Everything you said here is true, but I don't think it applies to Twilio or Jeff.
I don't think you can accuse Jeff of not caring about company culture. He built one of the defining dev cultures out there. Yes, this have changed as they've grown, but I've always found the people and offices of Twilio to be warm, productive and smart.
And Twilio was forged in the hardest time to raise money ever... 2008. If anyone knows how hard it is to build in a climate without easy money, it would be Jeff.
Memories are short, but Twilio was built when doing what seemed obvious - add an API to telecom services - was really hard. It's what Stripe is (doing, not done) to banking & payment, what countless companies have failed to do with Healthcare... I met Jeff in the early days and the fact that he (a) managed to stay the CEO through this growth & timeline, and (b) gave few enough sh!ts to maintain a hacker dev mentality makes him a notable standout. I'm not surprised that lots of people with legitimate viewpoints and perspectives DO/DID NOT like him or his approach. To me, that's a feature; we need less CEOs and senior executives who try to be all things to all people.
I don't think you can accuse Jeff of not caring about company culture. He built one of the defining dev cultures out there. Yes, this have changed as they've grown, but I've always found the people and offices of Twilio to be warm, productive and smart.
And Twilio was forged in the hardest time to raise money ever... 2008. If anyone knows how hard it is to build in a climate without easy money, it would be Jeff.