Uber should have come in as service to sell or license, either to cities or cab companies. They wouldn't have had to dealt with flouting regulations, dealing with insurance, driver relations etc. It all adds up to big costs for no real reason when they could have avoided all that.
I'm not really sure trying to run a taxi company in hundreds of markets against embedded incumbents protected by government is the best strategy. From what I have heard, the app really is the best part of it. Why bother with all the headaches of the rest?
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