How Tracking Every Second Took Rob Dyrdek from 0 to $405M in Exits | My First Million #224

I am human optimization. And optimized to be what though? To just be happy.

Yeah. I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.

All right.

Sorry we were late. We were recording another episode and—

Yeah, look, I got the context. I thought it was fascinating. I love the idea of like, your digital media company being acquired and then you have to do a podcast with the guy who acquired it who no longer works there or no longer the CEO. It's fascinating.

It's fascinating. Well, he told a story that was, I think, good. 'Cause I think most people don't want to hear necessarily from, oh, you're the CEO of some marketing company, some public company. It's not the sexiest story, but he just got in a crazy snowmobile accident and broke like every bone in his body. And, uh, was sort of like lying there on a mountain for an hour thinking I might die. Or, you know, maybe hopefully his cell phone had like one bar and he was able to call the police and get, get a firefighter to come save him. Um, and so he told that story and I was like, okay, this is good, this is good content then. I'm happy with how this turned out.

Wow, that's— that is fascinating, man. That's scary.

Yeah, it was good. He was like— it was like a movie. We were like, you know, Brian, this is like a movie, you know, like billionaire tech guy almost dies, quits, and starts meditating. And yeah, he became like a philanthropist afterwards.

He reevaluated his life while he was lying there, that sort of thing. All right, Sam, you want to do a quick intro?

No, you do it. You do it. I like— I've enjoyed you doing it lately.

Okay, I'll give the, um, I'll give the, like, the brief context of this. Okay, so Rob, um, I don't know if you know this, but your, your show on MTV, there's a, there's a kind of a meme about it on Reddit. Do you ever go to Reddit?

I do not.

Okay, so do you know of Reddit? It's like a popular kind of website or whatever.

Of course.

So me and Sam both watched the show The Challenge on MTV, and, um, and The Challenge has been around for like 15 years. It's kind of like our, our, you know, not even a guilty pleasure, frankly. I'm not guilty about it. I, I feel great about it.

It's a great show.

This is great. This is great.

And so me and Sam both watched The Challenge, and we're probably the only kind of like tech investor dudes.

Bro, it's only my wife. My wife watches it. I—

Sam hides behind his wife. I love it. I'm not afraid to say it. I came out the closet, said I love The Challenge. So on Reddit, there's this big subreddit about The Challenge. And the running joke is that MTV plays 23 hours of ridiculousness and then 1 hour of The Challenge on Wednesdays. And so because your show is— your show is always on TV. I don't know if you know this, but it's kind of like constantly on MTV. And so there's a running joke that that's all the channel is basically is ridiculousness. I don't know if you know about that or if you have any thoughts, but I wanted to start there.

Well, I mean, yeah, I mean, it's 60% of the total programming.

Is it really?

Yeah. And it's fascinating because it's like, you know, as I have evolved the program and my relationship with the network and ultimately sort of the business that I have with the network, it evolved into creating more content and airing more shows. And so they began to air more shows and the ratings went up higher and higher. So then now people are watching it in blocks of, you know, 2 and 3 hours at a time. So it, you know, and linear cable as a whole kind of faded to appointment television and you had hero content that pushed up to the fore on almost all the networks. And I just happened to be lucky, you know what I mean, of like finding that sort of resurgence. But I was also, because I control and own the the, the production. I have negotiated on the unit economics of the show and what the network needed as the cable advertising world was evolving. So I was able to control it at a higher level than traditional talent, which took me from getting 30-episode orders to 168-episode orders, which then eventually became 500-episode orders, right? It's a, a 9-year deal.

Were you always plugged into that? Like, I know with, for example, athletes, like Floyd Mayweather, right? Starts off as a boxer, but then the promotion, the production company basically takes all the economics and he's out here, the talent, the one that's drawn in all the viewers, but didn't own that piece. And then over time now he owns it all because he, he kind of like got screwed for a few years or sort of wisened up and said, oh, I need to own more of this stack in order for me to like benefit in the way that for the value I'm bringing. Were you, did you get it from day one or did it take some time for you to figure that part out?

Look, I think you guys know the complexity of making a successful business. Right. So, at the end of the day, there's arbitrage for talent and different aspects of business and it relates to entertainment, but the ability to actually monetize it, create value, and then in my case, sell it for a significant amount of money is extraordinarily difficult unless you really understand business at a really high level. So, it's way beyond— I started my first company at 18 years old. I went through basically years and years of making millions and losing millions through ventures where I ultimately created a system wisdom to grow into being a great entrepreneur. And then I capitalized on this unfair advantage that I had in the entertainment space to be able to look at the opportunity and maximize it both from a talent perspective and create a business that I was able to have acquired through that platform. You know what I mean? I think it's more rare than it is common for an athlete to have that mindset.

Yeah, and let me give a background here. And this is what I'm about to say is with no research, it's just as a fan. So I don't, you don't know this, but I still skate. So I've been a fan of yours forever. And so here we, I have here, look here, here it is. Can you see that? There's my tre flip.

Talking about a full tre flip right here. Fully caught. Yeah, totally.

Look, I could still, I still have it in me a little bit. Oh, my camera will come back in a second. But so you, you started skating very young. And I think you were sponsored by Alien Workshop when you were like 13, 14, 15, something like that, right?

Well, to give you more context, like I got sponsored at 11 years old, but I, I connected with the group and, and when they founded the Alien Workshop, and I turned pro for it when I was 16.

And you— but now I think you, you own Alien Workshop, right? Or you're part owner?

