Nat was originally on the Microsoft side when GitHub was acquired, not the GitHub side.

So how come he made so much money that he can waltz off to what sounds like a life of casual angel investing?

Does not change the fact that he stepped into the company he co-founded with vesting shares 3 years ago.

I still can't tell what you're alluding to. The company he founded was acquired 5 years ago, not 3.

Nat was not a cofounder of GitHub.

sorry my mistake, I had the idea he went full circle when were assigned as the CEO

Nat has had the privilege of working on some large projects and startups. I doubt money is something he's too concerned about at this point.

Why is that a surprise? All of the top tech companies have many public acquisitions and all of the leader info is available from multiple sources. In fact, you could use that leader info from LinkedIn to understand that Nat was already at MS from the Xamarin acquisition to know that his tenure at GitHub wouldn't be a good data point.