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According to http://www.bls.gov/data/inflation_calculator.htm, the $25,500 he paid in 1968 is equivalent to $174,419.27 in 2014. And, he paid that because (or despite) feeling he had few options ("stuck in the racket"). Further, this does not include his investment in his vehicle. The medallion fee is a huge (seems opportunistic and cruel, in fact) barrier to entry relative to the newer models of Lyft and Uber.
Uber is a perfect example of the inefficiency of the public sector: nobody can squeeze money out of you at all levels of interaction like a corporation.