20VC: DoorDash CEO Tony Xu on The Art of Great Leadership Today, Why The Best Give All of the Credit and Take All of the Blame & How DoorDash Have Won The Best Talent Against the Toughest Competition

Tony Xu is the CEO and Co-founder of DoorDash, the company empowering merchants to grow their businesses by offering on-demand delivery, data-driven insights, and better in-store efficiency. Prior to their IPO in December 2020, Tony raised over $2.5Bn for DoorDash from some of the best including Sequoia, Coatue, Softbank, Kleiner Perkins and DST, to name a few. Before co-founding the business in 2013, Tony worked in Product at Square, led special projects for the CEO and CFO at eBay, and began his career at McKinsey and Company. In Today’s Episode with Tony Xu You Will Learn: 1.) How did Tony make his way into the world of startups and what was that founding a-ha moment for Tony with the founding of DoorDash? What were Tony's biggest takeaways from seeing his parents work ethic at such a young age? How did it impact his operating mentality? 2.) Leadership Style: What does great leadership mean to Tony today? In what ways has Tony's leadership style changed over the DoorDash journey? How does Tony assess his own persistence and grit? Through what framework does Tony decide what to delegate vs what to control? 3.) Decision-Making & Risk: How does Tony evaluate his decision-making process today? What does Tony mean when he says, "you have to reduce the scope"? How does Tony think about understanding the interplay of different variants in a decision? Through what framework does Tony assess risk today? How has Tony's approach to risk and decision-making changed over time? 4.) Talent Acquisition: What have been Tony's biggest lessons in acquiring the best talent? What has worked well in the past? In what ways have they not acquired talent they should have acquired? What type of talent worked in the early days? How has that changed? Through what framework does Tony decide between a stretch VP and a stretch too far? 5.) Culture & Diversity: How does Tony think through the breakpoints in the scaling of culture? At what points did Tony feel the DoorDash culture was not what he wanted it to be? How did he react to change it? Through what process has Tony measured the success of DoorDash's diversity efforts? Which initiatives have worked? Are there any that have not? Item’s Mentioned In Today’s Episode with Tony Xu Tony’s Favourite Book: Score Takes Care Of Itself: My Philosophy of Leadership As always you can follow Harry and The Twenty Minute VC on Twitter here!

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  What an episode we have in store for you today. I'm going to dive straight into it because I'm too excited for this one. So I'm thrilled to welcome Tony Hsu to the hot seat today. Now, Tony is the CEO and co-founder of DoorDash, the company empowering merchants to grow their businesses by offering on-demand delivery, data-driven insights and better in-store efficiency. And prior to their IPO in December 2020, Tony raised funding for DoorDash from some of the best, including Sequoia, Co2, SoftBank, Kleiner Perkins, DST and CRV, to name a few. Before co-founding the business in 2013, Tony worked in product at Square. He also led special projects for the CEO and CFO at eBay and began his career at McKinsey & Company. I'd also want to say a huge thank you though to Peshman at Pair, Thomas at Co2, Alfred at Sequoia, Sarah at CRV.

• 0:43Harry Stebbings?

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• 1:24Harry Stebbings?

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• 2:10Harry Stebbings?

  And then receive the proceeds when the painting sells with more than a hundred and fifty million dollars in paintings purchased. Masterworks is the top buy in the art market. So build your diversified portfolio of expertly vetted works curated by industry leading research with Masterworks. And you can find out more at masterworks.io. But it's now time for the show and I'm so excited to welcome Tony Hsu, co-founder and CEO at DoorDash.

• 2:39Speaker 01

  You have now arrived at your destination.

• 2:42Harry Stebbings?

  Tony, it is such a joy to have you on the show today. I've heard so many great things from Sarah at CRV, Alfred at Sequoia and so many more. So thank you so much for joining me today.

• 2:51Speaker 02

  It's great to be with you, Harry.

• 2:52Harry Stebbings?

  I do want to start there with some context because we see the incredible company that is DoorDash today, but it's all got to start somewhere. So what was the founding moment for you at DoorDash and what was that aha moment in a very succinct two to three minutes?

• 3:04Speaker 02

  I wish there was one aha moment that happened over twenty seconds or something, but I guess if there was one, it really happened inside of a local macaroon store in Palo Alto, where the founding team met a store manager who had to turn down hundreds of deliveries. She literally showed us a notebook with payment information of customers and how she had to turn all of those orders down because they happened to be delivery orders. She was a single store manager and she had no ability to fulfill those orders. And I think what it taught us was it showed us that there was this huge challenge, which is more and more orders were not happening inside of her store. But she didn't just have to do with delivery. She obviously had to do that, but she had to figure out everything from acquiring customers to maintaining those relationships, to doing the deliveries, to even fulfilling customer service if something were to go wrong.

