How To Build a Media Empire with Sam Parr (Founder of The Hustle)

I believe in being bold and I believe in having fun. People move too slow.

What's your mindset when it comes to thinking like expansive and big and the potential that's out there?

I actually criticize myself for not thinking big enough. I just think that like huge successes are normal in my life, um, and I believe I can do pretty much anything I want. I know that the process is real.

What's your mentality when it comes to writing and thinking in headlines.

We're all persuading people to do things, and I think that it's like the most important skill set on earth. I like to box now, so I go to like boxing. We'll fight, and like there's times in the morning that I get my ass kicked. It's like this business decision or this career-related decision, that's nothing. I just got my ass kicked and I'm all right. And that's kind of like a really freeing feeling. You really got to like your shit. You got to like doing it. The key to getting a badass job or to creating something cool is to be a fucking animal.

I'm curious, uh, let's go back to 2014 for a second. You spent 47 days traveling 9,000 miles on a motorcycle. What did you learn from that time by yourself, meeting people along the way, traveling our beautiful country?

I was 24 and single, just just to give you some context. I had just sold a business and I was like one year sober. So I was like celebrating a bunch of interesting things. I met that meeting women on Tinder is awesome when you're riding your motorcycle across the country because you've got the best story to tell and be an entertaining date. I learned that I'm from the Midwest. I lived in the South and then at that moment I was living in San Francisco. Yeah, a lot of people in big cities stereotype the Midwest or the South as like rednecks, but all cities are the same. All suburbs are the same. All rural areas of America are basically the same. Like, it's really weird. You'll hear like people in like Northern California in the country have a Southern accent. It's like, so like we're all like pretty similar, which is shocking. I learned that you don't really need a lot to make you happy. I didn't, I basically had a little dirt bike and book bag and I was like, I don't need anything else.

I'm curious what made you do it? I mean, because like, I, that takes some guts. You gotta be willing to kind of get out there and live cheaply and also be okay with uncertainty, which I think is a great trait in a leader. But what, yeah, what made you do it?

Well, I'm very, that's one of my skill sets. I'm good with uncertainty. I'm very comfortable there. So I wanted to do it because I just wanted to explore. I'm very, I'm a very patriotic person. I love America and I wanted to see the entire country and I wanted excitement. I have a tattoo on my leg that says Bold, Fast, Fun, and I believe in being bold and I believe in having fun and I have no problem making life-changing decisions in a matter of days because something seems exciting and fun.

Bold, Fast, Fun. I read about that tattoo you have on your leg among other tattoos. Which look cool all over your legs. What does Bold, Fast, Fun mean to you? Like on a deeper level, like how do you live out being bold, fast, and fun?

Yeah, so BFF, that was like my motto for a lot of business stuff as well. I just think that when it comes to speed, I think people don't— I think people move too slow, particularly in business, but also being indecisive in life. And so I'm a firm believer of when I find an option that is at least good enough, I just 100% commit to it as opposed to thinking of all the alternatives. So I don't spend too much time like debating certain things because I believe in speed. I think that having a poor plan executed is a lot better than having an amazing plan unexecuted. And I believe in momentum. And so I always try to move and act really quickly. I got other tattoos that say "Act Now." I'm a big fan of action. And life's short and I want to like have an exciting life and I refuse to like let people box me into this like vanilla life that is unexciting. And so I'm always trying to do things just for fun. I think people are really analytical about certain stuff and I'm like, well, will it be fun to do this? Like, would you enjoy that? Then that's a totally fine, wonderful answer and reason why to do something.

I also view you, correct me if I'm wrong, as somebody who thinks really big. And I don't make that assumption about all people. In fact, I think most people don't think big enough. We are okay with mediocrity. We're okay with being average. We're okay with just enough as opposed to thinking bigger about whether it's ourselves, our own personal growth, and what we're capable of, or the companies we're building, or the, the peers that we're with. And I like being around people that push the edges of how big they're willing to think. What's your mindset when it comes to thinking like expansive and big and the potential that's out there?

I don't think I actually think that big. I actually criticize myself for not thinking big enough. I think that— but what I do, what I am good at is understanding that everything I see and everything that's surrounding me, whether it's a really big building, a beautiful piece of art, a huge company, some law created. I've been very fortunate that early in my career I used to have this event called HustleCon and I ended up selling the company that owned HustleCon for like tens of millions of dollars. But it started as just like this small conference and I got to meet the founders of like pretty much every cool startup from 2014 to 2018. So we're the founders of WeWork or Away Travel, Casper, like all types of like people who were soon to be or already were billionaires. And I got very fortunate that I got to spend time with these people in the green room. And what I noticed was that these people, many of them were not smarter than me. They were either as smart or a little bit smarter, or I was even a little smarter in some cases, but we were all in the ballpark of intelligence. But what, what they were really good at was, um, following through. And what it really did to me was it's sort of like, I don't know, like in Jamaica, why there's there's a small population, but they're oddly good at the 100-meter dash. It's like, because when you see your peers are doing something interesting and something big, it normalizes that. And I got really lucky in that I've firmly— I was inspired, but also like, I just think that like huge successes are normal in my life. And I believe I can do pretty much anything I want because like It's just got like this muscle of like, well, if you create this product that can get to a million in revenue and then you're going to spend a little bit more on marketing, that's going to get us to $10 million. And then the market seems big enough. So we're probably going to get to $100 million as long as we wait like 15 years to just do the same thing over and over and over again. You know what I mean? Like it became like, I just started, I'm really good at trusting this process because I've seen so many successful people and I've had some success as well that I know that the process is real.

But the idea of HustleCon and like for just someone to say, oh yeah, I'll get 2,500 people to show up, I'll get these amazing—

it didn't start with 2,500 people. It didn't start with 2,500 people. It started— so the business that I, one of my companies that I sold, the year we sold it, we were gonna do $20 million in revenue. Well, in year 1, we did $300,000 in revenue. And it started because I used to do these book club meetups where I would have friends come and visit. Or I would have friends at this book club and I did that for 2 years and then I did like a meetup that had like 200 people and I charged people $20 and then I was like, I'm gonna host a conference. And so I had been doing like some type of events or networking for like a year and a half. And then the first event that I did, HustleCon, I think I had 250 or 350 people come and that made like 50 grand. And then the second one made like 150 grand and then the third one made like 350 grand. And by the time I incorporated my business, I think year 1 we did 350, year 2 we did 2 million, I think. And then like it went from there, but it didn't start as like epic.