No, I acquired it for $4 million. And then I gave gave it back to the original founders free and clear, on top of buying a bunker in Ohio so they could run the company out of it, and gave that to them free and clear. That was the worst mistake I've ever done in my life, was why would you acquire a skateboarding business? Um, look, I, you know, I, I did it more— they were acquired by Burton, and I, I— every advisor around me was like, this company does not make money, it has terrible margins, like it burns cash, like this is a terrible investment. I didn't care. I didn't understand business well enough. I just wanted it for the story. The hometown kid buys back, you know, the Alien Workshop that he sat in the room and helped choose the name and create the brand when he was 16 years old and finds great success and comes back and acquires the business. And when I, I acquired it, I felt like I acquired a hornet's nest. And I, I learned so much about the operational side of business and culture and, and the dynamics of, um, what I'd consider a, a a toxic culture. And I just realized that my passion was to create, build, and create an ROI and IRR for the stuff that I created. And that doesn't align with skateboarding very much, right? They're really like, "Misery loves company. Let's all be broke. Let's all barely survive. Let's all keep it real." Starving artist syndrome. Starving artist syndrome. And I literally, like was on another call and was like, man, I don't even want to be on it. I don't want to put another bit of my energy in here. And I'm like, you want to know what the real hero story will be? I'm going to give back the original founders who built the company and sold it. I'm going to just give the entire thing back to them. And that's what I did.

So we have to talk about that in a second. That's crazy to me. Not in a bad way, but it's crazy. And so you're a skater. You know, I used to watch you in a lot of Transworld videos as a kid and a bunch of other stuff. And then you were early-ish at, I think very early at DC Shoes before DC Shoes was even named DC, right? That ended up becoming a pretty monster success. And so you've seen a bunch of stuff. Then you started some of the early shows, which crushed it. And then now you're telling, you're sitting here talking about Ridiculousness and the way that you're describing things. I'm like, it's just the evolution's crazy, right? From skateboarder to like talking about how you own 60% of the programming on MTV. And so I wanted to give like context there because it's amazing and it's inspirational. But at this point, you've got your hands in everything. It seems like you've got— you do, you dabble, you do a bunch of stuff. If I remember correctly, years ago you had like a food truck. Is that right?

I might have wrote an episode around a food truck, but it was probably fake for Fantasy Factory.

You had like a bunch of different, you know, you had a bunch of different stuff. You got your hands in everything. I think you even— did I read that you were— you do, uh, horse racing? You own racehorses?

I did, I did. When I got into horse racing, I jockeyed a horse for a race at Hollywood Park and won the race. Um, went on to own 12 or 13 racehorses, including a horse that I, uh, that got third place in the Breeders' Cup that I sold for $2 million that I paid $200 grand for.

That's crazy to me.

So is owning a horse a good, good investment in general? Like, that's a great—

obviously that's a great flip, but it's, it's not. But I, for me, I got out unscathed, you know what I mean? Like, for a lot of people I know that are in it, it's just really for the enjoyment of it. It's a lot of fun to go watch your horse race. Um, you know, I had a lot of respect in the racing community because they know I jockeyed a horse. They know how insane that is, right?

Did you do that as a skit or did you take it seriously?

I know, I mean, I did it as a skit. I mean, it's like the dumb— it's the scariest thing I've ever done. You're talking to a guy who's broke the world record for jumping a car backwards. I barrel rolled a car. I've been attacked by a shark, a tiger. It's like I've done, you know, broken 25 world records on a skateboard. But the scariest thing I'd ever done in my life is jockey a horse at Hollywood Park because it's just you on the back of this horse. You got a hold of its mane, you break the gate, you're going 50 miles an hour on the back of this giant beast, you know.

How do you— how is your current— your, your entities set up right now as well as your focus? Because if you have all— well, I was gonna— the reason I'm listing all these crazy stuff, crazy things that you do and all these projects that you've got going on, which are very substantial. How are you balancing all this? And what's your current business structure? I mean, do you have like a Rob Dyrdek Media, which only does the MTV stuff and you get some type of fee from them? And then you have, you know, I would imagine—

let me tell you, let me tell you, hey, hey, if you want to talk structure, let's talk some structure. Yeah, basically operate as a very Probably like a hybrid entertainment family office, right? Slash venture creation studio, right? So, I have a single entity, the Dyrdyk Machine LLC that owns everything, including Rob Dyrdyk Inc., which is the entertainment side of Rob Dyrdyk's business. So, all of that capital flows into this single LLC and then I distribute that capital into real estate holdings, right? The cash-flowing real estate holdings, or I distribute it into ventures that I co-find and create. Right, so I co-found and create almost every single company that I build, and I, I do— I co-founded with common shares, and then I do the initial funding, uh, usually in the $800,000 to $1.5 million, uh, sort of pre-money, and then I put $250,000 to $500,000 into every venture. I try to own between 25% and 70% of every single venture that I have at maturity. Um, I have built 17 companies, sold 6 for and netted $450 million since I launched the company in 2016. One of those is the production company, but all of these entities sit under the umbrella of the venture side of the Dyrdyk Machine business, including Rob Dyrdyk, the television business. So my production company that was acquired, my earnout goes into the LLC, um, that I own 100% of, right? And then, uh, my talent money lives in that same same thing. Then, I pay myself a salary that goes through that and then I invest all of that in basically non-correlated cash-flowing real estate investments, whether that's manufactured housing, multifamily units, storage units. I've been investing a lot of RV parks lately.

Dude, this is music to my ears.

