The Rob Dyrdek Story: From Skateboarder to Business Mogul

April 2, 2019
James Whittaker

Check out this episode on the Win the Day Podcast

“Everything you seek to achieve, build a believable plan."

Rob Dyrdek


In episode two of Win the Day, we spoke about how the right plan is far better than the right promise. After all, you can promise yourself anything you like, but you’ll continue to bounce from failure to failure until you’ve got a detailed plan for success. Purposeful action always trumps talk.

Importantly, the right plan encapsulates remedies for just about every adversity and obstacle you’ll face along the way, keeping you resilient, focused, and giving you the best overall chance of success.

As author of Think and Grow Rich: The Legacy, I was tasked with interviewing an incredible mix of people from all over the world to tell their stories from hopelessness to success. If you’ve read the book, you’ll notice that a bulletproof plan was a common thread. It got:

  • Jim Stovall to write 30 bestselling books and create the Narrative Television Network despite being blind;
  • Janine Shepherd to prove the doubters wrong, becoming a pilot/author/mother/speaker while still a paraplegic; and
  • Grant Cardone to amass one of the largest private property empires in the US after immense personal loss and a 10-year drug rampage appeared to have extinguished his spark forever.

A bulletproof plan creates relentless action, bringing superhuman levels of resourcefulness and resilience.

One of the most interesting people I’ve interviewed is Rob Dyrdek. Admittedly, I hadn’t really heard of him before the Think and Grow Rich: The Legacy project, but he’s amassed more than 12 million followers on Facebook and Instagram and appears on major television networks around the world every day. As I researched his extraordinary career, I was amazed at his eclectic cache of achievements and wondered what could possibly be left on his bucket list.

Two years ago, I drove to his penthouse office in Beverly Hills for our interview and could immediately feel the energy of the place. The elevator walls were adorned with his ’99 truths of business’ and the windows offered 360-degree views of one of the most glamorous cities on Earth.

Dyrdek greeted me like an old friend. He walked me into his office and, for the next two-and-a-half hours, shared his remarkable philosophy for life, success and business.

I was blown away, not just by how generous he was with his time and how candidly he shared his story with me, but how intelligent and insightful he was—a contrast to how many would perceive him, I’m sure.

It’s safe to say that I’m a fan.

Growing up in Ohio as an ordinary kid, it was a chance encounter that changed Dyrdek’s life forever. It happened at a skateboard tournament, where the 11-year-old followed around one of the pro skaters, Neil Blender, who was walking to his limousine. As Neil opened the door to hop in, Rob blurted out, “Hey, I don’t think there’s enough room for you and that board.”

“You know what? You’re right!” the pro skater replied, handing his board to the young fan.

At the time, Dyrdek had never even been on a skateboard, but this extraordinary course of events taught him one of the universe’s most valuable lessons: Whatever the mind can conceive and believe, it can achieve.

He became completely enamored with his new craft, practicing for hours on end while harboring dreams of turning pro. Dyrdek eventually moved to California and began shaping the culture of the burgeoning sport, both on the board and as a clothing designer.

But he wasn’t satisfied.

Fearless, he tried his hand at all he could, raking in millions of dollars, but the lofty highs were tempered by deep lows. To restore balance and stay focused on the bigger picture, Dyrdek began reading books like Think and Grow Rich and resumed asking for what he wanted, as he had done as a kid.

“What’s grounded me is the relentless pursuit of growth and having a bigger picture for what I’m meant to accomplish,” Dyrdek told me during our interview. “It’s knowing that these stages are just part of the process, and not a final destination.”

A lot of the unhappiness and frustration in our own lives stems from the contradiction between where we are now and where we think we should be, but Dyrdek reminds us that there’s lessons to be learnt in every situation and that your current circumstances never have to be your final destination. Trust the process.

Being crystal clear on what he wanted gave Dyrdek the fuel and inspiration to keep moving forward, even after his athletic shelf life was expiring. “As I’ve continued to level-up, I stop and decide what the answer is, and then build my life backwards from there,” Dyrdek noted.

That level-up came in the form of an unlikely career in entertainment, where he controls the full gamut: producing and hosting television shows, planning their distribution, and showcasing brands. To turbocharge promotion, he took the reins (quite literally in this case)—putting his body on the line and setting 21 Guinness World Records.

However, for all his success, Dyrdek’s crowning glory is the Dyrdek Machine, a venture capital company that invests in exciting startups with high growth potential. Aside from fulfilling the 99 truths that adorn the elevator well of his penthouse office in Beverly Hills, the people who most catch his attention are those who embody two simple attributes: zest for life and a bulletproof plan.

Many would argue that Rob Dyrdek has no right to be a major player in the entertainment world. After all, how many former skateboarders—or professional athletes in general—can you name who forged careers at that level of success after calling time on their sporting pursuits?

Despite what the haters say, being dedicated to a detailed growth plan has been the foundation of Dyrdek’s long-term success and why it would be unwise to bet against anything he does. Today, he owns companies in seemingly every industry, from virtual reality and luxury goods to clothing and plant-based foods.

To maintain harmony in his life, the 44-year-old focuses on three things: working on ventures he believes in, committing to mastery of the business world, and creating a platform of love for his young family. It’s this life plan—what he calls his ‘rhythm of existence playbook’—that maintains Dyrdek’s infinite well of energy and is what he regards as his greatest accomplishment:

“It’s creating your entire universe about you being at your best, living with energy each day, and just being happy. That’s the ultimate freedom. I have a clear vision for literally everything in my life and I think about it every day.”

Interestingly, Rob Dyrdek reads Think and Grow Rich every year because he recognizes that each time you read it, and have more life experience to bring, you don’t notice something new in the book—you notice something new in yourself:

“The foundational principles of achievement, you can only digest based off experience. When you begin to manifest based off applying these principles, and you begin to hone that, you read it [Think and Grow Rich] again and it’s like, “Wow, this really is what I’m doing!” I think self-help books should be read every year just to remind yourself. There’s no way to fully apply something that complex until you’ve had achievements to help you believe it.”

To conclude, let’s revisit his quote at the top of this newsletter: “Everything you seek to achieve, build a believable plan.” Think about the most important goals in your life and make sure you’ve prepared detailed plans to make them a reality. (Unsure of how to do that? Watch this issue’s video episode.)

Onwards and upwards always,
James W.

PS – You can learn more about Rob Dyrdek’s story, and many others, in Think and Grow Rich: The Legacy, available now on audiobook, ebook and hardcover.

Back to Newsletters >

Ready to win the day, every day? 

Actionable success, mindset and performance tips delivered to your inbox every two weeks 🔥
youtube-squareapplegooglespotifyfacebook-official linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram