Chris 'Drama' Pfaff - Dealing with Fame, Anxiety and Addiction
Guests: Chris 'Drama' Pfaff
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So, Chris, thank you so much for joining me today. I really appreciate it. It’s great to get to meet someone like yourself while I'm out here in LA and have a productive conversation about things that I myself am trying to uncover. But you, as a seasoned entrepreneur in this space, have been through it. My audience is predominantly young, aspiring Europeans, British people, slightly skewed to male, but we do have a strong female listenership as well. For those of the people listening that don't know your story, could you give us a topline overview of your personal journey?
Absolutely. So, first, thank you for having me. I'm excited. And that audience is exactly who I'm trying to reach and spread my message to, so it's perfect. Hi to all the new listeners. My story is this: I was born and raised in Akron, Ohio. Akron is a pretty small area, not complete farmland, but pretty close to it. I grew up with an older brother and two parents who are still together.
Everything was super simple. They loved family; it was all about family. Not so much entrepreneurship or really going above and beyond and doing anything crazy, but just a really nice, solid foundation. I fell in love with skateboarding at like 10 years old, I think, and me and my brother both. So that's all we would do is skateboard every day, all day. We would leave school as soon as we could, do whatever. I was always ditching out on doing any school sports or school activities because all I wanted to do was skateboard.
So, around the age of 14, I realized that Los Angeles is the skateboard capital of the world. It’s the coolest place on earth if you're a skateboarder. So around 14, I decided that this is where I was going to move, no matter what. As soon as I graduated high school, college was not an option for me. I was coming straight to LA and I was just going to try to make something happen. I wasn't good enough to be a pro skateboarder and I kind of had that awareness, but I started shooting video and taking photos and doing anything I could to solidify some sort of spot in the skateboard industry.
So when I was 18 years old, I was supposed to graduate high school and then move straight to LA. The weekend after graduating, I had a head injury from skateboarding where I was in a coma for four days and had brain bleeding and skull fracture and all this crazy stuff. So it derailed my trip about six months. Finally, after that six months, I was cleared to go. I left, I came to LA, and just kind of hit the ground trying to figure it out. I remember when I first got here, I was insanely nervous and scared and kind of overwhelmed, to be honest. It's embarrassing to say now, but like I just felt way in over my head. I felt like there was all this crazy stuff going on that I couldn't quite grasp.
How old were you at that point?
I was at the tail end of 18.
Did you have any money when you arrived here?
I had like $2,500. And I was like, first of all, at that time, $2,500 I thought was so much money, and it was gone like instantly. So I have a cousin who's a pro skateboarder, Rob Dyrdek, and he’s lived out here pretty much my entire life since I was, I think, five years old. So obviously we connected and I hit him up and I said, "Hey man, anything I can do, like I'll film you skating, I'll clean your house, I'll do literally anything, I just want to live in LA."
So we ended up meeting up obviously and becoming really close. And now he’s a lot more like my older brother. And I ended up taking a job as his personal assistant. At the time, I had no idea what personal assistants even did. He offered me the job because his assistant had just quit. Worst case scenario, I can just go get that job at a skate shop or whatever else I was going to do, but there's some action going on here. I want to at least give it a shot.
So I became his personal assistant. He was a pro skateboarder, and it was things like running around and grabbing shirts from his sponsors, putting together skateboards for him, and cleaning his house. Shortly after, around six months after, they came up with the idea of possibly doing a reality show for MTV. And that sounded crazy to us at the time. That was when like "The Hills" was on and all these weird MTV reality shows. It didn't seem like a place for us, but it ended up happening. Long story short, it ended up happening. It was called "Rob & Big," and it was based around him and his best friend/bodyguard.
And it was just kind of a funny comedy, like odd-couple show about them running around town doing crazy stuff. And they looked crazy together; he’s like 5'8" or something and the bodyguard was 6'5" and 300 pounds. And it was just hilarious. And the thing exploded. It just exploded into this phenomenon, especially here. And it was in a time when MTV was bigger than ever and these two guys were bigger than ever.
So I stayed on as his assistant, but life just got really interesting and really crazy. And now you're dealing with fame and you're dealing with endorsements and all these different types of things. So it didn't take long for me to realize that I didn't want to be a personal assistant forever. I also didn't want to be a reality TV star. I really wanted to create. I saw all the businesses that were being launched off of this marketing platform. And I wanted that. I wanted to run a business and I wanted to be able to be a somewhat normal human being, but to still be able to be successful and have fun and enjoy the success.
Did you become personally famous from that show?
I did, but not crazy like from the first show.
What are we talking in terms of following or recognition?
I’m talking like it was before the current social media metrics, really Myspace time. But I guess the best way for me to describe it is like, let's just say I go to a mall ten times. Probably two of those times I'm going to get recognized in the beginning. The only time that I would really get recognized crazy is if I was with the other two. Because now you're with the stars, and they’re like, "Oh, and you're here!" And it was cool, but to be honest, I've always been kind of introverted and kind of anxious socially. And so it felt more like scary to me than anything.
So that show did three seasons. Huge success, great. We were all finished with it, and mainly the two stars obviously, but finished with it because reality TV wasn't a path that we could see really continuing to go down. It wasn't giving anyone any time to do anything different. So we stopped doing that.
About a year later, MTV came back and said, "We want to do another show, and we want the familiar faces back on the network." His co-star had moved to Texas to raise his daughter, so it was me and Rob essentially together. And they came back and said, "We just want familiar faces back on the air, anything you guys want to do, let's do it." And so we landed on this concept of what was called "Fantasy Factory." And it was this concept about Rob and his 25,000 square foot warehouse in downtown LA that was like almost like a Chuck E. Cheese for adults—skate park, ziplines, foam pits—and then also all of his business offices.
