Matt beach worked for fed ex before trying to make a small comeback with his right foot forward part a few years ago, not sure if hes still skating.
I heard Evan Hernandez became like a drug dealer, and was slanging coke at a tradeshow, that was a rumor though.
Alot of pros do try to start a company hoping to cash in but most of time it doesn't work out unless they come up with something completely original which is rare now a days. Also by then they are in their 30's and are way behind today's non skaters who by then have over 10 years experience in any kind of workforce.