You assume a modest lifestyle. Knowing he had such a bankroll and spending $1M more a year than his income would explain turning $150M into $100M over 50 years. You can not demonstrate business failure by accumulated wealth.
I don't care if his results are due to irresponsible business decisions or an extravagant, indulgent lifestyle. Neither of those are traits I want in a politician with the keys to my tax dollars.
You keep making this argument that he might be the great businessman he claims to be (except no one can ever know, because you need all kind of financial reports that he's not legally required to release), but that he's just really irresponsible in his personal life. You're not helping.