I like the episode very much and merely pointed out the utter incompetence of this "business man".
I understand that people have this mythical idea about companies lasting forever but, well, it is just a myth. Excusable in the case of an uneducated John Doe, inexcusable in the case of a guy who prides himself in being a successful investor.
As long as he lays out a line of succession for his affairs, there's no reason his personal wealth wouldn't continue to grow while he was incapacitated.
You seem to pick on him because he's out of the loop. He has no historical context in which to evaluate his situation. He didn't know of cryonics being a fad and that him and the other two were the only ones to be revived. He has no way of knowing that a nuclear conflict would wipe out six hundred-million people and shattered the economy.
We never once see these people offered someone who could give them a history refresher. They're shown how to work the food slot and left in a room. They don't even show them how to work a computer station so they can find things out on their own.
Offenhouse was simply flying blind and without information assumed things continued on the course he thought they would.