The Exchanges

Q Do you believe there are benefits to naivety? And how do you think about good playbook learning versus bad playbook learning where you're transferring an experience that isn't transferable?

A And I think I understand what you mean with that. And I like to hire entry level jobs out right out of colleges. Yeah. Because you don't have, you haven't learned any bad behavior. You know, you haven't, you haven't gone to a company that's not very good at things and learned a bunch of foundational elements that Are wrong, are wrong culturally in our world. And so, you know, where we have opportunities to do it, I really like hiring people who are like day one in their career, because it, you know, you, you have more attrition in that because people are still, you know, discovering themselves and discovering what they want to do, but they become, you know, you hire somebody out of college in the Flexport, they're a Flexport. You're like, you know, they're, that's who, you know, they're here for 10 years. That's, That they're, you know, tried and true flexed work and toy, and they know the culture or their part of building it. You know, there's no better evangelist for it, and they learn what we're all about. You're not bringing in, you know, some other company's culture with them. So I, I do like a, uh, a sort of fresh out of school hire in the right kind of role.

AI assessment note: “you haven't learned any bad behavior”

Q Speaking of bringing in talent, uh, you also made some acquisitions that were very strategic. What's the thought process behind the acquisition, specifically, I guess, with Shopify Logistics, which also includes Deliver?

A I mean, it was a great opportunistic Um, moment, I think, you know, we, we have been, uh, we had a plan to do, we wanted to be Indian, so we want to be, you know, we're, we want to be in our now, Indian, the manufacturer, uh, supply chain technology and capability, uh, from manufacturer all the way to distribution center, store, or customer door. We had all the elements in place and or being built this year, except distribution and fulfillment. And we had kind of viewed it as not particularly a land rush in this year. And so we were going to start a team later in 20, 23 to build that. When we started having conversations with Shopify about the idea of, uh, that they were going to sell, or they were looking to potentially sell Shopify logistics and deliver.

AI assessment note: “We had all the elements in place and or being built this year, except distribution and fulfillment.”

Q When does it make the transition from operator to kind of bureaucrat and politician almost?

A I think it started changing for me a lot, probably around 2015 or 16. You know, we, when I took over, uh, leading the global ops team around 2011 or so in there, um, we had just started the growth curve of fulfillment. So you can go back and look at the square footage ramps, you know, there's sort of a big elbow in the curve around 2010, 11, 12. Where FBA growth really took off, the fulfilled by Amazon, where third party merchants were moving their products into the company, really took off in that time period. And so we grew a lot over the next decade. And so, you know, we were an enormous operating company by 2015 or 16. We were starting to build out transportation networks. And so it really came to a place to where my, my life became much more about delegating and managing, you know, a lot of global issues and less about building. Um, but you know, that's kind of, you know, that journey of, you know, decade or so from 2011 to 20 23 of building that for Amazon is, is what excited me about Flexport. You know, it was really this, you know, we built that at Amazon for Amazon and for sellers who were part of Amazon's infrastructure. And what I saw was the power of multi-tenant, you know, the power of Uh, you know, multiple companies being able to benefit from the scale of the total, and, uh, the rest of the world needs that, you know, the rest of the world needs that for the envi…

AI assessment note: “I think it started changing for me a lot, probably around 2015 or 16.”

Q How do you get through those moments actually when you're out of balance, how do you get through them?

A Well, first and foremost, I think it's, um, for me, it's been about Uh, like Leanne and I want the, we were on the same journey together. Like we recognize that like, uh, you know, I'm not successful without her. She's not successful without me. We accept that about each other and we want the same things. Like we were trying to, you know, we're on the same journey in life. So, you know, it's not like she's wanting to, you know, You know, go move to the beach somewhere and me not work. You know, like she, you know, like we're aligned on that. We want these things in life and we want these things for our kids. And so our base desires are aligned. And then, then you got to figure out how do you balance the time of the commitment? And, uh, that's, you know, it's hard. I don't, I don't know that the, you know, and that answer is different for every person. Uh, I've always said I could only be good at two things and, you know, that's work in my family. And, you know, sometimes I'm not even good at two things and, uh, you know, cause one takes place over the other. Uh, the key I found is just becoming more and more aware of what I'm doing with my time. More and more realizing, I think the older I get, uh, I recognize that the most, the only thing of true value I have is time. And so I become much more protective of it than I was, you know, a decade ago. And as a result, I, I reserve, …

AI assessment note: “I reserve, you know, structurally reserve in my calendar and with my assistant”

Q What do you mean by doing the effort and what that signaled to customers?

A Well, I think, you know, sometimes, you know, there are a lot of people who, you know, say they do things really, really fast, but that's really a small subset of what gets done. But it's a marketing message and customers start to believe that you have a perception of speed about you as a company. And there was a period of time there where, you know, I mean, today was like the, you know, you get anything you want in the world, basically in two days or less. And like, nobody was really competitive with it. And then all of a sudden there were all these companies who were like, well, today is for, you know, boomers. Like this is like, I'm gonna get it to you in, you know, 15 minutes. And that was where all the VC money went. That's where all the eyeballs went. And because of that, it made today The impression of two days slow, and because we didn't have the other offer, I feel like it made customers think we were not moving, we weren't on the edge, we weren't on the cutting edge anymore.

AI assessment note: “made customers think we were not moving, we weren't on the edge”

Q That's a decision that he makes, and when it comes to leadership, kind of, the ultimate element is decision making. When you think about your decision making framework, how would you describe your decision making framework today, and has it changed over time?

A You know, it's funny, I get asked this a lot and I always feel like, uh, uh, like I would give a really dumb Ted talk on this subject. Cause I don't know, I don't know that I have a particular, like, you know, but some people have these really robust, like acronym decision trees that they go through and I don't know, I don't have that. Yeah. I sort of just approach every document, like every document I review with, I have a lot of important news on things. So just particularly in the spaces I've occupied because I have a lot of experience in those places. And then I would just approach it with a lot of curiosity and trying to dig in, you know, and to understand what, again, what's the most important things, what's hard, where's the real innovation, what's the separation and what makes us better than the other. Uh, but I don't have a Sadly, you know, I feel like I need it. I like one of the things I should take as a personal improvement journey is come up with a smarter sounding answer to this question. Cause I get asked it a lot.

AI assessment note: “I don't know that I have a particular, like... acronym decision tree”

Q You brought in some very senior leaders into Flexport when you joined. What are one or two of your biggest lessons when it comes to bringing in really senior talent to join you at the C-suite?

A Yeah, it's a, I mean, it's a gift for me, for one. I mean, it's like Uh, I'm extremely grateful that these people are willing to entrust the next step of their career with me, you know, and, uh, so I, I think of it as, uh, especially at C, you know, big C-suite jobs or big executive jobs. I think there's a lot of mutual trust and mutual accountability in that hiring decision, which is, you know, I'm placing a big bet that you're going to come in and do the things you need to do to deliver in the company. And you're placing a bet that I'm going to support you. And then I'm going to live up to my end of the deal with help and support and resources and yeah, and guidance and whatever's needed to enable you to be successful. And it's a two way street, especially at a senior level, because those are big, big, those are marriages and might be much less, they are really You know, those aren't short-term hires. You're hiring somebody for, you know, that's gonna decide who these big teams are for the company for the next 10 years.

AI assessment note: “there's a lot of mutual trust and mutual accountability in that hiring decision”

Q Dave, what's the hardest part of parenting in terms of stage? When you look at children, is it when they're very young? Is it when they start to walk? Is it when they're potentially getting bullied at school for the first time? Which stage of parenting is the hardest?

A Well, I I'm only 11 and eight, so I can only speak to that part of it. Uh, and I can just say that the hardest part for me is that, uh, You know, there's never anybody in your life that you're more willing to go crush somebody into a million bits for hurting someone than when they hurt your child in some way. And it's like a different level of anxiety and a different level of protective sort of instinct, if you will. And, uh, I think that just, you know, it helps, at least for me, it helped Soften me, I think in a bunch of ways and helped me think about, you know, the whole person and think about, it just, I thought about the world in a different place after that. Cause my, you know, my kids, you, when something goes bad with you, you, you, you're only as happy as your happiest child is a, is a pretty common phrase that I hear a lot. And it, it's pretty darn true.

AI assessment note: “the hardest part for me is that... when they hurt your child in some way”

Q That's a decision that he makes, and when it comes to leadership, kind of, the ultimate element is decision making. When you think about your decision making framework, how would you describe your decision making framework today, and has it changed over time?

A You know, it's funny, I get asked this a lot and I always feel like, uh, uh, like I would give a really dumb Ted talk on this subject. Cause I don't know, I don't know that I have a particular, like, you know, but some people have these really robust, like acronym decision trees that they go through and I don't know, I don't have that. Yeah. I sort of just approach every document, like every document I review with, I have a lot of important news on things. So just particularly in the spaces I've occupied because I have a lot of experience in those places. And then I would just approach it with a lot of curiosity and trying to dig in, you know, and to understand what, again, what's the most important things, what's hard, where's the real innovation, what's the separation and what makes us better than the other. Uh, but I don't have a Sadly, you know, I feel like I need it. I like one of the things I should take as a personal improvement journey is come up with a smarter sounding answer to this question. Cause I get asked it a lot.

