Uber versus Night School is an example of this. Uber: Ignore taxi regulations, get tons of VC, get rich while being awful people. Night School: try to work with government and play by the rules, fail, get used as a cautionary tale.
Source: https://psmag.com/economics/night-school-failed-because-it-f...
I think something akin to GDPR is necessary and good, but GDPR as written probably isn't it. I look forward to seeing how it works out in practice, and how it develops/is replaced, and in the meantime feel bad for the developers and customers that suffer through the unintended consequences and misfeatures of it.
After the law gets clarified some, I think you're right that it won't be bad for small players. But I wouldn't want to be one of the test cases.