>I think he has a little nest egg saved up, and hasn't had to job-hunt lately.

Yes. Good insight. But I'd guess it's somewhat more than a little; apart from other things, he's also an angel investor. See the last paragraph here:

https://www.complexsystemspodcast.com/about/

It starts like this;

>Obligatory disclaimers: I'm a (tiny) angel investor. I previously worked at, and am still an advisor to, Stripe.