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> But Uber ought to be working to change the law, not breaking it in the hopes that the government eventually just gives up.

Very good point and well made.

Although, could one say this model has worked with regards to the legalisation of marijuana in Colorado and elsewhere? I.e. it's illegal, but we're going to do it anyway, so we may as well legalise it and regulate it?

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Sort of. In my opinion the major difference there is that the change wasn't driven by a particular corporate interest. I expect I'd feel differently about stings on ridesharing if hundreds of people individually decided it would be cool to start organizing rideshare services, and the government started running stings on them.

A similar example is content sharing. Leaving aside the debate on whether or not it should be legal, the community as a whole changed how they interacted with content and the market has begun to shift in response, with more and more content providers realizing that they need to adapt. (I know that's not happening nearly as fast as we'd like, but it is happening).

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