• 3:49Speaker 02

  And that was what we realized was the big challenge impacting all physical businesses. We couldn't solve all of that with just a few of us out of my apartment. So we chose one problem to focus on, and that was delivery. So that's really how we got started.

• 4:02Harry Stebbings?

  I mean, I absolutely love it. And I think we owe that dear macaroon maker a lot of thanks for that realization. I do want to ask that, you know, I've heard you speak before about your childhood and growing up, actually, and how instrumental seeing your parents' work ethic was. I want to touch on that. How did that impact your operating mentality and really kind of who? You are seeing your parents working at such a young age for you.

• 4:23Speaker 02

  Yeah, I think some of this is looking backwards on it because, you know, as a child, I think I was just as happy as any other child, even though I probably started work at a very young age. But in growing up, I guess there are probably the two effects as I look backwards. One of which was just the consistency and positive productivity that comes from relentless effort. You know, when I think about my parents' journey into this country, it kind of is that classic immigrant story where dad was getting his graduate degree. Mom was putting food on the table because we had a couple hundred bucks in the bank. And so she worked three jobs a day for 12 years to make things happen. All of those jobs happened to be inside local businesses, one of which was at a local Chinese restaurant where I got to at times moonlight as a dishwasher.

• 5:05Speaker 02

  So I think that industriousness and I think that just continuous sense of effort always led to better and better things for my family. And I think that's something that stuck with me. And then I think the other thing was really independence, you know, because my parents were always out of the house and they were always working. I was mostly left to my own devices, which I think had lots of positive effects, whether it be learning English or how to speak English by watching TV and playing basketball, how to make friends constantly because we're always moving around as my parents were trying to help me get into better and better schools as our socioeconomic status improved. And so while I didn't think about it and maybe it was actually difficult moving all of the time and trying to always blend in, I think that sense of independence gave me quite a lot of resourcefulness.

• 5:49Speaker 02

  Again, this is all looking backwards. As a kid, I was just happy, you know, playing my Nintendo and trying to start a lawn mowing business and doing all these fun things that sometimes kids do.

• 5:58Harry Stebbings?

  I mean, my word, Tony, you are such a self-aware little boy.

• 6:03Harry Stebbings?

  I do want to ask, so speaking of kind of your childhood there, I spoke to Alfred Lin at Secora before the show and he said, you've got to ask about Tony's children. They are such a pivotal and important part of Tony's life. How did becoming a father change your operating mentality? Because it is one hell of a transition in life.

• 6:18Speaker 02

  Well, I'm still trying to figure it out. So I have two young kids. And so I think even though I've had two times to have tried to impart or learn lessons. You know, I think so far it's really reinforced. One, what's important and where to really make sure I get great return on time. And I think number two, it's really taught me to rethink about all things from first principles. You know, it's amazing, you know, I, I think the best piece of advice I was given from our pediatrician was that a baby, so someone under the age of 12 months can develop a new habit in three days. And if you think about how fast that means for their rate of improvement and learning and how they look at the world and everything is new to them. You know, I, I wish I can always carry that beginner's mind.

• 7:01Speaker 02

  And I think it's a nice reminder with each of my kids.

• 7:04Harry Stebbings?

  My word, so you've got them doing new hobbies every three days. It's like meditation, gymnastics, you're going to be a pro by the end of this year. I absolutely love that.

• 7:11Speaker 02

  Yeah, I, I don't know if it's quite running a set of A B tests or things like this, but no, I think it's allowing them to their own devices and, and their own curiosities.

• 7:19Harry Stebbings?

  To us, on the children element, you know, when you compare your childhood and their childhood, naturally it is a different kind of financial world that they're being brought up in in terms of, you know, the wealth that comes from Dord Ash and your successes. How do you think about ensuring they have that same work ethic and ambition when brought up in very different circumstances?

