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This is a genuine question... isn't that his job? For a public company, the CEO has to be a public CEO. Everyone takes on a different persona (some sell themselves as business geniuses, others as creative geniuses, and others as someone you wanna grab a beer with). Some really like it, and some do it begrudgingly. But at the end of the day, you can't be the same CEO of a public company as you were when you were priva…
Only if you pretend that the CEOs job is purely for raising money. Nominally, CEOs are supposed to run the company and help brew the culture that makes that company productive. We've grown a bunch of celebrity CEOs because people stopped caring about how companies worked over the last 10 years of low interest rates. But now that it's harder to raise money, it's time to see these guys run the companies they built.
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.