If Spike Jonze counts as a skater then by looking at his IMDB credits, mostly for directing/producing features,tv and adverts, then I reckon he could be up there for sure. Part-founder of Crail and Viceland creative director isn't too shabby either.
Knowing how highly acclaimed and sort after he is in the advertising/film world I'm sure he could do a slew of big ads whenever if he wants to make dumb money.
There's probably some pro skaters out there who make nice investments as well though - that saint archer thing seemed to pay off well for everyone, a couple of those and you would be laughing