• 7:37Speaker 02

  Yeah, this is something I'm definitely still processing, but with two kids under the age of two, I'm not sure they're quite there yet in terms of, I think, you know, trying to find ways to challenge them or help them be resourceful. But look, I think when I look back on trying to learn from maybe success, looking backwards as a kid growing up, I think a big part of it was my parents really enabled me to pick my own curiosities. Nothing was ever pushed on me, you know, I don't think they even ever saw my report card, maybe ever, actually all the way through college, graduate school, and then certainly not in my earlier years. And so I think allowing me to pick my own curiosities, which obviously means making my own mistakes and making sure that there were constraints so that I had to earn,

• 8:22Speaker 02

  whether it was starting a lawnmower business to buy Nintendo and Duck Hunt and Mario Brothers and all the, you know, games that came with that console, or just making me earn, I think, the things that I had wanted. That's probably the general application of how I think about it for my own kids, but we'll see when we get there.

• 8:40Harry Stebbings?

  Totally agree and it will be a continuous thought, I'm sure for you. Um, having said that, I have absolutely no advice for you. I can barely look after myself, Tony. So the thought of educating children terrifies me. But, you know, speaking of kind of the independent mind to choose your curiosities there. I didn't want to get into your leadership style because I spoke to obviously many friends of ours. But it was specifically Sa and Pejman at Pa who said that you're one of the greatest leaders in the valley. When they didn't say that lightly. So I guess my thought, and it's a very broad and unfair question. But what does great leadership mean to you, do you think? And how do you think your style has changed over time?

• 9:14Speaker 02

  This is something I'm constantly still learning about. But I think maybe the succinct way I've, when I've seen great leadership, I've noticed is there is great followership. And it's not about how many direct reports you have. It's about how many people want to follow you. In fact, when I think about even people at DoorDash, there are many leaders at the company that have zero direct reports, but have lots of followers because of their influence and because of how they show up and how they show their work. And so I think a lot of times, some of the things I've learned about leadership is that you kind of have to be the first to do things. You know, we at DoorDash like to say that's about leading from the front. It's why in the earliest days, even to this day, all of the leaders at the company try to do all of the jobs in the early days. And actually, even to this day, that means doing deliveries.

• 9:59Speaker 02

  That means taking customer service calls. That means making menus for merchants. That means talking to customers every day. And I'm not sure there is quite a substitute for that experience because it ultimately is what allows you to outline the problems for a larger organization to solve and to hopefully have a point of view to be a thought partner in those discussions.

• 10:21Harry Stebbings?

  Can I ask, speaking of leading from the front, often the prohibitor or barrier there is people are afraid of failing. And then they went for it and they failed and, you know, there's internal ramifications. How do you create a sense of security where people feel they can lead from the front and try something ambitious? And if it goes wrong, that's okay, actually.

• 10:39Speaker 02

  Yeah, I think it is possible to have the leader actually get into the details and know the information. And at the same time, give space such that the person closest to the problem can own the decision and own the outcome. And I think the easiest way to do that as the leader is to give all of the credit and take all of the blame. And I think while that's difficult to do at times, because we're all human, even leaders are human. And I think we all want to see success. I think the only way to create that safe environment is, one, you actually know what you're talking about. So you can, you know, be there to commiserate at times with your team or to really help push the needle on problem solving. And then on the other hand, you know, have the team's back when things don't go as expected.

• 11:24Harry Stebbings?

  In terms of like the hard times that one does go through, it was Thomas at Co2 who said, there were many ups and downs. He asked, how did you not give up? And when you think about your persistence, how do you think about that today?

• 11:36Speaker 02

  Yeah, I don't know if there's a simple answer to this, you know, because when I think through the difficult moments that DoorDash has gone through. I don't think there was a singular motivation or motivating factor that got the team through it. I think there were a few things. I think, one, we always had a sense based on what we saw from customers that we were on to the right thing. Even though it was difficult, I think whenever you have something good, the question is like, why would you give that up? So it seems very counterintuitive that that might be an instinct. But I think, you know, more so than that, there's always been this desire at the company that we can do so much more. And that we're just at the beginning. And really, the measure of success isn't some dollar sign or valuation target or, you know, score.

• 12:21Speaker 02

  Actually, if we're doing this right, business is really an infinite game and it should keep going. The real successful organizations, they're generational because they have this enduring component about them. And it's really hard to do that because it's very against human nature, right? Human nature, we like it to have a start and a stop. We like there to be finite, even in competitions, you know, take sports. There's a beginning to the game, there's an end to the game, there's a way to keep score and then somebody wins. But that's not business. Business, there is no A to B. There's a general sense of true north, but if you're doing it right, you're going to be playing an infinite game. You know, our true north is to grow and to empower local economies, and we think we have a long, long ways to go.

• 12:59Speaker 02

  And so when I think about the mission, when I think about the team, the customer validation, when I think about our desire to just get better. I think there's few things, you know, that come to mind of why we would ever give up.

