My First Million: #224 - How Tracking Every Second of His Life Took Rob Dyrdek from 0 to $405M in Exits

All right.

Quick break to tell you about another podcast that we're interested in right now, HubSpot

just launched a Shark Tank rewatch podcast called Another Bite.

Every week, the hosts relive the latest and greatest pitches from Shark Tank, from Squatty

Potty to the Mench on a Bench to Ring Doorbell, and they break down why these pitches were

winners or losers, and each company's go-to-market strategy, branding, pricing, valuation, everything.

Basically all the things you want to know about how to survive the tank and scale your

company on your own.

If you want to give it a listen, you can find Another Bite on whatever podcast app you listen

to, like Apple or Spotify or whatever you're using right now.

All right.

Back to the show.

I am human optimization and optimized to be what, though, to just be happy.

Sorry, we are late.

We were recording another episode.

Yeah, look.

I got the context.

I thought it was fascinating.

I love the idea of 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.

Well, he told a story that was, I think, good, because 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 every

bone in his body and was lying there on a mountain for an hour, thinking, I might die

or maybe, hopefully, his cell phone had one bar, and he was able to call the police and

get a firefighter to come save him.

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 is fascinating.

Man, that's scary.

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.

Yeah, he became like a philanthropist afterward.

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've enjoyed you doing it lately.

Okay, I'll give the brief context of this.

Okay, so Rob, I don't know if you know this, but your show on MTV, there's kind of a meme

about it on Reddit.

Do you ever go to Reddit?

I do not.

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

So me and Sam both watched the show, The Challenge, on MTV, and The Challenge has been around

for like 15 years, it's kind of like our, you know, not even a guilty pleasure, frankly.

I'm not guilty about it.

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, dude.

Bro, it's because my wife, my wife watches it.

Yeah, Sam hides behind his wife.

I love it.

I'm not afraid to say it.

I came out to the closet and 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 one hour

of The Challenge on Wednesdays.

And so, because 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, two and three 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 forward on almost all the networks.

And I just happened to be lucky, you know, I mean, of like finding that sort of resurgence.

But I was also, because I control and own 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.

And 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 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 out?

Look, I think you guys know the complexity of making a successful business, right?

So at the, 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, it's way beyond, you know, I started my first company at 18 years old.

I went through basically years and years of, of making millions and losing millions through

ventures where I ultimately created a system to, 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?

It's, I think it's more rare than it is common for an athlete to, 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, I, 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 tray flip.

I'm talking about a full tray flip right here, fully caught.

Yeah.

Totally.

So 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, um, 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, uh, but now I think you, you own Alien Workshop, right?

Or you're, you're a part owner.

No, I acquired it for $4 million and then I 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.

No, it was the worst mistake I've ever done in my life was a choir, a skateboarding business.

Um, look, I, you know, I, I did it more if 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 Hornets 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, that my passion was to create build and, and create an ROI and IRR

for the stuff that I created.

And that's, that doesn't align with skateboarding very much, right?

Like they're really like misery loves company.

Let's all be broke.

Let's all barely survive.

Let's all like keep everything starving art of syndrome and I, I literally like was on

another call and was like, man, I don't even want to be on, 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, uh, not in a bad way, but it's crazy.

And so you're, you're, you're a skater.

You know, I used to watch you in a lot of trans world 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, believe

the name DC, right?

Um, that ended up becoming a pretty monster success.

Um, 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 is 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, it's amazing and it's inspirational.

But at this point, you've got your hands in everything.

It seems like you've gotten, 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?

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

The fantasy factor.

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 race horses?

I did.

I did.

I did horse racing, I jockeyed a horse for a race at Hollywood park and won the race,

went on to own 12 or 13 race sources, including a horse that I, uh, that got third place in

the breeder's 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, 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 jockey

the 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 the car backwards.

I barrel rolled the 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.

Cause it's just you on the back of this horse, you're, you got a hold of its main.

You break the gate.

You're going 50 miles an hour on the back of this giant beast.

How do you, how is your current, your, your entities set up right now as well as your

focus?

Cause if you have all the, the reason I'm listing all these crazy stuff, the crazy

things that you do and all these projects that you've got going on, which are very substantial,

how are you balancing all of this and what's your current business structure?

