Chris Keeffe has been skating since he was 10 years old. And while he no longer does it professionally, he is still very steeped in skater culture as the founder and owner of apparel company DQM.

“If I was going to describe skating in a word,” he says, “I think it would be: free.” And judging by the way he has lived his life, that feeling of freedom is crucial to him.

When DQM first started back in 2003, it was a very humble venture; its store boasted only a smattering of skateboard and sneaker styles, and just a handful of t-shirts donned the racks. But since then, it has grown into a very successful and highly regarded enterprise, even launching a second storefront, The General Store, in conjunction with the Godfather of skate footwear: Vans.

Keeffe knew something that all true entrepreneurs know, which is that fortune comes to those who seek it. Fortune follows the bold. He had already taken one bold step in his life, when he decided to skip college to try and go pro as a skater. That gamble paid off, so when it came time for him to sink every penny he had into launching DQM, he didn’t hesitate.

And though he’s already achieved some of his hugest goals in life, he still isn’t satisfied. “You know what you want to accomplish,” he says, “and then, as you reach those’s always changing. It’s always eluding you.”

Then again, if he was so easily satisfied, he never would have gotten this far to begin with.

For more from Chris Keeffe on how he found his fortune, be sure to watch the video above.