Leading with empathy | Keith Yandell (DoorDash, Uber)

Keith Yandell: Every business that you have heard of has gotten rejected by at least a handful of venture capitalists at one point or another. And so that drive to keep going if you believe in the business is critical, absolutely critical. I mean, we were weeks of runway situation and had been told no by everyone. And it was just Tony’s drive, really, to keep going. And the way he explains it to me is it’s just the difference between a founder and a non-founder. If you’re really a founder, you just have to find a way. You have to keep going. There’s no question. And I mean, that’s the only advice I can give folks, is it only takes one yes. But you got to keep going.

Lenny: Welcome to Lenny’s Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today’s most successful products. Today my guest is Keith Yandell. Keith is a longtime leader at DoorDash, where he’s been for about seven years. And in that time, get this, he’s led the legal team, the HR team, the marketing team, the customer support team, and currently he leads the BD and corporate development teams. Before DoorDash, he led litigation at Uber. He’s also managed folks like Gokul Rajaram, who was previously on this podcast and who suggested that I have Keith on. And damn, was he right. Before I had this chat with Keith, I didn’t know that much about him, but now you can count me as a huge Keith fanboy. I suspect you’ll feel the same way after you listen to this episode. I’m just going to jump right in and bring you Keith Yandell after a short word from our wonderful sponsors.

Keith Yandell: Thanks so much for having me, Lenny.

Lenny: First off the bat, I just want to give a big thank you to Gokul Rajaram and Micah Moreau for suggesting you be on the podcast, helping make this happen, and also just suggesting a bunch of questions to ask you. So, I hope you’re ready to be in the hot seat.

Keith Yandell: Definitely as ready as I’m going to be. And those are two good folks to talk to.

Lenny: Awesome. And Gokul’s been on the podcast. Maybe we’ll get Micah on the podcast at some point. I wanted to start off with a story. Apparently, there’s a story of you interviewing what is now your VP of engineering. And I hear that in the interview, you called him an asshole. And more interestingly, he joined DoorDash because you did that. Can you just talk about that story and share that story?

Keith Yandell: Yeah, actually, it wasn’t during the interview. We were debriefing. And for me, one of the top things I always hear about DoorDash from an executive standpoint when we do the internal survey is it’s a “no politics, no asshole” culture. And I’m not one to swear a lot, but after interviewing Ryan Sokol, who’s now our VP of eng, he was just kind of aloof. He came off as aloof to me, really curt answers. And I just didn’t have a great feeling about him. And I pride myself on being able to discern when people are really engaged or not. And I went to Tony Xu, who’s our founder and CEO. I said, “Tony, I think this guy’s a jerk. I don’t think we want him at the company.” And Tony was great. He said, “Keith, I want you to just have dinner with him, please, because I got a completely different impression. And if you have dinner with him, and you still think he’s a jerk, we won’t hire.”

And so I ended up meeting Ryan down the street. We actually live in the same general area. We went out to dinner, and I started right away. I said, “Ryan, during the interview you kind of seemed like an asshole. Are you an asshole?” And he was so great. It completely changed my perspective in a good two minutes. He wanted to know what he had said. He said, “I’m super embarrassed, and what could I do differently? Regardless of how this works out for me in this circumstance, that’s just not how I want to be perceived.” And we talked and joked about the things he had done, and he kind of told me the background for how he reacted or why he reacted the way he did. And by the end of the dinner, we ended up staying super late. We had a couple beers afterwards. Ryan and I have become really good friends.

And six months later, he told me that one of the reasons why he joined DoorDash was that we were going to blackball him potentially from joining just because of his attitude, because his perspective is life’s too short to work with people you don’t really enjoy, and a lot of people pay lip service. And he knew he was going to be a tough hire for us at the time. And the fact we were willing to go all the way down the path and have someone super qualified but didn’t meet the culture bar, for him was what pushed him over the edge to join the company.

Lenny: I love that. I love the directness of that meeting, of just like, “Are you an asshole?”

Keith Yandell: Think about it, right? And if someone really was a jerk, they probably wouldn’t have taken it very well. Right? It’s just like when you’re interviewing someone, giving them tough feedback after the interview if there’s an area of concern, but you otherwise like them, can be a really great way to see how they would interact with you personally as well as how they take feedback. And so that was my learning from the situation, is if you really enjoy an interview, except for maybe something on the culture side, to give the direct feedback and see how people engage.

Lenny: This touches on another question I wanted to ask you, which is just about DoorDash’s culture, which feels really unique, just feels very driven, very pragmatic. There’s a story I heard where when you guys celebrated one of your biggest milestones, you bought the cheapest champagne and plastic flutes, and I think the founders brought that to everyone. Could you just talk about what makes DoorDash’s culture so interesting and unique? And maybe if there’s a story of just a microcosm of what DoorDash culture is like, that’d be awesome to hear.

Keith Yandell: Founder-led companies tend to take on the personality of their founders. And if you spend any time with our founder, Tony Xu, you realize that he’s a humble leader. He’s competitive. He really wants to win, and he’ll do whatever it takes to win. And the example you’re referring to, I think, is when we raised our Series D funding, which was a really tough fundraise for us… We had very little runway left. We almost went out of business, and it was a huge relief when we had finally gotten the funding secured.

And I remember I was in a meeting. I was running policy and communications, among other things, at the time, and I was in the meeting with a couple other folks, and we were talking about the press release strategy. Tony was there. And someone ran down and got some, I think it was Korbel or something champagne and some plastic flutes. And one of the women who was in the meeting with me was going to leave to go put those together. This is a very smart woman, who I think Tony recognized could add more value. And he said, “Whoa, whoa, whoa. You stay here. I’m going to go put together the champagne flutes.” And he called the other two co-founders, Andy Fang and Stanley Tang. They came, stayed up all night, put together… I don’t know… 500 champagne flutes, plastic ones, for this cheap champagne and let the people who are closest to the problem try to work out the comms piece. And I do think that’s one great example of the culture.

