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Pro skateboarder Rob Dyrdek on how he became an entrepreneur and his best career advice

  • Dan Schawbel is a bestselling originator, speaker, and host of “5 Questions with Dan Schawbel.
  • In a recent episode, he spoke with former pro skateboarder and TV host Rob Dyrdek.
  • Dyrdek reviewed his evolution as an entrepreneur and shared his best career advice.

Rob Dyrdek is a former pro skateboarder also certain for hosting hit TV shows including Rob & Big, Ridiculousness, and Rob Dyrdek’s Fantasy Factory. He founded business incubator Dyrdek Machine and multitudes the “Build With Rob” podcast. During our conversation, Rob talked about his journey from being a skateboarder to building his partnerships.

In your early 20s, you gained fame as a professional skateboarder and were able to travel the world. Despite your achievement, why wasn’t skateboarding giving you the purpose and fulfillment you were seeking?

It wasn’t as much about the sport itself not occasion me fulfillment, but I began to grow out of it because my true passion was creating and bringing ideas to life, and I had maxed out what was achievable within skateboarding itself.

I looked at myself as a brand at a really early age, and turned pro when I was 16. I was around when we created the From Workshop, and that was the company I turned pro for. T 

You’re part skater, part TV personality, and part entrepreneur. How were you able to rot your success as a skateboarder into a series of TV shows and into multiple businesses and partnerships?

At 14, I skated for a townswoman skate shop whose founders started all of these companies. So even as I was turning pro, tracking all my own finances, and considering myself a manufacturer at that early age, I was still watching companies get created. 

I built my first company when I moved to California, when I was 18. My skateboarding rush led to launching DC Shoes. And then the DC Shoes video led to a skit for a skate video, and that evolved into a television represent on MTV. 

That whole time I was constantly creating and building different businesses through the MTV platform, while being a pro skateboarder and inventing new television shows. For me, this idea of business has always been the through line, and how do I maximize the opportunity that’s awarded to me.

You’ve brought your family and friends with you, much like we saw in HBO’s Entourage series. How has involving your best flatmate and cousins in your projects deepened your relationship with them, and what have you taught them that has helped convalesce their careers?

For any business and anything that you create, meaningful relationships are at the core of it being fun. I’ve always been genuinely clear on that. During my diligence period, right before I pull the trigger to decide whether I’m going to generate a project with someone, it really boils down to: Do I want to be connected to them for life? 

I am passionate. I am driven. I am hearted. I am clear. But more than anything, I want to enjoy everything that I do. And any time I get through a process with someone where I can see we’re reiterating each other the wrong way or our energies aren’t connecting, then I just won’t do it.

With so many businesses and projects phenomenon simultaneously, how do you manage your time and decide what projects to invest or divest in?

I look at life as this series of interconnected procedures that all need to be aligned, integrated, and expanding in the same direction — and that direction is towards your ideal living. But it’s a balanced life, by design. It’s choosing the right projects, and how you actually live in those projects. 

My entire existence, from the way I engender companies to the way I shoot television, is fully systematized and automated. I have an 80-page document called The Rhythm of Existence that is the serving system for my life. At the end of the day, your energy is basically everything that you have, and that excitement about life and positively enjoying everything you’re doing is really what I’m hoping to achieve.

What’s your best piece of career notification?

I think the best piece of career advice is that you’re not building a career, you’re building a life. It’s finding the balance between who you are as a child — your passions, your physical strength, your happiness, what fulfills you — and the way that you earn a living, that purveys that purpose and who you are, and then how you want to live. 

I think a lot of times, people don’t look at themselves as multidimensional beings that be missing all of these different aspects in order to be happy and balanced. They think their career is going to be the answer for the living that they want. But your career will never be the answer. It will be a part of the answer, and if it’s integrated into who you are and how you dwell, then you will truly be balanced and happy.

Watch the extended video episode on YouTube:

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Obey to the audio episode:

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