• 13:12Harry Stebbings?

  So I totally get you. The hard thing with like the ever going continuum that you mentioned there is there's no milestones to stop and celebrate or stop and go like, oh, we did a great job. And so can I ask like for you personally, do you ever like sit down and just go, wow, we did something great here and I'm not going to look at the next quarter and the next quarter. I'm going to appreciate that we had a great quarter and the team did awesomely and I did awesomely. Do you ever sit back and appreciate what you've done?

• 13:36Speaker 02

  Yeah, it's a, it's a great question. I, I think you're spot on in saying that when, and it's why it is, business is so tough because it's, it's very against human nature to think that long term and, and to have that infinite horizon in your, in your mind. And the real challenge is we like to celebrate. I think that's human nature too, and, and we should celebrate. And I think it's one of the things that, you know, candidly, I, I'm trying to work on to get better at, but do we look at the milestones? Sure. I think that, you know, the company has come a long way in our eight years thus far. And it's about celebrating when we do see those big accomplishments. And I think at the same time, also remembering that we're just getting started.

• 14:13Harry Stebbings?

  Can I ask, we, we spoke about kind of the good times and the hard times and in both times, actually, decision making and making the right decision is obviously front and center. When you think about your decision making today, I've heard you say a brilliant thing, which is, you know, reduce the scope, especially kind of with problems with high variance. What did you mean by this? And how do you think through tough decisions today?

• 14:33Speaker 02

  Well, I, I think on the first point, when problems are very high complexity, one of the most important things to do in the beginning is to understand what the problem you're trying to solve is. And I think that, you know, you take any very difficult problem, you know, whether it be a complicated math proof, autonomous technology, cancer research, some of the things that, you know, where, where I've seen very complicated problems. I've found that one of the reasons is because we don't actually understand. The scope of the problem. So what I mean by reducing the scope, it's almost formulating or manufacturing a set of milestones of you know where True North should look like, but you're taking a guess as to what each of the mile markers should be as you get to True North.

• 15:15Speaker 02

  And then if you can do that, what you're really doing is you're just trying to take a very big problem and break it down into several smaller problems. The hard part is you may not be right in defining the problem at each stage or in between each mile marker. And so when you reduce the scope, you're actually reducing the complexity and the variance of outcomes. And that way, hopefully you have a better chance at defining a well-defined statement so that you can actually work with your team to go and execute.

• 15:44Harry Stebbings?

  How do you think about understanding the interplay between the different variants?

• 15:48Speaker 02

  Yeah, there's no secret sauce here. I mean, this is a dynamic approach where you have to start somewhere and you have to put in writing ideally a perspective of how you think you can go from where you are to where the target is. As you climb each hill, as you progress from each mile, you're stitching together really whether or not you collected the right inputs to lead to the outcome. And the sooner you can write down that transfer function of how the inputs leads into the outcomes, I think the greater your return on investment will be. But it's this dynamic iterative learning process that starts with having a perspective of how do you move from where you are to where the target is, what the different mile markers in between are,

• 16:32Speaker 02

  reducing the scope of each one of those so you can actually make progress and then keep updating your learning algorithm.

• 16:38Harry Stebbings?

  Can I ask a tough one? It's a question related to kind of decision making around talent. When you hire someone and it's a stretch VP and then it dawns on you that it might be a stretch too far, how long do you give them to prove out whether it is a stretch too far, or actually you were right and it is a stretch too far? How long do you give them?

• 16:56Speaker 02

  That is something I'm still learning, I would say. And I guess if I were to document some of the things I've observed, I think one of the things that's going to matter is how important is this role? If this role is a role in which you believe you have more time in which you can give, and then that certainly would influence, I think, the answer to what you're considering. You know, something else I would think through is what is the potential of this person? Because perhaps you've actually fit them to the wrong problem. One of the beliefs we have at DoorDash is to try to manage people to their superpowers. But especially with folks who have maybe more talent or hustle than experience, you may not know what that superpower is. They may not know what that superpower is.

• 17:37Speaker 02

  And so you may have to trial a couple of different assignments before you can kind of lock on the target. And what a shame it would be if you gave up too soon before you locked on to something where they can 10x, 100x in that area. Those are some of the observations I've made. So I think the answer is going to be different by the individual. I think with leaders, you probably can get information a lot faster. But especially with folks who have maybe more potential than they do years of experience, I think there is when you may want to give it a bit more time.

• 18:09Harry Stebbings?