The other thing I think that really exemplifies DoorDash’s culture is a level of customer obsession. And that manifests in a few different ways. We have a program called WeDash, where, four times, a year all employees are required to go do deliveries. And I love doing it. I do it more than four times a year, and I usually take my daughters with me. And one time, I was out with my daughter, who was eight at the time. We got a delivery, and it was not the best delivery. There’s clearly something wrong with the system. We got a sandwich and a coffee, and we’re supposed to drive 18 and a half miles to drop it off. And that didn’t make sense for the customer. It didn’t make sense for us as drivers.

And she’d gotten to know Tony over the years, and she said, “I really want to call Tony and tell him this thing’s broken.” “Honey, I like my job. I’d like to keep my job. Can we not call Tony right now?” But she was adamant, and I was so proud of her for feeling so strongly that she wanted to fix this thing that was broken. I figured, “He’s not going to answer anyway. We can just call.” So call. Tony picks up on the first ring. And I’m like, “Oh, this might go badly.” And she just lays into him. She said, “This is going to take us 36 minutes to drop off. The coffee’s not going to be hot. How could you allow this experience if you really care about your customers?”

Lenny: Whoa.

Keith Yandell: And I kind of sucked in my breath and said, “Well, that’s how my time at DoorDash ended.” But Tony was great. He was like, “Hey, Alice, we have people who do deliveries for months. We have people who deliveries for years, and they’re always providing me feedback. And this is one of the most insightful pieces of feedback I’ve gotten recently. And you’ve only been dashing for a few different times.” And by the time we got home, he’d actually sent an email out to the product organization, calling out the problem, suggesting the fix. And they were already working on it. And that shows the bias to action that I think really is at the heart of DoorDash, alongside that customer obsession. And it’s not unusual for Tony to do customer support. It wasn’t like just because he heard this from my daughter that he actioned it. He does support every day. And again, this goes back to that level of humility and companies really taking on the ethos of their founder.

Lenny: What an awesome story. I want to chat a bit more about the, what is it called? WeDash? Is that the program?

Keith Yandell: Yeah. Yeah.

Lenny: So you say that you’re supposed to do it how many times a year, four times a year?

Keith Yandell: Yeah, at least four times a year.

Lenny: And then you said that you do it a lot more often. How often are you doing it? And then, is there any other fun stories of that experience, someone like you delivering someone’s sandwich?

Keith Yandell: I probably do it once a month.

Lenny: Wow.

Keith Yandell: And there, there’s all kinds of great WeDash stories, but I don’t know how interesting they’re going to be to the broader public because, for me, it’s just about getting out and experiencing the product. I almost always find something that’s broken, and I send an email to… We have a Slack channel that’s devoted to experiences via WeDash. It’s everything from, I found a bug once where it wasn’t routing you necessarily the fastest route. It was going using straight line as opposed to road. That was something that we fixed. And for me, the best parts about WeDash are the experiences, the interactions with the restaurants, the interactions with colleagues. So I’ll go delivering with Ryan Sokol, the head of engineering. I’ll give him a hard time about refining the product and things like that. But that’s, by far, my favorite WeDash story, is the one with my daughter.

Lenny: That’s a good one. So at Airbnb, we actually had a similar program, where Brian wanted everyone to be a host on Airbnb. But as you can imagine, that’s much harder. Not everyone is able to. Not everyone has a place to. So it’s always kind of a challenge to make people do that. I imagine DoorDash is a lot easier because a lot of people can go around and deliver things. But yeah, such a killer idea, such a good way of dogfooding your product.

Keith Yandell: Yeah, it’s a good point, but not everyone is able, for a host of reasons, at DoorDash to do it. And so there are alternatives. So you can do customer support, for example, in lieu of actually going and doing deliveries. It’s just about making people have empathy and get closer to the product. It’s also, going back to the culture point you raise, it’s a great way to weed out people that maybe we wouldn’t want to work with, right, because not every software engineer wants to hop in their Tesla and go out and deliver McDonald’s to some kids. Right? It takes a certain level of humility, a certain amount of customer obsession, to even sign up for that. So we’re really vocal during the interview process that this is something that’s expected. And it serves as a governor to attract the people that we think are going to be most successful at the company.

Lenny: I love that. Imagine all your programs have the Dash in there somewhere. Something Dash.

Keith Yandell: We try. I think when I was head of a marketing, we did a much worse job. I think we’re doing much better now.

Lenny: Nice. And Airbnb, it was always Air Something. Okay. So, I think one of the most interesting things about you and your background, and maybe unusual things, is the number of teams that you’ve led over your time at DoorDash. I have a list here. So over your time at DoorDash, you’ve led the HR team. You’ve led the customer support team, led the sales team, the marketing team. Now you lead the BD and corp dev team. Initially, I think, you were chief legal officer. So here’s my question. As someone that, I imagine, doesn’t have a ton of expertise and experience in a lot of these areas, how are you able to credibly lead these teams? And I ask partly because as a founder, you have to learn how to lead teams and people that you don’t actually know what they’re doing as well as they do. And so I’m just curious what you’ve learned about being able to lead teams in such disparate skill sets and functions.

Keith Yandell: Yeah, the one thing I’ll say is, I did not run sales. That’s maybe one of the very few non-technical functions I did not lead. But the question is a good one. And I had massive imposter syndrome the first time Tony asked me to take on something that I wasn’t a subject matter expert in. And I told him I didn’t want to do it. And he had me read this book called Range by David Epstein. And the general thesis is that generalists are better than specialists. And it goes through all these examples of about how Nobel Prize winners are usually amazing in something other than the field that they actually win the Nobel Prize in.