Yeah. It's a very sophisticated hybrid family office that I built. For myself. And, keep in mind, every venture that I create has a time structure. We call it the unified theory. At the very beginning, we lay out the entire capital path and growth path and when we want to sell it and how much we want to sell it for. And, that's our target. Everything is built to sell from the very beginning whether that's Pig Out Chips and Outstanding Foods or MindRight Bars or Lusso Comfortwear or any of the builds that I've done over the last 5 years. But, all of it is connected. To this idea of the capital that you've earned, the tax efficiencies on how you earn it, and then ultimately the IRR on every dollar wherever it goes inside the system. And what do you do then? You keep your expenses within the range of your dividends that come from your real estate. So, you basically play the entire game for free. And then, as you scale and have big exits and big big liquidity events, you just pump more money into the overall system and you basically live this extraordinary free life. Now, to that point, I do all of this with 30% of my time, right? Because I manage, I've mastered time, energy, and capacity, right? So, I live this extraordinarily balanced life by design where I only dedicate 30% of my time to podcasts and my shooting television and building my businesses. I spend 30% sleeping, 10% on my health, never compromise it, and then 30% with my family, you know.

How much is 30% for you? Like, how many hours are you looking at? 30% of a 40-hour work week or 30% of your—

he's saying my entire life, all hours, 8 hours basically, right? No, all life. Of the 24 hours in a day, I sleep 30%, so 7 hours, right? Like, I work 7 hours, I'm with my family 7 hours, and, uh, I spend 3 hours on my health on average, right? When you look at the overall balance. And then, I could show you this because I track it every day and it pumps all of it into this beautiful dashboard. Because what I've done over time, because to give you an idea, I shot 250 episodes of television this year. It's exactly 4% of my total time. That's how highly optimized it's become, right? Because you basically have a certain level of human capacity. And, in order to scale it, you either hire or automate it. So, I live this deeply automated life that hires people in to add capacity. And at the end of the day, I just live super balanced and happy. That's it.

So, give us an example.

What software are you using to track all that time?

Yeah. That dashboard. I created— I had a programmer write me a script that goes inside Google, the Google Calendar.

It's an app on your phone or it's just on like a spreadsheet basically?

It's inside Google Calendar and then it pops up. It populates a Google spreadsheet, right? And then, the beauty of it is qualitative data and quantitative data is what I live my life off of, right? So, every day for the last 5 years, I wrote down how I feel about my life, work, and health, 0 to 10. And so, I could show you by the qualitative numbers how I'm living a higher quality and happier life. And, the result of that is based off the optimization that I've done on my quantitative stuff. My quantitative stuff is that I get up before Did I brain train? Did I get in the gym? Did I meditate? Did I have a clean diet? Did I not drink? I could show you by my quantitative numbers that I have done all of those almost every single day of this entire year, about 87% of those quantitative things that have just driven those qualitative numbers, how I feel about my life, my work, and my health. Higher and higher. So by the numbers, I could tell you what a high-quality life that I'm living compared to just 5 years ago.

You're saying so many amazing things. I gotta dive into each one. All right. So you just said something, did I brain train? What's that mean?

I use the Luminosity app, right? Like where it's just adding flexibility and just letting your mind do all of these things that are different than just getting in and reading your emails and, you know, just going through your rhythm is really what I do that for.

And you wake up at 5:00. What's the morning routine like? Sounds like you're pretty—

Yeah, look, I'll get up. I, I get— I have to get up before 5:00, but depending on what time I go to bed, I'll get up, um, at 4:00 or 4:30 too, right? And then to me, uh, you know, always have that, that coffee pre-made so I can get up and get cooking. Um, and then I track all my numbers from the previous day, fill in all my time if I missed any time to make sure that all my data is there.

On your phone or on your computer?

On the computer, right? And then I try to just organize and knock out sort of my more executional work before the kids get up and all that. Then, at 6 o'clock, I brain train. 6:30, I meditate. When I jump out of meditation, I sent— actually, at 5:15, I bring my wife a coffee and I send her an email of every single thing that I'm doing that day, what it means to me, and with a love quote on top, right? Again, this is—

What do you mean what it means to me? Each thing you're doing?

Just like, while you're doing it.

Yeah. In my, in my, one of the, one of the pulls of our relationship was like, I do so much stuff that she would be, it'd be, I'd just be talking to someone, it'd be the first time she ever heard of it. And so she would just like, I would do so much stuff in a day. She just would, would feel disconnected. So I just started giving her an email every day of like what I'm doing, what it means with a nice love quote. Right. And, and that then settled down the energy of feeling disconnected from everything that I'm doing. Doing. Um, bring her a coffee at 5:15. God bless her, she started doing 5:30 calls for her business, which means she's going to be tired earlier. That means we can go to bed by 9:30, right? Which is another sort of blessing.

And this is happening in LA, right? You're—

this is your— yeah, yeah. And then, you know, I pop out of meditation at 7, wake the kids up, uh, get them both down to breakfast at 7:30. My trainer doctor comes to the house 7:30 to 8:30 training and then take the kids to school at 8:30, right? And then the day, depending on what the week is, you know, sometimes I go to breakfast dates with my wife. Sometimes it's, you know, on Mondays, you know, I basically run a flat organization, right? So I have, you know, 10 core divisions that are ran by an executive and I just spend Monday fully organizing from when I get up 4 o'clock into my chief of staff for an hour, into my president and COO for an hour, and then half hours for every single person that runs that division so that we can just be highly organized and then plan the rest of the week, which of course is inside Thursday night date nights and Friday night sushi night with my wife and picking my kids up and all of— I design balance and then I only work within the structure of balance. And then, depending on how I feel, feel, depending on how my wife feels, then I'll even adjust that to lean into making sure that my family is feeling priority above business always.