I mean, do you have like a Rob Deirdeck media, which only does the MTV stuff and you get

some type of fee from them.

And then you have, you know, let me tell you, let me tell you, if we, hey, hey, if you want

to talk structure, let's talk some structure, we operate as a very probably like a hybrid

entertainment family office, right, slash venture creation studio, right?

So I have a single entity, the Deirdeck machine LLC that owns everything, including Rob Deirdeck

Inc, which is the, the entertainment side of Rob Deirdeck's business.

So all of that capital flows into the 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-find and create almost every single company that I build.

And I, I do, I co-find it with common shares and then I do the initial funding, uh, usually

in the 800 to a million and a half, a million dollar, uh, sort of pre money.

And then I put two, two 50 to 500 into every venture.

I try to own between 25 and 70% of every single venture that I have at maturity.

I have built 17 companies sold six per 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 Deirdeck machine business, including Rob Deirdeck, the television

business.

So my production company that was acquired, my earn out goes into the LLC, um, that I

own 100% of, right, and then, uh, my talent money lives in that same, same thing that

I pay myself a salary that goes through that.

And then I invest all of that in, in basically non-correlated cash flowing, uh, real estate

investments, whether that's manufactured housing, multifamily units, storage units,

like I've been investing a lot of RV parts lately.

Dude, this is music to my ears.

Yeah.

It's a very sophisticated, it's a very sophisticated, you know, hybrid family office that I built

for myself right now.

And keep in mind, every venture that I create has a, has a time structure.

We call it the unified theory.

We, at the very beginning, we lay out the entire capital path and growth path and, and

when we want to sell it and how much we want to sell it for.

And that's our target.

Uh, everything is built to sell from the very beginning, whether that's pig out chips and

outstanding foods or mind right bars or Luso, uh, comfort, where any of the build builds

that I've done over the last five years, but all of it is connected to this idea of, uh,

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, uh, 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, 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, uh, building my businesses.

I spend 30% sleeping 10% on my health, never compromised it than 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 making

of my entire life?

All hours, right?

So eight hours, basically, right?

No, all life of the 24 hours in a day, I sleep 30%.

So seven hours, right?

Like I work seven hours, I'm with my family seven hours and, uh, I spend, uh, three 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

the 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, uh, that, 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, I had a, 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 basis.

It's inside Google calendar and then it pops, it populates a, uh, Google spreadsheet, right?

And then the beauty of it is, is I qualitative data and quantitative, uh, data is what I

live my life off of, right?

So every day for the last five years, I asked, I wrote down how I feel about my life, work

and health, zero 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 five, 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 five years ago, you know.

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You're saying somebody amazing things.

I got to dive into each one.

All right.

So you just said something.

Did I brain train?

What's that mean?

I use Illuminosity 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 just going through

your rhythm is really what I do that for.

And you wake up at five.

What's the morning routine like?

Sounds like you're pretty...

Yeah.

Look, I'll get up.

I have to get up before five, but depending on what time I go to bed, I'll get up at four

or 4.32, right?

And then to me, I always have that coffee pre-made so I can get up and get cooking.

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 dad is there.

On your phone or on your computer?

On the computer, right?

And then I try to just organize and knock out my more executional work before the kids

get up and all that.

Then at six o'clock, I brain train, 6.30, I meditate.

When I jump out of meditation, 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 with a love

quote on top, right?

Again, this is...

What do you mean what it means to me?

Like each thing you're doing?

Just like...

Like what you're doing?

Yeah.

In my...

One of the polls of our relationship was like, I do so much stuff that she would be...

I'd just be talking to someone to 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 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 that then settled down the energy of feeling disconnected from everything that I'm doing.

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, which is another sort of blessing.

And this is happening in LA, right?

This is your...

Yeah.

Okay.

You know, I pop out of meditation at seven, wake the kids up, 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 four 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, you know, I've designed balance.

And then I only work within the structure of balance.

And then depending on how I 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, you are like, yeah, you're like, you know, like people make fun of Silicon Valley

people because it'll like, like, here's my calendar.

I've got it adjusted 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 and you are more Silicon Valley techie in tune with this than like the stereotypes

of it.

And I, I love it.

I think this is awesome.

I mean, look, I'm, I am human optimization and optimized to, 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've 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, 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 get 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, right?

