PayPal

“You know, there are some great payments companies out there, Stripe, Square, et cetera, that I talked to very early and couldn't bring myself to kind of lean in to do, despite world-class great entrepreneurs, note to self, mistake, right? Because I was going, …”

“All startups go through a valley of the shadow. All of them, PayPal, LinkedIn, things that I've done personally, things that I've invested in, Facebook, Airbnb, all have valleys of the shadow where you're like, why did we think this was a good idea?”

“Within two months, a 200 person customer service department was up and running.”

“Back in PayPal's early days, we neglected customer complaints, even as users grew exponentially. And because we had a customer service department of three people, we quickly started going in the hole around 10,000 emails a month.”

“Our burn rate was tens of millions of dollars each month.”

“PayPal's co-founder, Peter Thiel, wanted to scrap the entire idea and break that early promise in order to keep costs down.”

“So for example, at PayPal, x.com was copying our go to market strategy. And I was like, well, it's more effective to merge with x.com than it is to compete with them.”

“No, it cost me 48 dollars. I got, a guy named Muhammad who I still talk to this day, 15 years later he helped me put the PayPal button on the website. And it was 12 dollars for the domain, that's part of the 48 dollars. And then I used Gmail as my back-end.”