You are like, yeah, you're like, you know, like people make fun of Silicon Valley people because they're like, here's my calendar, I've got to adjust it like this, this, and this. But I'm sitting here looking at you. I think it looks like you're wearing a black blazer with a black sweater and you got these slick AirPods in. You are more Silicon Valley techie in tune with this than like the stereotypes of it. And I love it. I think this is awesome.

Yeah. I mean, look, I am human optimization and optimized to be what though? To just be happy. You know what I mean? Like at the end of the day, that's why you're playing the game and you got to figure out yourself to understand what truly makes you happy because your goal is to not be happy in pockets. Your goal is to be happy every single hour of every single day of your life, right? And that's really what I've accomplished. And I'll tell you something, if you think about how you live, right, you can live in two places that'll get you nowhere. It's dwelling and being negative, right? Or it's being hopeful and like wishing, right? Either of gets you nowhere. But real, where life is lived is you're either problem solving, you're either creating the future, or you're experiencing the present. Present, right? And the truth is, whatever you're experiencing in the present is based off of the decisions you've made in the past. And it's your choice to create whatever your reality is that you're going to eventually experience. Or God forbid something hits you, rather than dwelling on it or hoping it didn't happen, if you problem solve and handle it, um, you're not going to— you can basically live a life with no negative thoughts if you learn to live in a state of either experiencing, creating, or problem solving in your entire life, right? But it's on you to understand that is to be able to live in that state.

I'm flabbergasted, Sean. Rob is just—

here's what I'm wondering.

Here's what I'm wondering.

We share a lot of philosophies, by the way. The things you're saying, these are a lot of philosophies I live by. Sam lives by as well. But I'm wondering this in my life, because I live by a similar philosophy, I've encountered a bunch of people and what I've found, maybe I'm wrong here with you, but what I found is it's kind of two groups. There's the group of people who kind of were this way from day one. From day one. They were sort of like optimizers from day one. They really cared about— they sort of recognized the importance of time early on. They recognized the importance of their mood and how they're feeling early on. And they said, cool, I'm going to design systems to make this work for me by default. So I'm not swinging from highs to lows. I'm not pissing away time. I'm actually making magic. So some people get it early. I don't know if that's nature or nurture, but they, they were this way from day one. And then there's other people who sort of live life in the exact opposite way for a while, and then it comes sort of screeching to a halt and they say, I got to make a change. I got to get some order and some organization. I got to like, I got to actually like take control of this, not just have it be so loosey-goosey. And I'm looking at you and I'm thinking, is he a skater? How does the skater guy become human optimization embodied the way you are? Were you always this way or was this, I lived a certain way and then I had a realization and a moment where I decided to kind of shift my path so that I could design my life a little bit differently?

Yeah, I was not this way. You're talking to a guy getting attacked by sharks, who's starting company after company, breaking world records, jumping cars, doing cartoons, television shows, doing all these things as you alluded to in the beginning. Like you were pulling into, I would say you were pulling energy from like who I used to be and what you know me of. Has, right? Just as a thing. Yeah, right? So, the way that you were viewing was in fact really how I was kind of living where I was being— I always refer to myself as going in so many directions that at once I was like pulled tight. And so, what happens? You swing from side to side in order for there to be some sort of give in whatever you were ultimately doing. And for me, I had built my league, my professional skateboarding league, and took it to market to raise capital. And these groups like, "Oh, we want a piece of everything that you do. Look at all that you do." They offered me a 360 deal. I thought, "This is it. I've just done this whole thing by the seat of my pants and finally, these people are going to recognize me and turn me into the billionaire I'm meant to be." And, when they did the diligence on how I ran my finances, how I ran my life, all aspects of it, they were like, "You're not even investible. You spend all the money that you have. You're not creating any value." All this stuff. And, it was this deep awakening. Of like, you're not who you think you are. You've attached yourself, this identity that you've created for yourself is actually false. And, the success that you've had by being so driven and so ambitious, despite all these other things you're doing that are failing, you're making up for it by other things working. You aren't actually what you think you are. And, I went on this journey to begin the discovery of how can I begin to put a system around myself to become— First, it was like, how do I learn business? I don't know business. And I hired a consultant to teach me how to build a company beginning to end. And in that process, I found this book called Start at the End. That was a business book about decide what you want out of a business before you ever start it. And then, it was like this sort of insane sort of moment where I was like, man, I need to start treating my life like that. What life do I want?

And how long ago is this?

That would have been in 2013, you know what I mean? So it wasn't— you got to understand, I—

this—

the evolution and the growth that I have gone through over the last 6 years is, is 4 or 5 lifetimes of growth, you know? You're talking about from, from saying you're uninvestable to creating generational wealth in a 5-year period. Okay, more, and, and, and now transitioning beyond, you know, self-preservation to generational preservation. What is my 500-year plan? How am I gonna affect Dyrdex for the next 500 years? And I couldn't even— in 2013, you know, I was single, partying, and like part of like when I looked at like what's my ideal life, I want to have balance and love and marriage and kids and these things. So I had to begin to change the way that I was living, to ultimately create the energy to attract the person, the people, the knowledge, everything that I would need to grow into the person that I, that I had designed for myself in 2014 and '15.

And was the— you said your production company was acquired. Was that the biggest win for you financially?