That's the cool thing though, is this willingness to take action on the idea, put it into play, and be okay with the fact that it's— it could take years, if ever, for the thing to be HustleCon with 2,500 people.

Yeah, I think, um, someone must have taught me this, but I was very in tune with the idea of in 5 years, I'm going to regret not having started today. Do you know what I mean? And so like, for example, whether it's sports or business or whatever, you're like, damn, if I started training 5 years ago, I'd be so sick right now. It's like, well, you're going to feel that way in 5 years from today as well. So we better start today. And so like really trusting that has helped.

And then you, you move that. To The Hustle, which became an online, like one of the first ever newsletters and certainly one of the first ones to sell for huge, or only one to sell for huge money. I feel like you, Morning Brew, I'm sure there are others.

I think it was just us. Maybe, you know, collectively we've sold our companies for hundreds of millions of dollars and I think we're the two largest.

How did it go from HustleCon to The Hustle to a newsletter that went to millions of people eventually.

I hosted this event called HustleCon. It was like a conference, like TED Talk for entrepreneurs. From the idea to the first iteration, it was 6 weeks. And the way that I got people to buy tickets was I started blogging and creating a newsletter and I got like 2,000 people to sign up to that. And then I did that motorcycle trip and I came back and I was like, all right, I should probably go make some more money. Let's do it again. And this time it did like $100,000 or $150,000. And I kept doing, I did the same process. I blogged.

Second event.

Yeah, the second event.

So, so the writing the newsletter was to basically promote the event. Yeah. And it ended up, it ended up being the newsletter became the actual really valuable thing.

Yeah. Well, after the second one I was like, oh sick, I've got 10,000 people who have subscribed to this newsletter, man. If it rains the day of a conference, like I'm gonna lose all my money. This is like, I don't, and then I don't see how this like scales becomes as big of a business as I want it to become. And then I started doing the math and I'm like, you know, BuzzFeed has like, let's just make it up, 100 million people coming to their website and they charge this many dollars per thousand impressions for their advertisers. With my newsletter, you know, if I get 2 or 3 million people, let's just round up and say 3 million people and I email 'em 26 times a month, for argument's sake, we'll round up to 30. That's like 90 million impressions and I only need like 2 writers to do that. And turns out email advertising rates are higher than just website advertising rates. If I do this right, I bet you I can get to $100 million in revenue. Like I'm just doing this math like really simply and I'm like, this could be a thing. This, the math works out that this is interesting. And then I told people who are older than me and more successful than me and worked in the media industry and most of 'em were like, Yeah, that, that won't work. Like, I know the math adds up, but like, that doesn't, it doesn't work that way. And I'm like, well, I don't see any reason why it wouldn't. Like, I can't find a good reason why this shouldn't, like, why this would fail, but I'll, I'll figure it out as I go. And so my math was basically, if I have like 3 million subscribers and I charge like $50 per 1,000 impressions, I mean, you could do the math now, but let's say if that would be 3,000 times, uh, $50, that's, uh, $150,000 every time I hit send. If I do that 26 times a month, that's, uh, about $4 million times 4, that gets me to $50 million. And I'm like, and then I bet you I could make some, uh, subscription revenue. This one product I have in mind, I think that can get to like $30 million. And I'm like, I think I can get to $100 million in 10 years. And I just like did that, like really simple math. And I sold the business in year 4 before I ever got there. But my good buddies at Morning Brew, they sold part of their business and they're approaching $100 million in revenue. And so my theory was on point. I just sold too soon. Not too soon. I'm happy I sold, but I sold before we got there.

When the HubSpot guys came calling, what made you eventually say like, okay, this is, is it just too much money? I gotta, I'm ready to stop. I'm ready to go to the next thing. What made you sell?

Two things. I had the goal that I made at age 22 to make $20 million by the age of 30 because I thought that was enough money that you can live a really good life forever. And so I wanted to make that money. I also had gotten sick, like really sick during COVID I got like Lyme disease and like my face got paralyzed and I was like, I want money because I wanna be able to afford the best treatment and I don't want the stress of running a company because if I die right now or if I get sick and incapacitated, I'm screwed. And so those two things combined, when I got offered by HubSpot, I was like, yeah, it's a no-brainer.

How has the deal gone now that time has passed? Because I don't, I don't know the full details of the earnout or if you had to, because they, they own My First Million, right? Which is a podcast you still do. And other things. How was that relationship going?

I basically, it's going great. I basically got like tens of millions upfront on the day of the deal. And then we did another deal for me and Sean. So The Hustle, we owned this podcast called My First Million. We did another deal to continue hosting the podcast and that was a performance-based deal and the podcast has like exploded. And so it like pretty meaningfully changed the price. And it's been awesome. I think that HubSpot has continued to grow the hustle. They make a whole lot of money off of it, I believe. I don't have any insider information, but I believe they make a whole lot of money off of it. And so they're happy and I'm happy and we still have a great relationship.

It's a win-win. That's the best one. But let's go back even a little bit before that because I think you asked me before we connected to remind you how we met and we met because I sent you a cold email. This is what I've been doing for 15 years, and it's a part of who I am, and I know it's definitely a part of who you are. So I, I want to focus on the importance of this skill, and I believe it's a skill that we all can develop, of being willing to reach out cold to people. And I think one of them from your earlier days was to the founders of Airbnb, I believe, where you're willing just to send a cold email to say, I, I could solve a problem, I believe. Can you, can you one, talk about the importance of sending cold emails as well as that specific story with Airbnb?

