Earlier quoted context omitted.
That is rationalization, where we try to apply "logic" to make ourselves feel better about a bad situation. The chances are low that life is better now, after losing out on a chance to be an early part of Instagram. That's like saying a homeless person's life may be better than if he had a home. Ya statistically that scenario is possible. But if you had a choice, do you really want that homeless person to stay homele…
I think the more brutal reality is that just because you had been there then instead of someone else doesn't mean Instagram would have done what it did. Maybe as a first hire you'd have jerked around more than the actual person, or missed deadlines or just made bad choices which lead to zero traction. It's egotistical to assume that it being you instead leads to the same result
I mean, what signals lead you to believe one scenario is more likely than the other?
It didn't sound like he was a weak employee in any way--if anything, he sounded like a strong employee because the founder of Instagram wanted to create a full-time role just to keep him, despite not having much money for the startup back then. I would assume the founder of Instagram is a better judge than I am, of who is good to hire.
It's possible that Instagram would have been more successful if he was there to support it back then.