  What do you think your superpower is, Tony?

• 18:12Speaker 02

  It's something I'm still trying to lock in and on. But I think in looking at things where it doesn't feel like work or where I naturally gravitate towards, I think one of them is actually in recruiting, especially identifying, I think, people before they're identified by everyone else as being world-class in some domain. And I think the second area is I really enjoy spending time on solving problems. Those could be technical problems, those could be business problems. But those are probably the two areas where I'm more naturally gravitated towards.

• 18:40Harry Stebbings?

  It's so interesting you said about recruiting because I think it's totally aligned within your ambassador base. I mean, everyone comments on your recruiting skills. And it was actually Sarah at CRV who said in particular, when we look at the war for talent that we have today, many well-funded, big-banned competitors, and I need to name them, like, when you think about how and why you won some of the best talent that you did, how and why did you win them in your mind? When you, I'm sure you do postmortems, what do you think you did that allowed you to?

• 19:06Speaker 02

  I wish we did more postmortems on the success cases. I think we do lots of postmortems on the not so successful outcomes. But I guess in looking backwards, I think first is taking a investment into markets and people that maybe others aren't, where others aren't looking. And early on, when I think about the team at DoorDash, it was mostly people with more talent than experience. And because we were venturing into a new field where we're trying to create this type of company where you have to be both excellent at engineering and operations. And it's very hyper local where you kind of have to go city by city to compete. And there wasn't a super well-defined playbook. It was being written, you know, as we were creating the company.

• 19:51Speaker 02

  It was actually more important to really bet on, you know, the general athlete, we felt. As a result, the pool for talent there was was actually quite big. You know, if we were all looking for the same machine learning or AI expert in the world, that's going to be a very, very competitive battle for talent. In our situation, we were actually looking for, I think, folks who are not scared about new types of problems, who can fit both business and product and engineering into the same conversation very seamlessly. And so really, we were looking for attributes as opposed to experience. It took us a while. It probably took a year, a year and a half before I started observing the most successful people at DoorDash and writing down what I call the six attributes of excellence.

• 20:33Speaker 02

  And those became ultimately the replicable set, or the playbook, if you will, of what we were looking for.

• 20:38Harry Stebbings?

  Were they immediately obvious? When you think back to some of those meetings, some of those interview proceeds, were those attributes obvious? And how do you draw them out of people? Because I'm constantly asking myself as an interviewer, both for the show, but also, you know, with talent. It's like, maybe they're brilliant and I'm just fucking up the questions, bunnily. So I guess, like, how did they show itself to you? And was it incredibly obvious?

• 21:00Speaker 02

  Well, first, I wouldn't be so hard on yourself. I think one of my mentors told me if you're the Michael Jordan of recruiting, you're probably going to be right sixty-five to seventy percent of the time. And this is coming from someone who's hired tens of thousands of people and maybe, you know, has managed out, you know, a similar number. And so I wouldn't be so hard on yourself. It's a good reminder at times when maybe things don't go well. But, look, I think for every company, whatever those attributes are, you're going to figure out the questions that I think are most successful at teasing out those factors for you. You know, one of the earliest, well, it's still one of our attributes. We call it the bias for action. Someone who's willing to do things in addition to just thinking about things or analyzing things when there's uncertainty.

• 21:41Speaker 02

  And the best tell there was we would ask candidates to acquire a hundred new customers in eight hours with twenty dollars. And that was the entire interview. And they would have twenty minutes to ask me anything they wanted to in order to prepare for that. But we asked many questions to get to that one as probably the best predictor of success against that dimension. And so I think the learning algorithm here is you have to figure out what culture is going to be authentic to your organization. Because that's the only one that you're going to be able to live and breathe, no matter what's written on the walls or on your website. Number two, you have to figure out through testing, I don't know how you would intellectually figure this out,

• 22:19Speaker 02

  through testing and documenting, you know, which questions and assessment methods are best at figuring out whether or not people fit with your culture. And then I think, you know, once you've hired, you know, a few people, one of the second order effects of doing the first two steps is that the initial group will really recruit the next group for you. You know, the first ten people will help you recruit the next ten and the next fifty after that. And that's really how your culture can continuously grow. Now, it also means, you know, the corollary to that is hopefully you set your culture up successfully. Because if you're growing really fast and you scale, you know, something that you don't like, if you, you know, copy something in your cultural DNA that continues to, you know, grow very, very quickly,

• 23:01Speaker 02

  that also has negative consequences if it's something that you didn't like in the first place.