And Tony believes pretty deeply in this philosophy, and the way he explained it to me is as follows. If you want to achieve a 10x outcome, hiring someone that’s an expert in the field, it’s maybe unlikely you’re going to achieve that 10x outcome, because they’re likely to do things the way things have always been done. So you might achieve incremental benefits, but the odds of completely reinventing the system and doing something that’s vastly superior to others is much lower. And he said, “I know you don’t know how to do this stuff. That’s why I’m putting you in the role.” And I said, “Okay.”

So, first thing he helped me do was believe that I could add value here. And then, the second thing for me was to go out and find the best people that really were the subject matter experts, and add the value I could to help them be successful. And I found that they were actually really attracted to wanting to work with someone like me, who came into the interview process and said, “Good news, bad news. I don’t know your field anywhere near as well as you do. Here’s the ways I intend to help you. Here’s what I think you can provide. And at the end of the day, I’m going to get out of your way.” And that’s really proven true. So, I ran marketing. Hired initially a head of brand, Kofi, who now is our CMO. Hired ahead of legal, who’s now our GC, Tia Sherringham. And these people have really just excelled at their function and, with the warmup that I was able to provide, have really proven that they’re much better at the jobs than I was.

Lenny: You don’t strike me as someone that is trying to build empires and take over all these teams. I imagine this kind of came at you because you’ve been doing a great job at other things. Is that how it worked? And, I guess, is there anything, any lessons there that you can take away?

Keith Yandell: Yeah, hundred percent. I run a 12-person org today. So I’ve gone from running 1,500 people in the company to 12. And for me, people talk a lot about hiring people better than you are. People don’t talk a lot about what you do when you hire those people. And if you really care about the company and your long-term brand as an individual, as a manager, you realize what you want to do when you find the person that’s better than you is you want to slowly get out of the way. And it’s really good for the company. It’s my favorite part of my job, is seeing people that either I’ve hired or managed be successful on their own.

And I think it’s a big part of our success, is this desire to be successful, regardless of who’s in charge. And that comes from the fact when I joined DoorDash, we were getting our tails kicked. We were in fourth place in the space. Uber had just launched food and rocket to market share leadership. And I think that was really good for us as a company because we realized unless we all worked together, and it wasn’t about who was doing what or things like that, we weren’t going to have a shot at being successful. And I think that ethos has really pervaded and persisted since then.

Lenny: Yeah. I think most people don’t realize DoorDash actually has the biggest market share in food delivery. Imagine that’s still true. I’ve always seen these line charts of market share, and DoorDash is always the top. And I think people kind of think Uber Eats is winning, but it’s not true.

Keith Yandell: Yeah, I mean, the category charts I’ve seen are consistent with what you said by a pretty wide margin. But we try not to focus on things like that. We try to focus on the customer experience. And it’s humbling in our space because we’re doing millions and millions and millions of deliveries a day, and those deliveries will go wrong, no matter how hard you try. And we read those experiences. We do customer support, and we understand that there’s a long ways to go. So we’re just getting started, and we know that.

Lenny: You mentioned that you ran this 1,500-person org at one point, and something that I’ve heard you do, that helps you do that, is you have this document that you put together that kind of explains how to work with Keith, and also, just broadly, how things work at DoorDash. Can you talk about this document, and why you thought it was necessary, and kind of the impact something like this has had? And then we’re going to share a link to a redacted version of this in the show notes.

Keith Yandell: One thing I’ve learned is it’s super hard to scale culture, especially when you’re growing as fast as DoorDash has since I joined. We were two or three X’ing the company, from a head count perspective, for the vast majority of my time every year. And so one thing I noticed is, it’s hard to come into a place and be new and understand how things work and what it means to be successful there. And so the idea was to do our best to scale that. And one thing that Tony taught me is one thing that scales really well is written work [inaudible 00:19:16]. And so I put together this document. There’s three basic subject matters. It’s my expectations slash what I’ve seen as traits in successful people within the company.

Two are how I can improve, like basically, feedback I’ve gotten in things I’m working on. For example, I’m a litigator by training, and so I tend to argue about things, even if I agree with people to the test levels of conviction. And I got feedback from my team that was really confusing because I’d be arguing against something, and then we would execute that exact thing. And so I try to be transparent about that and explain how I work through problems, but also in saying, “Hey, this is something I’m trying to improve on, is not being quite so argumentative for sport.” And then it talks about what my commitments are to team. So, “I’m committed to finding you your next job even if that’s not at DoorDash. Life’s too short to be in a job you don’t like,” things like that.

Lenny: I’ve heard from a few people how impactful this document ended up being. I guess, what impact have you seen this have on the org that you’ve run in the company and then, yeah, any other examples of just why this is powerful? Because I imagine some people listening are like, “Oh, I should do something like this.”

Keith Yandell: Yeah, I mean, for me, one of an executive’s main jobs is to attract and retain top talent. And going back to why people have joined DoorDash, Kofi Amoo-Gottfried, who’s now our CMO, joined me as head of brand when I was running marketing. And it’s comical because this person is a legend in the marketing space, and I had no idea what was going on. And so convincing him to join, I was really nervous about. And the point where he decided to join, I had sent him this document. He wanted to know what it was like to work with me. I said, “Well, I’ve actually written that down.”

Keith Yandell: And he later told me that that was a really important factor for him, that someone was so transparent about their areas for growth, how they thought they could be helpful, and he liked the fact that I knew that I didn’t know. And so he knew he was going to have a lot of autonomy on the role, and that was really important to him. But more broadly within the organization, how it’s been helpful is just being able to have people engage with me in a way, and with the company in a way that is so consistent with the culture from day one. I’ve had people come and tell me, that I’d never met before, that they’d read the doc, even if they’re on a different team, and just how helpful it’s been to try to acclimate to this fast-paced environment, where you’re learning while drinking from the fire hose, effectively.

Lenny: Yeah, that makes sense. Touching a little bit on it, you talked about all these amazing people you’ve led and how you’ve been able to do that. Something else I’ve heard that you do that’s pretty unusual is you help people that you manage find their next job, which may not necessarily be within the company, maybe at another company. You kind of help them land it and find something else to do. I’ve never heard of that before, really. I’d love to hear why you decided to do that, how you do that, and just the kind of impact, second-order impact, maybe, that has, maybe that leads you to be doing this.

Keith Yandell: It wasn’t a calculated decision why I started doing it. Then I gave it a lot of thought because I was afraid that I might get some blowback when people started taking jobs elsewhere. And as I thought about it, I realized it really is better for the company to have that type of open dialogue with people that work on your team. I think that’s true for a few reasons. In this “How to work with Keith” document, I say, “I will help you find your next job.” And what that means is, number one, people are going to be transparent with you, or more transparent, if they’re looking for something else or if they’re not happy. That’s going to allow you to lay the foundation for a backfill so you’re much less likely to get surprised when someone leaves.

Number two, what’s going to happen is if someone runs a blind reference on me at this point with someone that I’ve managed, which in the current environment is more and more common, people diligencing the managers, what they’re going to hear is, “Keith’s going to put you first.” And I think that’s really motivating for a lot of people. So if you’re thinking on a five-, 10-year horizon of your career as a manager, whether you’re an entrepreneur hiring people into your company, whether you’re a product manager who’s trying to build a team, building that long-term reputation, I think people take much too shortsighted perspective on that.

And so now if I get a blind reference, people are going to hear that, “It’s not all about the company. It’s not all about Keith. It’s about you and your career,” and that’s going to pay back 10x. Maybe you lose one really talented person, but they probably shouldn’t be there anyway. They’re probably going to leave anyway. And this way, you can participate in that and really drive value for them, as well as for the company in the future, by creating a much better reputation for the group of managers. So it’s been really helpful for me. I keep in touch with a lot of people who have left, and we get a lot of boomerangs, too. There’s a lot of people who leave DoorDash and come back. And that’s something I love seeing because it shows that people have gone out and seen what else is out there and realized this is the right place for them.

Lenny: Can you talk a bit about how you operationalize this? Because this is just out there. “Tell me if you’re thinking about a new job, and I will talk to you through your options and help you find something.” Or is there anything else there for folks that maybe want to offer this to their employees?

Keith Yandell: So, first of all, I put it in this document. And so I say how I run one-on-ones in my “how to work with Keith” document, and the last 10 minutes of my one-on-ones are career development conversations. That’s a really fertile ground for having the discussion. But for particularly more senior folks, if I get pinged for a GC job, or when I would get pinged by a recruiter for a GC job, I would forward that to Tia Sherringham, who’s now our general counsel but was basically head of legal for years before she got the general counsel title. And I’d say, “Hey, Tia, I don’t know when this job’s going to be available here. I’m still liking what I’m doing. I think I’m still adding value. If you think it’s time for you to leave, I think this is a really good opportunity.”

Lenny: Wow, that’s [inaudible 00:25:12].

Keith Yandell: And I say, in addition to that, “You’re going to learn the questions they asked during the interview process. You’re going to learn what type of qualifications they’re looking for. And if I’m not getting you that experience, you can tell me.” And thankfully for me, Tia decided to stay and has now grown into the general counsel of DoorDash, and doing a much better job at the role than I ever did. But she had the opportunity to leave, and I think she learned from some of those in-bounds and the experiences she had.

Lenny: Wow. That’s amazing, that your bosses forward you recruiter pitches to go work somewhere else.

Keith Yandell: Think it made her want to stay. Right? If I wasn’t invested in her success, she could have left any time and gotten a job, super qualified. But I think she felt a sense of loyalty based on my sense of loyalty, and I think it worked out best for all involved.

Lenny:

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Something else I hear about you, which I’m sensing as we chat more and more, and I could see why this is true, is that on the DoorDash kind of C-suite and board meeting and board in general, you play this really strong unifying force that helps the group come to fast decisions on really complicated topics. And I’m curious. One, would you agree with that? And two, what is it that you do that helps a lot of strongly opinionated people come to decisions on really complicated decisions?

Keith Yandell: I hope that’s true. I think that, for me, it all comes down to empathy. And what I mean by that is, you have to understand what different people’s motivations are in the room. Different people are goaled on different things. People come from different life experiences and different work experiences. And I think it’s really important to make each person feel heard. We had a situation, for example, where we were deciding between a trade-off between two business lines. It was a profitability question for one business line, to make one business line much more profitable to do a certain partnership, but it would come at the expense of the growth of another business line that was more nascent.

And so it’s hard when you get the GMs for all these businesses together, and they have very strong perspectives and good reasons on both sides about why path A is better profitability, path B is better for growth. And they’re arguing very strenuously, in part because they want to hit their numbers, in part because they believe it. One thing I found super effective in those contexts is I try to ask the other side. So, let’s take the profitability side. I ask them to make the growth case. I say, “Tell me the three best reasons why we should actually focus on growth here.” That generates instant empathy for the other side. And sometimes, they’ll even persuade themselves as they’re talking and say, “I think you’re right that we should focus on growth here. We can achieve this profitability measure later” or vice versa. And so generating empathy and having empathy for the other side, understanding how they’re goaled and what they’re bringing to the conversation, I think is the first step to having those really tough conversations.

Lenny: I love that. What other steps are there? I like that as a first step. Is there anything else you have that you end up finding is really helpful there?

Keith Yandell: Sometimes these conversations can go on forever. Right? People just want to keep going back to an argument they’ve already made, because they’re not willing to settle, and there needs to be someone that says, “All right. We got to be clear on who the decision maker is here. If we haven’t reached a consensus, who’s the tiebreaker?” And a lot of time that’s our CEO, Tony Xu, but a lot of times it’s the GM for a certain business line or a head of product or a head of engineering, depending on the decision to be made. I think being really clear about, “Hey, we’re all going to come together. We’re going to have a healthy debate. We’re going to make sure everyone’s perspectives are heard. We’re going to try to reach consensus, but the end of the day, here’s the person that’s going to make the decision, and we’re going to make it on this time horizon. And once the decision is made, we’re going to [inaudible 00:30:16].”

And I think that having someone that’s in the room that has run a lot of the functions that are trying to articulate the perspective is helpful, and someone who’s been at the company as long as I have and given up as much as I have… Right? To your point earlier, everyone knows I’m not trying to build an empire. I’m trying to find a way to win. And I think it gives me some credibility to call the question, figure out who decision maker is, set a time line, and move on. The only way it works is if there’s empathy on both sides.

Lenny: This is great, so I just took a few notes. One is there’s essentially the steel man component. Have them steel man the other side, argue why that’s the better decision. Clarify a decision maker. Make it clear like, “There’s the tiebreaker. If we can’t get there, this person’s going to make the decision.” And then create a time horizon of like, “We need to make a decision by this time.” Is there anything else, before we move on to a different question?

Keith Yandell: I think that’s the right framework. I can tell you’re product guy. You’re very good at distilling it down to the essence. I think that’s a good summary.

Lenny: Yeah, you got to do it. You mentioned the one-on-one meetings. And I took a note on this, actually, and I wanted to come back to it. You mentioned at the end of your one-on-one meetings you have this kind of coaching career conversation. Is there anything else you could share about just your approach to one-on-one meetings, your agenda or how you think about one-on-ones?

Keith Yandell: This is super tactical. It’s something I think is really important, is I’m very clear, in the document we talked about earlier, about how I like to work, is I demand feedback for me. And so we set aside time during one-on-ones where I want the feedback. First, constructive feedback. And I expect it, and if you don’t give it to me, I’m going to press you on constructive feedback. And then I give feedback. I tell this to managers all the time. If you create a space where you require constructive feedback, it’s a lot easier to give feedback. One of the top things I hear from managers, especially new managers, they don’t like giving constructive feedback. They want to be positive. They want to be liked and things like that. And so it’s a nice way to create space to have that dialogue.

And that’s something I actually learned from Travis, when I was at Uber. We had a system called T3 B3, where during reviews or pulse check-ins, you’d have to say three positives about your manager and three constructive pieces of feedback for your manager. And the first time I did it, I just did the T, the tough things, for my manager, who was the general counsel at the time. And Travis came over, and, “This is totally unacceptable. You have to provide constructive feedback,” which made me super uncomfortable but created the right environment, where people could have these tough conversations because, “My manager can’t get mad at me, because she knows the CEO’s going to come give me a hard time if I don’t provide some constructive feedback.” And I think having that as an expectation is super important to building open lines of communication.

Lenny: Wow. I like this T3 B3. So T is top good things and B is three bad things.

Keith Yandell: Yeah.

Lenny: Cool. I’m trying to imagine you in this meeting with the CMO you mentioned, and them having to give you constructive feedback. That’s always hard, even though you expect it. Is there anything else you do to help people feel comfortable giving you hard feedback in meetings like that?

Keith Yandell: You have to thank them for it. Right? I mean, there’s a saying, “Feedback is a gift,” but you have to say stuff, and you have to action. And that’s one thing I’ve found that can be really demotivating for folks. A lot of these companies have these pulse surveys, or they talk about what the company can do better, and they put the results on the screen, and, “We’re going to work on it,” and that’s the end of it.

And that was something I learned early on at DoorDash that people didn’t like, unless you were going to come back and say, “Hey, this was our lowest performing area in the pulse survey. Here are the three things we did to action it,” because that’s how you would treat the business. Right? If we got feedback from a customer or from another business line, you would say, “Heard it. We’re going to come back and report out on what we’re going to do differently, and then we’re going to track the progress.” And so I think that’s really important when you receive feedback. You have to show people that you’re actioning it and say, “I heard this from you. Checking in. Am I doing better? Here are the things that I’ve changed.” And so making sure that there’s that feedback loop, I think, is another important part of creating the right structure for a good, healthy culture.

Lenny: Another guest on the podcast had the same exact advice for getting feedback, and the way he described it is you want to be enthusiastic about like, “Thank you so much for that.” And the way he described it is even though you’re melting inside because you don’t want to hear, “Thank you so much. That was so helpful.”

Keith Yandell: It’s really good advice.

Lenny: I want to zoom out a little bit and talk about the DoorDash kind of journey. There’s been a lot of high highs with DoorDash. There’s been some low lows. I know that there was a funding round at one point, where it was very precarious and may not have worked out. Question I have for you around that is just, leading through hardships and through tough times, what have you learned, as a leader, about how to lead through challenging times? And ask partly because a lot of companies are going through that right now. It’s pretty hard for a lot of folks out there, a lot of layoffs. And so yeah, I’m curious what you’ve learned about leading through challenging times.

Keith Yandell: Yeah. I’m going to regurgitate some advice I got from some folks on our board at the same time, when we were having really tough times, which I really didn’t like hearing at the time, but I was kind of new to the space. And that is, “Tough times make companies,” for a host of reasons. I mean, this is super healthy for the start-ups out there right now. It’s because, number one, you’re going to find out who the mercenaries are on the team, that are people that are there for the mission, versus they’re there because they think this is going to be a quick road to riches. We had a lot of people leave the company when Uber launched food, and we fell quickly behind. And that was good for us because the people that stayed were there because they wanted to work on this team, on this mission, and they really believed in it.

The second thing is it forces discipline. It’s a good thing to focus on unit economics. And we didn’t have the funding that a lot of our competitors did, which forced us to be super focused on our unit economics and efficient and serve the customer in unique ways from the start. And I think a lot of our success, even to this day, emanates from those tough times. The last thing I’ll say is if you’re a founder, and you’re looking for talent, tough times are great because there’s a lot more talent out there. I saw… I think it might have been Bill Gurley. Someone tweeted, “This is the best time in recent memory, since 2008, to start a company.” And that really resonated with me because there’s a lot of talented folks out there who are looking for their next thing. And three years ago, it was tough to find talent. And so I think there’s a lot to like about tough times.

The last thing I’ll say is, one thing that I found surprising is, from our surveys internally, people actually like crises at DoorDash. And I dug into that recently, and I was trying to figure out [inaudible 00:37:10] like these crises, and it’s because there’s singularity of focus. You know what the job is. You know you’re going to get whatever resources the company has, when you’re focused on the main thing. And these tough economic times will create that work. It’s crystal clear. You got to cut, burn, and everyone’s going to be doing what they need to do to achieve that outcome. And I think talented folks really like that, one, resourcing, and two, singularity of focus about what the main thing is. And crises manifests those for folks.

Lenny: It’s interesting that there’s all these benefits to tough times. It’s hard to recreate artificially. Reminds me a little bit of Frank Slootman, I think his name… and his book Amp It Up, where he talks a lot about the importance of urgency, always creating urgency. And obviously, a downturn like we have today is an urgent situation. Have you found that to be true, the power of creating urgency? And then, is there something you’ve learned about how to create that urgency at a company [inaudible 00:38:07]?

Keith Yandell: Yeah, this is something Tony’s talked about since the day I joined, and he’s very good at, frustratingly good, at that, because just when you think you’ve achieved the goal, the goal might go up. It might get shorter if you’re from the product side. And speaking specifically on the product, compound interest is a really hard concept to fully explain to people, to make them truly appreciate. But that’s something Tony is fantastic at, which is, he understands that by pushing a road map up, even by a week, if you can continuously push up what you ship by a week, you’re going to end up lapping competitors who are just one week behind because you’re going to start the next thing a week sooner, and you’re getting that 1.1, 1.01x return. And then it grows and grows and grows.

And he’s as good as I’ve ever seen, combined with our president, Christopher Payne, at creating that sense of urgency and just pushing people. “Do we really need to test this thing again or can we ship it? How can we move that much faster?” Even if it’s by a small margin, understanding that you can compound those gains over time has been really impactful for our success.

Lenny: I saw the same thing at Airbnb. It feels like, “Things are going well. Maybe we could take a little break,” but it’s constant just like, “How do we go faster? How do we go bigger? Okay, what’s next? We launched this thing. Let’s move on.” And it feels like such a pattern across companies that do really well, is the founders continuing to keep that pressure on.

Keith Yandell: I remember our IPO day. We had this thing. I had to wake up super early. It was a virtual bell ringing, and the second it was over, we had our weekly business review, and there were tough questions being asked. There was not champagne being passed around. I mean, people were in a good mood, but it wasn’t like, “Wow, this is so great.” It’s just like, “Hey, how are we going to serve our customers today?” And I thought that was really emblematic of, “Hey, if we take too deep of a breath and are patting ourselves on the back…” It reminds me of the saying, “Somewhere, someone out there is practicing, and when you meet them, they will beat you.” It’s the same kind of thing. It’s if you take too long to be self-congratulatory, you’re going to fall behind the people who are still hungry. So it’s important to stay hungry.

Lenny: Wow. Reminds me, I think it’s Bill Gates talking about someone’s in a garage building the next Microsoft, and he’s always trying to stay ahead of them.

Keith Yandell: So true.

Lenny: The other thing this makes me think about is just, it’s wild that founders… like Airbnb founders have been at this 15 years. Tony, I’m not exactly sure. We’re probably a similar amount of time. It’s just like they have to keep that pressure on within the company and also keep themselves motivated and excited and continuing to push. Just such a hard path. There’s benefits to being that founder, but it’s such a challenging life, too.

Keith Yandell: Yeah, I think it can be lonely to be a founder, for sure. I know that Tony’s tried to develop a community, for him, of people who are similarly situated from other companies, and that’s been helpful. And the real founders that I’ve come across, that drive, though, is something they can’t turn off. They don’t have to try to keep it, because there’s a handful of traits I’ve seen that are pretty common. One is a level of obsessiveness. Two is hypercompetitiveness. And I think they’re good at manufacturing straw men, even if everyone’s saying nice things. It’s like Michael Jordan used to take things out of context and make bulletin board material. There’s definitely an element of that in the great founders that I’ve come across. And there’s just a raw curiosity. So it’s the competitiveness, but the curiosity in learning how things are working, and those all come together to create a drive that just never stops.

Lenny: That resonates. Coming back to the DoorDash journey a little bit, I imagine the pandemic was kind of this microcosm of high highs and low lows, where, as an external observer, felt like everyone needed DoorDash immediately, and it was just probably the best thing for your business. On the other hand, I imagine you had to scale like crazy and keep the wheels on the bus through this time. Can you just talk about that part of history for DoorDash?

