That's not what happened here.

Nat founded Xamarin which was acquired by Microsoft in 2016. Github was acquired in 2018 and Nat was already an Microsoft employee at time.

So Nat departing now is actually 5 years post the Xamarin acquisition (when he joined Microsoft).

https://www.linkedin.com/in/natfriedman/

EDIT: what's also interesting is that Thomas Dohmke joined Microsoft in 2015, moved to the Github division around the time of the acquisition (2018) but only became CPO 4 months ago.

We don't actually know one way or another. Golden handcuffs are very common in the industry and it's very easy to imagine that becoming CEO of very public and important subdivision of a cloud company comes with a very large stock option grant. Easily 8-figures worth. When/how they expire are also a mystery to us. I'm sure he didn't get the standard engineer vesting schedule of 4-years with a 1-year cliff.

Thomas' own blog sounded a bit like he was the special task manager. So do not read too much into this 4 months.

I wonder if he stick with Microsoft long enough would he have a chance of becoming the next M$ CEO.

Many people within Microsoft felt that he was a clear contender for Satya's eventual successor.

Damn. Satya is 54, within 10 years he could definitely be the CEO. But I guess most entrepreneur just dont like sticking around and not building.