Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)

So I want to start, what's your take on what is the difference about being an exec when you're running an atoms oriented business versus a bits oriented business? I was wondering when I joined DoorDash, which of my experiences were going to be most relevant to DoorDash. It turned out to be Amazon by a mile because of this reason. So at Amazon, that was my first experience working with atoms, to your point. And what are the key differences? One is like, you really have to understand the finances, like the unit economics. And so Amazon taught me how to look strategically with a finance lens at a business that is honestly a terrible business at first blush. And then you have to, like, make the math work. Same thing with DoorDash, right? If you launch in a geography, you start losing money initially, but as you get more scale, you then can improve the unit economics by lowering the cost of delivery. You can get merchants to pay more because you've got more customers. And then you can make the math work. At, you know, a Microsoft or other companies, the finance problem is like, you know, I don't know, add up the money if you build the right products. So you have to still build a great product with atoms, but you have to make the math work. And it turns out that my mind works, like I like those problems. I like the working on the make the math work. And so with DoorDash, we got the, we proved out Palo Alto. We could make money there. We expanded. For a while, there was a narrative like, oh, we're giving away dollars for 90 cents. Absolutely not. You couldn't do that because you would, you would lose money very, very rapidly. Too fast for a company that didn't have a lot of money. But what you, you do is you're expanding rapidly and you have to go through the life cycle. So you have to hit six months of volume to get the gross margin positive. And then you have to get to 12 months at a certain volume to get what we call contribution margin profit to flow through the bottom line. Once you figure that out and you know that it works for each of your markets, you can then expand very rapidly, which is what happened with DoorDash. So that I tend to like both types of businesses, but I enjoy the complexity of solving the atoms problem. A capable executive that works in bits can all be successful running atoms-oriented businesses. Definitely not, definitely not. Like what's the difference between someone like you that can play both games versus somebody that it's just not going to work for them? I always look for people that like to build things. I think you need smarts, obviously, but you can't have somebody that's like that, that runs businesses that isn't capable of going down to the lowest level of detail. If you've got somebody that like runs businesses and then gets bored and then starts building businesses, which is kind of what I did in large companies, you can do it. You can actually go down to the, to the business level, but not everyone, not everyone's going to be successful in doing that. We, Tony and I talked about this a lot, Tony, the founder of DoorDash, about how do you know during the interview process? And the truth is you don't. And so you just sort of have to try. What's as good as you've gotten at that question? Yeah, I often, I ask people these builder type questions. So it's like, tell me how you, tell me the problems with X. And so they can always do that. And then it's like, tell me how you built that. Like, go back, go back in your mind to the moment that you were thinking about building that and tell me what you're thinking and how you built that. I'll often ask people product questions. I take them outside of the business world. I'll say, tell me, tell me your most frequently used product, your AI. AI might be the thing right now. Oh, I use granola all the time. Okay, I make you king for a day. You get to add one feature to granola. Tell me what that is and why. And you'd be stunned. People are running 10,000 person orgs and they make no sense with their ideas. Totally. And you're like, well, my theory there is if you can't be empathetic about yourself and knowing you and how you use that thing, you say this is your most frequently used AI product and you can't make a feature for that, you know, come on, right? And you're, there's no chance you're going to be empathetic for a brand new customer. The atoms question, which you started with, I think that's teachable. I think you can learn. Do you think that that in all cases, a builder-oriented exec operating at mega scale will outperform, or there's absolutely a role for like, you know, the traditional large company executive? I think you need both. I think, I think you want the builder in a company because you want, you want the perpetual line of S curves. Like one of the first things I did at DoorDash because I had a lot of experience with this is I, I, even though DoorDash was very young, I founded the first new S curve at DoorDash, which was the platform business. So I worked at Microsoft. I worked at Amazon. So I was like, okay, we're going to, this can be a platform and there's going to be more volume eventually through the logistics engine of DoorDash than just the restaurant app. But as an executive that starts these new S curves, one of the things I've learned is that it's my job to protect those S curves because what's going to happen is even in a small organization like DoorDash and really in a large organization, everybody tries to kill the new thing. They just try to kill it because it's taking resources away from the main thing. And I always say, if you find yourself in a conversation where it's like, what's more important, the little thing or the main thing? You've lost the battle already. So what I tend to do is I reserve resources for the 10, I call it 10%, put it on the new S curves, protect those, don't let those in. And so you guys can deal with the 90%, but you can't touch the 10. Where it gets tricky is if you need, if you need some functionality from the main body in order to do the... Right. It's not totally cleaved off. It's not totally cleaved off. So you try to cleave it off and loosely couple to the degree that you can. Give it enough oxygen. Don't give it the same type of goals. Get the finance or get the right finance people in the room that are capable of helping you make the math work, find product market fit. And then later you can graduate it. So if you look at DoorDash, you'll say, okay, it's restaurants, it's grocery, it's alcohol, it's retail, right? It's DoorDash Drive, our platform business. All of these now are multi-billion dollar businesses that are... And so you have to have that. Now, to your point, it's okay. Like when you, when you have a large organization that supports that to have executives that run those organizations, right? They may not be good at building the next S curve. So you have to build a team that has a mixed skill set to be successful. But do you think for them to be successful, they have to be willing to get in the granular details? Like maybe an interesting thing is like when, when one part of what I heard you talk about builders is this ability to go zero to one, to get a business off the ground. There's another, there's this mindset of like being in the details, of having this sort of finger feel for every part of in your org versus an exec sitting on a fiefdom of 10,000 people. 100%. Well, I think, I think in general, like if you lose the ability to get into the details of the business, to go back to the, I'll call it the base metal, then you've become irrelevant. I fundamentally believe that that's independent. Everyone knows that Chris Fer would go look at the dashboard every day. And my, you know, I'd go down to the, you would, you'd be stunned by the amount of information I looked at, but it's easy once you know what you're looking for, you just go through and you're like looking for anomalies. You're looking for things that are going well, things that are surprises, and then you dig into them. So emails start to fly out. I think the thing that people get wrong though about details is that you need to be able to go down to the detail, but you must be able to then generalize that and then look at the data to find out whether that detail is interesting or important or not. I'll give you an example. One, one of the things I like to do when we were building the grocery business is I would, I would order groceries. Turns out grocery is a really hard problem. So we order groceries and invariably something would go wrong. Yeah, my, this is a ciabatta bread problem. My It turns out, this is the detail, right? The detail is there's two sections of bread. There's the normal bread aisle, and then there's the fancy bread aisle, right, or fancy bread area, and then the ciabatta rolls are in the fancy bread. And what was happening in the app is we weren't directing them there. Now, so that's a detail. So now I'm curious. So now I got to go back and run the queries and go, hey, is there a higher defect rate in these categories? Meats, so they have multiple areas, bakes. Turns out there are. Now I'm really interested, right? So now I start to, oh, it's 35% higher missing and incorrect or whatever the, whatever the quality stat is you're looking at. So now I've gone from detail, I've now generalized. I know it's a problem to solve. Now how do you solve it? And so my theory there would be that we need, unfortunately, we needed to get planogram information for every grocery on the planet and direct the dasher to the right location. We literally had to do that or they weren't going to be able to get the ciabatta bread and everything else that goes along with it. As an executive, you must retain the ability to go down to that level of detail. If you just stay up here at the 30,000 foot level and you become a manager or just a manager, I think you, yeah, you lose the ability to truly impact. Talk more about that. Like what is the problem with, it would be easy to hear the, what you just explained. It would be to say, you're a very senior operating executive. Someone more, quote, junior should get in their car, should become, you know, flip over to dash remote and go do this and go tell you what happened. And so like, what is the problem with that? They didn't do it. You know, I've got to go. I've got, it's the way I think about it is, yes, I want them to do that. And so my theory is that I can't do everything for sure, but I want to retain the ability to do that in special places where I'm like, I really would like this to succeed. So I'm going to go deep in this area. And my hope is that I help the team build that business, but I'm also hoping that you're training the next generation to say, oh, this is what's meant by being in the details. This is what's meant by, you know, solving how to solve a business problem and how to scale the business problem. So that, I can't do that in every. So one of the things I tend to do is like, you know, like say I'm running a complicated business like DoorDash, right? And the metaphor I use is a plate spinning metaphor, right? Let's say, oh, that that's, that part of the business is going really well, right? I'll help them with the goal setting, help them know, okay, that's your plan. I'll look at the plan. Great. Okay, let's spin the plate. This area over here, this is having trouble getting off the ground. We've tried this a few times. We're not getting product market fit. I'm going to prioritize that this quarter. I've freed up enough of my capacity. I'm gonna go deep with that team. And one of the things I like to do when I do that is like, you know, I'll sit down with the team and say, okay, I'm going to work this with you as if I'm a team member, not the president and COO of the company. I'll put that hat on if needed. But I am going to be a team member and we're going to work this problem. And so the, the, the, the ask I have of the team is that they share the sausage making process with me. What doesn't work? What does it? So then, then I can get involved at a level that's necessary to try to help. Then I can back away from that. That plate is spun and you can go do something else. It's a strategy I've used in my career to scale myself. And so every quarter I might have two or three of those special areas that I'm going deep on with the hope that I can kind of scale myself into your question. I'm hoping I'm, while I'm doing that and helping that product area succeed, I'm helping train the people on how to take it forward. When you're diving into different parts of the business at that level of detail, what is the benefit when you're back up at altitude? It's like, you know the business, right? So it's like, let's take the, the DoorDash example, right? So it's like the initial challenge with DoorDash was like, how do you make these markets profitable, right? And so to use our working model, you got to go figure out how to make Boston work and how to make Philly work and how to make Palo Alto work. And it turns out these things are kind of different from, from one another. And so you then start to say, okay, I need a playbook that's common. And then that's the 80. And then I need some 20 because it's different. The big cities are different than the suburbs, right? And so now when you copter up and you're at the, at the high level, you now are like, okay, now I understand, here's how I'm going to roll out the United States. Here's how I'm going to go from 16 markets to 50 markets to 500 markets to a thousand markets, right? You can use the playbooks that you've gleaned by working the problem. I tend to call this crawl, walk, run. You know, that's the crawl phase, right? And then it's like, okay, I figured this out. Now we're gonna, we've made it work in one market. Now I'm gonna, I'm gonna try different flavors, right? And make it work in three markets. And then I'm gonna go from there. Then you're up at the top level. Now you know how to allocate capital. You know how to build teams. You know how much personnel you need. You, you then can build the machine that can go scale that thing across the country. If you just try to run to the end, you won't have the lessons that are necessary to be successful because the problem is not homogenous. How much of it is also the way in which you're able to work with your directs or their directs that you have a better sense of sort of ground truth and discussion and debate and guiding sort of on a day-to-day basis? Yeah. I mean, one of the things you realize running a lot of these companies over the course of time is that at the end of the day, it's all about people. Like you have to have the right people, the right teams. Earlier in my career, I would say that I was sort of like a one-size-fits-all manager. I kind of, I was like, oh, here's how you manage people, right? And set the, help them set goals and do the one-on-ones and everything like that. And then as I went through time, I became much, I think, better at being a manager in the sense that I, I realized that each person kind of needed different things. And so I was always trying to figure out, okay, I'm coaching this person. What does this person need to be successful? And obviously you're asking them and you're like, how can I help you be successful? I think earlier in my career, I let go a lot of people because they weren't performing. I read some book. I can't even remember what book it was now. And it told me it's like, like the first failure is on you. It's your fault as the manager. I was like, that's kind of cool. And so I really took that to heart. And so I was like, okay, that's, that, we didn't, that didn't work. Okay, that's on me. I didn't do, I didn't give you the right goals. I didn't give you the right information. Let's, let's try a different way. Holy cow. I was blown away by how much I could. So that, that then became a philosophy of like, okay, I'm not going to be one size fits all here. I'm going, it's my job to make this person successful. And I think that one technique that we've spent, you know, time talking about the data piece of it, I'm often trying to teach that. I'm trying to teach how you go low to the data. I don't like the phrase in the weeds. I always say that that's, that's kind of stupid. It's like, because like if you're in the weeds, it seems like you're not, you're not like, you're not like getting it, right? It's like, no, I