• 23:05Harry Stebbings?

  Can I ask, one often challenge that I see is when there's a exec role within a company and there's a lot of people internally who want it. How do you think about how to bring in an external leader without disincentivizing internal talent who maybe wanted that role?

• 23:20Speaker 02

  Yeah, it's a tough question. I don't think there are perfect answers. I think the only success criteria here I've seen is you have to hire someone excellent where it's so obvious for the person on the inside that this person on the outside can really help their careers and really grow them. You know, because if you think about it, the person on the inside is going to help the external candidate by learning the organization, how the company works, how to get things done. Ideally, the person on the outside is have seen one or two orders of magnitude of scale ahead of the person on the inside such that they can turbocharge the careers of the people on the inside. I think when you can get that to work, I've seen it work really, really well. Otherwise, it can be a challenge.

• 24:00Harry Stebbings?

  I think it's one of the bigger challenges. When you bring in those amazing people, there's the element of delegation and the ability to delegate. I'd love to hear, how do you think about your decision-making process around what to delegate versus what remains in your purview? How do you think about that?

• 24:14Speaker 02

  I don't know if I've thought about the zero to one. I've more thought about, I guess, the degree of delegation, you know, how much of something. And I guess, you know, we can dream big but start small, right? If the ultimate goal, you have to have a point of view and hopefully this is well articulated as you're, you know, starting your recruiting process, what you ultimately like this person to grow into. And it doesn't have to be like super detailed, but you have to have some general sense to both, I think, be honest with yourself as well as with the candidate. But I think when the person is in the door, in order to set them up for success, you probably want to start small because of the information asymmetry of how your organization works versus how they may think your organization works is very, very large. It's almost impossible to estimate. And as a result, I think you're

• 24:58Speaker 02

  probably better served if you start by giving a small scope, something that seems embarrassingly small, but then to grow that quickly as they start garnering success. Because the number one thing you're trying to do for the executive coming in is to optimize for success quickly. That way, they can garner the trust of, you know, those that they've inherited as well as the peers, as well as others in the organization. And that's really how you set them up on a journey to, I think, achieve that north star that you communicated during the recruiting process.

• 25:28Harry Stebbings?

  It's actually Keith or a boy who has the milkshake. Test internally, which is like you start by getting a milkshake for them in in twenty or thirty minutes. And once you do that, it scales and scales and scales. So I totally love that in terms of kind of reducing the scope there. In terms of culture that you mentioned earlier, when you think about the scaling culture that you've had at DoorDash, the company did scale and has scaled so fast. Was there ever a moment when you were like, ah, culture's not where it ought to be or where I'd like it to be? What was that moment and what did you do to turn it around?

• 25:57Speaker 02

  Yeah, this is a constant question, right? Where you're always evolving, I mean, just like your product. You know, I think an organization would be embarrassed if their product looked the same a year later versus today. Why is that not true for your culture? You know, maybe it changes more slowly because, you know, you're talking about people ultimately when you talk about culture as opposed to, you know, software or other types of products, but it ideally is always improving. When I think about, you know, some of our operating principles, maybe it wasn't that our culture went south. I think those instances are maybe when we didn't recruit the right people or we promoted the wrong behavior. And those are few and far between, actually fairly easy to correct if you hold yourself accountable.

• 26:37Speaker 02

  I think the harder parts of improving culture are trying to actually change and add to the culture. You know, for example, in twenty fifteen, maybe between twenty fifteen, twenty sixteen, so year two and three of our company's life, we realized that the early team was not very diverse. So very early on, we added this value, actually, we added it in twenty seventeen about making room at the table as one of our operating principles and thinking outside the room because we started becoming more and more decentralized, where we had, you know, general managers physically located inside different cities. And so we weren't always in the same room anymore. And adding those wasn't a way to just, you know, make ourselves feel better about our culture.

• 27:18Speaker 02

  I mean, we added those values by also adding operating metrics and trying to create mechanisms internally in which we can actually make true those values. And so that was a lot harder though, because you're now almost saying, okay, add something to your personality. That's like what, you know, culture is like a team's personality as opposed to an individual's personality. But changing or adding to your personality is very, very, very difficult versus adding some feature to your product, right? And so that was something that only could happen top down. But then it took the organization to bottoms up, create the mechanisms that they would organically adopt and see not only the positive organizational outcomes, but also the positive business improvements.

• 28:00Harry Stebbings?

