"He obviously feels he is owed something"
Does he feel he is owed something just now? Why didn't he feel he was owed something at their sizable Series A [1]? It all just seems Opportunistic, someone just waiting to maximize their returns.
not the "This is the right time to start a certain business" kind of way
This fully describes most of the VC-backed startup world. 95+% of the businesses fail and a few get lucky. Part of making that happen is trying just about anything and shooting for the moon.