To be honest,
I don't think it is such an awful idea, we have all seen Captains move from Bizjet, t'prop to airline, and the other way. There are some who can make the transition. Bear in mind I'm sure that the interview will be based not on hours and experience exclusively.
I think the learning process of reinventing the wheel will be the hard part of this plan, I can't help thinking the use of all the capital raised would be better spent acquiring existing operators with existing fleet / management (profit)contracts / aoc etc, defracturing (is that a word?) the market and generating extra profits by the economies of scale of a single fuel purchase account, single Ops base and the other bits that reduce the threats to an AOC holder like TRTO, Maintenance and suitably qualified CP's.
Phil