  What were one or two of those mechanisms? And I ask you because I I hear a lot of companies that say, oh, we instill diversity and inclusion as a core culture point. And it's like, great, how are you measuring that? Like, what does that actually mean? Like, what mechanisms did you put in place?

• 28:14Speaker 02

  Yeah, I mean, the first thing is you have to actually be able to measure these things. And for example, what's the first thing you can measure this can start small and say, what's the representation inside your teams? Does that match the representation inside the decision makers? You know, it's a it's a very easy question and and then you can go team by team, that same question. And that one question, or or I guess two types of data points to collect will probably take years to make improvements on. I mean, we're almost there where the representation at the company and the representation of the decision makers are even. But we're, I mean, twenty fifteen, twenty twenty twenty one, so six years out of our eight years, we've been working on it. Seventy five percent of our lifetime history, and we're still not there. And so it takes real work.

• 28:57Speaker 02

  And then it's just going through that funnel, you know, who are the people that you're recruiting? Why are the funnels the way they are? Because we're all always gonna hire those that look like us or sound like us or more in our circles and et cetera, et cetera. That's gonna be the general bias. And so how do you enforce diversity in the funnels? How does that diversity carry through the funnel? And then how does that diversity then translate into someone's career at the company? When it comes to things around promotions, assignments on key projects, et cetera, et cetera, et cetera. You know, thinking outside the room, for example, that was one where, I mean, it's less relevant during COVID. But in a pre pandemic and, you know, maybe post pandemic world where we're gonna be in some hybrid version, all of us of sometimes being co located, other times being dislocated.

• 29:41Speaker 02

  How do you make sure that the person who has maybe the most disadvantaged voice, because they're not in the room, actually gets to speak first? How do you make sure that the most junior person, maybe closest to the problem, speaks before the senior person, who has the quote unquote overview or oversight of the team, speak first? I I think those are some of the mechanisms that you really have to practice in order to make true the cultural belief.

• 30:05Harry Stebbings?

  Do you wanna come back to the office?

• 30:06Speaker 02

  I do. It's one of the things I miss. I think this is such. A organizationally specific question. I definitely can see it working for for for different groups. But, you know, at least for us, DoorDash always had very electric kinds of energy levels in all of our offices. And this isn't just, you know, the the San Francisco office, but across all of our offices globally. And I think that it's one of the things that not just in hearing about it during some of our internal team conversations, but also seeing it in some of our employee voice surveys, it's something that a lot of people want to do.

• 30:37Harry Stebbings?

  Speaking of the relentless energy there, final one before the quick fire. Little birdie tells me that you work every Sunday. Talk to me about working every Sunday. Like, has it always been that way? Why? How do you think about the working every Sunday?

• 30:50Speaker 02

  It started because we just didn't have enough drivers. And so it was really, you know, part of just making sure that we had enough drivers on the road and doing deliveries. But since it's morphed into, I guess, two areas. One is a reflection on my return on time. If I looked back at the week, did my week actually reflect the priorities for that week or the priorities for a slightly longer time horizon? And if the answer is yes, then that probably was a pretty good week. But if the answer is no, I probably shouldn't wait. I should just change my upcoming week such that my priorities can align with where I'm spending time. And so I found Sundays to be useful for that. You know, the other thing I found useful for Sundays is is candidly just some thinking time

• 31:33Speaker 02

  and how how important and sometimes increasingly rare that can be. And so those are the times in which I've spent Sundays. But it's that balanced with family time, right? And that's kind of how the weekends are spent.

• 31:45Harry Stebbings?

  I totally get you. I do want to move into my favorite, though, which is a quick fire, Anthony. So I say a short statement and you give me your immediate thoughts. Does that sound okay?

• 31:53Speaker 02

  Let's do it.

• 31:54Harry Stebbings?

  So what's the favorite book and why? What's the must read?

• 31:56Speaker 02

  I guess the one that has had quite a lot of influence on the building of DoorDash is The Score Takes Care of Itself by Bill Walsh. And just this notion of trying to chase excellence as opposed to the scoreboard. That has been, I think, the defining history of the company and how and a big part of how we operate.

• 32:13Harry Stebbings?

  What's the hardest element of your role stay with DoorDash?

• 32:16Speaker 02

  Management bandwidth. Making sure that I'm giving the right amount of energy and attention to the right projects, especially when projects have different capital allocation, different horizons in terms of, you know, time investment before you actually can expect to see a return and just we have so many great people.

• 32:34Harry Stebbings?

  How many direct reports do you have, Tony?

• 32:36Speaker 02

  Ten, so it's manageable.

• 32:38Harry Stebbings?