Oh, you know, I mean, there's no doubt, you know what I mean? But you got to understand, like, even, you know, it's, it's such a significant amount of capital, um, and I own 70% of it, right? So it's just a, it's a much, it's a, it's a big acquisition, um, you know, you know, the final numbers aren't— we're still in the middle of the earnout, but it's, it's, oh, it'll, it could be close to, you know, you know, $125, $130 million for just me now. right? And so that, that unto itself is a really significant single transaction, um, that is— that very few people ever experience, you know what I mean? So again, it's a— and it, to me, it's the first company that I built that was in the built-to-sell structure, right? Of when I just taught myself business completely, built a system for how I would create businesses. It was the very first one that I built to sell and built it and sold it in 3 years, right? And went first to the investment bankers, said, I'm going to build a production and sell it to people that only sell production companies. They're like, okay, here's how you got to do it if you want to build it and sell it. Then I went and hired a person who just went through a build and acquisition, who was the number 2 at the company, to help me build it. Then I went out and began to build it. Now, what happened? A whole lot of magical shit happened, you know what I mean? Like, because like, like all of these different things like occurred that allowed me to go from zero revenue to $50 million in the first year. That allowed like the trajectory of the growth and the EBITDA in the company to scale based off of Ridiculousness having a second resurgence and me being able to negotiate the value of the company based off of now understanding the production and the unit economics of what the network would need. These unpredictable things that in the beginning, but I set it where I would build it and sell it in 3 years and then took it to market, went back to those bankers 3 years later. Here's the numbers. Let's take it out and see who would be interested. Now, as fate would have it, the group that acquired it was the same group that offered me the 360 deal that said I had no value in 2013. And, when they acquired it, part of the acquisition, I made them also acquire my professional skateboarding league as part of the roll-up that they created. So, it was a very poetic justice and beautiful sort of 360 moment as it relates to they as the single sort of private equity group that drove me to reevaluate and really push myself to design my life. And then, they come around and also provide the opportunity that sets me up for the future. Instead of owning half of me for the rest of my life, they acquired the only two assets I kept from that era.

And, you don't know this, Rob, but Sam is kind of a nut like you.

He—

I think at the age of— he showed me the spreadsheet and he's like, I made this. I think he was 23, 24 maybe. And basically what he did was he said, okay, I want to have— I forgot what it was. I want to be a millionaire, self-made.

I said I wanted to make— I wanted to make $20 million by the age of 30.

By the age of 30. I want to have $20 million by the age of 30, liquid cash that I actually, you know, I own liquid, liquid net worth. And so he then created a list list of all the rich people he could find in tech, because we're in the tech world, right? And he's like, okay, from Jack Dorsey, who created Twitter and Square, to like whoever. And he mapped out how many years did it take them to make their first, like their first nut of like a million bucks. And then like, how long, how long before they got their big win? He's like, he's like, okay, the median time of 7 years. The average person is getting this, I need to be on this trajectory at this. And so he's like mapping it all out.

So I was like, I need my business to be at this revenue with this EBITDA inside years because that means the growth rate is this. And then if I own this percentage, that means I'm going to make this after tax so long as I'm in this state.

Yeah, everything. And then, you know, when Sam—

did you do it?

Yeah, he did it. He pulled it off. He just sold at 31.

I sold the company when I was 31.

A year late.

Yeah. Good for you, man. And you want to know why you did it? Because you started at the end. And then, you know, you know, hey, hey. And you know, hey, like, it wasn't about how the path actually went. Event you could have never predicted. You're like, whoa, I would have never expected it to be in this one, whatever it may be. But your mentality was there on what it is. And you're very young, because you got to think the way I'm talking, I didn't do this till I was 40. 10 years from now for you guys, you know what I'm saying? But go ahead. So I didn't mean to cut you off, I just wanted to get another payout. No, you had— you know, you had a point for me on that, or no, I just— I just jammed you.

Yeah.

Yeah.

No, no, you're good. The other things I was going to say is that we, you know, one of the first messages Sam ever sent me, I met the guy, you know, kind of in passing. And then, you know, 2 days later on Facebook, he's like, so how much do you pay yourself out of your company? And he started talking money in a way that most people don't. Most people are very afraid to talk money. And I thought, at first I was taken aback. I was like, who the hell is this guy? And then I was like, actually, it's pretty powerful if I could have some friends like this. Where we could openly share what are we making, how, you know, what did we sell for, what are we investing it in, share some—

What are we spending? And is spending that much money each month actually making you happy?

Yeah, that sort of thing. And so—

Oh man, this is amazing. Yeah, go ahead.

And so we got to know each other that way, created a friend group that way. Do you have like a set of peers like that in your world where you kind of learned the game together, came up together?

No, but let me tell you what, uh, who I do have as a peer group that I think you'll find fascinating. Have you ever heard of Tiger 21?

Yes, we've, we've broke down that business a ton. I actually think that you can build a new Tiger 21 because it's pretty old school. It's like all old rich guys, right? So like, it's not very young.

Yo, so I'll tell you what my Tiger 21 experience is, right? So To me, it's not about the business model of Tiger 21. It is about the peer group. Yeah. And so, this is what you do in Tiger 21. So, in my group, they've really expanded it since they took on private equity and they're really trying to grow it. So, it's probably a little bit different whenever you had looked at it. In my group, there's 15 people of varying ages, right? Really young guys that have made hundreds of millions, really young guys that have a billion, couple billion dollars in worth, right? Really interesting group of guys. Now, this is what you do in Tiger 21. Each month, one person has to show all of their assets and it's called portfolio defense, right? So, each person has to lay out, "This is every single thing that I'm doing." So, what are we doing as a group? Not only do we understand each other's philosophies, what they're spending, their life philosophies, all these things, but understanding seeing how they manage their wealth, their wealth, not, not, not making money but managing wealth, right? All, all of the latest things through their own advisors that we share and all this stuff. But at the core of it, it's the realest of the real because you have to be very real in order to open up and show everybody what you actually have. And to me, when I first heard about it, I'm like, oh my God, this is the group for me. Like, this is what I need. Like, I know that only like the realest people would be willing to share all of their investment strategies and all of their assets. And so, for me, I actually have been in it now for 2 years and it was life-changing for me because part of that very first portfolio defense, it was like, "What was your 100-year plan?" And it was like in an instant, I shifted from self-preservation to generational preservation. But of course, I had created enough wealth to be in that mindset to that point, right? And now over these last couple years, it is just— it is a depth of knowledge of wealth building that I've like— that's so personal that I've just never experienced on— that I could never experience through just people that were my friends that weren't like open to this being part of the structure of a club, if you will. So, you know, look, I would even say for, you know, you guys to even consider it, you know what I mean? Just because it is an extraordinarily eye-opening and you just learn and learn and learn because at the end of the day, you grow like this, right? Your entire life as you grow and evolve, you expand. And, what you want to do is be expanding in one direction because that's where exponential growth and greatness and mastery and all these things lie when you grow into a single direction. So, I I think that it's something like that as a peer group has been massive for me that I didn't have before that because I just don't have anybody that because I come from a sort of a different world, I just didn't have any relationships with people that were thinking like that.