want you to be in the data and now I'm going to teach you how to copter up. And part of it's judgment. You have to have judgment where to look. I was in Microsoft during the early nineties. You know, I talked about this before we started talking. And at that time, there wasn't a lot of data being used. And so it was all about persuading. I would get a big ideas, product persuasion, you know, this. And then I got to Amazon. It was all about data. It's all about like, like running experiments, A-B tests. And I learned a lot during that period of time. I was like, oh my God, my instincts are dead wrong often. And now I would say in the last 10, 15 years, I've been teaching people to not just use data, but to use their judgment to actually like, don't, don't overlook the human judgment. I think this is very important in this era of AI. You know, the metaphor I often tell people, I said, so it's like we're running a store, grocery store. And there's this That art and science duality, I think, is critical. But at the end of the day, if you've got the right people underneath you, you can do anything. You can pivot, you can do whatever. If you don't, like, it don't matter. You can have the best strategy. And so you don't think if you're star talent, you can work sort of in any environment. The manager doesn't have to coach you in a certain way. Or you found that the opposite is true, that the way that you work with people really changes what they can do. Well, first of all, I think I agree with both points. So I think there's stars that can be successful everywhere and in any environment. And then there's people that need coaching. And often you'll get people that will be like, they want to be the, everybody wants to get promoted, right? Everybody wants to get promoted. They want to be managers and all this stuff. And it's like, and I might be incredibly good at what they do. Sales is the example. Engineering is the example, right? And sure enough, you promote them and they're just like, they're not good at that next function. That's a good example where you've got a rock star that's incredible that you're going to have to help them get to that. If that's what they want. If they don't want to still be like super coder and eventually, we should make that possible too. But if that's not the path they want, if they want to be a manager, it's like, no, we're going to have to, you're going to have to go back to school. You're going to have to study this like you did engineering. And this is going to be hard. And that needs to be helped and taught. And so if you advance to a level and some people do, and you don't get that coaching or mentorship or experience, and people are not helpful with you, you can easily run afoul. And it's too bad because you were a rock star. Who were some of the people that did that for you? And, and what were those moments that they took you aside that had some real impact? At Amazon, I would say that David Resher was my boss. He's now the head of Lyft and Bezos. It was a very small company back then. And I learned so much from them. So I was in Microsoft coming into Amazon and Microsoft's a very challenging environment, very competitive environment. And when, you know, Bill challenges you, you respond with force. You know, you gotta, you gotta be, you know, behind your idea and everything. First day I was at Amazon, Jeff challenged me on something. And I, you know, I was like fired back and Jeff was like, you know, just to ask you a question. I was like, Oh God, this is, I'm in a different environment. Right. And I need to, I need to learn a different system. Jeff was, he always was teaching customer, customer, customer. Like it was like, that was the, the foundation. I had never been in an environment like he started literally the orientation day, there's much, much about this on the internet where he like had an empty chair. Why does he have an empty chair? You know, every, he was doing orientation and it's like the empty chair is for the customer. You want to represent the customer and everything you do. Like that's an example where I was like, oh, okay. Like I've been thinking of this the wrong way. Like I had, you know, strategy, product, business, all of the, it's like, no, no, you put, you put it around the customer and then you build the strategy. And once I, once he helped me get that and then I helped build the video business, I led that. Then I helped build the electronics business, which was crazy making stuff up as we were going. I liked that. There is without that sort of guidance, mentorship, focus on how to do that, there's zero chance I could have done that. What do you think about yourself has allowed you to be so successful at sort of the top level exec jobs? If you introspect, like what's going on or outside of maybe what you shared thus far, what's like your working theory of yourself? Well, first of all, it hadn't all been roses. So I think, I think it's very important to be able to look at things that were failures and label them as such and learn from them. And so it's easy to talk about the DoorDash experience. Yay! But then there was the Tinder experience where, you know, it was a disaster. I got fired after six months and I, you know, it just didn't, didn't, I didn't fit there. I should have known that. I ran web search for Microsoft, what became Bing. And it was a great experience on the one hand. I went from like, you know, zero to a thousand engineers. I got to work on the coolest problem. I mean, it's all called AI now, but it was called machine learning back then. But did we fulfill what we wanted to do? No. I told you before we started about my little startup that, that I founded right into the teeth of the Great Recession. I ended up having to basically sell the company in an aquihire. Now it was great. I enjoyed my chapter at eBay, but it wasn't the dream that I had. And I think so to your question, I, I like to look at things. I was a U.S. history student at Dartmouth. And one of the things you learn quickly by studying history is that like the best people learn from their mistakes, right? And they're not afraid to make those mistakes and learn from those mistakes. And so I, I try to do that. I try to always look back and say, what did I, what could I have done differently? How can I own this situation? Yes, there were externalities like a, you know, great recession, but what could I have done differently? And I think that's, I think that's helped me. So that's one thing. And then honestly, like putting myself in, like putting myself in different chairs, like the, the one I talked about earlier, that has been the most, like the most important because at some point you go from being like, oh, Christopher's the Microsoft technology guy to, okay, well, Christopher solved that problem. He tried, he worked on that problem. They worked on that problem. You then start to have like a, a repertoire of, oh, I can solve business problems. It doesn't really matter what the domain, it has to be tech. I mean, I like tech, but other than that, like, I feel like I can, I can dig in. Right. I can go to school on the problem and then I can bring to bear all this experience. I'll pull from that, pull from this, and it won't be exact. It won't be right, but we'll go for it. And then maybe lastly, I'll say, I like to iterate and learn, like crawl. I call it crawl, walk, run. So if I'm tackling a problem, if I can break it down into sub parts where I can work on a problem. DoorDash was great for this because you, instead of trying to launch everything across the United States all at once, you're like, no, I'm going to start this project in Phoenix. We'll go see if it works there. And once we get it working there, then we'll figure out how to expand it. And so I think that you can't do that with everything. You know, if you're going to change pricing or do a subscription model, you have to do it writ large. But I think that ability to compartmentalize and shrink problems down and then walk and then run, I think has been very helpful to my career. What do you think is the difference between somebody who taps out at the number two spot? They're the VP of finance and they, they never, other than maybe bad