So I have a PhD, and do empathize with being "transgressive", but I'll say I think it's less about the PhD than it is about being right.

If you are bull headed and drive really hard in a new area, you better be right because you are taking responsibility and accountability for that area (whether you think you are or not). High risk, high reward - sound familiar? This is true at Google, at startups, in academia. So it's really more of a personality thing - if you're ok being obedient, you also don't need to bear the stress of accountability. But if not, well, no degree will alleviate that stress.