So that ended up getting picked up by MTV and we went into that. For me, I said, "This is my chance." I wasn't a big enough star in any of the other stuff to really kickstart a business or to even get a good endorsement deal. This was my chance because now the co-star's gone, it's me and Rob. I watched everyone, how they played the game, how they did these different things. This is my shot. And that's where I came up with the concept for Young & Reckless. And that's my clothing line.
And so what I thought is I had dabbled in a bunch of other businesses and other ideas. I was a music producer for a while. But this would really allow me to create a brand that meant something, fill a gap in the market, and also be able to market it directly on this TV show that we're already doing that's going to millions of people. So I'm just—everything's working together. That’s what ended up happening. I went and got the trademarks, I figured it out, I wore the samples all over the show, and long story short, it worked.
And it started taking off and I was able to build a real business behind it and really make sure that it lasted beyond this hype of a reality show. We ended up doing eight seasons of that reality show. That's where I became more—at that point, I would probably get recognized ten times out of ten at a mall. That's where it kind of changed. But yeah, and then that ended about four years ago and I ever since then have just been building this business and doing it right and readjusting and moving and shaking. I've tried a bunch of other businesses—some have worked, some haven't—and that's kind of like my journey.
That's incredibly inspiring, by the way. I think there's a lot of people who wouldn't have seen the opportunity in the platform you had there to build something even bigger than that. A lot of people will naturally concede for what they have there, but it was very entrepreneurial to want to build more. What does Young & Reckless stand for?
I want young people to break out of the status quo and live the best life that they can live. And what that means is, go start a business if you want to start a business. You don't have to go to college. You can listen to podcasts, you can read books, you can figure it out. If you want to go travel the world, let's figure out how to do that and go travel the world. If you want to go jump off the tallest cliff into the water. Whatever your dream is, I support these young people saying, "Wait a minute, these rules don't apply to everyone and they don't apply to me, and I'm going to kind of go around them and make my dreams come true."
Were you naturally an entrepreneur? Or do you think there is such a thing as a natural entrepreneur? Because one of the questions I get asked a lot is "Are entrepreneurs born or created?" What's your thoughts on that?
So that's the go-to question. I've been asked it hundreds of times, and sometimes I feel—not to be defensive—but I want to make sure I stick up for the right people. Sometimes I feel like that question is a question that allows entrepreneurs to disassociate themselves from everyone else and get to say that they're special and like, "No, I'm different than you." And I think that I don't know. I think there's obviously some traits in people—risk tolerance, courage—there's all these things that do make entrepreneurs some better or some worse, strengths or weaknesses.
But I don't know that it's some crazy combination of gifts. I think that if people can be woken up to it, I think that something can happen to someone that didn't maybe look at themselves as an entrepreneur up until age 32, and then they can become one of the best entrepreneurs that ever lived. I think that can happen. For me myself, I was always trying to find ways to pay my bills and get by without having a normal job. I didn't like normal jobs, normal sort of authority. I don't know if that was birthed in skateboarding.
Why didn't you like normal?
I just didn't. I didn't like—something felt like just becoming one of the people. If you're going to go get a job at like Starbucks or whatever, you're just becoming the same as Todd and Tim and Stephanie and you're just one of the people and you're taking orders because somebody said these are the orders and you're just doing it. And I didn't like that. I always hated that. And I do will say something with skateboard culture is it's very anti-sports culture. And they're very like core and "screw corporate America trying to get into our thing," and "screw the rules and we do what we want."
And there was something really cool to me about having no hours, having no coach, having no teammates. My own progress relied 100% on me and how many hours I was going to spend trying a trick in my garage in the freezing cold Ohio winter or whether I wasn't. And when you landed something or when you made progress, it was your progress to enjoy.
I'm going to try and play devil's advocate. Obviously, I agree because I'm an entrepreneur as well and I completely understand what you're saying. But I'm going to try and dismantle some of the things you're saying or try and argue with them. The point that entrepreneurs don't have a boss? You probably have more bosses than anybody in a sense because you have customers, right? Do you have any investors at all?
No.
Okay, so you have thousands and thousands of customers. A lot of entrepreneurs have investors. You have to work harder than everybody else. The person you referenced that's sat in Starbucks cleaning tables as a barista clocks off at 6:00, goes home, lives the rest of their life. You have chosen to sacrifice friends, probably family, probably a huge amount of other parts of life—romance, these kinds of things. Why?
You want to know why? This is the difference. You're 100% right. And if I did have investors or board members or any of that stuff, I'd have a lot more bosses. The difference is: yeah, you work for them, but you get to decide what the best answer is, and you get to live or die on your own choices. Not "this coffee machine has to be cleaned at 9:00 AM, noon, and 3:00 even if I know it's not dirty." Why? Because Jim said so.
That's what I'm saying. It's doing things not because you believe that it's the best way to go about them and to do it; it's doing things because that's what the system says that you're supposed to do. And I think that being able to—there's an insane amount of pressure, of course, way more than I ever thought, and an insane amount of missed time and relationships with being an entrepreneur. But man, when there's a problem, I get to try to solve it with my own thought process.
I completely get you. I'm going to come back again. Part of the bullshit that comes with being an entrepreneur is all the problems are also yours to solve. No matter how much you want your team to love the business as much as you do, you know at the end of the day they get to go home, right? And that bullshit, no matter if it's Sunday, you're on holiday, if you're sat with your mom, you're sat by your father's bedside, that bullshit is coming to find you and it's asking for you, Chris, to solve it at all times forever as long as you're in this business. And you love that, right?
I love it and it’s more than I thought. I'm not going to act cool like, yeah, I can take any problem. It is more than I thought. It's stressful, it's overwhelming. There's days when I hate everything and I wish I just had a nice comfy job. But you feel so much more connected to your life when the results of your life, good or bad, are a reflection of your own decisions.