Yeah, by the way, it's like 3 parts. So I think that you said you have a bunch of young listeners. So it's one, cold email people. Two, provide value to them or like tell them such an interesting story that they want to follow along. And number 3, follow up a ton of times. Like 10 or 20 times, or follow up or die. Like, you always follow up. And so when I was 20, I had heard about this company at the time, it was called Air Bed and Breakfast. And in college I had a hot dog stand, that was my first business. And then on nights and weekends I created like a little e-com website that was doing okay. And I was like, man, the internet is like way better than being outside when it's 100 degrees. And I'd heard about Airbed and Breakfast and I'm like, this concept's amazing. And I'd heard about them when they first launched and then like a year or two passed and they probably at this point had 200 employees. So I cold emailed the founders and I was like, you know, I have this cool tool that I use called Reportive and I've hacked it to do X, Y, and Z. I think you guys could use that and it could help your company. And the founder was like, yeah, whatever, but that's cool. Like, I don't, He like was just impressed that I had the initiative. And so he was like, you know, he passed me out to someone on their team and they were like, are you, you know, you live in the Bay Area? And I, at the time I was in Nashville, Tennessee, and I didn't know what the Bay Area was. I had to Google like, what's Bay Area? I thought it meant LA. And I was like, yeah, yeah, I'm here. And he's like, cool, come to my office on Monday. I was like, great, see you soon. And so I basically had to get a flight and it was like one of the first times I've ever even been on a plane. And I like flew to San Francisco and I got a job interview with them and I eventually got hired. Why I didn't end up working there is a whole nother story. But yeah, I got the gig and then I went back to Nashville and I sold all my stuff and left school a little bit early and I eventually finished online. But like I sold everything within a week's notice and moved out there.

And just did it. Took action. Given your stature now, you would say, well, you might not have to cold email as much. You can get introduced by friends, you know, or is that a muscle you still exercise?

Oh, I cold email and cold call all the time.

Yeah.

Yeah. I do it on a regular basis.

Yeah. What about for who, to who, why?

I created this website called Sam's List last, a few months ago, and I just did it for fun just because I like making things. And I basically tweeted out to my, like my 300,000 person audience. I was like, who's got a good accountant that they love? And I got like 300 replies. And so what I did was I phone called all of the accountants that people recommended and I would be like, hey, you don't know me. This is kind of weird. I'm not trying to be a customer, but like I might be a customer, but I just want to let you know that I asked my audience like this and someone said you, and I'm going to build a website where I aggregate all this information on accountants. Can you like tell me how much you charge? Like what services do you provide? Things like that. And I'll just put you on this website for free. And so like I called like 300 of them.

You did it yourself. You could have easily farmed that out to somebody else, but you did it yourself.

I did the first 100 and then we hired this young woman named Kimmy to help me run the website and she did a bunch as well. But yeah, I did the first whole bunch. Yeah. And then when I started Hampton, my current company, that's like my main company, the first 300 customers I called.

Why is it important for you to keep that muscle strong and growing it?

Well, because cold email and cold calling, that's really a subset of just convincing people of something. So you're like convincing your— this girl to go on a date with you, or you're convincing this employee to come join your company, or a customer to trust you. We're all persuading people to do things, and I think that it's like the most important skill set on earth is, uh, like, that's the highest leverage thing, is to convince a whole bunch of people that your idea is good and to work together and move together and Persuasion's at its core. Like you can look at this at like an evil way of all the people who have done like horrible military leaders who have convinced a whole bunch of people to do evil things. And you can look at on the positive way, all these people that have convinced people to do good things. Like it's all comes down to being a good persuader. And so I just, I'm kind of obsessed with making sure that I always have that. And I'm not like the best at it, but I just like, you need to have it on, on you, like in your toolkit. And so And if you don't use your tools, they get dull.

How much of that were you born with versus how much of that have you developed?

I was born decent at it. My father was a small business owner, so my parents owned a fruit stand in Missouri where I'm from, and he was always good at making clients and customers love him by like, he would call it the gift of gab. And so I learned it from them. But then starting at the age of like 6th, 7th, 8th grade, I started reading like How to Win Friends and Influence People. Because I was like a dorky teenage kid and like I wanted girls to like me and I wanted like guys to be my friends. And so I was like, I'm awkward. I need to adapt and get people to like be my friends. And so I read a lot of books on how to do it. And then I practiced. I used to do this one exercise where I would cold call someone from the Yellow Pages and try to convince them to recommend a movie that I should go see. And it'd be like, hey, uh, uh, Eric, what's going on? It's Sam. Oh, this isn't Eric. I'm like, oh wait, who is this? And they're like, this is, you know, Rashad, whatever. I'm like, oh, hey Rashad. Sorry. I did not mean to call you, but look, this is kind of weird, but while I got you in the line, I'm on my way to see a movie. What should I see? I would like do these like weird drills to learn how to do it. Or when I was a teenager, I would just like, if I saw a woman that looked cool, I would just, I would be like, within 3 seconds of seeing her, I have to walk up and say hi. I would do this stuff all the time.

Forcing yourself to be uncomfortable because it makes it a little bit less uncomfortable each time, right?

And you get more skilled at it. Yeah, but like, I want it to be— I want it to not be fearful of it.

It's just, it's— there's one thing to say like, I want to get better at this. There's a whole another thing to actually create games and push yourself and force yourself to do it. I have to believe like all of those—

yeah, talk's cheap, baby. If you want to get better, you got to do the damn thing.

Yeah, exactly. You also were very fast, competitive collegiate Division I runner. You know, now the Olympics are happening now. This is an evergreen conversation, but still real time with these distance runners are insane to watch or middle distance runners. So I'm sure you got to be getting juiced up watching them. But I watched your YouTube videos of how well you ran. I'm curious what you learned from your time as an athlete that has helped you as a leader as well as a business owner and entrepreneur?

Yeah, I was a very, very elite 200-meter runner in high school, and then I had the potential to be a very elite 400-meter in college, but I, I partied too much and I didn't take it as seriously as I wish I would have. But I ran for a long time and I would run sometimes in front of tens of thousands of people. You know, no one cares about track, but every once in a while there'd be a big meet where there'd be a lot of people. And the cool thing about sports particularly track and field, there's a few cool things that I love about it. One, it's objective. The time doesn't lie. Same with business, like the numbers don't lie. And it was really cool to have to face the reality of like, you is or you ain't. Like, you know, you ran the time to win or you did not. Like there is no politics and putting that pressure on you is pretty awesome. I also loved, I kind of wish I had more team sport experience, but I love the fact that With individual sports, there's no one to rely on. It's just you and you're out by yourself. And I kind of liked that pressure. And then the last thing was what's cool about, or interesting about fitness sports. A lot of times people think that the better you are, you feel less pain. You feel the same pain every time. And so before a 400-meter race or an 800-meter race, you're at the starting line and you're like, in 30 seconds, I'm going to be really in a lot of pain, so much pain that I'm going to want to throw up and potentially quit, or I'm going to question what the hell I'm doing with my life. And I'm going to do it anyway. And I love that idea of like, uh, kind of being a man and saying, this is going to really stink and I'm going to do it anyway. Same thing with business and a bunch of other things where it's like, this is going to be hard and we're going to do it anyway. And I really loved that muscle.

