> I think by definition free software won't win while remaining free.

The Linux kernel is widely adopted and remains kind-of-free.

LibreOffice is widely adopted and remains quite free.

> If a tech becomes main stream, corporations (and people) begin commercializing it

Not necessarily. That is, they may engage in commercial activity surrounding it, but that's not the same thing.

> So, the only way to win, in the sense of surviving and thriving, would be for that tech to fly under the radar.

Your "winning" requires not-winning, i.e. most people not using the relevant software.