Keith Yandell: I mean, it was just a wild rollercoaster. We were trying to get ready to go public, first of all, and so there was that overlay. And then, what you saw was our volume dropped right away, like the first or second day of lockdown. And I was like, “Well, this is going out of business because no one wants to order food from restaurants anymore.” People didn’t know how COVID was transmitted. And so just basically volume dropped out a cliff. And I was like, “Oh, went from a super high. We’re getting ready to IPO. Super low. Volume’s going to zero.” And then, all of a sudden, volume doubled. And that was really exciting for a second, till we realized that our customer support center… I was running support at the time. All the support centers around the world shut down. So you’re doubling volume. You have no one to serve it, from a customer support perspective.

And our infrastructure, we weren’t planning to grow that fast. We didn’t think there was a chance of two or three exiting in a very short window. And so every Friday night, the app would crash. And if you’re running customer support, there’s few things you like less than the app going down. Set aside what it means for the customers and for the business. Selfishly, it’s just super painful. The irony of it was, is our NPS was going up and that people were just so grateful to have the product, to be able to safely get the things they needed, for people to be able to earn money at times when they really needed it because maybe their job had been shut down, or they weren’t allowed to go in. It became a really essential service for folks. And that was really motivating for me, and I think for the team, is to really be able to fulfill the big part of our mission of empowering local economies in a very unique way in a very special time.

And the last thing I’ll say on the pandemic was, one of my most vivid DoorDash memories was being on a Zoom call, where we were trying to figure out what to do to help restaurants. And again, we were trying to go public. And Tony made a decision, and I admit, I’m on the wrong set of history. I was arguing that this seemed extreme, just to cut commissions by basically 100 million bucks for restaurants, to help them stay in business. And I’m like, “Hold on. We’re trying to go public. This is going to completely change the bottom line perspective. No one’s asking us to do this.”

And Tony says, “Keith, you think too short-term.” He’s like, “This is the right thing to do.” And reminded me of the Ted Lasso quote, which is, “Doing the right thing is never the wrong thing.” And talk about how sometimes there’s healthy debate. He didn’t want to hear any debate on this one. He said, “Just shut it down.” And he’s like, “Founder-led decision. This is the right thing to do. We’re going to cut these commissions.” And I woke up the next morning and never been happier to kind of been overruled in a debate before than there. It was just such a meaningful moment for the company, and I was so proud to be a part of the organization.

Lenny: Is there anything else you took away from that experience of just living through this up and down of pandemic times at DoorDash?

Keith Yandell: It actually reminds me of the best advice I got when we were having our first kid. And everyone thinks they’re going to give you the insight that’s really going to be transformative. But one that stuck with me is, “For better and for worse, everything’s temporary. So the highs, you can’t get too high. The lows, you can’t get too low.” That really resonated with me during that period of time, as well as this general idea that you have to try to find opportunities to reach the potential for the business. And decisions sometimes have to be made in very short time horizons, and being able to seize those moments, I think, is really important.

Lenny: I have a few questions about product that I want to get to. But one bigger question about DoorDash is, you’ve been involved in a lot of the bigger fundraising moments, DoorDash. I think you’ve worked probably with every major firm out there, raised large dollar amounts for DoorDash. Are there any memories or lessons that you can share from that experience?

Keith Yandell: We’ve definitely tried to raise from everyone, been told no many, many times. I mean, raising the Series D was really difficult. Tony and I worked together very closely on that one. And there was a lull in the tech market publicly, and it translated pretty quickly to the private markets. And people didn’t believe in either the TAM or the profitability of the business model. And it was difficult. I think one thing that process taught me is after we raised the D, almost every round, or I think every round ended up being led by someone who had passed in a previous round. And that was because we put up numbers we were highly confident we were going to hit.

I’m an operating partner at a venture firm on the side, and I see that most people put up stretch plans, but they [inaudible 00:46:31]. But that was just not in our DNA. We wanted to make sure that we put forth numbers that we knew were going to hit, and that cost us some dilution upfront in the form of lower valuations, I think. And there’s just a trust that builds from that, where when we tell people we’re going to do something, that they have conviction that we’re going to do it. And I would trade a couple of points of dilution for that level of trust with the right investor base over time.

Lenny: For founders that are going through fundraising right now, maybe having a hard time, any just advice from that period for founders, yeah, that are having a hard time raising these days?

Keith Yandell: It’s fortunate because you only need one yes. Right? And you see all the people post the how many rejections they got. Every business that you have heard of has gotten rejected by at least a handful of venture capitalists at one point or another. And so that drive to keep going, if you believe in the business, is critical, absolutely critical. I mean, we were weeks of runway situation and had been told no by everyone, and it was just Tony’s drive, really, to keep going. And the way he explains it to me is it’s just the difference between a founder and a non-founder. If you’re really a founder, you just have to find a way. You have to keep going. There’s no question. And I mean, that’s the only advice I can give folks, is it only takes one yes. But you got to keep going.

Lenny: Awesome. Shifting a little bit to a few product questions. Most listeners to this podcast are product builders, growth people, founders, and so I have a couple questions here. Today you’re currently leading the corp dev and BD team, and I imagine you work closely with the product team. And so I’m curious what you’ve found to be an effective relationship between BD and product and from the experience you’ve had at DoorDash doing that.

Keith Yandell: Yeah, I joke that our head of product, Rajat Shroff, is actually the head of BD, because he’s both interested and good at it. And to do impactful BD, the two really have to go hand-in-glove. So when I think through how to make that relationship work, the first challenge I’ve confronted, and maybe mistake I made, is trying to figure out what the right cadence is. When do you bring in the product team? Because if you bring them in too early on a deal that really has no chance of getting done, you waste valuable cycles. And our tech talent is our most precious resource, probably, at DoorDash. And so you have to be really mindful about when you bring them in. But if you bring them in too late, it may be a situation where you’ve given on terms that you really shouldn’t have, and that can be really detrimental to the partnership as well.

