In the decade leading up to Tony Hawk's historic landing of the 900 at the 1999 X Games, he had attempted the trick countless times to no avail.
"I'd never pursued a trick as long as I had doing the 900," the 48-year-old skateboarding legend told CNBC.
"There were times that I thought it wasn't possible," Hawk said. "I broke a rib, I threw out my back and I'd tried every technique."
Hawk said he didn't expect to land the trick that night, much less in front of a crowd that size. But he knew it was a make or break moment for him: "I was either going to make it or get carted off in an ambulance. Those were the only two choices."
Normally, it becomes too physically taxing to keep making attempts at a trick that technical, but Hawk said it wasn't a problem that night.
"The adrenaline was high," he said. "I just knew that I was committed to do it. It was either going to happen or I was going to get gravely injured."
After a few attempts, "it finally worked," he said. Hawk landed the elusive 900 and won first place in the "best trick" event. The breakthrough came when he realized how to correct his technique and shift his weight.
Hawk's dogged persistence and willingness to push through failure also helped him excel in the business world with the launch of his apparel brand, Hawk Clothing, and the popular "Tony Hawk's Pro Skater" video game series.
"The mentality from being a pro-skater definitely crosses over into being a businessman because I'm not afraid of challenges," he said. "I'm not afraid to take risks."