I know that you've been famous for forever, it seems, and you've always been doing cool shit, but you mentioned earlier that when you were going through due diligence that the buyers were like, dude, you're running your, like, you're spending too much money, or you're, maybe you're, you're buying things incorrectly and you're not, you know, you're mixing personal and work. Maybe, I don't know. But were you, were you making a significant income leading up to your big exit? And also, I mean, judging just off purely off TV, so who knows if it's real, were you, it seems like you spend a lot and you like to, and you, and you like to ball out and you like to do fun stuff. Were you spending a significant amount? And so like, were you actually financially successful prior to the deal?

And you're saying when they offered me the 360 deal? When they went in—

Like you sold your production company recently, although that's still kind of mid— it's not entirely done, right? But prior to like your— where you said you read the book in 2013 or whenever it was, were you actually doing well, or was it like you're still getting by but you're, you're, you're, you're making debt?

I was not crushing. I was making a significant amount of income, right? The, the problem was I was spending so much and not managing it properly, not, not looking at what I was doing it. I would like, you know, I put $2 million, $4 million cash to buy the distribution company. I put $2 million into building the first ever Street Dreams skateboard movie. I put $2 million into building my league. I was just making millions and investing in building any, any which way but loose, on top of having, you know, a $5 million a year overhead and bodies in my— in running the Fantasy Factory, and then all the people that, that were underneath me as it— as part of the management team.

So Fantasy Factory costs $5 million a year to maintain and, and run?

No, like, like having the building itself was like, you know, $750, right? And now you, you put all the bodies in there, you know what I'm saying? I had, you know, president, CEO, like, like full-time, like general counsel, like CEOs. Like, I had like, you know, a 30-person team. I was like running like an agency almost the way that it was built in that era, you know what I mean? But let me get—

were you making any profit at all, or, or was it breaking even and you're just spending it as you're going?

I was like, I was, I was breaking even because, yeah, I was, I was making profit and paying taxes, but after taxes, I wasn't saving any money. I kept reinvesting reinvesting in new projects and bigger ideas because I thought that's how you do it. You know what I mean? You just keep taking shots. Back then, I used to say, like, our money's fearless. Scared money doesn't make money. And it's like, you want to know, dumb money doesn't make money.

You know what I mean?

Like, that's like the reality of how I was running. And again, it was because I was still— I revolutionized skateboarding and built Street League Skateboarding. I launched and built a cartoon on Nickelodeon. I had multiple shows on MTV. I owned my integration rights, so I was doing Chevy deals and Microsoft deals and making millions of dollars. So, I was having extraordinary success, only like the way I was reinvesting in it, I was still essentially make— rather than creating value, I was really almost like a created services agent.

You just kind of flopped. Just you weren't tight.

Was not only not tight but wasn't creating value with intention, wasn't looking at markets and market sizes and trends and how could I create a business that could be acquired one day. I'd never even heard of a venture. I didn't know what an investment banker was in 2013. I thought it was someone that dealt with high net worth individuals. When they told me my league was worth $30 million and we did $7 million in revenue, I said, "How?" They're like, "Oh, it trades at like, you know, 4 to 5 times revenue." And I'm like, "How? How does business even work?" That's how little I knew about business in 2013 when the 360 deal was offered to me. I knew nothing of the capital markets, capital staging, private equity, venture. I didn't know anything. It was the first time I'd ever even heard about about it. And compared to who I am today and how I look at creating value and managing capital staging and treating myself like a family office, not that many years later, it's an exponential amount of like unprecedented growth. That almost doesn't even seem real. You're like transferring through universes. You know what I mean?

You've been pretty phenomenally successful. I'm very impressed, by the way. Way. Uh, but I almost feel like you were too early. I feel like if you were 12 years old now, because you didn't have, you know, TikTok and YouTube, where you, you would have been the, you know, the Nelk, the Nelk Boys. You would have been bigger than the Paul Brothers, right? Like, because you didn't have social media when you were doing all these stunts. You, you did it in TV, you, you know, you did it before TV, and then on TV, but it kind of helped him in a way, right?

But like, yeah, I bet—

I think you would have gone viral like nobody's business. I think you would have been—

TV, for the amount of views that they get, I bet MTV pays more than you.

Of course, of course, of course. It's— he monetized as well. But I think fame-wise, if you were a teen today with the tools they have and you had the same kind of gunslinger mentality of like doing stunts to attract attention, attract viewers and challenge yourself and have fun and have a blast in public. That model works today with people who I feel like have done like a fraction of the level of stunts that you've done. Do you think you're early?

