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Skateboarding Legend Tony Hawk's 3 Tips to Take Your Business to New Heights Life is too short to not enjoy what you do.

By Nina Zipkin

Johanna Siring
Tony Hawk

While Tony Hawk is known today as a record-breaking skateboarding icon, the 48-year-old -- who went pro when he was just 14 -- vividly remembers a time when his career in the sport, and even the fortunes of skateboarding itself, were uncertain. It was during that period in the early 1990s that he co-founded his skateboard and apparel company Birdhouse.

Looking back now on 25 years in business, Hawk says that at the time, even though skateboarding was going through a fallow period and he was seeing his own own income take a significant dive, he had the conviction that the sport would make a comeback.

"It took longer than expected and we definitely had moments of extreme doubt and serious conversations about quitting altogether," Hawk recalled to Entrepreneur at the American Express Success Makers Summit in New York City.

Related: 6 Stories of Super Successes Who Overcame Failure

Now Hawk is a multimillionaire. But he says that his passion is what drove and inspired him during the rough patches. "When you're that young and you're making six figures, you seem invincible. It seems like there is no ceiling to that or no end to that. When it does come, it comes very harshly," Hawk says. "Those years were lean, but what they taught me most is that I truly love the act of skateboarding. I'll do anything to keep at it."

Hawk says that in order to channel what you love into a viable business, you need to be able to learn everything you can about your industry. "Even if it doesn't interest you, it's going to benefit you in the end," he says. "You're going to have a much better understanding when bigger opportunities present themselves."

The skateboarding superstar offered his best advice for aspiring entrepreneurs.

1. No job is too small if it helps you do what you love.
Hawk bought his first house when he was 17-years-old at the advice of his father to make an investment in his future. But as his pro career stalled, he learned that the highs don't last forever and you have to account for that in your plan. On the flip side, if you're making millions and aren't happy with your work, you can find yourself just as stuck.

"I was doing odd jobs too, but I was doing skate jobs like in a parking lot doing three shows a day outside of a Six Flags for 100 bucks. Now that seems crazy, but I paid the bills and I got to skate," Hawk says. "If you really are following your passion, you're doing what you love and you're able to get by doing that. That to me is the greatest success."

Related: 7 Tips for Loving Your Career and Working With Passion

2. Make sure that your partnerships are authentic.
When your name is your brand, you have to be careful of how it's used. Hawk says that while for him it's very much an instinctual, gut check decision, it's important that you enjoy the process and challenge of coming up with inventive and genuine collaborations. He cited an upcoming partnership between him and a luggage maker that he is a fan of.

"The guy who created the luggage saw a picture of me traveling with it and hit me up. He said "I'd like to send you a new bag' and I said I actually had an idea for a marketing campaign, using my skills and my reach," Hawk says. "We collaborated on something I'm really proud of. It's coming out soon. The way to combine them could have been really sterile or cheesy. I feel like we did a really good job of using both of our expertise."

3. Don't be afraid to go big.
If you are afraid to take risks in your business life, it's likely that fear will end up becoming a self-fulfilling prophecy. So if you want to pursue your passion, you have to go all in, says the guy who pulled off the first 900 degree spin on a skateboard during a competition. If you stumble, instead of being discouraged and deciding to quit, use the experience of being tested to come out on the other side stronger for it.

"You have to go at it with confidence. That is something that translates directly to skateboarding. If you go out to take a risk and you don't do it with confidence, you are going to fail because you've already created the worst case scenario in your head, and that's what's going to follow," Hawk says. "When I try to do something, I think I'm fully capable of this and I'm going to make it work. Sometimes it doesn't go the way I planned. But going through that learning process and embracing the mistakes, in order to approach them from a different direction is I think what the key is."

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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