And the truth is whatever you're experiencing the present is based off of the decisions

you've made in the past, and it's your choice to create whatever you, 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, 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?

It's on you to understand what that is, to be able to live in that state.

I'm flabbergasted Sean, Rob is just shocked me.

Here's what I'm wondering.

We share a lot of philosophies, by the way, the things you're saying, the philosophies

I live by, Sam Lizby 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 found, maybe I'm wrong here with you, but what I found is it's kind of two,

two groups.

There's the group of people who kind of were this way 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 recognize 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 a bedroom.

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 take control of this and not just have it be so loosey-goosey.

And I'm looking at you and I'm thinking, is he a skater at early?

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, doing all

these things as, as you related to in the beginning, like you, you were pulling into,

I would say you were pulling energy from like who I used to be and what you know me as,

right?

Just as a thing.

Yeah.

Right.

So, so the way that you were viewing was in fact really how I was kind of living where

I was, I always refer to myself as going in so many directions that at once I was,

I was like pulled tight.

And so what happened?

You swing from side to side in order for there to be some sort of give and whatever you were

ultimately doing.

And for me, I was, I had, had built my league, my professional skateboarding league and took

it to market to raise capital and, and these groups were like, oh, we want to, 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.

You know, I've just thought, you know, done this whole thing by the seat of my pants and

like finally like 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 investable, you're just like, you spend all the money

that you have, like you're not creating any value, like all this stuff.

And it was this, this deep awakening of like, you're not who you think you are.

Like you, you've attached yourself, this, 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, like

as, you know, despite all these other things you're doing that are failing, you're making

up for it by other things working, like you aren't actually what you think you are.

And I went on this journey to begin the discovery of like, 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, 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 started.

And then it was like this sort of like, like, you know, insane sort of moment that where

I was like, man, like I need to start treating my life like that.

What life do I want?

And how long ago was 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 six years is four or five lifetimes of growth.

You know, you're talking about from, from saying you're uninvestable to creating generational

wealth in a five 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 going to affect Deardex 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 and I own 70% of it, right?

So it's just a, it's a much, it's a, it's a big acquisition.

You know, you know, the final numbers aren't, we're still in the middle of the earn out,

but it's, it's, 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 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 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 three years,

right?

And went first to the investment banker 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 an acquisition who was the number two 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?

Because like, like all of these different things like occur 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 and 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 said it where I would build it and sell

it in three years and then took it to market went back to those bankers three years later.

Here's the numbers.

Let's take it out and see if, 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 rollup that they create.

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 like reevaluate and really push

myself to like 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 it 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.

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 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, okay, the median time of seven years, the average person is getting this.

Uh, I need to be at this trajectory or this, and so he's like mapping it all out.

Well, so I was like, I need, I need my business to be at this revenue with this EBITDA inside

four 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.

Yeah.

Everything.

And then it, you know, when did you do it?

Yeah.

He did it.

He pulled it off.

He just sold it.

I sold the company.

It was 31.

And you're late.

Yeah.

Good for you, man.

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.

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 out of the payout.

No, you had, you know, you had a point for me on that or no, I just, I just jammed you.

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, two 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 taking it back.

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, what are we selling for?

What are we investing it in?

What are we spending?

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

Yeah.

That sort of thing.

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, you came up together?

No, but let me tell you what, who I do have is 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.

Yeah, 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 Tiger

21.

And so this is what you do in Tiger 21.

So in my group, you know, 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, 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 net worth, right?

Really interesting group of guys.

Now this is what you do in Tiger 21.

You each month, one person has to show all of their assets and it's called portfolio

defense, right?

So each person has to like 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 of the latest things through their own advisors that we share and all this stuff.

But at the core of it, you're to 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 them, 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, their

and their investment strategies and all of their assets.

And so for me, I actually have been in it now for two years and it was life changing

for me, right?

Because part of that very first portfolio defense, it was like, what was your hundred

year plan?

And it was like in an instant, I shifted from self preservation to generational preservation,

right?

Because I had created enough wealth to be in that mindset to that point, right?

And now over these last couple of years, it is just, it is a depth of knowledge of wealth

building that I'm like, that's so personal that, 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, for, for, you know, you guys to even consider it,

you know what I mean?

Just because it is a, an extraordinarily eye opening and you just learn and learn and

learn.