Doing hard things on a consistent, regular basis I think has been— is a key to life, man. And now you as a dad, I think about this as a dad because of— and I got it from playing sports, namely football— of you have these 270-pound guys who are probably about as fast as I am coming after me on every single play. Like, why do you do that? "why do you do that?" I'm like, "I love the feeling of being able to compete and to test yourself on a daily basis." Like, how good is that for you to put yourself in tough positions, to be a little bit unsure— I'm confident, but a little bit unsure, like, "How is this gonna go?" And then to be triumphant or to handle the pain or the hard and push through it. I think that creates evidence for yourself to be very confident. And you can take that confidence and it's portable to all different areas of your life. And so that's why I, I'm like you, like I love sports, I love doing hard things, I love being around other people who regularly do hard things and push themselves because I believe that they're going to have a greater chance of making it happen, whatever it is. And it seems like, like that's been the story of your life.

Yeah, I can't imagine playing football. That's like way scarier than anything I did.

I can't imagine running a 400. I see the— or an 800 or whatever. I'm like, oh, that was just so painful because you, you, you got to be hurting so bad, I have to believe. But then you still put it into another gear after you're completely dead. I, I can't imagine. I mean, we ran around the track to to prepare, but it was to prepare to play football. It wasn't like to take it to another gear to hit this time or whatever. I can't imagine that part of it either though.

Yeah, it sucks. But yeah, like, and I, I like to box now, so I go to like boxing. And when I say boxing, I don't mean like fitness boxing, like we'll fight. And like there's times in the morning that I get my ass kicked and it's like the greatest feeling ever because you get beat up. Like you could relate to football, if you get your ass kicked, it's like this business decision or this career-related decision, that's nothing. I just got my ass kicked and I'm all right. Like, I ain't afraid of this other little nonsense. And that's kind of like a really freeing feeling.

Yep. I had an old mentor of mine named Luke Gaffney. I was at a QBR, quarterly business review, when I was working as a sales leader in corporate America. And he's like, dude, there are no 265-pound 4'5" running guys coming after you in this meeting. You're going to be fine. "Just go do the meeting." I remember it just like put me at such ease as I was leading, going in with all these like senior VPs or whatever to give some presentations. Like, worst case, you just walk out of the room. You know, like, it's not like you're getting killed. And I'm like, in a way, that doing hard things makes other things that maybe some people would think are hard, it makes them easier. And so, that's why it's good probably for all of us in whatever way you can to to regularly put yourself in positions to do hard things, manufacture hardness. And I want to actually ask you this, it's a little bit of a shift, but you as a dad now, you have the opportunity to raise your daughter and maybe future kids to have whatever they want, to be able to provide for her for her whole life if you wanted to. But I know you don't want that, right? You want to raise somebody who's tough, and resilient and it's got a lot of the skills that you have had to develop on your own to be gritty and, and, and keep fighting, I think, through the hard things. And I know she's still pretty young, but, but you and Sarah, your wife, what do you, what have you talked about in order to raise kids to be tough, resilient people?

I'm scared. I'm very scared about that. So basically, like, compounding is like a crazy thing. If you make money when you're young, like, it becomes like potentially billions, like in a lifetime. Like it's pretty insane. And I'm fearful of that. And I think about it all the time. I think that as I've had a little bit more career success, we're relatively frugal still, but we have some nicer things. We have a bigger house, have a nanny, we fly differently. And as my kids get older, I think we'll likely, like for a long time I was like, I want all these amazing services. I want like someone doing my laundry all the time. Which is what I have now. Like, I have like services, service providers. And I'm like, as our little girl gets older, we're gonna, we're gonna say goodbye to this stuff. I'm, we're actually gonna, I'm not gonna have that shit around because I need her to see me doing things I don't want to do. So she knows what grit means. And so I'm enjoying things now because she's 9 months, but in the next handful, a couple years, we're gonna like purposely dial things down, I think. Um, and that's like a, that sucks for me because when I could finally afford all this stuff.

That's hard to do, man. I feel like that's gonna be hard to do.

It's not that hard, I think. Um, I mean, yeah, it is hard, but like, I mean, I've been really poor before. Yeah. Like I've had like a lot of, I've had a handful of things happen in my life where like I've experienced what it was like to have nothing or to be destitute. And so I'm like, dude, like I could, we could, we'll be fine. And so yeah, it'll be hard in one sense of like, it's not gonna be as cushy, but it'll be easy in the sense of like, you know, I read a lot of history books. I love reading about war and like people who have experienced hardship and I'm like, hey, compared to like these other people, like I've actually kind of always been good at that of like comparing myself to like a global audience of like the best or the worst of everyone. Do you know what I mean? So it's like reading a biography of a billionaire and you're like, oh, I see myself in him. I could do that. And so, and similarly where it's like, I'm reading about kids in Afghanistan and I'm like, well, we're like crazy wealthy compared to them, even if we just make 50 grand a year. So we're fine. So what we're going to downgrade like big time, like, hey, look, we're not sleeping on dirt. Life's good. And so like, we're pretty good at that as a family, I think.

Yeah. That's a really good skill to develop. I think too, you brought up earlier in the conversation. About the fact that you would meet these super wealthy people or CEOs in the back, in the green room for HustleCon, and realize that they're actually not like, like that much smarter than you, or they're not even as smart as you are. And I found that to be one of the number one things over almost 10 years and 600 episodes of doing this, is not that people aren't brilliant and do amazing things, it's the fact that almost every person I've met is figuring it out as they go. And I think that's really inspiring. I think that's an inspiring thing to think about.

I find it very inspiring.

That people are— basically all of us are just figuring it out as we go. And so, it is possible to do big, amazing things, but you got to be willing to act. And I think that's one of the key learnings. I'm guessing you have too because you've interviewed a lot of people, you've met a lot of people that We really are just all figuring it out as we go.

