes it bothers me in a good way. I used to be a little bit I used to be kind of fat and I'm like I would see like photos of myself and people were like, "This guy looks fat." And it helped me. That's why I got skinny or skinnier.
Ken Rideout
Well, if you think you were fat and the guy said you're fat, it's like
Sam Parr
Yeah. I was like, "That's a good point." But
Ken Rideout
I always think for the shitty commenters out there, how [ __ ] bored are you that you have time to disparage another man, try to hurt their feelings. I wish that I had enough time in my day that I wish I had a few free minutes that I had time to scroll other people's content and leave nasty comments for no reason other than, "You triggered me. I don't like you." Like, what? Get the [ __ ] out of here. Keep scrolling. Get out. Like if you don't have something nice to say, scram.
You never see successful people leaving the comments. You never see Jeff Bezos being like, "Sam, you suck." By the way, my the guy who edited my book, I
Sam Parr
Was going to ask you, did you write this whole thing?
Ken Rideout
I did it oldfashioned way like uh like the guy from Eastbound and down, Kenny Powers. Spoken word.
Sam Parr
He goes, "I'm the best.
Ken Rideout
I'm doing it the
Sam Parr
I can throw the ball fast as fuck."
Ken Rideout
Dr. Cockin balls. I'm doing it the oldfashioned way. Spoken word. No, I I basically my editor would interview me, transcribe the the the text, then we would write it together and we he he he would type it and then I would go through edit it. But the guy who did it, Mishka Shubali, who's a superstar writer, he has a bestseller. He wrote a book called The Long Run, Recovering Addict, ran a marathon. He cold emailed Jeff Bezos with the with the manuscript. Bezos wrote the forward for his last book.
Sam Parr
No [ __ ]
Ken Rideout
Yes. Incredible.
Sam Parr
That's crazy. How did you um how did you get um Reggie Miller to write the uh write a little testimonial?
Ken Rideout
Great question. I would see Reggie Miller when I was running in the Palisades in the mountains. Reggie Miller is he's a savage on a mountain bike. He's like a legitimate
Sam Parr
He's skinny, right?
Ken Rideout
Super skinny, but like he's like an age group champion mountain biker. Oh, he's incredible. He's got endurance. Like you can't imagine.
Sam Parr
How tall is he?
Ken Rideout
Tall. 6'5, 67.
Sam Parr
There's like no tall guys doing that.
Ken Rideout
He's huge. U but skinny. So he would see me running and you know when you're running and mountain biking up a hill you're going basically the same speed and it would be like misty super early in the morning I'd see like what's up champ and we would just start chitchatting and then I I think I must have sent him a DM like hey man good seeing you this morning we became friends you remember you
Dude he would run a race in Hawaii and and just send a random Instagram post like channeling my in Ken ride out this morning at this race and he wrote that crazy post to me like if I'm walking down a dark alley with my life on on the line. I'm choosing Ken Ry out as the man I'm going to battle with every time.
Sam Parr
Dude, that's awesome.
Ken Rideout
There's a great one from Dustin Porier.
Sam Parr
He wrote He wrote one in here.
Ken Rideout
Yeah.
Sam Parr
Where?
Ken Rideout
What did he say?
He wrote um Dustin wrote something like the best part about Ken's story is he not that he has never been knocked down, but that he keeps getting up and uh crowd-pleasing knockout or something. Is it
Sam Parr
Oh, and Trey Hardy. I know who that guy is. He's a man.
Ken Rideout
Two time decathlon world champion.
Sam Parr
Yeah, he's like the most athletic guy on earth.
Yeah. Best athlete in the world. He probably still
Ken Rideout
He's a dude. He's incredible.
Sam Parr
How long did it take to do this?
Ken Rideout
Probably took me nine months to like write the manuscript and then the editing, you know, you send it to an editor. So Simon and Schustster, I put the proposal together.
Sam Parr
Do they pay you up front?
Ken Rideout
Yeah, good question. So I for people interested I write you create a proposal. At first I got an agent. I told my book agent at UTA Bird Level I'm like here's what I have in mind. Here's who I am. Like people had Rich Roll had connected me. and John Bear had vouched for me, connected me, and and I met with him. He's like, "I think you have a book in you. Let's do a proposal." So, you pay an editor/go writer to help you prepare a proposal.
