Board Thread:Episode Discussion/@comment-410526-20160116155944/@comment-26872876-20160121195316

Grimm Eclipse mentions a company went out of business in Mountain Glenn. They hinted in the Livestream some things from the game will appear in the show. So perhaps Roman was a business leader or investor in Mountain Glenn or something. Of course, that depends on when Mountain Glenn happened... Which has been suggested to be "before team RWBY's time."

Either way, I think he was a wealthy individual who ended up losing his fortune, or his family lost their fortune when he was a child. Would help explain a lot. Leadership, planning, money or time to learn piloting for several vehicles. Could afford some level of self defense training.