Yeah, it's like the most fun thing ever is to like see your heroes cry. And I've like seen that a bunch of times where I've seen them like cry, or I've seen them confess to like being committing adultery or to being fearful of firing someone. And I like see all these things that bring them down in my eyes, and that sounds negative, but it's actually super positive where it empowers me. And I think that it makes it, it makes it normalized that it's cool to do great things and it's normal to suck at many other things, but I could still be great in general.

Yep. Now that you've built multiple businesses and are currently building multiple businesses, you have to make hiring decisions. And I think this is one of the most important things that leaders do is choosing the people that they're going to surround themselves with, they're going to work with. I'm curious, Sam, when you think about, let's say you're hiring for a leadership role like to run Hampton, for example, right? Because you hired somebody to do that or senior leadership roles as that company grows. What are you looking for in a leader? What are some of the must-haves you're saying, "Yeah, they got to have this, this, and this in order for me to want to hire them to be a leader at my company." I tend to like freaks or weirdos.

Like, I think of myself as kind of quirky and weird, and I like people who were the others growing up. I really like that type of personality. And another way to put it is I like people who are passionate, like, about their hobbies. And so when I interview people, I like to ask them— I call it the bottom fourth of the resume. So for example, let's just say you went to a 4-year university and you majored in philosophy. I don't really care about philosophy, but I'll be like, hey, what was your favorite class and why? And if they can't passionately entertain me on a story about something they spent 4 years and hundreds of thousands of dollars on, why that's interesting, then I don't want to be around them and I think they're losers. And so I really care about people who are passionate about a hobby, about anything. It doesn't even have to be work-related. So people who have, are high energy and focus on something that interests them. I, I love those types of people. Um, when I hire for a lot of roles, I have it like two categories. Category one is like people who have been there, done that. And so like with a CEO or something like that, I want someone who I'm like, look, I'm not trying to give you a chance. Like, I just want to find, like, it'd be like hiring a quarterback who like has never played quarterback before. I'm like, no, no, no. I want someone who like, you are already good and we'll give you room to be even better. But then there's other roles where it's like a junior role and it's like, I'm looking to buy people's stock before it becomes overvalued. And so in those cases of the second one, that's when you really find some of these weirdos. And like, I want to hear, like, like for example, I interviewed this one guy, Jacob, who ended up working at my company. He now works somewhere else and he's amazing. And I was like, what do you do for fun? And he was like, you know, I have acid reflux and I've been like working to find the best ketchup. And so I went, 'cause I saw a bunch of boxes in his back of his house and I'm like, what the hell are all those boxes? He was like, So for fun, I like am trying to use these beets to make a new ketchup so I can eat ketchup. And I'm like, tell me everything about that. And he walked me through his experimenting phase. And I'm like, you're, you're brilliant. You're the best. Like you have the it factor. And so we hired him. And so I hire people a lot of times because if they have these like weird hobbies or like they're passionate about something, I'm really into that. I also I want people who are skilled at something. I think that far too often people are think that being a generalist is cool and everyone starts unskilled, but people who you have to have a little bit of a promising ability to be skilled because you're being intentional about getting better at something. So I care about people who are skilled. I think far too many people fall back on the generalist mentality and I think that's bullshit. I think you, you have to be, highly skilled at something.

I know it probably depends on the role, but how important is them being an effective writer/communicator?

Dude, it's like the most important thing ever to me. So a lot of people think because of the way I talk on podcasts that I'm like a bro or whatever, and I'll get people who email me and they're like, what's up, MFer? And there'll be like typos in their email, and I'm like, not a chance. Don't ever talk to me again. I'm very into effective communication because effective communication— there is a 100% correlation between how well you communicate and how clearly you think. And if you can't— if you communicate clearly, by definition you're very likely, or you are thinking clearly. And so Clear writers are like, it's like the most important skillset. Like, 'cause writing, particularly copywriting, is again, just another arm of persuasion. Not always, but a lot of types of writing are, are like persuasion. And I'm like, if you can't get me to read what you're saying and get the thoughts into my brain from your brain. Effectively, then like you're a nobody. Like you're going to be nothing. And unless you can like communicate to me, then I don't want to be around you.

I think your writing is very enjoyable to read, even whether it's sampar.com or the Anti-MBA. Like you've written, you have blog posts that go back that are enjoyable to read, or even like a yearly review of last year. I just reread that one today and I think one of your skills that you can make it look really easy, just like a great keynote speaker, they make it look really easy, or a great stand-up comedian, they make it look like they just wander out and talk even though it's like very crafted to the syllable. I would say you write like you talk. From having listened to you talk and reading your writing, you write like you talk. And that sounds like it should be easy. Well, just write like you talk. But I don't know if it is.

Can you, can you, I'd love to do that.

Yeah. I'd love to hear more about your process on writing like you talk, because it sounds way more authentic than trying to be like a writer. It's just, I'm just going to write like I speak.

No, I learned how to do that. I, that, and when I talked about being a generalist, people are like, cause I actually don't like generalists and they're like, well, you are. I'm like, no, no, no. I'm a. Like I'm self-trained, but I'm a trained copywriter. I know how to do that. I can always get a job doing that. And I taught myself how to do it the right way. I taught myself how to do that was doing this thing called copywork, which is where you find other people's writing and you just copy it word for word just to understand like their flow and stuff. And I did that for months, every single day. I would word for word write what people's, other people's work. So I would do it with entire books. I would do it with bestselling advertisements. I would do it with scripts of Saturday Night Live. And so in the same way that you learn guitar, you play other people's music for a long time and then you're like, oh, I like this, I like this, I like this, and I'm gonna combine all of that to make my own flavor. That's what I did with my writing. So I just copied other people for a long time and then I, in copying other people, I were like, oh, you know this, you know, the way he phrases, that's very authentic to me. I would, I, I would use that. And same with this person, this person, this person. I'm gonna combine all of it to make my own thing.

How does it, like, literally handwriting is— I believe there is some science behind this, right? Yeah, other people's, like, because you think, like, I'm gonna handwrite other people's stuff, like, why would I do that? Like, how does that help you become a better writer?