I’m not waking up—and the other thing is, you could wake up and you could get yelled at all day at work for something that somebody else did. That sounds crazy to me. That sounds so miserable to me. I would rather at least take the blame and take the heat and say that I'm getting punished and I'm getting beat on because I didn't pay attention or I didn't focus or I made the wrong decision. And this is a learning experience and I'm going to then go and win, and I'm also going to reap the benefits of that progress and that win personally. But your life is just connected to you so much deeper when everything hinges on your own stuff. That's the part that I loved.
I tried—I tried everything that I could. I realized this when I was younger. That’s why I say, to take it all the way back, I can't say I was born some super entrepreneur. But I have instinctually always tried to avoid that, and I've always tried to learn and have wins or losses on my own. Like when I was younger, I said I was learning how to film for skateboarding. But what I started doing because I had a camera and I had editing equipment is I started going and filming Little League football games. It came because one of my cousins played Little League football. And I realized like, hey, these people don't have Final Cut and cameras at their house. I can go film these games, edit them, burn them to DVDs, make cool little covers and sell them to the parents. That was my first time in seeing like, oh, this is working, or you know I'm making a little bit of money, but the margins aren't good or whatever, and there was all these little hustles. And so I always tried to do that. And I think that is a very entrepreneurial quality.
For sure. I also think—I'm playing devil's advocate. Even with the question "do you think you're a natural entrepreneur?", the reason I ask that question is because the world is such a different place now with technology and the ability to work remotely, that you can literally be an entrepreneur sat at home on your computer alone. Or you can be the more stereotypical version of an entrepreneur, which is this big charismatic leader of a big business. I wanted to ask you that question because personally I think the definition of an entrepreneur should and has changed in many respects. Knowing the pressures that you've gone through building this business and starting your own company, do you think that anyone could do it? Or is it just for a select few people that are tough enough to deal with the bullshit?
I think that the same way anyone could run a marathon, anyone could start and run a business. I think it's possible. I think and that is part of what I try to do through my podcast and my message. Because what I don't like and what I try to shy away from is people saying, "No, I'm different because I was born special." Don't get me wrong, there are qualities that are undeniably needed and practiced and—but people can change. People can become more resilient. People can learn how to deal with adversity.
I've seen people that I—there's a guy in my office ten feet out the door who promised everyone he was going to run the LA marathon three months ago. And if you looked at him, you would think there's no chance. And everyone in the office was like, "Man, there's no chance." And I even was telling him just kind of being devil's advocate, like "Hey, there's just no chance." And he did it. And he trained and he buckled down and he ran this marathon.
And it's like, I just compare the two things. I think anyone can do it. I just don't think anyone will. But I think that if you want it, if you truly want it, if you watch all these podcasts and you soak in all this content and you say, "That's for me, that's for me, that's the life I want," then do it. You can do it. This is something that I think. I think there's a huge growing contingent of people that are becoming fans of the rockstar lifestyle that's attributed to entrepreneurs. And they never ever do anything, but as you said, they'll watch and listen to this podcast, they'll listen to Gary Vaynerchuk, every possible type of content out there that will talk about the entrepreneur lifestyle, but they'll never take action.
On the other side, I've met—and this is one of the hardest things I've had to deal with with producing content and advocating entrepreneurship—I've met people who—I'm really only thinking about one guy who watched all my stuff and was a big fan of, you know, being an entrepreneur, all these things. And he would just show up outside one of our offices in the UK, Manchester, 6:00 AM in the morning every day just to meet me and get photos or whatever. And then he came to me one day with a business idea.
Now, this is a guy that—I'm going to be completely honest, right—he could barely communicate, he can't communicate articulately, he bursts out hysterically laughing almost every five seconds. His ideas that he showed me on this piece of paper, which he'd literally scribbled with a pencil to show me his business plan, was horrendous. He couldn't sell, he couldn't hold eye contact with me, he couldn't do anything. I told him, I was like, "Listen, I think you've got to go back and work on the fundamentals a little bit more." And he came back at me with my own advice, which is the whole, you know, "do it and fuck you to everybody who doubts you." And I realized at this moment I created a bit of a monster because the truth was for him, he was—there was so much more work to do.
But everything that I say about, you know, doing it regardless and discounting strangers' advice and believing in yourself was also true. So what do I do in a situation like that? But here's my question: do you think that if—let's just say—will this happen? Probably not. But if that person got the right insight, the right coach, the right guidance, the right mentor, the right whatever, that he could be an entrepreneur? Or do you think he's just doomed?
He could be some type of entrepreneur. He could be selling something in a shop.
There you go. So that's all that I'm saying: anyone can. It's just that most people won't. Because what it takes to actually do that is insane and intense. And some people—I think that the same way—it's a scale, right? Life is a scale of sort of personality types. Some people are just born and raised and whatever closer to the traits that are needed to do that. Some people are way further. But I think anyone is capable of learning what it takes. It's just will you do it? And you have to be willing to learn and put your ego completely aside and just take a beating and think that maybe you're potentially wrong in any circumstance.
The worst thing that I always see is people that think they know it all now. Maybe Jeff Bezos could say he knows it all and I would be like, "Oh, you probably do." But anyone under that? You can't. And part of being an entrepreneur is you can't have that attitude. You have to constantly be learning and constantly be curious and constantly be potentially wrong. And I think that some people are really far from that.
But my point is, I think that at least here in America, the way that we put people through high school, the way that college is structured, the way a lot of parents raise their kids, is not conducive to the qualities that it takes to be successful at anything, but especially to be the type of person that goes out and stands on his own sort of ideas and stands at the front of the ship and steers and works harder than everyone. I mean, we're just not raised that way, but that's part of my thing.