I don't know. No, look, I'll tell you what, it makes me tired just even having you say that. It's just like, God, think about being on YouTube. You know what I'm saying? And like, look, if I— even when I look at the world, right, forget about sort of being early or whatever it is, like an extraordinary exist— I've lived an extraordinary life, a handful of lifetimes. But I've never been happier than I am today talking to you. Because at the end of the day, there was so much angst and ambition and I want to do something so big and I just kept trying and trying. And my will to execute and my ambition and drive kept just breaking me down. Highs and lows, highs and lows, highs and lows, where now I am just in this perpetual state of high growth in a clear direction. Right? And, and inside that is complete happiness, right? And not saying that I didn't enjoy what I, I went through, but it was too much highs and lows and chaos. And for, for, for what it's worth, right, like, it's— and it's all experience, and I really love my life way more at 47 than I did at 27 or 37, right? I— and that's really what your human mission is, right? At the end of the day, you want to live this peaceful, happy, effortless, like, fulfilling life. That's what you're chasing, right? You want a life of infinite abundance and love, right? And the only way you can actually get to that is through learning mastery of self. And that is mastery of your energy and all the things that give and take from it, your time, and ultimately your capacity, right? And the only way you can master all those is to really learn yourself at a high level and what you really love to do. And the difference is back then, I had to do so many things that I didn't enjoy to feed that beast. At least, right? And continue to find the next thing and constantly struggling with like, I got to do another show and it's got to be bigger. It's like that sort of thing where now everything's so much more controlled and done with purpose inside Balance that you just enjoy every moment of the process, right? But yeah, could I have done that on YouTube? No, because I also had an $800,000 budget. That allowed me to like, you know, go and do a deal that could, you know, rent out, uh, you know, Six Flags so that I could flip a car ramp to ramp over the world's biggest skateboard that I designed.

That's how much that stunt cost, it was $800,000?

Oh no, shoot, I don't— that stunt probably cost like altogether all of those were a few million dollars, you know what I mean?

That's crazy.

That's like stunt teams and groups and like test cars and like, I mean, I like, you know, then, then the day comes and what do you got to do? You got to flip a car. And you want to know what, you want to know what happens on the day that you got to flip a car? You're like, this is the dumbest idea ever. Why am I even here? I have so much going on in my life. Like, why would I even put myself in this position to like flip this car? And then you flip the car and it actually works. And now it's a Super Bowl commercial and it's part of the, the, the season premiere of season 5 of Fantasy Factory and this giant Chevy partnership. And you made millions of dollars and now you're a legend and you're going to all this stuff. It was genius and the best idea. But the day of when you got to do it, it's like, that ain't even that cool. This is so dumb. You know what I mean? That's basically all of those, all the stunts that I did in that era. It would always be like, this is the worst idea. It's not even funny. And then when it was over, I'd be like, I'm a legend. I'm a legend.

Earlier you said that you track trends now and you start at the end and you work backwards. What trends interest you at the moment? What business opportunities are intriguing to you? If you had a little bit more, like, even if you aren't going to do it, but you wish you had more time and it's just kind of on the side and you're like, this interests me. I think someone should pounce on this opportunity. Maybe I will, maybe I won't, but I'm interested.

For clarity purposes here, now I have a business that builds businesses, right? So I build 5 to 6 businesses a year, right? And although I've kind of really pushed into all the builds I'm doing at the end of the year here are all in the beauty industry, adaptogenic topicals, water filter system, saw a real opportunity and sort of in the beauty space of how important water is and how many chemicals there are. And when you shower, but then you go and spend all this money on your hair. And makeup and skincare, but you wash yourself in chlorine. So, found a real opportunity to develop a real innovative sort of shower purification system and water filter system for beauty. And, you know, really looking at superfoods and plant-based sustainable beauty products is a big opportunity in that sort of space. You know, we launched a nootropic footwear or a nootropic and adaptogen plant-based bar and drink mix and coffee mix line this year that's been really successful. We looked at the $3 billion in market share between Uggs, Crocs, and Birkenstocks and created what we consider the sleeker ugly shoe, the pretty ugly shoe, and Lusso Cloud that we launched this year that's there last year that, that really has ridden this wave of sort of comfort, this comfort wave and casual wave in the comfort footwear world that we think is gonna be on track to do really, be really big too. For, because to me, at the end of the day, like, what's happening in a market is important, and it's, it's going to be where you live and die, right? You're too early, or, you know, in the case of Ultracast, you know, I launched this company that was a a live 360, live 360 and VR video platform that put 360 videos all over the world and where you could jump on your phone and travel all over the world and be in different bars and clubs and all these different things, like right on the conversions of live Instagram and live content and live streaming and sort of VR coming in together. And then what happened to VR? Like, just died.

Died, nothing, right?

And it's like, I was like, and what did it end up being? Like the new 3D TV, right? And so 360 video became like the new, like the 3D TV, right? And so even though I built— I got it right on the wave, and like it was super innovative with an amazing CEO who, once the company went out of business, built and took a company public in like 9 months. But I'm— that, that fails, right? So you're trying to time markets and look at trends and all of that, but at the end of the day Okay, like you got to get a little bit lucky. So, you want to be in the right place, white space, and an opportunity that's investible. There's so many nuance to a white space and where opportunity is. I can tell you from someone that's built 17 companies in the last 5 years that the greatest lesson I had in years 2 and 3 was founder market fit. You know what I mean? Like where it's like when the The biggest red flag you will ever hear is when somebody comes from, you know, one industry and wants to be in another because this one's so much easier, right? This one's— it's the margins over here, it's the shelf stability over here, it's though there's not sizes. Like, they all have a position based off of how hard their particular industry's sort of structure is, and they're all hard. They're all hard. And you don't want to invest, build companies with people that have to learn the industry as they go, right? And I think that's— I would get caught in seeing great opportunities and ideas and build with really relentless, well-experienced founders who get crushed in the learning curve of trying to learn and understand a new industry. It's something that I've really— it's very hard for me to build a company with somebody that's getting into an industry for the very first Rob, we've, we've had like billionaires on.

