I think asking this question without addressing the overall cost/benefit to society is not very productive. The overall goal, I think, is to allow startups to grow and thrive while at the same time being a net plus for society. I would argue that "ask for permission later" mentality of some US based startups is a net minus to society overall. While I don't have any love for the taxi industry the regulations around cars for hire were put in place for consumer protection. These are some of the same regulations Uber is currently trying to get around (surge pricing in particular). Similarly, while I don't have any love for the hotel industry the regulations around short term housing exist to allow ample housing supply for long term residents of that city.

While inconvenient for the entrepreneur/investor/1%class most regulations exist for the common good of society. If a startup can prove that the regulation is outdated and doesn't make sense in the context of a new technology they should be able to convince the regulators that the regulation needs to be adjusted.