Rob Dyrdek Talks Celebrity, Wellness and His Future Ventures

In 1991, Alien Workshop released Memory Screen, their debut full-length video that introduced a cut-and-paste, multimedia aesthetic to skateboarding that somehow felt as familiar as a fever dream; it made you want to ride a skateboard. At 16-years-old, Rob Dyrdek was part of Alien’s new sect of street skaters who were then still largely unknown and unestablished in the industry. Memory Screen’s artful irreverence, along with the brand’s mystique and visual direction, became a cult hit still referenced and lauded today. 

In 2021, it's hard to think of Rob Dyrdek as niche or underground. For some, they hardly equate him with skateboarding and that’s partially by design. In the beginning of his Memory Screen part, Dyrdek is shown in grainy Super-8 film, juxtaposing wires into a console. It's a subtle if not accidental metaphor for an approach that made him a successful entrepreneur—connections, patterns, and a splash of hyper enthusiasm, albeit aided by sped up film. 

That energy led to Dyrdek starting several businesses, having successful television franchises on MTV and eventually owning Alien Workshop before returning it to Mike Hill, one of its original founders. Rob Dyrdek is a skateboarder and if you question that, go back and review the tape. He also has the awareness to not only put himself out there but make moves other skaters would deem as “corny” without worrying about perception. Why? 

As I learned in my interview with Rob Dyrdek, a skate career is part ambition and part illusion. Whether he realized that through intuition or experience, skateboarding’s taken him from a pro making less than four-figures a month to a franchise, expanding into the wellness market and determined to “grow rich not get rich.” You can also explore what he's up to with the Dyrdek Machine here.

There was a point in skating post-Jackass where every skater thought they were a comedian or a potential celebrity and everyone wanted a piece of it. While you never shunned from the spotlight or taking huge risks, how were you able to optimize opportunities and make decisions you felt good about while balancing the corporate machine that goes along with those choices?

The balance was always something I have considered throughout my entire transition from pro skateboarding core industry to pro skateboarding mainstream media. Skateboarding just wants to be represented in a real way. I was hyper aware to stay away from corporate projects that would use skateboarding and its culture in a way that was disrespectful or inauthentic. I used a lot of those corporate relationships to fund skate plazas and invest in Street League so pros could make more money. It was always a balance for me. 

Skaters aren’t known for financial prowess. Was there anyone you met in or out of skating that changed your outlook and got you thinking about how to invest and make sure you had stability after skating?

I am cut from the same cloth that most skaters are. I am a creative and athletic person that didn’t connect with team sports or school. I left high school, like most pro skaters, at 16-years-old with no real education and no understanding of money. I was blessed with the drive and desire to learn and evolve, and I learned all aspects of finances and business through the fire of experience. I created my first company, Orion Trucks, at 17-years-old and began to figure out ways to make multiple revenue streams, but it took many many years to understand how to invest and grow money. I never really thought about life after skateboarding because my ambitions have always been about how I can continue to grow and evolve into bigger and more exciting opportunities.

The nature of skating is trying something thousands of times before you do it once. Failure is part of the DNA, do you think that made you bolder or more liquid in business?

There are a few key aspects of skateboarding that I think built the foundation for how I approach business. Once you have a clear outcome and understand what you need to do to achieve that outcome, failure becomes part of the process. Failure is not so black and white. Trying over and over again and it not working is not failure because you are slowly progressing towards your goal through failure. You have to keep adjusting and adapting your strategy until you learn the trick. It doesn’t matter if that trick takes five tries or a thousand tries, you are failing towards your goal. You only truly fail if you quit trying, and even in that case, you have simply learned the range of your limits which in itself has great value. I build each business with this same framework and mindset. 

Is there anything you regret about “Peak Rob Dyrdek the Celebrity?” or anything you’d change?

Peak Rob Dyrdek Celebrity, I will always look back on fondly with no regret. It’s a remarkable transition from pro skater to mainstream recognition. I am thankful that it happened for me so much later in life so I was much more prepared for it. I was able to really enjoy it without it ever disrupting my passion and drive to continually elevate and evolve. I am not really someone that lives with regret about anything because there are clear lessons in all things you experience.

We’re in an era where everyone considers themselves an entrepreneur. How do you define entrepreneurship and what keeps trying new things exciting?

I feel like if you create any service or product and sell just one, you qualify as an entrepreneur. This is the American way. There are many different ways to be an entrepreneur. My approach is different because I want to master the process of curating amazing entrepreneurial talent, validating their ideas and then creating and shaping the idea into a successful thriving business. I absolutely love all aspects of the process and just want to keep doing it over and over again. Each time I get better and better.