Well, if I said, hey, to learn how to play piano, here's, like, you've never played piano before, uh, but Write me a song. It's like impossible. You know what I mean? Like, it's really hard. Like, I've tried to learn how to play piano. If you told me like, we're going to learn by you writing a song, I'd be like, dude, can you like teach me how to do chords first? Can I like learn Happy Birthday? And then like this other band and this other band so I could just like see how they do it. And when I was a kid, I used to play drums and the way like you learned was I would just put headphones in and I would play with Green Day all the time. And like, oh cool, he does this fill all the time here. Like I get it. Or like, oh, you see how he like hits the cymbals twice here? Like that adds this really cool like bit of emotion. Like I feel kind of cool. It's the same exact way with writing. And so a lot of people think, oh, that's ridiculous. Why would you copy other people's work? And I explain it with music and they're like, well, that makes perfect sense actually. And so, and there is science behind it. I don't know all the science, but there's been like large sample size studies where they like teach people this way and it is effective. It's very effective.

I heard you talk with David Perell about this. Big, good, good buddies with David. I love his work too. And you talk about writing in headlines and thinking in headlines. And I think from a leadership perspective, this is important because you got to say things that are memorable. You're at a town hall leading 1,000 people. It's got to be memorable. It's got to be sticky. It's got to be entertaining. Like it's got to be motivational and inspirational. So I think leaders need to think about this. What's your mentality when it comes to writing and thinking in headlines to be clear and to help people remember it and take action based on what you're saying?

Yeah, look, like we're inundated with new data like all the time, and the only way to make people or make anything you're thinking stick, whether it's in a leadership perspective at your company or writing, you need bite-sized memorable phrases. And there's a lot of examples of this, of like great advertisements where you like only remember, like you like don't remember a lot of it, but you remember there's 5 words and boom, that's stuck. Like I got it. And so that is true for headlines, but the reason why headlines are important when you're writing is if like basically anyone who's ever ran anything on the internet, they know that the like 3% conversion rate for some reason. That's like, it's kind of arbitrary, but we'll, that it's kind of a threshold of like, if 100 people come into your website, if you're lucky, 3% of them will buy something. And it's always like the best websites in the world. Maybe we're talking like Amazon is like probably 8% or something like that. So like on the ballpark of 3 to 10, whatever. Same with articles. So on Facebook, if I were to post an article, The click-through rate, if I'm doing kick-ass, is going to be 3%. And yet people will spend 100 or 99% of their time writing the article and only 1% on the headline. And I'm like, well, if you do the math, like the headline actually reaches most every, like reaches way more people. And if you were to change your click-through rate from 0.5% to like 5%, we're talking 10 times more people. Are gonna like read this. So like your headline's like a huge deal. And so when I say think in headlines, I mean, I mean it one out of being practical, like your headline's actually more important than the article because that's to get people in the door. But two, if you think in headline, that also forces you to write a certain way. So like, for example, I had this article go viral and it was like, uh, I lived on Soylent. So for people who don't know, Soylent is like SlimFast for nerds. It was like a meal replacement thing. And it was like, I lived on Soylent for 30 days straight. I knew in my head that that would go viral. And so I made the article to fit within that context. And so when you think in headlines, you think, what can I create that can fit within a headline? Which is like I said, practical, but also gives you a really good framework to like, cause any good content or good email or good speech or good anything, you need guardrails to like stay within and finding those guardrails is hard. That's why I did copywork, cuz I was using someone else's work there. I didn't have to make my own guardrails. When you have that guardrails, that's where art is made. When you like have this little box to stick with inside of, do you know what I mean?

Yeah. I mean, that's why I think it applies so much to outside of just the world of writers or copywriting, but, but it applies to people who are leading teams, leading companies. Is because the communication element, that part, like, I don't know if you—

well, yeah, look, like think of all these famous speeches. I have a dream. Yeah. Or ask not what your country can do for you, but what you can do for your country. Like, right. Like Martin Luther King, uh, his legacy is defined, uh, defined, yes, as civil rights, but it's like boiled down to like, I have a dream that one day might, you know what I mean? Like that line, same with JFK, that line, like, that like when you think of these one-liners, you, they have to be memorable. They have to be repeated a ton. And same at leadership at your company. Like you want your company to behave a certain way, you gotta repeat the same shit all the time. You gotta make it memorable.

Yep. One of our, I think mutual guests from our podcast is one of the best in the world. That's currently Scott Galloway. Like he has so many memorable turn of phrase sayings. And I heard you and Shawn talking to him and it was the same feeling I got, like talking to him a few times of like, how does this guy have so many memorable sayings? And it's like a lot of practice, a lot of reading, a lot of writing, a lot of preparation, very smart. But I think that is why somebody pays you $150 grand to go give a speech or why somebody would pay you to consult or why somebody would pay you to be the CEO of a company is because you've really worked on thinking in headlines, Writing, speaking, communicating. That's what moves people.

And Scott's good at it. So often, for example, he was like, I work out so I can kill and eat everyone in the room or to be able to outrun them. And I'm like, yeah, that's mine now. I'm stealing that one. He like has these like beautiful phrases that I freaking love. He's very talented at that.

Yeah. Sweat more than you sweat more than you watch other people sweat. I was like, oh yeah, I should be working out more than watching some game on TV. I was like, oh, and that leads to the eat and kill everybody and be able to take over a room or whatever.

Yeah. He'll say, you should be signing the front of checks, not the backs of them, meaning you should give more money. And I'm like, yeah, that's like a great, that's a great line. I love that. Like he, he just has lines. He's very good at it. He's a wordsmith for sure.

I know it's something for all of us to, to think about from a communication perspective. Hey, there was a cool post online that you and your co— I believe co-founder of Hampton. That I like that you were very clear on what you both wanted going into it.

Oh, yeah.

And you posted this and I was like, oh, okay, what Sam wants, like a certain amount of net worth in 7 years. You talked about fame and influence. You talked about freedom, right? You talked about what that could provide you. And I think this idea of documenting what you want, it has two purposes. One, it helps you get very clear on like, what am I trying to do? What am I trying to accomplish? And then if you are going to work with a partner or with anybody else, make sure that they have vivid clarity of where you're coming from, you have clarity of where they're coming from, so you're on the same page. And so, I'd like to hear more. I think it was— his name is Joe, right? That you guys wrote each other like, "This is what we want. This is what we're all about. This is what we're striving for," and how that's benefited you.

