Uber founder he passed on
Gary explains he passed on investing in Uber twice because it looked like Garrett and Travis's side hustle rather than their main focus — a lesson that he had played too conservatively until 35 and that 'defense always loses.'
“What I learned there was defense always loses. I bought my first apartment in Manhattan. I played so conservative up until 35.”
After Shaan and guest Daniel Gross brainstormed a public, crowdsourced org-chart tool on the pod, a stealth startup called The Org launched doing exactly that and raised $8M from Sequoia and Founders Fund.
“There's actually a startup that came out of Stealth that is doing this after we talked about it. Clearly stole our idea. It's called The Org. They raised $8 million from Sequoia and Founders Fund, and it looks like they're doing exactly this.”
Sam notes that Uber founder Travis Kalanick allocated roughly $500 million toward building ghost/cloud kitchens through his new venture.
“Travis Kalanick raised a— well, I don't know if he raised it. He probably used his own money, but he allocated something like $500 million to creating ghost kitchens or services for ghost kitchens.”
Chris Sacca tells how, while CEO of Uber, Travis Kalanick hustled Sacca's dad at Wii Tennis — playing left-handed, then switching hands ('I'm not actually right-handed') — and was ranked #2 globally. Sam uses it to show competition is Kalanick's fuel.
“And later in that story, Chris actually says that he did the same thing with Angry Birds. He was ranked really high with that. But this is just how he's always been.”
Before Uber, Travis Kalanick's first company at 18 was SAT prep outfit New Way Academy. Sam notes how Kalanick lights up bragging he could finish a 30-minute math section in 8 minutes — competition was always his drive.
“My first company was when I was 18. It was actually a company called New Way Academy. It was SAT prep, old school, no technology. I burned out on filling out bubbles, you know, with a pencil, A, B, C, D, etc. But man, I can kill the SAT. I've been timed 8 minutes on a half-hour math section.”