The bad thing is I can't stand just as much as the next guy the dreamer wannabe entrepreneurs that just soak in YouTube videos all day long and think that they're entrepreneurs. I hate it. I think it's toxic, I think it's really bad. But I do think that what's happening is the internet and all of that content is allowing more people who are real and are serious and are hungry to get a little glimpse into what is true and closer to the truth and further from the bullshit that maybe their parents taught them or whatever, and therefore allowing more people to live their dreams.
And I think that's the part that's really important. And that's what's so important about what you're doing is, forget—I mean, when we used to have a reality show, there'd be people waiting outside the gates of this thing all day long throwing their terrible business ideas over the fence. Like, "Please just give me a shot, this is the best idea ever." Terrible idea, over and over and over. But the point is, I do believe that forget about all that, there were people that started businesses or became inspired to do something better than what they thought they could because of that show that otherwise wouldn't have. And that's the same thing you're doing and all these people are doing.
For sure. So I think that what you just said there has inspired a question I had. You talked about when you were doing the reality show and people were throwing their business ideas over the fence. When you put yourself out there as an entrepreneur, what will happen quite naturally is people will flock to you with their business ideas under the assumption that you're the enabler, you're the investor, you're the person that holds the wisdom that can help them make these ideas come true. I'm sure if your DMs look anything like mine, it's full of a lot of young people and older people hitting you with their elevator pitches and their business ideas in your DMs. What has someone got to DM you or send you via your private inboxes to get your attention?
Yeah, it's hard. It's hard because it's a bit of a case-by-case, but like number one, if it's an ask first, you have no shot. It’s just not possible. "Help me with this" or "help me come up with a business plan" or "give me some money." I think that it's like some sort of value proposition. It's "Hey, I have this thing that is really, really valuable." I mean, what happens the most now is podcasts. Because all these young people have these new up-and-coming podcasts and it's great and I like having the conversations. But they say "Hey, I have a podcast, this is what it's called, this is how many listeners I have, this is what I plan to talk to you about, and this is why it would be really good. Is there any way that you'd be willing to give me an hour of your time and do this?" Of course. I would love to.
What's the worst type of DM you get? The ones where you just roll your eyes?
"Yo dog, can I have 20 grand?"
Yeah, okay. So the things—I've never talked about this publicly before, but I honestly get annoyed, not annoyed at the person for them messaging me or offended. I'm annoyed because I'm disappointed in them. And I read these DMs and it will literally be "Yo, any jobs going?" I'm annoyed because I want this kid—whoever, I don't even know this kid is—I want them to get a job. Total stranger, I want them to win, but I'm so disappointed that that's how they're applying to the CEO of the company. And sometimes I tell them. Sometimes I don't have the time to, but sometimes when I look at their profile, as we all do, and I think, "For fuck's sake, Clive," I'll just tell them. Do you ever feel that way?
Absolutely! You know what we should both do because I just had this idea? Okay, so here's the good news. The good news is we are truly both—I can already tell by talking to you for 10 minutes—our goal is to inspire and educate young people to start businesses and to do what we've done. Because we know the feeling, we know it feels great, we know that it's incredible. Naturally in the pursuit of doing that, you're going to have some lost ones and you're going to have some people who just don't get it. But I think what we should do is make a video about how to properly reach out to somebody in a direct message and what certifies a proper reach out. And then when people reach out with the wrong one and we have time, just copy and paste them the link and say, "Hey, I made this for you." Because all we're doing is continuing to educate and inspire. We're not being assholes. We're not saying, "Yo, you messed up." Like, we're just saying, "Here man, you're just not getting it."
But that's my point. That's why I say like, sure, anyone can be an entrepreneur. Whoever raised that kid, or whatever high school he went to, or whatever way that he got that into his head that that's how you approach a person, is just terribly, terribly wrong. But he could be taught the right way. He just doesn't know. And in their mind, they don't know. They think that that was probably a great idea. I literally set up a—do you guys have Venmo?
Yeah, I know what it is.
So I set up a Venmo account. I will get—I don't know, I'm going to have to figure out how to change my name or whatever—but I will get random requests for like 50 bucks, 100 bucks, whatever, from people saying like, "Hey, I need to fix my car," "Hey, my mom's in the hospital," "Hey, whatever." Like, you're just requesting money from me on this money-sending app? It's crazy! But they don't know. And I think that our goal at the end of the day, if we really look at it, is to teach more people how to know how to navigate this weird world. Why? Because us now sitting across from each other having the joy of traveling and doing a podcast with other successful people know how incredible it feels. And we want everyone to have that feeling.
Completely agree. Jumping back a little second to some of the tough times, especially in your personal journey. One of the things I've, as I said earlier, that I think about entrepreneurship these days because of movies and Instagram is that it's glamorized into being this rockstar thing where you get to fly on private jets and eat lovely food and you're rich and therefore because you're rich, you're happy. Talk to me about the toughest time you had as an entrepreneur.
So there's been a lot for me, and I think more than—you know, I really suffer a lot from glamorized life syndrome. Like, when you're on a TV show and then you have this big social media following and whatever, obviously on our TV show all we did was show fun and just having the time of our lives. And the way I even showed starting the brand looked so fun. But it didn't show any of the real like struggles of any of this stuff. And so I have this thing where I think that a lot of people think that it's just been a reality show—like my life has just been this great sort of thing.
And what they don't see is what happens underneath all of that to make all this happen. So I think that my first—there's probably two. And I think the first one was just when I moved to LA, to be honest. I was just lost and scared. And like I said, it sounds so embarrassing to admit now, but I need to be honest that I just was in over my head and I felt this urge to try to chase this better life, but I was just lost. And it felt terrible. And I was having anxiety attacks and I was fresh off this head injury and I just didn't know.
But the worst part by far was probably three years ago. It was this convergence of all these weird things. Like, it was a combination of I think that I had filmed a reality show for the last like nine years and then it was over. And I was so happy that it was over because I didn't like being on TV, I didn't like performing for a camera every day. I didn't like that stuff. But what I didn't take into consideration was that it was literally like leaving a business. Because every day we would go down to this team of people and we had been with this team for nine years and there's people that care about us and that are happy to see us and we're skating together and whatever, and then they're just gone.
And I didn't think about that. I was too busy happy about the show being over and not thinking about "Okay, I need to fill this gap in my life with something." I also was just got out of a bad relationship. I also had a couple friends that had recently got married and were just kind of off in married land, so life felt really lonely. And then on top of all of that, it was right when the worst of like the retail collapse here in the US really started hitting.
And for us, I had spent the last six years focusing on building my business in retail—in PacSun, Tillys, Macy's, Dillards, all these places. That was my whole life was traveling around, meeting with buyers, making sure I could slowly but surely gain more shelf space. And then it really felt like kind of all at once, there was this collapse. And PacSun filed for Chapter 11 bankruptcy and a lot of our other guys were cutting orders and all this crazy stuff was happening.
And it wasn't because we had done anything wrong. That was a hard one, when we talk about like owning your losses and stuff like that as an entrepreneur. That was a time when I had to own somebody else's losses and I had to own a market shift. And it hurt. It didn't make sense to me and I felt like it wasn't fair. And then you put all this personal—all these personal issues on top of it. And I literally for about—realistically, I would say a hard six months—felt like nothing was worth anything. This life that I had built was worth nothing. Getting up every day to come to the office was worth nothing. My relationships I had built were worth nothing.
And I was literally—I say it now, but I was literally going home every night and I would wait—my only self-sort-of-management tool was I would wait until 9:00 PM to start drinking. Because for some reason if I drank after 9:00, that felt like I didn't have a problem. So every day of the week, I would drink, just chug bottles of wine and take Xanax to go to sleep, take the occasional Vicodin that I had laying around. It got pretty—not like I'm not a—like never turned into like having a drug problem, thank God. But like it got pretty brutal.
It was filling a gap, right?
It was, and it just felt like—I don't know, it just became kind of the routine. And it really came from all of these things making me feel like nothing was worth it. And there was no upside and this was it and I had chosen the wrong industry and I had blah, blah, blah. Just feeling sorry for myself and feeling stuck. And whatever, so that was probably—that was like a six-month time frame that was by far the worst part.
It’s really reminiscent of my co-founder Dom who I started the business with. In our second year when things were really tough, we lived together and I would go downstairs most nights and pull a bottle of alcohol off him and he was sat there in the dark drinking. He was 21 at the time, 22. But the pressures of the business and trying to pay people's wages—and we had at that time about 100 different wages to pay and you're looking at the bank balance all times and it's not working out and then there's all these personal pressures and having to keep it together for everybody else—I just think it was just too much for him at that point and he started doing drugs, as he said in the podcast. Started going through mental health battles as well. And came out the other side of it and he's not drunk since then, he's not—he runs marathons, he runs like a marathon like last week, he ran 10K yesterday for charity. He's an ambassador of mental health charities. He's been completely sober ever since then and he's just a completely different person. But it just goes to show the untold stories of taking on the pressure of running a business whilst also having the pressures of life, right?
It’s insane! And I was even like you said at that time, because this is the thing: I've always been able to keep this business relatively small. So we've never had hundreds of employees, but we had probably 52 or something like that and right now we have I think around 42 if you count the warehouse and everyone. But the point is, I had built like—apparel can be a really fun industry, right? It's a lot like being like a rapper sometimes. You're doing parties and you're hanging out with celebrities and blah, blah, blah.
And so what happened was I had built this team of friends and we became really close friends. And so everything we're doing, you know, we're going to South by Southwest in Texas and going to all these festivals and it's so fun. The problem is when times get tough like that, unfortunately your friendship doesn't pay the bills. And I'm coming in every day feeling like crap and you're sitting across from your friend who you had all this fun with and you're having to fire them day after day after day, not based on their performance, not based on your friendship, not based on anything but these kind of outside sources.
And when we're glamorizing it on YouTube, we're not talking about that. And we're not talking about sitting across the table from your best friend and saying, "Hey, there's just not a job here for you anymore," which inevitably ruins relationships. And yeah, it's a rough thing. But kind of like your friend, I feel so much better having gone through that. Because now I feel like there is no issue that this business could face that would put me back into that place. Because now I get it. And I feel stronger and I feel like I know why I'm doing all the things that I'm doing. And if I see a problem coming, I'm able to adjust a little quicker because I know how things can get. And it just gave me such a clearer, stronger foundation for how I run a business that I wouldn't trade for the world.
And how, if anyone's listening that's going through a similar feeling to what you went through then, what advice would you give them?
The advice is simply this: take the first step to positive. Whatever that is. Like literally if you're like, "Man, one day I'm going to start running," like literally just go right now and run around your block. Don't worry about how big the goal is or "Oh, that's not even a real thing" or this or that. Literally just start the first thing. Or here's a book that somebody recommended, screw it, I'm finally going to read that. Or here's a podcast, whatever it is. Just do the first thing. And the first thing will lead you to the second thing, and the second thing will lead you to the third thing, and so on and so forth. And that's how it will happen.
Don't try to sit—a lot of times you sit and you come up with all these plans of how life could be better in a different world and all these things that you could do or what you lost or whatever, and you make this like mountain for yourself to climb. And that's why you feel like you're in this horrible valley, because look at what you're looking up at. You just have to start with one piece of forward momentum and let that build and you will be shocked in a year what happens to your life.
What did you do?