So I think one thing to do is just give visibility. So without actually bringing them and having a full discussion, like, “Here’s the pipeline. If you see things that are super impactful, let us know. If you think things you’re not so sure that are going to make a difference, please let us know.” That’s been really helpful.

Another thing that Rajat’s taught me is the importance of building platforms, and whenever you can. So what we used to do is, I’d go out and negotiate a deal. We had a lot of deals around DashPass, which is our subscription product, and I’d ask the product team to go build a bespoke thing for this particular partnership, Chase or whatever partnership we were negotiating at the time. And Rajat said, “Why don’t you figure out what the scalable solution is for this? We will build you a product. You won’t need to come ask us every time to build something. And then you’ll know the parameters in which you can negotiate. You can negotiate a better velocity. We might spend more time on the first version of this, but very little effort for the next. And we’ll have a high return on the product hours and the engineering hours spent.” And so that was a super valuable insight that I garnered from him, is to try to figure out how to create these type of platforms.

Lenny: Any other lessons of just building an effective BD team within a product company, especially at the scale you’re at?

Keith Yandell: A few other things. Number one… This is something else that Rajat taught me. One of our core values is, “Dream big, start small.” And he really brought that to the BD product org. And there were some painful times. We invested heavily in a partnership with a hotel chain. We thought we were going to build, “Hey, we’re going to make sure that this is the new dine-in experience when you’re at a hotel. We can actually replace room service.” And asked for a lot of product worked. And it was a total flop. And the realization I had is that we should have gone out and tested this at one hotel with just some hacky operations and seen what the uptick was. And what I would’ve realized is this particular hotel chain was franchised. So even though corporate thought this was an important thing they were going to prioritize, if the franchisee doesn’t care about it, they’re not going to give you the visibility, in room or otherwise, to make it work. So we built all this great integration [inaudible 00:51:32] that was totally wasted because the operations weren’t right.

And I have probably two or three other examples of situations where I learned I should have just gone out and stood out front with a promo code, and handed it out in certain forums, and seen if that changed customer behavior, before going and asking for the product resources. And Rajat correctly was like, “Hey, this is how we have to think about these things going forward.” So yeah, definitely building platforms, “Dream big, starts small,” use operations to test a thesis around a deal before you actually expend the product resources, I think has been super helpful. And then, the last thing would be to engage early, but not too early, on deal opportunities.

Lenny: It’s interesting how the advice of doing things that don’t scale just continues to be useful, even at the scale of a DoorDash. Like you said, you could just stand out there and see if people want room service through DoorDash before building a whole solution.

Keith Yandell: Yeah, early DoorDash, that was a core value. Do things that don’t scale. It’s as relevant today as it was then.

Lenny: Same at Airbnb, is something the founders brought up all the time. And speaking of that, another area that you have a lot of expertise on is legal. So, you led legal for a while at DoorDash. And I was thinking, as thinking about this question, “I wonder what’s more difficult, to be head of legal at Airbnb or head of legal at DoorDash,” both fraught businesses and ideas. But we’ll avoid that question for now. So my question is just legal and product. It’s always this interesting relationship, how much legal has say over what happens versus how much product has final decision-making powers. Any lessons there about just how to set up a product and legal relationship within a software business?

Keith Yandell: Yeah. And both for the product folks that are listening as well as the entrepreneurs who want to be founders, I’ve had the pleasure of working with two founders who are very product-driven, product-first folks, in Travis and Tony. And I’ve found that the way they engage on the legal side is with the curiosity I referenced earlier, which is they’re both hyper curious, and they will ask questions until they understand the law in the particular area about as well as the lawyers. And then they will apply a first principles product mindset to their understanding of the law, and they will push the lawyers to make sure that they’re not being overly conservative, which sometimes they can be.

Keith Yandell: And so, when you’re on the product team, especially if you’re in a consumer-facing business, it may not be as pronounced for SaaS businesses, but if you’re in a consumer-facing business, working on a consumer-facing product, you had better have at least a general understanding of what type of regulations are going to apply to your business, and what type of constraints there are, and how to push those constraints. Yeah, and so for me it’s just about that level of curiosity and actually engaging in the profession. Right? There’s nothing magic about the law. There’s a finite number of things that you can learn. And just like all the other functions I’ve learned, I think you can engage them in a way, till you are proficient and actually really accretive to your business.

Lenny: Keith, this has been incredible. I can see why people want to work for you, why they keep giving you more teams to run. I learned a ton. I’m really excited for folks to listen to this and learn from you. Two final questions. Where can folks find you online, or if they want to reach out or learn more, where do you point them? And then, two, how can listeners be useful to you?

Keith Yandell: If you want to find me, LinkedIn is the place you can locate me. You can locate me there. I don’t do any other social media. It is maybe unusual in this day and age, but that’s my preferred medium. And then, as far as being helpful, always looking for referrals for great people. That would be the number one thing. And everyone has an opportunity to use our product. So if you have product feedback, I always welcome that as well.

Lenny: For folks that maybe want to join DoorDash after hearing this, is there specific roles you’re hiring for? Anything you want to share there, folks that might be interested?

Keith Yandell: Yeah, I mean, select roles definitely on the product and engineering side is a place we’re focused right now. But even if there’s not a role open today, I like meeting great people. I’ve found that building relationships over time, even when you’re not looking, is impactful.

Lenny: Awesome. Keith, thank you so much again for doing this.

Keith Yandell: Thanks, Lenny.

Lenny: Thanks for listening. You can find the full episode on YouTube, or head on over to lennyspodcast.com.

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