How a Skater-Turned-Business-Builder Figured Out the Cheat Codes for Life (And How You Can Steal ‘Em)
So, Who Knew Rob Dyrdek Was This Dialed In?
Alright, so you probably think of Rob Dyrdek as the guy pulling off wild tricks on a skateboard or, you know, cracking jokes while watching people wipe out on Ridiculousness.
But, turns out, there’s a whole different side to him — one that’s got a ridiculously methodical grip on money, time, and getting what he wants out of life.
This dude isn’t just making things work — he’s got everything wired in like a high-performance machine.
He’s built more than a dozen companies, flipped a handful for crazy money, and somehow only “works” about 7 hours a day.
How? By taking all the randomness out of success and turning it into something that runs on autopilot.
So, yeah — this breakdown? It’s gonna have you rethinking how you run your day, your money, and maybe even your whole damn life.
1. Getting Paid Like a Boss: Why Owning Stuff is the Only Way to Win
Most people working in TV are, let’s be real, just faces on a screen. Someone else calls the shots, collects the big checks, and the “talent” gets what they’re given.
Dyrdek? Didn’t play that game.
✔ Negotiated to own a chunk of his show’s production instead of just collecting a paycheck.
✔ Figured out what MTV actually needed (endless, cheap content) and gave ’em exactly that.
✔ Locked in massive episode orders — from 30 to 168, then 500.
✔ Eventually sold his production company for something like $125M+, while holding onto most of the equity.
🔥 Lesson? If you’re bringing in the value, make sure you’re also cashing in on the upside.
Whether it’s equity, licensing, or owning a piece of what you build, make sure you’re stacking chips that’ll keep paying you long after you’re done working.
2. Building an Empire That Pays You in Your Sleep
So, instead of running 15 different businesses all over the place, Dyrdek pools everything under one big umbrella.
📌 All his money flows into one single company: “Dyrdek Machine LLC.”
📌 From there, he moves cash into things that multiply on their own — like rental properties and companies he co-creates.
📌 Doesn’t just throw money into random startups — he makes sure he owns somewhere between 25% and 70% of every business he backs. 📌 Every company he touches? Built with a clear plan to sell it at the right time, for the right price.
💡 Take this and run with it:
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Stop treating your income like a pile of cash you just dip into whenever.Instead, funnel it through one main business.
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Use that company to stack up investments that generate money while you sleep.
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Only start businesses that already have a clear way out — whether that’s selling to a bigger player or setting them up to run without you.
3. The Secret to Selling a Business Before You Even Start It
Most people start a business and just, you know, hope it turns into something worth selling one day.
Dyrdek? Decides the exit plan before the thing even exists.
📌 Every single company he builds follows a set process:
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Find an opportunity that actually makes sense.
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Make sure the founder knows their industry inside and out.
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Map out every step of the company’s life — from launch to sale.
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Lock in a clear target price for when it’s time to cash out.
📌 Has already built and sold 6 companies for a combined $450M+.
💡 What you can steal from this:
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Don’t build something just because it sounds cool. Build it because you know exactly how it’s gonna make money and who’s gonna want to buy it.
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Make sure your first hires fill in your weak spots. If you’re great at product but clueless about marketing? Bring in someone who lives and breathes it.
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Exit strategies aren’t just for when things go bad. The best time to sell a business is when things are going great.
4. Stealing Back Time: How Dyrdek Tracks Every Hour Like a CFO
So, this is where things get borderline obsessive.
✔ Logs every single minute of his life into a custom-built tracking system.
✔ Rates his happiness, work-life balance, and energy every day (literally scores them from 1–10).
✔ Wakes up at 4:30 AM, does brain training, tracks his habits, and even emails his wife a daily schedule with a love note.
✔ Only works 7 hours a day — but those 7 hours are locked in and distraction-free.
💡 How to copy his setup (without going full psycho):
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Start tracking where your time actually goes. Most people think they’re busy — until they see how much time they waste.
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Automate the stupid stuff. If you’re making 6 figures but still running errands you could pay someone $15 an hour to do? That’s a bad trade.
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Make your schedule boring, so your life can be exciting. The fewer decisions you have to make in a day, the more brainpower you save for the stuff that matters.
5. Hanging Out With Billionaires to Learn How They Keep Their Money
Making money is one thing. Keeping it is a whole different skill.
✔ Joined Tiger 21 — a group where ultra-wealthy people break down their entire financial lives.
✔ Sits in rooms where people straight-up share what’s in their bank accounts, where they invest, and how they structure their wealth.
✔ This is where he realized wealth isn’t about working more — it’s about stacking assets that work for you.
💡 Takeaway for the rest of us?
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Get around people who actually know what to do with money. Your friends who just buy stuff when they get a raise? Not the ones to copy.
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Learn about tax-efficient investments. If you’re paying full price on taxes, you’re getting fleeced.
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Make sure your money is making more money, without needing you to show up every day.
6. The “Happiness Stack” That Keeps Him From Burning Out
After decades of chasing success like a madman, Dyrdek figured out none of it meant anything if he wasn’t actually happy.
📌 Only does work that gives him energy.
📌 Cuts out anything that feels like a grind.
📌 Lives in three mental states: creating, problem-solving, or enjoying the moment.
💡 You could take a page from this book too:
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Audit your work: If something drains you, automate it, delegate it, or drop it.
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If you can design your business in a way that lets you live how you want, you’ve already won.
Bottom Line: Dyrdek Cracked the Code, And You Can Too
✔ Make sure you own your time and your money.
✔ Only start businesses that are built to sell.
✔ Surround yourself with people who make smart financial moves.
✔ Track your time like a mad scientist.
✔ Automate the things you don’t want to do.
✔ Build a life that feels like winning — every single day.