The problem with success is even when success is a reality, it's effects are temporary.
You get hungry even though you have just eaten.
The most telling moment for understanding what's going was Matt responding to successful critics by saying they weren't successful enough
I can't remember exactly what he said, & too much has happened for me to find it with 5 minutes of Googling. Something like "oh yeah well you only got to $2B valuation and it took 1000 engineers, what do you know"
If there is a breakdown here, it's one I've seen before, but wasn't cognizant of until I saw it 100x over at Google, sometimes tragically: you got everything you thought you wanted, but you're bored enough to need a new challenge, but you're not cognizant enough of it to effectively make that choice _before_ your actions show you that you need to.
Doesn't help any that it would amount to "backing down" in this scenario, he can't say that now without people thinking he was forced out somehow.
When I think about this, I also remember:
- the somewhat odd acquisitions over the past few years, Tumblr, that one cross-platform messaging app that got a ton of press for insisting they'd do iMessage....another strong indicator of boredom with the day-to-day, IMHO.
- His clear, repeated, focus is on money. It's never in primary focus, but it's always there, in everything lashing out that is publicized. If you're unhappy, and you're not sure why, and you have everything you thought you wanted, one easy thought train to jump on is "the compensation is not commensurate for the work"