I originally did it with my wife. So like when my wife and I, yeah, when my wife and I were dating, you know, we got to the conversation.

Same type of template or is it different?

It was similar. So we got, we got to dating and like when it was getting serious, we were like, hey, I think like I would like this to end in marriage and a family. Would you? And she was like, yeah. And I was like, that's wonderful. Let's like, do you wanna like do an exercise where we like write down, like tell me what do you want in 5, 10, 20 years? And it's okay if it changes. But like, tell me what you want and I'll tell you what I want and what values we stand for. And when we said, when we say what I want, it was like, how many kids do you want? Like, where do you want to live? What type of lifestyle do you want? And in order to have that lifestyle, how much money do you think that we need to make? And like, what jobs, like not necessarily careers, but like, you know, like for, for example, it could be like, well, you know, so maybe I'll be the one who earns the money and you could be the one who like Supports us in this other way. But like we basically mapped out, we're like, you know, tell me all of your wants and dreams now and what you stand for and what you are willing to sacrifice and what you're unwilling to sacrifice. And I'll do the same. And as long as there's mostly overlap and we're willing to compromise on the things where we maybe don't align on, sounds like we're like, we're good. Like this, like we're both, we're aligned. And I did it with my wife and it was like really helpful. And then now I do it with, you know, Joe's my only business partner, but we did the same thing where it was like, hey, so it's this business that we are kind of tinkering with, it might have some legs. Um, you know, what type of outcome would you want to have? Would you want to sell this company? Would you want to own it forever? Do you want your family to work here? Do you not want them to work here? Do you want to have lots of employees or not lots of employees? Do you— how, how many hours a week do you want to work? How many— what type of vacation would you like to have? Uh, what What would your, your net worth, what would you like the outcome to be in 5 or 10 years? And we outlined this and we mostly overlapped on everything. And the things that we didn't overlap on, it was like, well, is this a deal breaker for you? No. All right, cool. This other thing that you said you want, I don't want to do that, but I'm cool going along with it if it makes you happy. And so this way, like there's no surprises and of course we maybe will change. But it's important to be intentional, I think.

Yeah. I think with any relationship, communication, clarity, and understanding of the desires and wants of each other is critical. And you see problems arise when people aren't good at this. So that's why I want to highlight it. I actually wanted to drill down on one of them if you're cool.

Here's an example. Yeah. Well, you drill down, but I'll give you one example first. Like for example, what I said was like, I don't wanna do this right now, but once my kid gets a little bit older, I'm gonna take, I wanna take the summer off. I don't wanna work in the summertime. And he was like, yeah, I wanna work all the time because I love it. But, uh, I'm okay if you wanna take the summer off. And then this way, if I wanna take the summer off, I'm fucking doing it because I told you that's what I wanted. You're cool with it. And I know that you have my back and I have your back. I'm doing it and I'm gonna be guilt-free.

And you're very clear upfront. Like you both are like, yeah, we're good. We're good. I think that's critical for any relationship to go well. One of them you wrote about though was fame and influence. You said, "I want a seat at the big boys' table and for people to think I'm wonderful at my job." And then you wrote, "I wanted it to be clear to Joe what my insecurities were. Being taken seriously as an entrepreneur, not just a content creator, was one of them." Can you go deeper there? What is that about?

Well, you know, it's funny. It's changed. Now, I don't care about fame at all anymore. I actually would like to, I don't want any of it. If I could just disappear on the internet, I'd be fine with that.

But because that you didn't write that that long ago, or did you? When did, when did you write that initially?

So what, a couple years ago, but, but it's still rooted. What I wrote is still partially true. So I don't want fame, but I do like, like I didn't come from a lot. I came from Missouri and like, You know, I live out here near New York and I'm like, I see all these big shots. I want, I'm like, in my head, I'm like, I want them to take me seriously and to know that like, I'm the real deal. I'm not just some dude on a podcast. And so I'm still like, that is still true with me. Now I don't care about like, if I was never on a podcast ever again, I would be totally fine with that. So the fame thing is not true anymore, but the taken seriously by big dogs, I still feel a massive chip on my shoulder. Where it's like a guy from Missouri with nothing. And then like, you know, I relatively knocked it out the park by the time I was 30, but even still I'm like, it's not enough. I made my money on a stupid newsletter. That's such a silly small idea. You know what I mean? Like I still have that like chip for sure of like proving to myself and others.

So you don't think that that will, make the big dogs take you seriously? Like, what would make them take you seriously?

Well, that question is similar to the an— or the answer to that is similar to like, how much money is enough? It's like, whatever you say is probably not true because the answer is probably like, it already is enough. Or like, you know, like, like they probably do take you seriously, but like, you, you know what I mean? The answer is like, it's a me problem, not a them problem. But I don't know, like it would be nice to have a billion dollar outcome.

Do you think that having a billion dollar outcome would like, how would that change things other than you fly private and do whatever you want?

I already do whatever I want now.

Right. That's what I'm saying. So how would it change then?

Oh, it wouldn't change at all. It's just that I have like an ego issue and I still have insecurities and that's just something I'm trying to convince my, or I have convinced myself to be true, even though I can logically say nothing will change. Like the only thing that will change with more money for me now is just how much I can give, I think. But just like sports where it's like, if you want to bench press 300 pounds and you finally hit it after 4 years of practice, you're not a different human being. You're a little bit different because you went through all the effort and you improved like your mindset a bit, but you're not a different person from 295 to 305. But once you hit 305, even though that's all you ever wanted, You're like, dude, I could get 330, I bet, if I like give it another 8 weeks, you know what I'm saying? And so that like competitiveness, like that scoreboard mentality, while I think it's unhealthy for a lot of things, and in many ways it's very unhealthy, it is what it is. Like it doesn't go away, or at least it has—

What do you mean by ego problem?

Well, Like it's never enough. You know what I mean? Like I'm not great enough. Like I need to build a legacy. I need to be all-time. That's all rooted in your ego. And the fact is, is in 200 years, none of us are going to exist or be remembered. And so I should live life a little bit differently, but you still, like, even if I know this to be true, like you still fight these, these insecurities and these, the devil on your back of like, but I could be better. I could, I could be great, you know what I mean? Like, and I recognize it's, it's not important, but it's still like, that doesn't— like, I know that I should eat a certain way to look great, but that's still like, it's— that's a simple thing, but it's still hard.

