Supra's team is pretty large. The brand stays alive the more Muska/Penny shoes they sell, and that translates into supporting more riders.
They're not milkin' it. Muska owns part of the company and Penny isn't milking anything...they're on tour, don't see a lot of guys their age on tour. Plus they still back Greco, who is old too but is obviously still putting some great skating out there to those of us who care.
Lastly someone said skating appeals to people of all ages nowadays...that couldn't be more true than ever before. I grew up watching Penny skate when he first came on the scene and so now I still get stoked to watch his clips even if though they are pretty chill. That means I end up buying more skate shit. It helps grow the industry dollar pie and everyone benefits. When the economic sea rises every boat does too.