luck, they're never capable of being a great CFO. They're a great VP of ops or however they ended up in the, in the path to COO. And they just don't have the capability. It's funny. I decided I don't want to be a CEO. Like I was a CEO of my little company, but the truth is I watched Tony and I was like, holy cow, I don't really like this job that he has. Right. I like my job. Right. And so one of the things for me is like, I've been taught all my life is you, you, you should aspire to keep going all the way, tippy top. And I realized in, at DoorDash, this was late, right. That I was like, you know what? I'm good at being the president and CEO. That's like, that's what I'm good at. I want to build. So that's where I want to spend my time. I don't want to raise money from investors and all that stuff. That's hard work. That's, that's stuff I don't like to do. Tony's brilliant at lots of things, including that. Part of it is like, it might be okay to be the VP, the best VP of finance on the planet. Do you know what I mean? Now, if you want to be the, if you want to go to the next level, a lot of times I think people don't take the risk to get there. I don't think they take the, they don't take the path. They don't take the risk. It's like, what does it take to get there? Often you might be the, on the controller side of finance, right? You need to figure out, I got to go learn the strategic side of finance. Are you willing to take a step back in order to do that? A lot of people aren't willing to do that. And very few people get the generalizable skills, the general I want to know about Eng, right? And I want to be able to bring it all together in a coherent strategy and a coherent go-to-market. The problem is we got specialists, specialists, specialist, specialist. And you can sub-specialize. I was doing that on the finance side. And so that was a little bit of the exercise of, like, let's get in a different seat where you're uncomfortable, and let's see if you can learn that skill. That pushes you, certainly, your skills. It will then increase where you can go and up in the company, but boy, does it make you a better leader. Because now, if I've run Eng and I'm now running DoorDash operations, I'm not overseeing engineering. But guess what? I know a lot about engineering, so I now know how to hopefully align myself with the engineering organization. How can I help you be successful? How can I get you the data you need? And I know all roads lead to engineering, right? That's how you scale. Technology business. Exactly. And so, if you don't know that, if you've never had any experience with it, I think it's very difficult to do that. So, we live in an era of specialization, but at some point, the people that have generalist skills, I believe, become more valuable. And that is one of the things that helps you break through to get to the chairs that you're talking about. You sort of said this as a passing comment, but if you go back to sort of Microsoft in the 90s, you talk to a lot of people, it was very competitive internally, battling out of ideas. Do you think there's a lot of environments where that's actually great and that's absolutely the way that a company should be run and people should behave? Yes and no. So, on the one hand, I'm very... I feel very privileged to have been at Microsoft in the 1990s. So, that was like, if you want to know my origin story, that's got to be central to it, right? Brilliant people, big vision, reinventing the world. Like, love that. I thought that was the only way to work, right? Because that was my only experience circa 1998. Then I learned that's not the only way to do it. And so, like, so I could have easily been a lifer at Microsoft and probably answered your question... Answered this question differently. Now I realize, actually, you know what? You don't need to... You don't have to necessarily have as much competition internally. You can... There's other systems, perhaps friendlier systems, perhaps better systems. Although I was at Amazon, which was a tough environment as well. So a little bit of both. Like, I don't... And the truth is, like, I pick from, like, now running a company or a division of DoorDash or whatever. Like, I'm trying to pick the best of. I want the customer focus of Amazon. I want the marketplace nuance of eBay. You know, I want the technology optimism of Microsoft. It's a best of. There's no one-size-fits-all. But it doesn't have to be an ultra-competitive place. How do you end up with not just a watered-down culture then? I think the key from a leadership perspective is to set aggressive objectives, like full stop. Tony and I talked a lot about this. Like, big, hairy, audacious goals. And I coach this a lot. I'm on three boards now, and I coach a lot of founder CEOs. And I'm like, like, set ambitious goals. So we were talking... I was at the one company, and I said, so this is your, so what's your best AI feature? This is the best AI feature. I said, what percentage of... It's very new. Okay, 5% of people use it today. Okay, great. But they like it. That's great. So we're getting product market fit, right? What's the goal for, you know, the next six months or whatever? We're going to increase it by 20%. I'm like, oh, no, that's not gonna work. Because, you know, in order for this to become mainstream, that would take the rest of our, you know... Existence. Exactly. So, no. You, what you need to do is set, let's 10x this. Why don't we want to go from, you know, 5 to, you know, 0.5 to, you know, 5, and then we'll see how to go beyond that. It was 0.5, actually. And so it's like, okay. And that sounds like hard, but the thing is, the team then thinks differently about that. My contention is they don't all have to be assholes in order to achieve that objective. They can work well together. They can be friendly with one another, but they have to be ambitious and driven and bias for action and get stuff done and aim high. But I don't think you have to be competitive and combative, which is the... And if I'm overreading into your question, that's what I'm, that's what I'm... But you have to work hard. You have to work hard. You have to work smart, but you don't have to compete. Yes, you have to be competitive, but you don't have to have a culture where it's dog-eat-dog. I don't believe. You said that Amazon was very hard, but hard in a different way. What way? Well, I think part of it was the time that I was there. So it was the dot-com boom and the dot-com bust. And so on the one hand, this is why I think people should work in a hyperscale situation. You are forced to learn. So, you know, Amazon was like in 98, 99, 2000. Like we would go from like, I'll say my first week there, I was trying, he goes, Christopher, go build the video business. So it was me and Jason Kyler, who ended up running Hulu, and we're like, Okay, we're going to go figure this out. And so we went to the Video Software Dealers Association, and not a soul would meet with us. Like, literally not a soul. I think Artisan met with us because they felt sorry for us, but no one else would meet with us, right? This is in, you know, March or April of 2000, 1998, right? And Jeff wants us to launch in October. And so roll forward. October of 1998, we launch Amazon. I'm in every mahogany boardroom for every movie studio. So I went from can't get a meeting at a dealer association with any, to literally talking about the future of e-commerce to Warner Brothers, Columbia, Sony. And so on the cool thing about that, I had experienced that type of growth at Microsoft, but not that acutely, not that like crazy. And so you're forced as a up-and-coming executive, you got to up your game. And it's not, it's not just like, hey, you know, give me some tougher goals. It's like, it just happens. It's just like, oh God, you know, build the electronics business. Go figure out how to do that. I don't know anything about electronics. Okay, go figure it out. Right? There's no playbook to do it. And the pace is electric, right? Jeff just said, we're going to launch electronics in July of 1999 and toys at the same time. Why? They're big and they're really different. I swear to God, that was the, that was the rationale. And it was cool because