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Steal the Playbook

Hey, Josh here. I’ve been itching to write about this one for years. Let’s dive in.

The Rob Dyrdek Money Machine: How a Skateboarder Built a $200M Empire (And You Can Too)

You're about to discover the exact blueprint a skateboarding dropout used to make $200 million while working just 40 hours a week.

Most people think Rob Dyrdek got rich from skateboarding tricks and MTV shows.

They're dead wrong.

While everyone else was watching him goof around on TV, Rob was quietly building what he calls "The Machine" – a systematic approach to life and business that's generated hundreds of millions of dollars.

And here's the crazy part: He tracks every single hour of his life.

The Time Tracking Obsession That Made Him Rich

Rob doesn't just manage his time. He owns it.

Every 5 minutes of his day gets logged into a system he calls his "rhythm of existence." Work time. Family time. Gym time. Even bathroom breaks.

Sounds insane, right?

But here's what happened when he started doing this: His productivity shot up 80%.

Think about your last week. How many hours did you waste scrolling your phone? Watching Netflix? Sitting in pointless meetings?

Rob figured out that most people are bleeding money through their time. So he plugged the holes.

The result? He films 336 TV episodes per year (that's almost one per day) but only works 40 hours a week. The rest of his time? Family dinners. Gym sessions. Building his empire.

Here's his secret: "What gets measured gets managed."

Start tracking your time for just one week. You'll be shocked at where your hours actually go. Then you can start fixing it.

The $4 Million Shower Head That Almost Nobody Knows About

While everyone was watching Rob joke around on Ridiculousness, he was secretly backing startups.

One of them was Jolie – a company that makes fancy shower filters.

Sounds boring, right? Who cares about shower heads?

Rob did. Because he saw something others missed.

The founders created a genius marketing tool: customers could type in their zip code and see exactly what nasty chemicals were in their local water supply. People were horrified by what they found.

Year 1: $4 million in sales
Year 2: $40 million in sales
Rob's return: His $800K investment turned into a $200 million valuation in 18 months.

That's a 25,000% return.

But here's the kicker – Rob almost passed on this deal. It seemed too simple. Too boring.

The lesson? The biggest money is often hiding in the most mundane industries. While everyone chases the flashy tech startups, the real money is in solving everyday problems people actually have.

The $300K Nightmare That Taught Him Everything

Not every bet pays off.

Rob's biggest failure was Momentous – a premium supplement company he co-founded with an 18-year-old Harvard dropout.

They thought they could charge 35% more than competitors for "Ferrari-level" protein powder.

Nobody bought it.

For 8 years, Rob sat through brutal board meetings watching the company burn cash. His original 30% stake got diluted down to 4% as they kept raising money just to survive.

After nearly a decade of pain, Rob finally made his money back. But barely.

The brutal truth? Even smart people fail 90% of the time in business. The difference between winners and losers isn't avoiding failure – it's making sure your wins are so big they wipe out all your losses.

One Jolie pays for ten Momentous disasters.

The Media Empire Hidden in Plain Sight

Here's what most people don't know about Rob's TV success:

He doesn't just star in his shows – he owns them.

While other celebrities get paid once to appear on camera, Rob created his own production company called Superjacket. Every episode of Ridiculousness puts money in his pocket as both the host AND the owner.

Then he pulled off one of the smartest moves in media history.

In 2020, he rolled up his production company, his skateboarding league, and Nitro Circus into one giant company called Thrill One Sports.

The exit: $300 million sale. Rob's take: $200 million.

But here's the genius part – he didn't walk away. He reinvested $10 million of his own money back into the company that just bought him.

Why? Because he knew Ridiculousness was still a money printer. He wanted to get paid twice.

The lesson: Don't just be the talent. Own the content. Own the company. Own the distribution. Stack multiple revenue streams from the same work.

The Forever Estate That Almost Bankrupted Him

In 2015, Rob made what he calls the "worst financial decision" of his life.

He spent $10 million cash (almost everything he had) on a piece of empty land in Beverly Hills.

For 8 years, he paid $200,000 per year in taxes and fees just to own dirt. No income. No returns. Just bleeding money.

His friends thought he was crazy.

But Rob had a bigger plan. He called it Forever Estates – a multi-generational compound where his family would live for centuries.

Here's the brilliant part: He's putting the entire estate into a trust with an endowment fund. His family will pay rent to their own trust, and that money will cover all the expenses forever.

The result? A family legacy that never becomes a burden.

The lesson: Sometimes the "worst" financial decisions become the best if you think long enough. Most people optimize for next quarter. Rich people optimize for next century.

The 1,000,000 Hour Life Plan

Rob has a goal that sounds impossible: Live for 1,000,000 hours.

That's 114 years old.

Most people would laugh at this. But Rob's dead serious.

He wakes up at 5 AM every day. Meditates every day. Hits the gym every day. Hasn't touched alcohol, sugar, or junk food in 9 months.

His consistency rate? 100%.

Not 90%. Not 99%. Perfect.

Here's his secret: He stopped relying on willpower.

Instead, he engineered his environment. His schedule. His habits. Everything runs on autopilot now.

The result? He says he wakes up feeling "extraordinary" every single day.

The lesson: Most people try to change their habits. Rich people change their systems. Design your life so the healthy choice is the easy choice.

The Cash Flow Secret That Funds Everything

Here's how Rob actually stays rich: His assets pay for his lifestyle.

He's built a portfolio of rental properties and investments that throw off enough cash to cover all his expenses. His active income (TV shows, business deals) gets reinvested.

This is the difference between being rich and staying rich.

Rich people buy assets that pay them. Poor people buy liabilities that cost them.

Rob's real estate alone generates about 15% returns per year through a combination of:

• 5-6% cash flow (tax-free due to depreciation)

• 7-10% appreciation

When he sells properties, he uses something called a 1031 exchange to roll the profits into new properties without paying taxes.

The result? His wealth compounds tax-free forever.

The Billion Dollar Plan

Rob has a spreadsheet that shows exactly how he'll become a billionaire by 2050.

No guessing. No hoping. Just math.

He models out his real estate returns, his business investments, and his media income over 25 years. Even with conservative 7-8% growth, the numbers work.

The secret? He thinks in decades, not years.

Most people want to get rich quick. Rob got rich slow. Then fast.

The Machine Method You Can Copy

Rob calls his system "The Machine Method." Here's how it works:

1. Track Everything
Time. Money. Health. Happiness. You can't improve what you don't measure.

2. Own, Don't Work
Build assets that pay you instead of trading time for money.

3. Think Long-Term
Optimize for 25 years out, not 25 days.

4. Stack Revenue Streams
Never rely on just one income source. Build multiple pipes flowing into your bank account.

5. Compound Everything
Let your wins reinvest and grow. Time is your biggest advantage.

The Choice That Changes Everything

You have two options:

Option 1: Keep doing what you're doing. Work harder. Hope things get better. Retire broke at 65.

Option 2: Start building your own machine. Track your time. Buy assets. Think long-term. Compound your wins.

Rob was a skateboarding dropout with no college degree and no rich parents.

If he can build a $200 million empire, what's your excuse?

The best time to start was 10 years ago. The second best time is right now.

Stop making excuses. Start building your machine.

Your future self will thank you.