It's like 15 grand. And the agent's like, "Do it. Uh, if you spend that money, like I'll sell this book." So, I did it. And I mean, I told this story before, but like in the beginning, if you told me Simon and Chuster would publish my book, I would have said, "I'll pay them 100 grand. No problem." So, when it went made the rounds, people started bidding on it. He's like, "Okay, we got an offer from I I might be mistaken the name of Hashet, uh, Penguin." I was like, "Holy shit." And then he's like, "We got this offer, you know, hundreds of thousands of dollars." And I'm like, "Do you think they'll get Do you think they'll do 500?" He's like, "Let's not be greedy." And I did the deal.
Um,
Sam Parr
How many do you think they'll sell or you'll sell?
Ken Rideout
I think the first week I sold like six or 7,000 copies, which is a lot. like 5 to 10,000 you have a chance to be on the New York Times bestseller list on the bottom of the list. So the way it works is like let's just say your deal is 300 grand. You might get 100 grand when you sign the deal, uh 75 grand when you turn in the manuscript, 75 when it publishes, and then whatever the balance is a year later. So it's like it's spread out.
And then if you have an editor like I had, you got to pay him and he's like I don't know 80 grand, 100 grand, something like that. So it's like you don't
Sam Parr
How much time was it? A 40hour a week thing.
Ken Rideout
No, no, no. We would talk like two three times a week for two to four hours and we'd bang out a chapter at a time.
Sam Parr
So much work.
Ken Rideout
It's it it's it's it's manageable. It's like anything. It's like how do you eat an elephant? One bite at a time. It was like that and we just grinded it out and it became like a bit therapeutic. The childhood stuff, the early life stuff was hard cuz I don't like remembering it. I don't like talking about it sucked. But the stuff about the running and [ __ ] I enjoyed and and about my wife and my family, then you turn it into an editor and then the editor takes a long time.
Sam Parr
Wait, so how old are you
Ken Rideout
Now? Yeah,
I'll be 55. Uh,
Sam Parr
What if you do more dope [ __ ] between 55 and you die?
Ken Rideout
I wish I would love to. I will say the book is good. The the the reviews that I've gotten are incredible. Like if I show you the DMs of people like, dude, this book is incredible. This is the guy who was the CEO of Kevin um Oly's Wonder Funds. He sent me a DM this morning. He goes, "This is the [ __ ] best book I've ever read."
Sam Parr
And do you think so? What's the game now then? You going to get like speaking gigs or something?
Ken Rideout
I got a bunch of speaking gigs coming up. Uh
Sam Parr
But you got to travel there.
Ken Rideout
Yeah.
Sam Parr
Are you okay being home away from home?
Ken Rideout
I think it's a nice break for everyone involved. I think
Sam Parr
I think my kids aren't old enough to annoy me yet, but once they get old enough to annoy me yet, then I'll be like it'd be nice.
Ken Rideout
I think it's nice. Like I think that there's a part of my wife that's like it's a little bit easier when you're not here cuz I have a system with the kids. Everyone is on the program. My wife's super soft and gentle. When I'm there, it's like there's a monster in the house.
Sam Parr
Dude, I hate I don't I don't like leaving home. I I haven't slept away from my my my kids only two and a half two and a half and two or two and a half and five months. And I haven't like I think there's only probably been two nights that I've slept away. So
Ken Rideout
I would say this, I definitely don't like it, but I have I'm not rich. If I had $20 million, I wouldn't [ __ ] sleep away either.
Sam Parr
Well, I what I'm but but my my eldest is just getting old enough where the other day I was like, "Go to your grandma's house. I need a night off." So, like I can understand why I would uh like I if I particularly if I had boys, I'm like, "You're [ __ ] insane."
Ken Rideout
I don't really like being in the hotels, but I do think that it's good break for my wife and the kids cuz like someone will slam a cabinet. I'll be like, "Oh, slam that effing cabinet. I'm on a call." You know?
Sam Parr
Which authors did you copy? You think?
None. I don't think my book is like anybody. Well, but like you get inspired rather by
Ken Rideout
Honestly like when I you ask me I would tell you the truth. Like I don't think of anyone to be like I wanted to be like that guy.
Sam Parr
Well, which memoirs have you read that you thought were the [ __ ]
Ken Rideout
I think David Gogggins book is a lot of similarities minus the military stuff, but like the rough childhood and then feeling like an obsessive drive to like feel validated. I just think he's his he's much more intense. He's doing like long races and like just competing in like crazy.
Sam Parr
Dude, it's pretty crazy to be famous for being like tough. That's kind of like an insane thing. That's like telling someone in the 60s you're going to be a famous you're going to make a living like being a skateboarder. It's like imagine you telling me 10 years ago you're just going to be like popular just for being a for like exercising.