it pushed us. Harrison Miller was running toys. I was running electronics. And so the environment that we were in, the goal setting that we were in, the fact that we were making up stuff as we were going, forced a level of crazy. Like I had, I don't think I've worked that hard and learned that much in a period of time in my life. Then on the other hand, the boom and the bust. The bust happens as well, which you probably didn't go through, but it was an ugly time. Like it was the dot-com and Amazon.com and all that stuff. What's the goodness for you personally of feeling that? Yeah. I mean, what happens is you learn that these cycles ebb and flow, right? And, and once you have perspective on that, then you're, you're a little bit less flustered when they happen to you. Jeff took me for a walk and said, you know, Christopher, they build you up just to tear you down. And the best you can hope for is the comeback story. And I think that's right. I think that was wise, wise words. I was talking to somebody about, you know, a reporter or whatever about DoorDash and the stock has been down a bunch or something like this a few years ago. And he's, you know, how do you feel? I'm like, I don't care. And he's like, oh yeah, you do. I know you do. And I'm like, no, I don't. Like, because this is like, you have to have a long-term perspective. Like this comes and goes. But, we went through a period of time where it was like basically of late, not, not the pandemic sort of changed that, where it was like, everything was like... You're the one old guy. Wheel them out. Exactly. Wheel them out. It's gonna be fine. Don't worry about it. But you do get perspective that, and in fact, have you gone through it enough, you begin to realize that the downturns are actually the time where you can, you can gain the most share if you keep your head about you and you've got resources, you can gain the most share. What do you think the role of experience is? I think it's a mixture. I think that, like, in starting a new business where you're trailblazing, I think often having experience in that particular industry is a negative. So, like, if you're, if you're gonna reinvent electronics, you probably don't necessarily want to hand it over to an existing executive from, from Circuit City or Best Buy. And it's not disparaging on them. It's just saying, like, it's an advantage to be able to go, you know, say, okay, we're gonna reinvent this thing and it's gonna be different than the current thing. It's almost an advantage to not know the business. Now, with that said, there's been many cases in my career where, like, I, you know, having gone through things, I realized the pitfalls. And so now I can apply that experience. I'll give an example. So when I, when I joined eBay, they said, Christopher, go fix search. That was my thing. This was 2009. 92% of the sales went through search at that time. So I was like, OK, this is a pretty high leverage situation. I set the goal, right? I set the goal and, and I said, well, I want, I want to optimize conversion. So if I get one point of conversion, I get a bunch of money, basically, for the company. And, and customers are happy, presumably because they can find what they're looking for, right? Well, we didn't have the technology to do this quite right. And so I could only optimize item level conversion, not item times price. And so I said, well, I'm going to go build that system in parallel so I can actually use auctions for the complexity. But I knew in the back of my head, I knew in the back of my head that I could drive item growth and not drive sales growth. I knew item times price, but I said, I'll get away with this for six months and then I'll add in the price component. Sure enough, six months goes by. Bought items is up by some nice amount and sales are basically flat. And the CFO's looking at me like I'm insane, right? So, okay. Now I get the system online, item times price. Oh, sales go up, but you know what? I didn't think about the trustworthiness of the marketplace, right? So what happened is a bunch of the sellers that were good at manipulating the thing, but were not necessarily the best products, were getting to the top of the list. Okay, item times price with a trust constraint. That's it. I went through that for like 12 to 18 months before I got that right. But what did I learn as an executive? This is your experience point. Okay, now I learned, okay, I got to be more thoughtful about goal setting. I've got to, I've got to think about what can go wrong with the goal and how do I set the goal so it's not too complicated because if there's too many constraints, I won't get anything. But if I don't constrain it to some degree, I won't get the outcome that I want. That's a situation where experience helps me tremendously. So I don't think it's a one size fits all answer. I think it's the, I think it's the problem that you're looking at, whether you want to look at it with fresh eyes or whether experience. And the truth is they both can help in. And is it mostly when you're thinking about the different backgrounds, it's just sort of a judgment call. Is it like you're putting together a jazz band and it's very sort of finger feel or you have a way of like, okay, I need somebody who's done this 20 times in this role. I'm willing to take more risk on an up and comer here. I want a fresh, somebody with fresh eyes here. I think a lot of pressure gets put on the recruitment process. I think people think they can figure out in the span of 45 minutes, whether the person's going to, going to be great at this or not. In my experience, it's a, it's very noisy. It's a batting average thing. I think people spend too much time thinking that they can engineer that process to be perfect. I'd much rather, yes, we're going to interview, yes, we're going to look for skills, but then we're going to bring them in and we're going to see whether they succeed or not. And I think where, where organizations fail is they often then don't, when it's not a fit, they don't move on. Everybody says that. What's, why is that? It's very easy to just get complacent, unfortunately. I'll give you an example where it's like, I, you know, you put somebody in charge of something and check in on like week one and they'll be like, oh my God, this thing is so messed up. We got to do A, B, and C. That sounds, that sounds freaking great. That, that makes a lot of sense to me. Let's go get that done. Check back, right? A month later, is A, B, and C done? Nope. Nope. And they moderate. What happens is, you know, it's often they can't, they can't translate it into the doing. And so people don't fix the problem. And as I alluded to earlier, step one shouldn't be to fire the person. Step one should be, I'm not giving the person enough information or enough guidance or enough help to succeed. And, and you got to lean in. You got to lean into that. And then if it doesn't work, you have to move. You have to move on. Being in a company that's growing like a DoorDash or an Amazon circa that period of time forces you to get good at that because you, you're going to fail, right? So you're forced to fix that problem one way or the other. What do you think is the difference between an effective executive at a rapidly scaling company versus an effective executive at running an at scale business, if there is a difference in your mind? It's certainly the ability to adapt and change is the, is the tippy top in the hypergrowth scenario. I think that I like to teach this. I say the thing you're doing now is guaranteed to not work six months from now, right? Guaranteed. And the problem is a lot of human beings, myself included, they're inertia. Like you want inertia, right? You don't like change. You're in a situation where if you don't change, you're, you're not gonna. So I give you an example at DoorDash. So we used to launch cities by sending in college students basically into town, into cities. It was to be a fun job, right? I'm gonna go launch Miami. We'd send a team in there and they would, you know, recruit dashers and train dashers and sign up restaurants and do the marketing. It was a fun job. But then, you know, Tony wants to launch 3000 cities, like you can't, I, we