Wrong side of the tracks?

I just finished Crossing the Road to Entrepreneurship, the autobiography of Bart Wolstein who passed away just before it was published.

Wolstein made millions in real estate developlment - starting on the then undeveloped suburb of Twinsburg. He developed many similar outlying suburbs, got into big box stores likes Kmart and eventually shopping malls, hotels and country clubs.

Two things really jump out at me from the book. First is how relative “humble beginnings” can be. He was raised in the 1940’s on Taylor Road in Cleveland Heights. Even today, that is not exactly the inner city or a depressed area. In the ‘40’s, living in Cleveland Heights would certainly not be considered a hardship by most. Yet in the book he constantly talks about (and the title refers to) crossing Taylor Road. Eventually he did – ending up in Beachwood and Pepper Pike – but Cleveland Heights was certainly not the 3rd World in the ‘40s.

The second thing is how this multi-millionaire with all his connections and acclaim (he owned the Cleveland Force soccer team) always felt like an outsider and/or that he was being betrayed. He cites disloyalty and dishonesty from his closest partners and workers, in many of his business deals and just about everyone he ever dealt with except his wife Iris.

He felt he never was accepted in Cleveland’s inner circle and uses his rejected plans for a downtown arena, buying the Indians, a convention center, the Rock Hall and many more as evidence. In particular he was stung by his treatment by the board of Cleveland’s Jewish Federation. He tells of being silenced at a meeting when he didn’t want to increase his contribution and says “I kept quiet with tears in my eyes. It still hurts when I think about that moment.” He speaks of being ostracized by part of the community after that and the thread running throughout the book is that he never felt accepted or that he fit in.

On the surface you would have thought this guy had it made - tons of money, sports team ownership and so on. But you never really know what's inside someone's head I guess.