Ken Rideout
It's crazy. It's crazy cuz when I started exercising I was just in survival mode.
Sam Parr
What did Kenny Power say? I'm not trying to be the the best at exercise. I play real sports.
Yeah, that's it. I tell my that's what I tell my kids
Because I when I first started you you were like do you shadow boxing and then you'd go for a 13 mile run and I'd be like boxer or runners are dorks. This guy is actually shadow boxing kind of good. I'm like who's this dude? I can't believe he's going to be like famous just exercising.
Ken Rideout
And I ran and race like that like a [ __ ] bully like a monster. I mean I was nice to people at the end of the race but during the race I was not trying to make friends.
Sam Parr
Well I like the story of you like running in the Sahara Desert or somewhere in Mexico I forget. And you and you catch up to someone and you're like, "You should quit."
Ken Rideout
No, I said I said, "Dude, how you doing?" Oh, good. Good. Dude, I did I ever tell you I never get tired. I feel I feel [ __ ] awesome. It was a 50 mile stage. And that's the day I won. I won by 90 minutes that day and won the whole race by 90 minutes.
But I wasn't like trying to be a dick. I was just I genuinely felt good. I'm like, "Dude, I never get tired. It went on the fourth day. It's 50 miles stage. I never get tired." And the guy was like, "Oh, this [ __ ] guy." And I looked back and he was walking.
Sam Parr
I love that story. He told It was a great story.
Ken Rideout
Yeah. Yeah. Yeah. I'm trying to do it, man. Well, listen. I want to be sensitive to your time. I could talk to you forever. I hope everyone enjoyed our uh bro conversation. It's not my normal I think it's a little broy, but I like it.
Sam Parr
What was bro? I'm Dude, I get accused of being a bro all the time. I think I'm the least bro. Like, first of all, I have been married to the same woman for a long time. I'm incredibly
Ken Rideout
What does does broy mean? You're unfaithful.
Sam Parr
I'm incredibly like dedicated family man. I don't drink alcohol. We exercise.
Ken Rideout
Do you think I'm any of those? I'm not any of those things, too. I am so not a bro. I think I look like a bro, but I would when people call me a bro. I'm like
Sam Parr
I don't know what you're like thinking broy is like a negative. I think we're like bro all the time. I'm like dude I like [ __ ] read a book a week.
Ken Rideout
You have the we have a different definition of bro then. I think you are my bro. I like I love you. I love talking to you. We're talking just a normal conversation. Normally in interviews like tell me how you over you were in prison for [ __ ] 3 years on a wrongfully convicted. Then what happened?
Sam Parr
You had people like that
Ken Rideout
Dude. I had a kid who was did three years for child sexual super aggravated sexual assault on a child that he didn't do and he did three years in a maximum security Texas state prison.
Sam Parr
Oh,
Ken Rideout
I said they know you're you know you're innocent. The inmates don't know you're innocent. You're a rapist. What happened? Kid was going into his senior year of high school. Division one scholarships up the ass to play football. Good-looking kid. big.
Sam Parr
What? He like fool around with like a high school or something.
Ken Rideout
No, he he another kid had sexually assaulted a kid at this daycare where he was staying at his buddy's house. And the kid looked exactly like him. And the the prosecutor never even investigated the possibility that it was someone else cuz the little kid said it was Greg and that was his name. But the other kid who did it
Was it was his mom's day. It was a cra dude. It was like the second third or fourth episode I did. You should listen to it. The kid's name is Greg Kelly. It's a very famous case from Austin. Crazy. And I've had I had other people that have done crazy prison time. And it's like all about how they overcame this difficulty. And I think this is just two friends talking. And I'm interested in like how you did hard things, but had fun doing it. And it doesn't have to be like this painful like prison life story.
Sam Parr
It's
Ken Rideout
No,
It's a grind.
Sam Parr
I'm soft, dog.
Ken Rideout
No, you're not. I' I'd argue you're the opposite of soft. Anyway, thank you for doing this with me. I appreciate it. I'm looking forward to reading your book
Sam Parr
Monday.
Ken Rideout
I appreciate you for doing this. Thank you everyone for being with me.
Ken Rideout
Thanks a lot for being with us and we'll see you next
Key takeaways
- Sam says an owned email list gives a media company more control than depending only on algorithms.
- A useful event can create the relationships that later support a company.
- Sam's early Airbnb opportunity ended after a lie caught up with him.
- Building Hampton around founder relationships required choosing a price that members could justify.
- Sam describes sobriety as a turning point that changed how he managed fear and risk.
Nowhere to Hide
A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.
It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.
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