can't do that. So six months from now, I need to have a model go-to-market where I can launch cities and not set foot in that city at all. And we don't know how to do that. And so, but, and Tony wants to keep going. Like he wants the current model to keep going. We can't stop, right? So I now need to do that while I carve out some capacity to build the new model, right? The new launch model. I need to figure out how to get that right. And then I need to put the pedal to the metal as it were to launch. You, like, you need the adaptability to deal with that pace of change. And it's very difficult. It's like, well, this is working, right? Well, yeah, it's working, but it's, it's gonna, it's gonna, we don't have money. We don't have the money to do that. And this gets back to the goal setting. You know, you're like, I want to launch with no people and I want it to be better than the model with people. And then you got to put the right people on that to our conversation about people who've got to go figure out that and DoorDash cracked that. That was our, we figured out how to expand economically remotely and that, that allowed us to expand across the country. Everybody calls it the suburb strategy, but it really was an expansion strategy. That's how we did it. But to connect the dots, if you're an executive that, like, you can be amazingly effective at running at a billion dollar business and like I pull this lever and that lever, but the pace of change there is not necessarily great. That's fine. You're, you're good at that, but you may not be good at dealing in this type of an environment where it's like, it's built in. You have to change. It turns out that's, that's what I like. I like it because you're always like this. I always like to learn and every time I've moved in my career, I've been kind of bored. That was the reason you moved. I get bored often, the reason I moved. And, and I, I felt like being in those environments, there's zero chance that you're going to get bored. Do you agree with the idea that that a lot of these AI first companies or Cursor or Anthropic are sort of much more flat orgs, much more empowered ICs, a much higher expectation for everyone regardless of how up, how high up you are in the org? The IC-ness of the job is much more. Or is, no, there are all thousands of people and general management is general management and that type of thing. Well, I think in the world we're living in and about to live in, I think that the ability to get stuff done, I'm blown away. I'm just absolutely blown away. I don't know about you, but I did not necessarily think we were going to get to where we are in my lifetime. It also says your comment you were saying a second ago, which is just, we don't understand exponentials. And if technology is on a curve, you check in on a year, a lot changes. We are. Yeah, somebody is saying, Claude Code's been out for like nine months or whatever. I was like, really? That's all? You know, just, and so, uh I think that that's going to have huge implications for how organizations are run and your ability to manage teams of humans and AIs is going to go through the roof. I do think organizations will likely be flatter in the future. I do think that even higher up executives are going to be capable of doing things, which is just astounding. I think that, yeah, but at the end of the day, like if you're still managing humans, which you will be, I believe for a long time to come, those are going to require a lot of the skills. I think that generalist skills of building businesses, understanding customers, I don't think those go away. In fact, I think they get more important. More, the value of a generalist goes up for specialist. Yes. If you were to go back to Dartmouth where you went to school and you said, hey, got to go create a course and the title of the course is How to Be a World-Class COO. What's the syllabus and, like, why? Why are those classes on there? I think I would teach how to build, which I think is the job of the COO. Because I think and so the thing that would be on that syllabus, of course, would be we build something and we'd probably start with AI first in this world. We build it with agentic AI. But like, I would teach how to build. I, I would teach how do you go from zero to one? How do you set goals? How do you scale once you find product market fit? How do you build a viable business? That's what I would teach. And I think if you, if you teach that, then you can be a successful COO. The trouble with the COO title is it, it means, it means so many different things to different, different people. And each company sort of has a different definition of what it is. For me, I viewed my job as my job is to build the business. And that's, that's what I would, that's what I would try to teach. Do you think most of those things you actually could teach? Or you would teach them by telling to go build something? I do. I do. In fact, one of the things I enjoyed the most last year is I got to go to the University of Oregon where my son went and I, he just graduated. And I got to help a group of young entrepreneurs who were building phenomenal, like, ideas, like, fantastic ambition. But not necessarily, they didn't know all the, you can teach. And some of them still follow, literally follow up with me weekly on, here's what I'm doing. Here's what, you know, here's, so like, what are some examples of that? One person's building a, it's a, a marketplace to help people with mental disabilities. And if they're building a network of, of it's using video and stuff like that. And, and it's, it's going fantastically well. I'm, I'm super excited about that. Another person was building like, you know, T-shirt marketplace. It was, you know, basically in real time figuring out how to do that. Another person was writing, literally writing, they were writing, writing books using AI and, and trying to figure out how to go to market with, like the range was just like, astonishing. One of the things I learned from this, I'm curious about, I taught this class once where I was at, at Wharton and it was, it was half undergrad and half business school students. And you didn't have to tell me who was who. You know how I could tell which one was which? The innovation level for the undergrads was like off the hook. Like it was like, they were so cool. The ideas were so cool. And, but the business school students had the, the polished, like, yeah, here's the plan. Here's the, but the ideas had been, like, somehow watered down during that process. And so it's like, I wonder if, like you, if there's a way to, like, keep this, this ambition, but maybe then figure out how to. That was, It goes all the way down to growing up. Like you see the creativity and curiosity in a nine year old. Yeah. And it's just beaten out of them year by year. Totally. So in my fake, you know, curriculum, I would hope to keep that enthusiasm and great ideas, but maybe help them figure out. But when you, when you were trying to help the students, what are some of the, like, the ways that you actually taught or explained how to build? Yeah, a lot of times it would be like the one vector would be they didn't understand who the customer was. So like, who's the customer? Who have you talked to? What problem were you solving? Those are the, that's where you start on most of these things. Some people had that kind of nailed, but they were going so slow. You know, I was like, oh my God, this could take forever. So but I teach them how to set goals. One group, the, the marketplace I was talking about, I, you know, I basically told them they had a 10X by December, I think it was. And they're like, well, where, you know, where'd that come from? I'm like, I made it up. And so I'm like, but it seems like a good goal. Like it seems like a reasonable goal. And then I said, and then I said, well, okay, you kind of laughed at that goal, but like, let's talk about it for just a second. Like, what would have to happen to get to 10X? So then, and then they start beginning to work the problem. So, okay, you've got to hire this person. You've then got to get, okay, your bottleneck would be medical or whatever it was. And so, okay, how do we get a hundred of those