Exactly that. I literally started—I think the very first thing I did, I'll be honest, I remember. The very first thing I did is I went to dinner with some of my friends and I was having like terrible anxiety at dinner because of course all of those feelings and then drinking and all that stuff just give you this terrible social anxiety if you already have it. And my friends, thank God for them, recommended this book—they asked if you've ever done any meditating. And I was like, "No, meditating seems crazy to me. Like, I'm from Ohio. Meditating seems like some weird funky like religious stuff."
And they're like, "You should really read this book called *10% Happier* by Dan Harris." And they're like, "Trust me, just read it, it'll change your opinion of like what meditation is." So I read that book. And it's about a guy who was a news anchor who just had a mental breakdown on air and found meditation and it made him 10% happier. Didn't change his life, it helped. And so I was like, "Oh, this is cool." So then I started dabbling with meditation. And then I started reading why meditation works. And then that led to this and that led to that, and literally it just led to then I started this podcast.
And I didn't realize the first 10 episodes I did of the podcast were a nightmare for me. Like, I was panicking. I'm like, "How do you carry a story? How do you—like this is all on me, I gotta sit here for another hour." Like, I'm looking at the clock. But then, you know, you have one conversation where somebody says something cool about a cool book and you go home and read that book. And then somebody else says whatever. And then you're just stacking all of these things. Then I started working out. I started going to cycle class, to SoulCycle here in LA because I was like, "Man, I hate running, it sucks, it's miserable." And I had a friend who was going there and I'm like, "Yeah, let me try it." And then now you're doing that and you're sweating, you're getting some cardio, and it literally just led to this entire shift from following the next thing in front of you to where now I can go on and on for hours about how I structure my day and how I keep track of things and what I do in this and that. And it's all just from experimenting and trying the next thing.
I imagine your motives for doing what you do have shifted. They have for me. When I was 18, I wrote in my diary that I wanted to be a millionaire before I was 25. Did you make it?
Yeah, I'm 25 now. Yeah. And the next thing I wanted was—I've got this diary and everyone's seen it—the next thing I wrote in my diary was that a Range Rover Sport would be my first car. Was that true? Yes, it did. And then my other two, I think I'm still working on. Number three was I wanted to have a long-term relationship because I just was allergic to girls because I thought that they impinged on my freedom. I had a girlfriend for a year which I thought was pretty impressive for me. And the other thing was working on my body image. Back then I was super, super skinny because I wasn't eating, I was completely broke. But my motives for wanting to succeed have shifted. Money has come around in my life, as I'm sure it has in yours. My view on relationship with money has changed. I want to know from your perspective what role money plays as a motivator in your life.
Yeah, money for me now—and I'm similar to you, right? I think it was my 26th birthday, I bought a Lamborghini for myself for my birthday. Ridiculous. And obviously I was much more driven by kind of the fancy things, which I also think is like it's a big part of everyone's early dreams and I think it's important to own those dreams and to go out and to chase them, but it just won't get you to the end of the race.
And I think that for me in the beginning, it was much more driven by that. And now, I'm sure similar to you, it's much more driven about how can I continue to spread that message and add real value to the world. Not to be too dramatic, but like, how can I add some value? As far as what role money plays now, it's simply like a megaphone to, or an accelerator to, anything that I want to do. Like, yes, if I want to start a podcast now, thank God I am able to buy the best equipment, build this cool-looking little set here in my office, get the fancy computer, and pay someone to do it. That's incredible. But I use it to simply put fire on a good intention.
And I try to do that. I try to really now only spend real money on things that I think I'm just expanding a good intention. But money allows me to do that faster. I don't do the—at least right now—any crazy outlandish spends and just for the sake of doing it or to show off or to show how successful I am. You said "at least right now." I'm just saying. I don't want someone to hit me up in two years and be like, "Oh, you just bought a Ferrari, huh? Real cool." But no, that's not my main concern. It's how can I use money to expand my goals.
And does money make you happier?
That’s a tough one because yes. I mean, the answer is yes. It does allow me to—you know, my mom is sick at the moment. I can fly home next week and visit her and sit in a comfy little first-class seat and take my girlfriend with me and, you know, I have the ability to do that. That's incredible. That is definitely happiness. Also, I can set a goal of creating a podcast, doing these different things, and I can pay to at least get it started. So it definitely does enhance my life. But if everything goes bad and I lose all my friends and my family and everything, can I just sit at home in a bathtub full of money and feel alright? No, that'll never work. So it's kind of to that extent.
So what are the things that do give you your personal happiness? You've talked about having a positive impact and creating value for the world. What are the other things that you think as an entrepreneur—because here's the question I'm trying to get at: much of the narrative that I got fed I think as an entrepreneur when I was building my business was that you do it for the money, you become this internet rockstar if you become a real successful entrepreneur, and then you just sacrifice everything else because nothing else really matters as much. And one of the things that I've come to learn over the last probably like six months is the importance of creating a sustainable life outside of just hustling my life away. And I'm somebody who doesn't see my mom and dad. Like, I probably not seen my mom and dad for—maybe a year. I probably only see them in December at Christmas. Same applies for like my friends. If you don't work at Social Chain in one of the offices around the world, you're probably not my friend. I have one friend outside my company. The more and more I've read, the more and more I think maybe I've got it wrong to some degree because I've put too much emphasis on the working part of my life in this kind of false assumption that at some point it'll all be over and then I'll just go back and sort of re-ignite those friendships. But I'm going to be an entrepreneur forever. So I have to build a sustainable life now. I just wanted to know your thoughts on that.
Yeah, I think you're dead on and I think that for whatever reason we're taught that like hard work wins. So if you just scale the hard work and you just work harder and harder and harder, you're going to win bigger and bigger and bigger, and that makes you a better and better entrepreneur. And I think that that's a false story. And I think that it's unfortunate that it is part of the story. And I think that when you talk to truly smart, successful, stable human beings, they know that. They know that that's a sham. And they are balanced and they do have happy families that they care about. And that's what keeps them going. And I think at the end of the day, if you don't have good friends and family and relationships, what are you even doing it all for?
