Stanford game disaster led to refunds and 5AM cookie deliveries
“This is the third month of our operations September 2013 where it was a Saturday. We had no ability to fulfill the orders that came in. We had no ability to even shut down the website, so we couldn't even, like, stop the floodgates. We were late on every single delivery. Nobody asked us for the refunds. I'm sure they were pissed, but nobody asked. We did we did the refund right away, and then we stayed up that night actually baking cookies, and we deliver those cookies at around 5AM, before we thought when customers would wake. And the idea was we'd rather die trying to be excellent or at least die trying to do the thing that we wanna stand for than to live to be mediocre.”
Palo Alto delivered faster than San Francisco due to simpler logistics
“One of the earliest experiments we ran at DoorDash was doing deliveries in Palo Alto versus doing deliveries in San Francisco. And one of the fascinating things we found out, and we didn't understand why initially, was we were actually completing deliveries faster, inside Palo Alto than we were inside San Francisco. Obviously, San Francisco is a more dense place. But one of the things we learned early on, though, was that, obviously, you know, in Palo Alto, you had much easier parking. You had a lot, fewer apartment complexes where you had to go up and down the stairs and figure out where the lobby was or the right elevator entrance, things like that.”
Run two operating systems: scaling business and paper-airplane experiments
“When you look at, I think, and one of the reasons why I think Amazon is inspiring, a lot of these big tech companies now actually, is they tend to do two things at the same time. One is they continue to build the core business. But they also do new things. So it's like you are flying the airplane. It's a big airplane. You're carrying lots of passengers, and you're gonna do a mid air engine transplants. And then there's new stuff. It's not even an airplane. It's like a paper airplane. There are no passengers, no nothing. You're in search of product market fit all over again.”
Jiu-jitsu teaches holding firm strength and total relaxation simultaneously
“Jiu jitsu is a fascinating activity. It is like some version of physical chess. And it's almost like an exercise where there's so many opposites that you have to hold at the same time. The best jiu jitsu athletes can both be extremely firm and strong, yet at the same time extremely relaxed. They're very capable of being intentional with their game plan, but then give up and release their agenda within a nanosecond if they see that they're losing their position.”
Competitors faxed orders while restaurants did their own deliveries
“They were mostly, honestly faxing orders, believe it or not. So they would be a website that would receive orders if you can believe it. They would fax the orders literally, into machines that would sit near the kitchen or the payment systems inside these restaurants, then the restaurants would actually go out and do the deliveries themselves. So they were lead gen companies at the time.”
Three years of brutal fundraising required controlling his own psychology
“In the spring of 2016, a few things happened, and this is probably when I first started learning about the importance of dealing with your own psychology. The markets actually tank, the public markets. All of a sudden, the narrative for DoorDash was this really hot company, now is a company that can do no right. You can't ever make money. You can't beat all these competitors who are better funded. That happened for about three years, though, where we were kinda stuck in this one of these cycles where the company could do no right. The sector was viewed as toxic, and that was certainly probably the three years in which I certainly had to learn how to deal with my own psychology.”
Engineering candidates were interviewed while doing deliveries in his Honda
“On the engineering front, we looked for engineers who certainly were great at coding, but we looked for engineers who would be willing to do deliveries with us. In fact, the interview with me, if you're an engineer, is the final round interview was we would go and do deliveries together. So the interview would literally take place in my Honda, and we would be doing deliveries for maybe an hour or two or something like that. And I'm walking you through the flow of literally the order and asking your opinion of how we could productize this.”
Tony still personally does customer support every single day
“I still do customer support every day. I see them literally every single day. I think one of the easiest things as companies get a little bit bigger, perhaps earn a little bit more success, is there are more obstacles between them and the customers or the jobs to be done. A lot of what I'm trying to do is building as many reinforcing and repetitive mechanisms and motions, including things that I do individually, that will allow this company to always recognize that the number one job and the only religion at this company is to solve problems for customers.”
DoorDash launched in 43 minutes as paloaltodelivery.com with PDF menus
“Well, whenever you can ship something in forty three minutes to test your idea, I think that's pretty good. So we shipped to paloaltodelivery.com. That alias was available for $9, and so that's why we got it. It was a static page, where you saw eight PDF menus of restaurants that we frequented in Palo Alto. And the only way you can in which you can order is you can read through the menus. You can call a Google Voice number that would ring the cell phones of the four founders, and one of us would pick up.”
Best insights come from 2,000-word emails about edge cases
“The ones I love the most are actually, the really long ones, actually. The ones where there's a lot of gold. I love the 2,000 word emails, especially from Dashers who will give many use cases of why the logistics algorithm broke for them. And it becomes almost like a debugging exercise, right, of both physical world things that have occurred, things about our systems that, you know, probably broke, and things in our products that couldn't interface well enough between the physical world and our systems. And so then I go into our debugging tools, and I actually literally track the order.”
Christopher Payne self-assigned a 4-hour delivery shift before being hired
“Christopher Payne, our first chief operating officer, I didn't ask him a single interview question, but after a two hour discussion about our logistics algorithm, he went home that night, it was Friday, drove with his son for four hours doing deliveries. I didn't ask him to do that. I also didn't ask him the next morning to write me a 3,000 word email about why our logistics algorithm sucks, but he did it. And that told me more than any set of interview questions.”
The Wright Brothers solved flight with $100 from bicycle profits
“Have you ever read the biography of the Wright Brothers by David McCullough? Human powered flight was a centuries old problem. Like, people were trying to figure it out over and over again. The Wright brothers at the same exact time were trying to do it. They had better funded competitors, better brand names. I think it was Samuel Langley. Samuel Langley was, I think, backed by, like, the Smithsonian. I think he'd raised, like, $500,000. There's a great line in the book where, like, essentially, the Wright brothers solved the centuries old problem with the modest profits from their bicycle business, and they tallied up how much it cost. It was, like, $100.”
