Earlier quoted context omitted.
I think they are more lucky than privileged. Multiple IPO stock options, both well educated and high paying jobs and shared interests. They seem to have hit right timings multiple times. Things compound.
Do you think there's any good decision making and hard work involved too, or just pure dumb luck?
Yes, luck. Hard work is table stakes. It is necessary but wholely insufficient. We shouldn't make the mistake of over-attributing our successes to hard work and ignore the massive social and economic advantages that let us capitalize on the work we do. Everyone else works hard too, they just don't get to reap the benefits of that labor.