At 50 years old, Tony Hawk remains a skateboarding legend. His career helped popularize the sport with mainstream audiences and helped him launch a variety of successful business ventures that have made him a wealthy man. Forbes named him the highest paid action sports star in 2009, and the popular "Tony Hawk's Pro Skater" video game franchise generated an estimated $1.4 billion in sales since it was launched by Activision in 1999.
In fact, Hawk has been a skating star since he turned pro at 14. He spent many of his teen years pulling in about $100,000 per year between prize money for winning competitions and company sponsorships (he skated for the Powell-Peralta skateboard company and did commercials for companies like Mountain Dew). Hawk was making more money than his teachers when he was still in high school.
Hawk even bought his first home when he was a senior in high school.
"That was one of the smartest things I ever did, because it definitely put my money away [and] made it grow eventually," Hawk tells CNBC Make It.
Aside from investing in a house, the legendary skater admits he often got a little carried away with his spending when he was young.
"When I first started earning money, I was in my late teens and I thought, the sky's the limit. I thought this was never going to end," Hawk says of his early earning power.
Hawk admits now that he "had no compass" with regard to being financially prudent, and he often bought "a lot of ridiculous, frivolous things."
"I would go to Sharper Image and go crazy and buy, like, the new small camera or the tanning bed," he says.
Fortunately for Hawk, his dad, Frank Hawk, convinced him to put some of his growing income into a more sound, long-term investment: real estate.
"My dad was the one who encouraged me to put [my money] away, in terms of investing in a house," Hawk tells CNBC Make It.
The only problem: Hawk was 17 at the time and, legally, you have to be at least 18 years old to sign the contract to buy a house.
"[My dad] cosigned a house with me, because I had the money but I wasn't old enough to actually sign a deed," Hawk says.
Putting his money into a relatively stable investment proved an invaluable move several years later when, in the early 1990s, the sport of skateboarding saw a sudden drop-off in popularity. At the time, Hawk says, his income fell off precipitously as his "royalty checks started getting cut in half every month," while fewer and fewer fans were showing up to his skating competitions and demonstrations.
"At some point, when my very quick cycle of popularity in those days ended, I still had that house to go back to, to live in, and it saved me in a lot of ways," Hawk says.
Indeed, Hawk says he even took out a $40,000 second mortgage on that house at one point to help finance the Birdhouse skateboard brand that he founded with fellow skater Per Welinder in 1992.
"Those years were a struggle," Hawk says.
But skateboarding's cyclical popularity soon resulted in another upswing. In 1995, Hawk starred at ESPN's first-ever X Games competition, a nationally televised event that put skateboarding back on the map for millions of viewers. Four years later, at those same X Games, Hawk became the first skater to ever land a "900" — an iconic trick where he spun for two-and-a-half revolutions in mid-air — which cemented his legacy as the world's most famous skateboarder.
Hawk's popularity soared with the sport over the next couple of decades and, even though he says he eventually sold his first house years ago, Birdhouse became one of the sport's most popular brands.
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