Cause at the end of the day, you're, you're, you grow like this, right?

You, you're at your entire life as you grow and evolve, you, you, 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 you know, I, I think that, 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, I don't have anybody that, that

because I come from a sort of a different world, I just didn't have any relationships

with people that, that were thinking like that.

Were you doing, I know that you, I mean, you've been famous for forever, it seems.

And you've always been doing cool shit, but you mentioned earlier that when you're going

through due diligence, that the, the, 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 where you seemed 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, the, the deal?

And you're saying when they offered me the 360 deal, uh, like, like, like you sold your

production company recently, although that's still kind of mid, mid, it's not entirely

done, right?

But prior to like your, when 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

making debt was not crushing.

I was making a significant amount of income, right?

The problem was I was spending so much and not managing it properly, not, not looking

at what I was doing.

And 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 dream 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 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 of like, like full-time, like general counsel, like CEO's

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?

So were you, were you making on any profit at all or, or was it break even and you're

just spending it as your goal?

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 rein and reinvesting in new project and bigger ideas because I thought that's

how you do it.

You know what I mean?

You just keep taking shots.

In my back then I used to say, uh, like our money's fearless, scared money doesn't make

money.

And it's like, you want to know, uh, dumb money doesn't make money.

You know what I mean?

Like that's like the reality of how I was running.

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 I wasn't the way I was reinvesting in

it.

And I still, um, essentially make rather than creating value, I was, I was really almost

like a created services agent.

You just kind of floppy.

Just you weren't tight and was not, not only not tight, but didn't, wasn't, wasn't creating

value with intention, wasn't looking at markets and market sizes and, 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 I, when they told

me my league was worth $30 million and we did seven million in revenue.

I said, how they're like, Oh, it trades at like, you know, four to five times revenue.

And I'm like, how the, how does business even, how does that work?

I, that's how little I knew about business in 2013 when, when the 360 deal was offered

to me, I had, I knew nothing of the capital markets, capital staging, private equity venture.

It didn't know anything of the first time I'd ever even heard 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, you know, that almost doesn't seem real.

You're like transferring through universes, you know what I mean?

You, you've been, you know, pretty phenomenally successful.

I'm very impressed by the way.

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 milk 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 did it in TV, you know, you did it before TV and then on TV, but it kind of helped

them in a way, right?

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 in TV pays more than the, the new course, of course, of course it's immunitized as well.

But I think fame wise, if you were a team 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, 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 existence.

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 like, like angst and ambition and like,

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 like perpetual straight state of like high growth

in a clear direction, right?

And inside that is complete happiness, right?

And not saying that I didn't enjoy what 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?

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 really 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, and the only way you can master all of those is to really learn yourself at a high

level and what you really love to do.

And the difference is back then I was, I had to do so many things that I didn't enjoy to

feed that beast, 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.

You know, it's like, 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, could I have done that on YouTube?

No, because I also had, you know, an $800,000 budget that allowed me to like, you know,

go and do a deal that could, you know, rent out, you know, six flags so that I could flip

a car ramp to ramp over the world's biggest skateboard that I designed for a world record.

That's how much that stunt cost was a hundred.

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 was 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

fives of fantasy factory and this giant Chevy partnership and you made millions of dollars

and now you're a legend and, and you're going to all this stuff.

It was genius and the best idea, but the, the day of when you got to do it, it's like,

cool.

This is so dumb.

You know what I mean?

That's basically all of those, uh, 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'll be like, I'm, I'm a legend, I'm a legend.

Earlier you said that you track trends now and you, and you start at the end and you

work backwards.

What trends interest you at the moment?

But, uh, what business opportunities are, 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 is this, this

interests me.

I think someone should pounce on this opportunity.

Maybe I will, maybe I won't, but I'm interested to, to, to, for clarity purposes here now.

Now I have a business that builds businesses, right?

So I, I build, uh, you know, five to six businesses a year, right?

And although I've, I've, you know, I've kind of like really pushed into all the builds

I'm doing at the end of the year here are all in the beauty, beauty industry, uh, adaptogenic,

um, um, topicals, uh, water filter system, so a real opportunity and, and sort of, um,

in the beauty space of like how important like water is and how, how many chemicals

there are.

