Re: "His take could have been close to 5Mil+[1] had he joined the team."

So let's say he was hired. Maybe his engineering decisions send Instagram on another trajectory - one that doesn't involve a billion dollar exit. Maybe his impact on candidate interviews causes Instagram to end up with an entirely different-looking engineering team, one that isn't as successful. Maybe he develops considerable influence within the organization, and convinces the founders to take an earlier exit.

This isn't a knock against Robert. This is just suggesting that things could have played out entirely differently were he onboard - even if he was by every measure a successful employee.

Maybe an asteroid strikes their headquarters. Maybe this is a pretty good argument^H^H^H^H^H^H^H^H justification for why every decision someone makes is the right^H^H^H^H^H wrong one.

I mean, sure, those things could have happened, but I was focusing on outcomes that might likely have been impacted by Robert as the 2nd engineering hire - not random acts of god.

I know Robert and he genuinely does embody the "money doesn't matter" philosophy. Besides, he sold to Zynga and he's an early employee at Quora, I somehow doubt he's hurting right now.

You write that as if cognitive dissonance were a bad thing...

It is when trying to explain one's motivations in a structured and informative way. Not so much when trying to emotionally deal with a missed opportunity. But this is presumably meant to be a reasoned response.

It's too early for a reasoned response. He has to pass through anger and depression first. Cognitive dissonance might get him there.