It's just the balance is so fascinating to think about because, you know, you know some of the issues and some of the problems, but You also know that some of that is why you've become who you are and why you accomplished so much in a, in a, in a short period of time.

Yeah. And for anyone who's like, like, I'm, I'm pretty paranoid about certain things and, um, it's hard to let go and not be paranoid even because you're like, well, that's why, like, I'm a baller is because I'm fucking paranoid and I'm, I think it's all gonna go away.

Paranoia, Jim Collins stuff, right? Don't you think? It's like—

I've never heard of that, but that's awesome.

Well, a great choice. It is. I am a— I live with productive paranoia and I use that intentionally because of like whether it's before a keynote speech or a podcast or whatever, it will eat me up and spit me out. But I also know that it is very productive, that pair, that productive paranoia then can lead to excellence on the stage or on a podcast or writing a book. And so I try to be like, be grateful for it, but also at times I'm like, oh God, like, why can't I just relax? You know? And so it's like, it's never ending, dude.

The strength is the weakness. Like, and for example, I love the UFC. Yeah. And like the other day, someone to Dana White, like one of the UFC guys got arrested for fighting. And then another one got like a DUI. And the media was like, hey Dana, like, does this bother you? He's like, dude, I'm getting guys who want to fight in their underwear to the death in front of millions of people. In order for them to be great at that, I must accept that they're going to be insane in other aspects. That's just part of the personality. And I think that's true for— now that doesn't mean you should accept that. It's DUIs, beating, getting fights. That's not acceptable behavior. But it's accepted behavior a little bit, you know what I mean? Like, yeah, I accept that, that you could understand it. You could understand, like, yeah, I expect that that might be part of the territory.

And yeah, football teammates like that, it was tough, you know, you got to be good character guys and do the right thing. But these guys are maniacs on the field and sometimes they don't turn it off. And because we're humans and we're messy and we mess up and We make, we make mistakes. Like, so it's like, I gotta have, we want to do the right thing and be good people, but we also know like we're maniacs out here and sometimes like it spills over and that's, that's life.

And by the way, I know you got a lot of young people listening. Like, I think the key to getting a badass job or to creating something cool is to be a fucking animal.

Yep.

Uh, like that's like an animal is how I would describe the best people I've ever hired. They're animals.

Say more.

Nothing stops them, or they're insane a little bit. And when I use the word like freak and weirdos, that they're cousins to being an animal. Sometimes the best people that you hire, they're almost uncomfortable. You're uncomfortable a little bit being around them, and you're sometimes fearful. Like, I have people work for me, I'm like, dude, you, you're Like your belief in this thing is almost scary to me. And I love that. And you're pretty ruthless and I love that. And being an animal is something I think you should dive into and like lean into.

I love that. I was just going to ask you to close here. You've been around some of the highest performers in the world. You've interviewed them, you've hung out with them, you've been backstage with them, you've seen them at their highest and lowest. What have you found to be the commonalities among leaders who have sustained excellence over an extended period of time?

You really gotta like your shit. You gotta like doing it. Um, you know, there's like a lot of passion versus what you're good at type of advice, and I don't know anything about that, but in order to do something for decades, you you really got to enjoy it. You got to like get— now it's sort of like you could start a business selling tires and you cannot care about tires, but you just love like building an organization or you like, you can, you love feeding your family or you love hiring people and watching them develop, but you have to find joy in what you do. If you're going to be pretty good, you're going to be in the 1%. You got to really enjoy it, I think. And I think that's really important. I think that having endurance and being a cockroach and like surviving a nuclear bomb, like that type of mentality is a real competitive advantage. Willingness to do something for decades is like a huge competitive advantage and you gotta enjoy what you're doing in order to last that long. I would say that like the world in general wants to make people be vanilla. So like my wife went to an Ivy League school and, and they they were like, you got to go into finance and do this. And like, everyone faces that. But the people who like do dope shit, whether that means career-wise or they're just like generally happy, you can't let that influence get to you. I think that far too many people get nervous about making a decision that's authentic to themselves to please people that they don't really give a shit about. And I would encourage like young people like to follow their gut a lot more and be willing to be different.

Be a weirdo, dude. This is awesome. I really appreciate it, man. Big fan of your work and I would love to continue our dialogue as we both progress, dude.

I appreciate you. And we'll have to do a mock combine.

Mock combine. I don't know. You're in pretty good shape, man. I don't know. It might be tough to— what are you benching? 225 now? You still getting like 16, 18 times?

I did that last year. I can't do that today. No, I couldn't do that today.

4.640, is that right?

Yeah, it used to be a lot faster, but yeah, I ran a 4.6 this year.

But 4.6 at this age, like that's super fast. That's fast when you're in college.

It's all right. Yeah. Like I, the fast twitch don't go away.

I don't know. I think it does for some people.

At least it doesn't go away. Like you got it or you don't a little bit, but I, um, attributes. So like on a video game, like some of the athletic attributes, I've always been good at that. But then when it comes to like handling the ball or like running with the ball, I'm like the least coordinated person.

Oh, so you're fast. You would've been a good receiver though. You would've been a good receiver.

Well, I can jump high, I can jump far, I can lift heavy things, I can run fast. But then if you ask me to like catch a ball while I have a helmet on my head, I'm like, dude, this is like, I, I'm just simply not athletic enough.

So what about basketball?

No, it's all horrible. I can't do any of it. Like, like I could, like I could dunk a ball, but if you ask me to like dribble in between my legs, I'm like, dude, I can't do this.

Skateboarding though.

I could do that. But like anything that involves like traditional sports of like holding a ball, for some reason on paper, it looks like I should be good. I'm horrible at all of them. If we were to play basketball, it's embarrassing how bad I am. Huh.

Funny. Interesting. All right. Yeah. We should record one in person and do a little combine. We could figure some stuff out. I'd have to throw a few ball sports in to make up for the other, other areas where I'd lose.

It wouldn't even be close. You would absolutely destroy me. Okay.

We'll figure it out. Awesome though. I really appreciate it, man. Thank you so much.

Thank you.