I wonder if he held the same utility function for the entirety of his life, because the beginning and end of his life is quite dismal. Not one bit of reflection in his life seemed to change his tone.
A recent observation, and this could be a biased one, you mentioned:
> we’ve spent a bit of time learning more about moving off the cloud to a managed data center. But the nice thing is not feeling like we need to.
That SaaS's are moving/thinking/completed to running their own infustructure away from managed services like digital ocean and aws, like 37Signal(Basecamp & Hey).