I worked at Twilio for nearly 10 years and it's hard to overstate what a gift it was to work there and see Jeff operate as CEO up-close. He created an environment where (at our best) we could have fun doing work that had a real impact, and we could it with people we enjoyed doing the work with. He pushed us to be creative to authentically empower and inspire developers. Wanna build a video game that teaches developer…
> Wanna build a video game that teaches developers how to code and use Twilio? Let's try it! Wanna build an AI application with Tony Hawk and have Tony Hawk debug the code live on stage? Sure! These are the strange effects of ZIRP and infinite QE. Many companies never had to care at all about profit and could just do things "for fun", and still see valuations skyrocket as long as they hired more people. What a time.
The fact that the music continued so long and led to incredible valuation inflation over the last 15 years made the excesses look a lot worse, but even in a more sane financial environment I'd argue you'd still want to do these things to be competitive in an attention-economy, just maybe not to the extremes we saw.