The rabbit hole for me was the 2007 Ron Paul Revolution. I was already vaguely libertarian, but that's when I started reading political philosophy and economic theory. By the time Bitcoin came around, my concerns were rooted in economic theory.

Basically, I was skeptical of the claim that it was truly scarce. I got that Bitcoin specifically had a limited supply, but there's no reason any number of other identical cryptocurrencies couldn't be created.

I guess my orange pill "moment" was seeing Bitcoin firmly establish itself and develop network effects.