Yes it is possible Caldbeck is a cunning predator who knew exactly what he could get away with and used his clout as a VC to grope and harass many women, but it's far more likely that he is not. Far more likely he isn't all that smooth with women and ham-handedly attempted to woo his victims.
He failed to realize how the power dynamic influenced things. This is important for anyone in a position of power to realize. My moment of realization was when I noticed that every single person on a team I led laughed at a joke I made. I realized something was off. The joke simply wasn't that funny. It's easy to see how simple flattery (which is quite normal when dealing with VCs) might have thrown off Caldbeck's compass. Yes I'd expect someone with his level of experience to be aware of it, but some people can go years without realizing they are being flattered.
This is in no way meant to minimize the poor judgment Caldbeck used or to cast any blame at all on his victims. VC is a unique world that is fad-driven and reputation-driven and so the founder of a very hot company has tremendous power over investors, but all other founders are essentially beggars.
I know Jonathan and he's an exceptionally gracious person whose behavior is completely reserved and respectful. I imagine he's quite disappointed about being lumped into all this and having his company's brand ruined by it and his name dragged through the mud for Caldbeck's poor judgment.