  It is, that's close. I've heard that eight is the sweet spot for direct reports from thousands of employees, that is what I've been told.

• 32:45Speaker 02

  Yeah, I think as, as I'm sure others who've been on your show will tell you, there are certainly, I think academically correct answers here, but most of the time you can make any org model works as long as you're actually solving problems with whatever your organizational model is.

• 32:59Harry Stebbings?

  One from Samuel Shah, what's the greatest personal sacrifice you've made in the pursuit of DoorDash?

• 33:04Speaker 02

  Hmm, mental consumption, I guess. I mean, building a DoorDash is an all-consuming effort. There is one hundred percent, a hundred and twenty percent of the time, you know, spent thinking on it, even if I'm not spent working at the company, especially for someone who is very curious, you know, has done everything from cancer research to other things and like a lot of different areas and, and different types of problems. You know, that's one of the big sacrifices and obviously a, a big part of that is sacrificing time with friends and family at times.

• 33:31Harry Stebbings?

  What three traits would you most want your children to adopt?

• 33:34Speaker 02

  Resilience, curiosity and kindness.

• 33:38Harry Stebbings?

  Which leader do you most look up to and why?

• 33:40Speaker 02

  I'll have to think on that one. Most, you know, I, I think people who have done big things for the first time, that tends to be the type of leader I really respect because there probably are far more things they had to overcome in order to get to where they are. One of those leaders that comes immediately to mind was Barack Obama. That's a, you want to talk about a tough job, that is a job where I'm not sure what the definition of winning is. But, you know, I think his personal ascendance into that job and the probably circumstances I'm not even aware of that he had to have overcome are, are historic to say the least.

• 34:15Harry Stebbings?

  Now, you can have a choice here, penultimate one. You can either choose best board member and why, political, may not want to do that one, or you can choose the most memorable board meeting and why.

• 34:26Speaker 02

  I think one of your earlier questions was something to the effect of why DoorDash never gave up or why it doesn't continue to give up. And I think that there was, um, one of these opportunities that came up in which we're discussing as a board and I think. I think it took thirty seconds for the board to look at one another and said, why would we ever give up on DoorDash? And I think that was unexpected, because I think it was a small group of folks at the board meeting, but it was also like, you don't talk about these types of things all the time, right? So you don't exactly know what to expect when there might be an opportunity to partner or to take a different strategic direction with a company, how everyone would react. And when it was so in unison, what the response was, it was a pretty incredible feeling.

• 35:11Harry Stebbings?

  Yeah, that's a pretty special moment. Final one. What do the next five years hold for you and for DoorDash? Paint that picture for me, Tony.

• 35:17Speaker 02

  Well, I mean, for DoorDash, we have a long ways to go. We're trying to build the biggest local commerce app, and we're also trying to build the biggest local commerce platform, in which we're giving tools to merchants so that they can create their own digital businesses and really compete in today's digital economy. And so when I think of both of those aspirations, there's a lot of work to do. And I think it'll probably take longer than five years to achieve those goals. But if we can do that, then I believe we will achieve the mission of both growing through our marketplace and empowering through our platform, these businesses to compete. And so for me, I've always had a very simple decision-making framework for my life choices versus, say, some of our business choices, which is where am I going to have the most fun and the least regret?

• 36:02Speaker 02

  And I think that's going to be exactly where I am. And so it's going to be, hopefully, evolving as a leader. It's hopefully I'm trying to add to our team's personality, so improving our culture and making sure that our best people get to do the best work of their lives at the company.

• 36:19Harry Stebbings?

  I love that as a decision-making matrix, the way you spend your time. But Tony, I've wanted to see this one for a long time. So thank you so much for joining me today, and I've loved the discussion.

• 36:27Speaker 02

  Thanks, Harry. It was fun.

• 36:31Harry Stebbings?

  I mean, I think one of the most humble and kind leaders I think I've ever had the joy of having on the show. If you'd like to see more from Tony, you can find him on Twitter at T underscore X U. Likewise, it's always great to see you behind the scenes at the show. You can do so on the 20 minute V C dot com. However, before we leave you today, Mercury is building full stack banking for startups, applying in under 10 minutes from anywhere for FDIC insured bank accounts, physical and virtual debit cards, domestic and international wires, and integrations with Gusto, Stripe, QuickBooks, Plaid, and basically every other tool your startup uses. They also offer unusual features like API access, custom team management, and their newly launched Mercury Treasury, a cash management product for high growth startups. And they'll even help you build your startup

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