He's very, very good with his money.
He runs his outerwear sponsorships on contracts, and maintains the image needed to get contracts with JL, Cross, and other super ridiculously expensive outerwear contracts. He doesn't get caught up in loyalties either. He's gone from JL, to Cross, and I'm pretty sure he's back on JL right now. Big money at that level of clothing.
On top of that, he's a businessman - he runs two of the biggest competitions in skiing, one of which produces some of the best shots of the year. He has a contract with redbull which I'm sure brings in some cash, and he's always off on a film shoot or photo shoot somewhere. And now he has YNIQ goggles, which I'm sure will take off and bring in huge cash in a few years. Before you hate on YNIQ, remember that Jon is trying to sell to the rich skiing crowd. He's not making goggles for NS.
He's also a damn good skier, and has done a ridiculous amount for the sport. He popularized the double flip, invented several of them, and is basically known as the double flip guy. With that putting him on top of the skiing world, and his knack for handling money, its not surprising that he's been so successful.