people? Right? And so, okay, I got to do a BD deal. Okay, great. Let's go do that, right? Did they hit the 10X? They did not. I think they got to 8X or something like that. But that's the, again, there you're hoping where you're like, okay, now I've taught you, you can move way faster than you thought you could. Now what's your next six months goal and see if they've learned, see if they've learned the lesson. So it, you know, the good news is once you've seen enough businesses, you can pretty quickly ascertain, Oh, this person doesn't know who the customer is. This person doesn't know how to run. This person has no technology person and they don't know what they're doing on the tech side of the business. I need to tell them how to do that. So pattern recognition, this is your experience point, matters a lot. You've talked a little bit about this. I can't imagine how much time you've spent setting goals in your career. A lot. It has to be a lot. And debating goals and getting into arguments about goals. Yes. What else can you share on the art of goal setting other than one of the most important things, which is most people are probably not ambitious enough. And when you have incredible things happen when you set a really ambitious goal and expect a lot of people. What else are like do's and don'ts or things that people get confused about when it goes to goal setting? Well, one of the things that I do is I tend to be very initially top down in goal setting. A lot of companies are in teams are bottoms up in goal setting. And I found that that is not a great way to have ambition. So what happens if you say, well, tell me what you can do. Everyone goes off and they, they kind of say, well, how about this? Well, that'll go wrong. It'll come back and be, we can do this. It's not bad. It's achievable. But the problem is they didn't necessarily think as expansively as I would think they should. So I found the following much, a much better process. What should that team do? I think they should do X. I'll make it up. This is where experience comes in to play. I know enough about the area. They moved it, you know, this, this rate last year. I think they can move faster. This thing came online. I'm gonna push them to do X. Now, here's the thing. You got to push them to do X with Y amount of resource. Because if you say do X and X is ambitious, they'll come back and say, great, I can do X, but I need 4,000 people to do X. You say, I want X with Y dollars and people. Come back and tell me Can't get to X, but I can get to, you know, 80% of X. Let me explain why. That's great. This is one of the big tensions with ambitious goals, is you feel like people feel like they're not winning. This happened in in one of the companies I coach, and I said, I said, You should promote that person. You should promote that person and say, That's exactly, because you, you think they did stellarly. And oh, and you should take it on yourself. I said, I set the goal 10% too high. Sorry about that, but I'm so glad we got to 90%. The best execution in the company, I'm going to reward that with promotions and dollars and whatnot and send a message to the company that it is okay to strive for these ambitious goals, even if you fall short. The how you did this, you know, really matters. Like, I've even rewarded teams that like got nowhere near the goal, but like pivoted, learned, didn't make the same mistakes. But they, they had the energy and effort to try to get there. They'll figure out how to get the, the batting average up over the course of time. So that, that, the tops down philosophy, I think is, is very important and you'll get much further faster than if you do, you do a bottoms up. And I talked earlier about the, you know, the, the figure-out the nuance of make, make sure you're going to get what you goal, or you're going to get directionally what you goal, to be, be sure that that's what you want. Where a lot of companies get it wrong is they can be, the goals can be antagonistic to one another. It's like, I need to do X, and you need to do Y, and they don't intersect with one another. And so you, you want the top level goals to galvanize as much of the company. Like, you know, DoorDash just got DashPass, our subscription model, right? That's super important, right? So if you're running, yeah, the grocery business or you're running the restaurant business, you're driving DashPass, right? How are you helping add value to either grow the number of DashPass subscribers or retaining DashPass subscribers? And that unites the teams together. So that's another element of goal setting that I think the bigger your company gets, the more you want to align the teams together. And you're always looking for pockets where you've got, you got it wrong. What do you think about the topic of charisma as it relates to executives? Do you think about trying to be charismatic? No. It's just who you are. You have a way of, of really engaging someone, of leaning forward. That's what you mean by that? Yes. I think that it's developing followership. It's getting someone excited. Yes. That's what you mean by charisma. Yes. Like that, that idea is a job of a leader. The job of a leader is to get people excited about the, the problem that we're, you know, solving or the customer need that we're going to meet. Like, I think that's, I think that's part and parcel of the thing, right? There's some dark times. You invest in a lot of companies, right? And it does not go smoothly. Most of the time it doesn't go smooth. And you're like, you know, there, there were periods where DoorDash was running out of money and couldn't raise money in 17. And, and, you know, people were like, oh my God. It's at those times, you've got to be like, you know, we're good. We're going to get there. I think there's different models of leadership. One is that we're going to sugarcoat everything. Everything's hunky-dory. The other is that, no, people see through that instantly and you lose credibility. Once you lose credibility, you have nothing. Having gone through these things, like, I often just point back to these things. Like, look, lots of people left Amazon, myself included, actually in 2001. Amazon.com. That was the end of Amazon, right? Go back and look at a stock chart. Have some fun with that one. And that wasn't the end. Now I left for other, other reasons, but like, that is a good teachable moment. And there's been lots of those in my career. I'll give you an example. Like, so Uber entered the, this was back in 2017 or whatever, entered the restaurant delivery space, right? And some people were like, you know, oh my God, Uber, they've got unlimited capital, unlimited money, incredible talent. They've got all the drivers, right? Ambition. Travis is gonna, you know, it's over. And so it's in those moments where you got to say, come on, this is a harder problem. This is a different problem than rideshare. We're going to be best at this, right? And then some people are not going to believe you, not going to believe you. I can share examples. I'd be like, you know, many people when I was at Microsoft, like we would enter a space and they'd be like, Oh my God, Microsoft, Microsoft's in the personal finance space. Well, ask Quicken how that went for Quicken. Oh, they won. Oh, okay. Just because you have unlimited money and great people doesn't mean you win. Why is that? I think you got to solve the problem. And often when you're in a company, this gets back to the new stuff as well. Often what happens is that just because the team solved this problem, doesn't mean you solve this problem. It gets back to the, often you don't put the right people on the problem. You don't put enough resources on the problem, you know? Like you can imagine like Tony and I, who, who was showing up at the Cheesecake Factory selling the Cheesecake Factory? It was Tony and me, right? We were the little engine that could. We were like, we're not in rideshare. We're, we're in, we're in food delivery. We're gonna, and so they went exclusive with us, right? It was Travis going to the Cheesecake Factory, pick, no, not a chance. And so elevating that in terms of like the people you put on the problem, making sure those new S curves get