We typically don't do, do guests. We typically just Sean and I, but we've had billionaires. We've had, you know, Gary Vaynerchuk was on recently. He was, he was really fascinating. We've had some famous people. We've had all types of people on here. You might be the most interesting that we've ever had. Um, you're definitely the most surprising, you know, and I hopefully this isn't— you don't take this the wrong way, but I judged you based off of just as a skateboarding fan and what I knew about you on TV. Obviously I knew you were the this slick-ass businessman and you always had some cool shit going on, but you are way more dialed in than I ever would have imagined. And you might be one of the most interesting people I've ever spoken to. And, uh, yeah, I, I, I think you're my new hero.

You—

I, I— this, this has been amazing.

Look, I, I, I could tell by the questions you asked me, um, that, that it was coming from that sort of lens. And I thought to myself, man, let me, let me feed this guy kind of the, uh, the angle and the evolution of where I'm operating at, right?

You've evolved like a motherfucker. Is what—

You know, and think about it too. It's extraordinarily concise and clear, right? Because it's like I constantly am seeking clarity. So, I'm always operating from a place of intention. And then, I consider myself to have an evolutionary mindset where it's like, "How can I purposely keep evolving and evolving and evolving with purpose in a singular direction?" And one of those is literally human optimization. And being happy as could be, you know what I mean? At the end of the day. But no, I thank you and I appreciate it 'cause you guys also had me do work, right? You guys said, "Hey, can you write an agenda of what you wanna talk about on today's show?" I'm like, "These guys are like having me write an agenda to be a guest on their show?" And I wrote out an agenda and we never even covered any of the subjects.

Can you come back? We didn't cover it because—

You blew our mind early on and it was kind of, yeah. Took the first 3 things you said and said, okay, I have 2 hours here where all I need to do is just let you expand on that. Because if I'm listening to this and somebody says something interesting, there's nothing more annoying in the world than the guests going back to their preset agenda and not asking about the really interesting thing the guy just said. And so we had to do it.

And look, it goes back to what you said about building towards the end. Yes, we had you planned just I planned my exit, but like what you said was you don't really know what's going to happen in between.

Yeah. Yeah. And look, even with all this, this, this planning and structure, I'm, I don't let it— I'm not controlled by that calendar. You know what I'm saying? Like I still allow myself to like, but the beauty of the system is I could just shut down 3 days and everything continues to move and then picks back right up when I get there. You know, even as I operate my life, I, with the same group that helped me develop my system for the Dyrdyk Machine and my business creation system, I had them develop my life system. And, I have this 50-page document called the Rhythm of Existence that's managed by my 2 assistants and my chief of staff. And, it's basically the operating system for my entire life. And so, that allows all aspects whether it's from my food to my haircuts to how I deal with birthdays and how I deal with all these different things is put into this system that's that does what? It's automated and gives me back more capacity to be able to do more, be more present with my wife and kids, be more present when I'm working, be more focused, be able to get more done because I keep adding more and more automation and optimization to my life that allows me to just live and do the things I love to do, which then gives me more energy to be more successful, more clear, have more intention, and push things further and farther along.

Would you be willing to come on again and, and talk more about like pretty much everything you've discussed and also the things that we've planned? Because this is, this is going to be a home run.

Yeah, look, you know what I'd like to do? I'd probably like to like send you all of my— I'll send you all the stuff that I do so you could read it and see it and have like, okay, here's a life conversation of how Rob lives and runs his life optimization. Then send you all of my business stuff, including my machine method and how I, I run my businesses through a discovery, diligence, build, um, uh, uh, launch and scale phase. Yeah, my 7 core capabilities of business and brand, product, uh, marketing, sales.

Sounds like you have a new product coming out.

Yeah, this is the program.

No, it's It's just so I can build businesses efficiently and consistently. You know, this morning I told my head of media, I said, look, I think I'm going to come up with a Drake equation for business. And are you guys familiar with the Drake equation? You know, the Drake equation is essentially the probability of intelligent life inside the universe, right? And to me, I do believe that there's an equation that I can put through market, through founder experience, founder age, like all these different things that add up to a probability number on this company that I'm about to create with this person's potential successes. And it's because I've pointed my mastery towards— I want to master curating individuals and ideas and building them into sustainable, profitable, acquirable businesses. And I just get better and better at every single one that I build because that mastery is going in a single direction. So, my depth of knowledge in building companies is getting so wide, which in turn is doing what? It's making me more intuitive. I can have a 5-minute conversation with a potential founder and fill all their holes, know that they're a more operated-minded, like, product person, like, not a brand person, doesn't understand marketing, doesn't understand media. Oh, it's a financial mind that understands product. Oh, it's a brand mind and product person that doesn't understand operations or marketing or finances for sure. Like, you become— you're driving yourself, if you want to save energy, you become extraordinarily intuitive, right? Like, that's where your mastery shows itself. So, I digress. Where I would— we could do a life show and a business show. You know?

I mean, they're very similar. Dude, this is so good. I'm so thankful that you came on. Thank you so much. We're going to do this again, I hope. Hopefully, you'll do it, but we're going to do it.

Yeah. Yeah.

This has been our pleasure. Thank you so much for coming on.

Okay, all the best now. Cool.

I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.