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I've found this video from 2011 to be kind of interesting in terms of illuminating how his history as an entrepreneur has shaped his attitude running Uber today

I've found this video from 2011 to be kind of interesting in terms of illuminating how his history as an entrepreneur has shaped his attitude running Uber today (TL;DR - he failed and got screwed over a lot). https://www.youtube.com/watch?v=2QrX5jsiico https://www.youtube.com/watch?v=2QrX5jsiico

x0x0 9y ago
video summary Scout * preyed on by predatory vcs (sued by first vc to improve terms even after LOI expired; vc leaked lawsuit to WSJ to scare off other investors) Red Swoosh * cofounder tried to sell team behind his back; * team went without pay for multiple months * cofounder fucked up and didn't pay witholding taxes to IRS (NB: IRS can and will personally pursue officers of the company) * nearly went out of business multiple times * last eng quit via twitter / AOL saw this and spiked a deal * got a 4-way deal (worth watching at about 25:00 or so) * acquired by akamai for $23m It's worth watching