My personal thesis is some combination of Bezos’ “regret minimization framework” and working on “cool problems with the smartest people”

This job application cycle I encountered three tranches of roles:

1) Great WLB companies — fully remote, ~$200k salary, if slightly less exciting work

2) Big tech companies — typically hybrid, much higher salaries ($300k+), if possibly less WLB and more boring day-to-day work in service of an exciting larger goal

3) Early-stage — super exciting work, smart people, at cost of WLB, salary, and brand

Not having gone to a prestigious university, brand was a big factor I considered — esp for future fundraising and roles. Some of the big tech companies were also likely to IPO for some quick cash, and obviously had smart people there.

Having a family leaned me towards the great WLB roles too, but ultimately I went with the early-stage because life is just a pure joy when both the work and people are great.

Another reason is community. I lacked true peers/mentors much of my life until I joined a really solid early-stage with smart people, who became great friends. So when I sense a chance to recreate this experience, I jump at the chance.