started, get to where you need them to go. Not every company's great at, matter of fact, most companies are not great at the, at the hit parade. And so you have a distinct advantage when it is your only business. What else can you say about the, the dynamic of being an executive in the context of an executive team and what, when that's really high functioning, what that looks and feels like. The number one way you can tell is ask them what team they're on. And if they don't say that team, if they say, I'm on the Eng team, or I'm on the marketing team, I'm on the product team, then you've got a dysfunctional team. So you want the leadership team, whatever you call them, M team, executive team, or whatever. They need to be a team, right? They need to work problems together. They need to have each other's back. They need to not be political. I think as I've gotten older, it's, it's become easier for me because I don't want anybody's job. Like I'm not asked, I'm not trying to do this or that. Earlier in my career, you know, I was trying to, I was kind of like a wrecking ball earlier in my career because I wanted to get stuff done. And I realized that was perceived as, as self-serving, got some good feedback from, from a leader at Microsoft about that. And I, at one part of me resisted that because I was like, my goodness, we're not moving fast enough as an organization. But then I realized that my inability to get the executive team aligned or to help get the executive team aligned was holding me back. And so I ended up realizing that that was, that was holding me back to your earlier point. And so I had to figure out how to work within this executive team in order to, to thrive in my career and to get the things done. I think a lot of people don't make that. They don't make that leap. That's a litmus test for you. So next time ask that of somebody, so what team are you on? And see, and see, see, see if you get a range of answers, but you want that executive team to feel like they are, that's their, that's their primary team. Do you generally find it's productive when CEOs want to dive down in and around a functional lead, a VP of this or that, and they go and work on a problem low level? Or do you think it's generally the job of the CEO to work with the executive team, let the executive team express themselves on the company, on sort of their org underneath? I do both, obviously. Like I, you know, I think the default mode should be, should work within the structure that you've built. But then you should also reserve the right to go work the problem. I've learned so much by doing that, by the way. Like you go, then you, you, you know, you go down, you're like, okay, this team's working on this problem. That team, that, that problem has not gone well for the last quarter or whatever. Why? I don't know. of the culture that's developing down in the organization and obviously solve the problem. But like, I try to coach that a lot to executives to maintain that ability to go to the lowest level of detail. And Tony, he can do that all the way, all the way down. Bill Gates is like that. I mean, I used to be terrified to go into a meeting with him because you'd be like, what's he gonna ask? I have no idea what he's gonna ask. It's gonna be, literally, you could come in and be talking about, I don't know, the architecture of the search index. And the next thing you know, you're off on some search business strategy conversation. His range was like astronomical and he was conversant on everything. Asking, you know, you'd find your weakness, which is very impressive. Someone, maybe a former version of yourself or a friend of yours, is joining a company as the COO scale-up company. Yep. Like, I'm starting on Monday. What? And your job is to sort of give them advice, make them, increase their chances of success. You got to study the business. So you, you need to understand the business, right? So it's like, somebody built this tool at DoorDash that was just like unbelievable. It was four hours arrives. It's called dispatch. And you literally could like watch an order happening at real time. And it was the greatest tool ever for this. Literally, I would like pull it. I would order. I'd pull up the tool, you know, or a restaurant has confirmed the order. Right. And then it's like Dasher assigned the order, right? Dasher drives, you see, Dasher drives to the, and then, you know, your food. And so in some, we invariably go wrong, right? There will be customer support interactions and one Dasher locked the keys in his car. And you know, literally I was watching this unfold. This is what during my first week at DoorDash, it was invaluable in understanding what we do. That's the lowest level of detail. And then there was like the aggregate detail, right? And so it's like, and I always coach people to look at data on a, on a daily basis. Don't aggregate it to a month or a quarter or look at it on a daily basis because you'll learn so much more about what's actually going on in the business. So I built this report straight away that had, you know, all the cities and all the, the numbers and the quality and stuff like that. And it, what's cool is it looks like a lot of information, but you're, you're really just like, oh, like something interesting happened in Boston, right? It's like, oh wait, the marathon was yesterday. Oh my God. The quality just fell through the floor. We didn't handle remapping DoorDash correctly because of the, the routes, right? And then you have customer churn and on and on and on. Yeah. And, but then you're like, Hmm, actually there are lots of marathons that happen. And then there's this parades that happen and then there's like, so like how do we handle that? And then you, you know, you go on off and you figure out how to do that. So it's an, it's like an insight generator. Like one of the things I did, I love sorting things. So like I sort, you get the worst gross profit orders from yesterday. And I was like, click, you know, you look at that detail and you're like, oh my God. And then you look at the customer orders and you realize that this person's creating fraudulent orders. Email, right to the, you know, is this what's going on here? Right. Is there a fraud? And then you could, the other side is, oh my God, this is a great order. We should do more of this. I didn't realize that was happening. The Phoenix team did something or the Seattle team did something. Let's take advantage of that and spread it across the country. you know, so understand that, understand the company and what it does. I went on like a journey because DoorDash was very distributed. So when, like my first weeks, I was in Orange County visiting in LA. And then I was in Seattle. I was visiting all the teams trying to get a sense for what was actually happening. The gentleman that ran our local team left in the first three months of my arrival of the company. Kevin, if you're listening, I miss you. No, he came, he came back. Ironically, he did me a huge favor. So I was like, Tony, this is the center of the company's go-to-market. I've got, so I basically said, you're going to have to do these other things. I'm going to go run the local teams for a while. And so it allowed me to actually go and understand the company at a, at a very good level. And it was kind of the heart of the go-to-market. So I got to understand what we do. And I, he did me a, he did me a huge favor. As in hindsight, I was like, oh, that, that actually was great. And then I came back and did the, did the COO job. So it's like, if he's, if your person's coming into a startup, it's like, don't, don't be afraid to like do any job that's necessary because you're in a, you're in a startup. And the other thing, the advice I think I would give is like, you can't solve all the problems immediately. So like pick something, solve it and then solve the next thing is the other thing. You can't solve it all overnight. Oh, great place then. Thank you so much. Thank you. Enjoyed it. This is great. You're very good at this. Oh, thank you. And you're very charismatic. Oh, thank you. You really are. Thank you. I appreciate it. You, you have a way to, to be excited and get people excited. At least that's my experience.