And we all have that same notion that one day you're going to be able to just hang it up and just bask in family time. And that day never comes. It literally never comes because even if you sold all your businesses and you made hundreds of millions of dollars and you went and spent time with your family, you'd last how long? Six months? At best? Until you'd be like, "Alright, well what's my next business idea?" It's just how we're wired. So I think that to kind of blend those two questions together, what makes me happy is this: yes, friends make me happy, family makes me happy, all that stuff.
But I think that what really drives me more than anything is figuring out how to do this whole thing better. And if every day I feel like I truly became a better human being, then I feel good. I feel happy, I feel content. Like if we know, okay, we're both really busy, but I love my mom, and I know how much I mean to my mom, so how can I make that work? And there's a way. It sounds messed up to like schedule your mom into your day, but if that's what you have to do, that's what you do. And you schedule that time and you have a phone conversation or a FaceTime or whatever, you're just getting better. You're being a better son, a better boyfriend, a better husband, a better whatever. And I just want to continue to become a better human. And I want one day to be able to sit on a podcast and say or have a conversation with you and say, "Man, like this is what I do with my family, this is what I do with my children, one day, this is what I do with my business," and you'd be like, "Damn, that's it. You've got it figured out." But that's only going to come from small progress every single day.
Speaking about children, are you in a relationship?
I have a girlfriend.
How has being an entrepreneur and being ambitious and pursuing your goals impacted your ability to hold down romantic relationships?
So it’s hard. It’s been hard my whole life. It is extremely hard, no way around it. I think that the biggest thing is, especially in LA, one of the biggest things I've faced is like girls can't understand that I just really care about my work. And it always is like you're cheating or like "where are you really?" And it's like, man, you can't understand. And I've actually had multiple girlfriends come back years later and say like, "I wish I knew. I wish I knew that this is truly what you were involved in." And I think that's the hardest part—is understanding that there are no hours and understanding that I might be leaving here and say, "Hey, we're going to go get dinner at 7:00," and I have to go to a meeting at 7:00 that comes up 30 minutes before, and I have to.
And that's just an ongoing, everlasting struggle. But I will say this: the girlfriend that I have currently is amazing and also has dreams of starting a business, and so she understands that. So far. Five months? Okay, so we'll see. To be determined. But so far it's been very because she understands the work that it takes and the whatever, and she's like happy for those. If a meeting comes up and it's whatever, she's like happy that an opportunity came up that's worth it. We'll see. I have not experienced it yet. But that's the only reason I'm in—I wouldn't be saying all this and then say I'm in a relationship now that has the same problems; that would just be stupid of me.
Do you think part of the reason why so far it's gone well with this particular relationship is because she came into your life at this stage?
Yeah, I do. I think that's definitely a huge part of it. You know, I think one thing that's funny is like, once again going back to reality show days, and keep in mind I was the same guy that had a Lamborghini at age 26. You're not exactly attracting the most level-headed, understanding—you know what I mean? And I think that like this is the first one that I've dated since I had a podcast and since I've been posting on my Instagram like what cool books people should go buy. And so I think she came into it with a little bit of a different mindset. I think that you are right. Yeah. I think if you attract someone through the means that you actually care about and you're actually you and you're not popping bottles at a club and like "Hey what's up girl, you want to be my girlfriend?", I think it helps. But I'm not going to claim to have the solution.
Do you think this is the least chaotic part of your life?
Yeah, I love this part. This part's great. Because you just get to talk about how great everything is and try to spread some positivity and some words of wisdom and have a great conversation with somebody else who's interesting. I love it. When I do my podcast, I love it. It started off as pure fear and terror and anxiety and now it's like so relaxing because you get to just have a conversation, there's no agenda. I don't need to impress, I don't need to sell something.
The girl you're dating at the moment, is she independent? Here's a theory that I've been sitting on for a little while. I'm trying to diagnose why all my relationships haven't worked. I think I've gone into relationships in moments of my life which have, I would say, high chaos. But I also think that because I'm such a naturally independent person—I stopped going to school when I was 16, I dropped out of university or college when I was 18—I've always, much like you by the sounds of it, wanted to be my own boss and control my own destiny. My whole model of what a relationship is is just this drain. So that's part of the reason why none of my relationships have ever worked. But in more recent times, I've come to believe that when you're an independent person, if someone is dependent on you, they challenge your sense of independence. And really, I want to be my girlfriend's second priority. I want her to be so preoccupied with her life, her own things, her own future, that she doesn't even know that I missed the 7:00 PM date because she's also got to miss it. That kind of thing.
Oh, I think it's true! I think that like one of the worst things are relationships that I've been in where like 4:00 PM you start getting the text of like "Hey, where are you? Like, what time you think you'll be home? Like I'm just here on the couch" and you're just like "Oh, I need to work." You know, I don't want to feel obligated to entertain this person. I don't want to claim to know the secret formula or—I need another year before I'll start to give advice. I don't want to jinx myself. But I will say that I think that there is a special combination that makes the perfect entrepreneur's girlfriend that is very much so that. And I think at the same time—let me tell you a weird thing about myself. I also, when I do get a moment to relax and spend time with my girlfriend, I want a lot of affection and attention. And so that's another hard thing—it's hard to find a girl that will let you miss the dinner because she's going to miss it too, but she's not doing anything shady. Because yeah, there's girls that don't care, but those girls are not the type of girls you want to date. Being there and being supportive and being affectionate at the right times and being extremely understanding is a really hard balance to find. But I think that somebody that truly understands and is truly proud of that meeting that you had to cancel your dinner because you are making progress and that makes her so happy. And then when you get home, is going to just love you like nobody else. That's a dream come true.
