FC: You write a lot in your book about the challenges of working with corporate types. What's been the toughest part?
Trying to convince bigger businesses and traditional companies that what we do can be done right and well without having to go through their cookie cutter. We want the creative freedom and the opportunity to do it our own way. Their mindset is still so old-school, even with social media. Last year and the year before, there have been companies that say, "Okay, we've got to buy airtime." Guys, it's not about airtime anymore. Even the whole viral thing is, to me, played out, because it's clearly forced. It's got to be real.
Authenticity is one of the themes that you keep coming back to.
The real problem is that some people put in charge of product development and marketing aren't beholden to their products — it's just their job. But passion really shines through, especially with all the information that's out there now.
What was the biggest mistake you've made as a businessman?
I was 18 or 19 — I was just signing my name on the dotted line everywhere I went. This one company was making Velcro wallets — really bad pink and blue ones. Probably the worst part for me was it ripped off the Vision Street Wear logo and made them say tony hawk gear. I didn't even see them until they were in the store. That was the tipping point for me: I learned not to allow someone else to use my likeness and my name like that.
Who's your business inspiration?
It's not that he's an inspiration, but I recently met Tony Hsieh from Zappos, and what he has created and his attitude toward business, being so customer-friendly, is unique and great. I also have a deep respect for what Lance Armstrong has done with Livestrong, transforming his celebrity and helping to change the world.
How often do you still skate?
Almost every day. At the moment, though, I'm nursing a fractured pelvis. I'd just come off a three-week European tour, and I had to do this exhibition. The jet lag finally caught up with me.
When will you fully retire from skating?
If I can stand up when I'm 80, I'll be happy to cruise around on a skateboard. If I feel like my skills are fading, I just won't do it publicly.
A version of this article appeared in the October 2010 issue of Fast Company magazine.