And when you shower, but then you go and spend all this money on your hair and makeup

and, uh, skincare, but you wash yourself and chlorine, uh, so found a real opportunity

to develop a, a real innovative sort of shower purification system and, and, and water filter

system for beauty, um, and, you know, really looking at superfoods and plant-based, um,

the sustainable beauty products as a big opportunity and, and, and that sort of space, you know,

we launched a new tropic, um, uh, footwear or new tropic, um, um, in, in adaptogen, uh,

plant-based, um, bar and drink mix and coffee mix line this year that's been really successful.

We looked at, you know, the, the $3 billion in market share between UGGs, uh, Crocs and

Birkenstocks and created what we consider the more the, the sleeker, ugly, ugly shoe,

uh, and Lusso Cloud that we launched this year that's, that, or last year that, that

really has ridden this wave of sort of, uh, comfort, this comfort wave and casual wave

in the comfort footwear world that we think is going to be, uh, 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, um, 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, a live 360, um, uh, live 360 and VR video platform, uh, 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, and live content and live streaming and sort of VR coming in together.

And then what happened to VR, like, just died, 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 wants to company went out of business built and

took a company public in like nine months, but I'm, um, that, that fails, right? So you're,

you're trying to time markets and look at trends and all of that. But at the end of

the day, 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 investable. Um, there's so many nuance to a white space

and where opportunity is. I can tell you, um, from someone that's built 17 companies

in the last five years that the greatest lesson I had in years two and three, uh, was founder

market fit. You know what I mean? Like where it's like when the, the, the, the, the biggest

red flag you will ever hear is when somebody comes from, uh, 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, uh,

sort of structure is and they're all hard. They're all hard and you don't want to invest

it, build companies with people that have to learn the industry as they go. Right. And

I think that's, that's, I would get caught in seeing great opportunities and ideas and

build with really relentless, well, uh, experienced founders, uh, who get crushed in the learning

curve of trying to learn and understand a new industry. It's something that I've really

very hard for me to build a company with somebody that's getting into a, an industry for the

very first time.

Rob, we've, we've had like billionaires on, we typically don't do, do guests. We typically

just shown a night, 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, 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 slick ass business man 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. Yeah. I, I, this has been amazing.

Look, I, I, I am, 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'd be involved like a motherfucker is what, you know, and it's, 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'm, I'm considering

myself to have an evolutionary mindset where it's like, how, how can I purposely keep evolving

and evolving and evolving with purpose in a, in a singular direction? And one of those

is like 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 want to talk about

on today's show? I'm like, these guys are like having me write an agenda to be our 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 were mind early on and I could have took

the first three things you said and said, okay, I have two hours here where all I need

to do is just let you expand on that. Cause 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 pre preset agenda and not asking about the really interesting thing the guy

just said. And so we had to do it and it goes back to what you said about building. Yes,

we had to plan just like 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 the beauty of the system is

I could just shut down three 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 Deirdre machine and my, my business creation system, like

I had them develop my life system, right? And I have this, this 50 page document called

the rhythm of existence that's managed by my two assistants and my chief of staff. And

it's basically the operating system for my entire life, right? And so that, that allows

all aspects, whether it's from my food to my haircuts to, to like how I deal with birthdays

and how I deal with all these different things is put into the system that's managed 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 further along.

Would you be willing to come on again and talk more about like pretty much everything you've

discussed and also the things that we plan? Cause 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,

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 run my businesses through a discovery

diligence build, uh, uh, scale launch and scale phase and my seven core capabilities

of business and brand product, uh, marketing sales, like you have a new product coming

out.

This is your program.

No, it's not. It's just so I can build businesses efficiently and consistently. You know what

this morning I told my, uh, you know, my, my head of media 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'm, 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 and building

company is, is getting so wide, which in turn is doing what it's making me more intuitive.

I can have a five minute conversation with the potential founder and fill all their holes,

know that they're a, 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, we could, we could do a life show and

a business show.

They're very similar. Dude, this is so good. I'm so thankful that you came on. Thank you

so much. Um, we're going to do this again. I hope, I hopefully you'll do it, but we're

into it.

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

Okay. All the best now.

I feel like I can rule the world. I know I could be what I want to put my all in it.

Like no days off on a road. Let's travel. Never looking back.

Machine-generated transcript that may contain inaccuracies.