I completely agree. So taking it in a—I'm just going to try and hit you with some tough questions. I don't know what they are yet, but I'm going to think of some. Okay, so first tough question: if you were to die today, would you be happy with the life you've lived and what would you regret?
Yes. I will say yes because I do believe that like I pushed it. Am I content? Am I ready to go? Absolutely not. There's so much more for me to do. But would I like have any major regrets or be like, "Man, this isn't fair, I didn't get a chance to—"? No. I think I've pushed it. I've lived way beyond what I ever thought I was going to live, meaning experiences and success and the love that I've received. I'm really humbled by that. What would I regret? Maybe that thing, maybe not spending more time with my family and loved ones. Yeah.
Are you doing anything about that?
Yeah. I call or text my mom every day. No question about it. I started that eight or nine months ago. I would go like three or four days without calling or texting, and I just didn't think about it. And now it's literally a note on my phone every day that I have to do. And she loves it and it's been great. And now I just do it out of habit and it's amazing. But I need to go home more. I only go home for Christmas and December. I need to go home more, I need to just do those things. Go home three times a year, call every day, FaceTime every Saturday, whatever it is, but just up that.
What do people give you credit for that you don't deserve? This is kind of trying to sniff out the fraud in all of us, I guess. Because that fraud exists in all of us. What are those things within you that you think you might get credit for that really you don't deserve credit for?
That’s a tough one. I think that the part that makes me kind of feel that way is when people say like "Your podcast changed my life" or "Your this thing changed my life." I don't—I think that's a little premature and a little over-exaggerated. I think I'm doing an okay job and I'm getting there and we're getting some real stuff, but to say that I changed someone's life is a little aggressive. That's the one that I feel—hopefully one day I want to receive that compliment or that statement and believe it and say like, "You know what, I think I did. Because I've been doing enough stuff that I'm out here changing lives." Right now I don't feel that way.
So that's just relative to your own ambition, right? And because you're so far from where you want to take it that you just don't think they're—I just think people are real quick to listen to a good podcast and say "Bro, you changed my life." It's like, did I really? Like did I really give you enough actionable things that you made a difference or are you just inspired right now? And my goal is to honestly give enough actionable advice and direction and whatever to where I could say I actually did that.
In my little sort of notes for meeting you today, one of the things I had written down on there was "Jake Paul copied your design." Yeah, that little bastard! So just for context, someone sent me photos of it. I was actually going to meet Jake Paul out here; I was going to meet him yesterday before his tour rehearsal. I've got no beef with Jake, power to everybody doing their own thing, whatever. But I saw the design that Jake did for his merch and it's identical to some of your stuff, yeah. How does that make you feel? What did you do?
I’m going to be honest, I just think it's corny as shit. And I think that the one problem that I have with those guys is the Paul brothers. This is the thing: I support anyone making a name for themselves, getting money, doing their thing. I really do. And those guys are from Ohio and when I started Young & Reckless, they used to hit me up all the time and ask for gear. We used to send them gear. And ask if they could do anything to support, and it was great. The only thing that I don't like about how they operate and I don't think is a good example is they operate sometimes at the detriment to other people. Like that thing happened with Logan Paul and the suicide thing and then all this different stuff and it's like, man, you don't realize—I'm no Mother Teresa by any means—but like you don't realize that there are fundamental values here that you are teaching people that it's okay to disregard. Like other people entirely. And I think that that's really whack and really lame. So when it comes to the shirt, I think like, eh, it's just you guys being you guys. It's just corny and cheesy and you just you don't care about other people's stuff and what you took. And the fact that I used to send you clothes. Like just be like "Yo bro, shit's crazy, sorry about that." Like do anything. But they don't care. They're just—they're just you know. I posted an Instagram post and said like, "Damn bro, I thought we were friends." But that's it. I don't care. I'm not going to like sue you or like, you know what I mean? I've made my mistakes. I've had designs that were copyright infringements close to other people's stuff. Yes, that was a direct knockoff, no way for that to be a coincidence. But like whatever, they're young and stupid. I don't really care. It's flattering.
It’s good that you can see it that way, that's a sign of maturity for sure. Dinner party. There's six seats, right? So I'm in one of them because I'm cooking burritos or whatever. You're in the other seat. There's four seats remaining. Who do you invite to this dinner party, dead or alive?
Barack Obama. I don't have to ask why. Tupac. Oprah. And then I think Steve Jobs as the last one.
Interesting! It shows your influence I guess.
Yeah, because you know what—I'll tell you: I'm fascinated by what the through line is in those people is overcoming everyone telling you you can't do something, like literally everyone in the world, and like completely pioneering uncharted territory. Those are two things that I am fascinated by.
And on that point then, you meet 18-year-old Chris today. What is it you say to him? What are the if you just had 60 seconds to talk to him and just tell him the things, the real sort of secrets, the keys that you know now, what would you say to him?
I would say to spend more time learning and more time soaking in the things around you and the things available to you. And the time will come to apply it. You're going to use that information once you have it. And I've never had a problem doing. But I think like just shutting up and learning a little better and asking more questions and stop acting like at 21 you're too worried about being the dumb one at the table and trying to shine, trying to output when you should just be in-taking. You know what I mean? Just shut up and take in and learn, and you'll have plenty of time to shine later.
Amazing! Well, that's all my questions. Thank you for taking the time, I appreciate it. Where do people find you on Instagram?
The main place on Instagram where I'm the most active is just @drama.
And if they want to hear more of you in a vocal sense, what's your podcast?
*Short Story Long* on everywhere where podcasts are. Incredible podcast I hear. I just did 100 last week.
When did you start?
It was just about two years ago.
Nice. Amazing! Well thank you so much! I'm sure you're going to get a lot of new followers and fans I hope you do from this. I'm sure we'll on a personal level reconnect much more because of this. So thanks, I appreciate you.
Yes, thank you!