Rob Dyrdek's Street League: An Entrepreneurial Fantasy Becomes Reality

Over the past 20 years, Rob Dyrdek has built a thriving business empire on the back of skateboarding. Turning pro at 16, Dyrdek emerged as one of the sport's premier stars, became an early ambassador for brands like DC Shoes and Alien Workshop, and parlayed such commercial sponsorships into his own clothing lines (Rogue Status and DTA), a toy line and animated series (Wild Grinders), a feature film (Street Dreams) and other successful ventures.

But despite the 36-year-old's ever-expanding resume and two hit MTV reality shows (Rob & Big and Rob Dyrdek's Fantasy Factory) that have made him a household name, Dyrdek's vision for a professional skateboarding league remained an elusive goal that he long viewed as the potential cornerstone of his entrepreneurial legacy.

This summer, after six years in the works, that vision finally became reality.

In its inaugural season, Street League Skateboarding brought together 24 of the world's best skateboarders, including Paul Rodriguez, Ryan Sheckler and Chris Cole, competing for a $1.2 million purse in a "for skateboarders, by skateboarders" tour sponsored by DC and Monster Energy.

After competitions in Phoenix and Ontario, Calif., the league closed out the season in Las Vegas on Sept. 25 (set to air on ESPN2 tonight at 8 p.m.) on its third-straight buzzer-beater finish (spoiler alert!), with Shane O'Neill taking the top spot and Nyjah Huston claiming the overall title for the season. Street League drew more than 15,000 fans for its first three events.

For Dyrdek, a member of the AOL Small Business Board of Directors, watching Street League take shape was no doubt rewarding. But like most can't-sit-still entrepreneurs, he's already focused on next season and how to refine his product. In an exclusive interview, he highlights what went right, what went wrong and what it's like to build a professional sports league from the ground up.

You just wrapped up the inaugural season of Street League. What's your first reaction?

For me, I wasn't even through the last one and I was already focused on 2011. Just the reality of such a massive undertaking, you can already feel how many holes are in it now that you're doing it. Obviously, I'm excited. We've taken street skating and brought it to this rock-star level.

But I'm very unsatisfied. I don't know if I have a problem, or if this is the nature of the beast, but I just see the grand potential. Now I have eight months to just refine the aspects of the whole property.

How gratifying has it been to see a project you've been focused on so long finally come to life?

It's thrilling. It's definitely thrilling -- the grandness of it all, standing in the middle of it all in this concrete plaza. It's absolutely incredible, to say the least, because of how crazy executing the whole thing really was. Maybe it's because I'm still burning a bit from the fire, but now I see the potential and just want to make it bigger and better.

Was there a specific moment during the competition where the whole thing clicked?

More than anything, for me, it was that first contest when we had four guys with a shot to win it and just being on the edge of my seat. It was like, "Ahhh!'" It was really, really shocking. It's one thing to do all the testing, it's one thing to pitch it. But we never thought we would get three back-to-back buzzer-beaters. It's the same way I pictured, but it's still almost unreal.

Standing in that arena on that first day, when the course was completely finished, I was just like, "How the hell were you able to pull this off?"

This was a whole new type of venture for you. How did it differ from your past business experiences?

I think more than anything, it's a combination of my business maturity, in the sense of really understanding how and when I decided to spend money and what was the smartest way to do it. I could've cut a lot of corners and cut none. Knowing that you're building this for the long term, spending a lot of money up front and a lot of extra money to make sure that it's done right and it's executed properly and you've got the support to ensure success in the first year -- that's how we did it.

You're the face of a lot of different brands. How did you integrate those with Street League?

Obviously, this year was a mega integration, where I had my movie that comes out on DVD in October as part of it, and the telecast features all my brands. DC and Monster sponsored it. You could not have intertwined it any more. We virtually intertwined every single thing that I have. I don't think that's part of the long-term strategy of the brand. I think it'll be survival of the fittest with something like that -- it'll always end up going to the highest bidder -- but as it grows, it'll evolve.

I really used myself to push it and promote it and use my embedded audience, but I really want to build the brand around these skaters.

You recruited the best skaters in the world for your roster. How big a role did they play?

There's already such a fraternity around it in year one, and I think they understand the magnitude of what it really is and what it can really be. It's really the first time taking the very best and just showcasing them. It's something that has just never existed in our world before, and I approached it as, "If I were them, how I would want to create this?"

Did you study other professional sports leagues in preparation for this?

The only thing I've really watched that really hit home was the story of the USFL. Those guys created a true niche with spring football and began to overtake the NFL by paying guys way more money. So they had Steve Young and Marcus Allen and all these gnarly guys. And instead of slowly attracting the talent that would've legitimized their league, they tried to go hard and started suing for free trade and that left them with nothing and the league collapsed.

When you have the elite in the world, you have a true property. Who did I call on Monday morning after the Street League finale? Every single one of these dudes. What did you like? What didn't you? I want to make sure we all get on the same page.

What was the biggest surprise?

I certainly didn't expect there to be three buzzer-beaters. Three buzzer-beaters and three winners and three guys who haven't won a contest? It's pretty shocking.

As far as the event, I think I sort of lost sight of the fact that you're putting on a show. No one who was really in this with me prioritized that. But that's just one of a million holes. It's 10 percent of what it will be.

What would you do over?

First and foremost is figuring out the television schedule and number of events and toying with ideas on what makes the most sense for marketing it. I want to restructure and figure out how to pace it and keep it more exciting.

Seriously, this was like just running in front of a giant snowball.

As you focus on next season, do you think it will be easier this time around?

Absolutely. I don't think it'll ever be perfect until year five. But like anything else, as we go into next year, I'm sure we'll find more holes -- but it'll be 20 times better. It's a long-term thing.

Is there a professional sports league you look at as a model you'd like to emulate?

I think the NBA, in the sense that it's Lebron James, it's Kobe Bryant -- the dudes you're seeing are the super upper echelon. But as far as the events, it's more the UFC model of putting on big shows.

If I'm flipping through the channels tonight, why should I stop on Street League? What's your sales pitch?

More than anything, for those who think that skateboarding is cool but never watched it because it never made enough sense, now you'll finally be able to watch skateboarding and watch a true sports story unfold. It's a true competitive sport that's exciting -- and skateboarding just happens to be the centerpiece. We've got to build the understanding.

The original version of this article appeared on AOL Small Business on 9/29/10.