AI assessment note: “I would just approach it with a lot of curiosity and trying to dig in”

Q You brought in some very senior leaders into Flexport when you joined. What are one or two of your biggest lessons when it comes to bringing in really senior talent to join you at the C-suite?

A Yeah, it's a, I mean, it's a gift for me, for one. I mean, it's like Uh, I'm extremely grateful that these people are willing to entrust the next step of their career with me, you know, and, uh, so I, I think of it as, uh, especially at C, you know, big C-suite jobs or big executive jobs. I think there's a lot of mutual trust and mutual accountability in that hiring decision, which is, you know, I'm placing a big bet that you're going to come in and do the things you need to do to deliver in the company. And you're placing a bet that I'm going to support you. And then I'm going to live up to my end of the deal with help and support and resources and yeah, and guidance and whatever's needed to enable you to be successful. And it's a two way street, especially at a senior level, because those are big, big, those are marriages and might be much less, they are really You know, those aren't short-term hires. You're hiring somebody for, you know, that's gonna decide who these big teams are for the company for the next 10 years.

AI assessment note: “there's a lot of mutual trust and mutual accountability in that hiring decision”

Q Well, we ask you a weird one, but it's, you know, you're bringing your children up in a, in a fantastic environment, but also a financially affluent environment. I speak to many very, very successful founders. I asked Toby at Shopify this, um, how do you bring your children up with the same hunger and ambition when brought up bluntly in very lovely and financially secure environments?

A Yeah, we talk about it a lot. Uh, you know, my wife and I both come from backgrounds that, you know, certainly it looked nothing like the lives we have today. And, and it's a challenge. Our number one rule is, you know, we have two rules in our house, which is basically, uh, do the best you can and don't be an asshole. And so we want to like our kids when they're third. Like, I don't want my kids to be assholes. And, you know, I want my sons to be like happy. Polite, good to people, caring, empathetic, well-rounded humans. Uh, and if they do that and they don't want to go to Harvard, I don't care. You know, I, I, I'm not worried about whether that, like, I was a terrible student in life. I mean, I hated school. School was the most boring, pedestrian, like, check the box. I hate it. I did terrible. Right up until I had to be good at it, and then I did really good in grad school and went to Amazon. It's fine. Like, I, I don't think school, and I'm personally not a big believer that, like, ah, you need to go to Harvard to be successful in the universe, and so I, I mostly want my kids to be curious and learn and be nice, well-rounded humans, and I want to like them. I want to want to have dinner. I want to live to when they're 30, and I want to be able to have dinner with them and enjoy it.

AI assessment note: “I mostly want my kids to be curious and learn and be nice, well-rounded humans”

Q What's the most painful lesson that you've gone through, that you're pleased to have gone through?

A You know, I've earned a lot of money over time. I don't regret it too much. Uh, I, I, most of the time, I, I don't, I'm not very backwards looking. Uh, you know, quite honestly, uh, I think I grew up in a way where I didn't have a lot of, well, like, I was kind of like, I didn't care about school. I just wanted to work. Uh, but my mother passed away when I was a junior in high school and my dad passed away when I was in grad school. And all right, it was very, it was very painful to lose your parents early. Yeah. But I don't think I would be who I am had I not gone through that. Like, I got started with a can and it was like, you know, like I realized I'm fine without a nap. It was on my own. I tell my kids a lot, I hope I have one need to die for them to feel the need to be really successful over time, but it is a, it was very painful, but transformative in a way that I think, um, shaped my independence and self-reliance and desire to succeed in a very powerful way early in life.

AI assessment note: “it was very painful, but transformative in a way that I think, um, shaped my independence”

Q What did you learn at Amazon then that you've not taken to Flexport, and what did you learn at Amazon that you have taken to Flexport? Like, what worked that is replicable, and what worked that isn't? Or what didn't work that you don't want to do again?

A Yeah, I, I mean, I, I love so much about Amazon. I sort of view myself as, uh, somebody who helped establish parts of the culture on Amazon over, over that time period. And I, what I would love is that most is the customer centricity, you know, this place of like, and I really do make a decision for a customer. You know, a lot of people say they do, and they really do, relative to the point where it's a trade-off between money and the customer. You know, like, you know, you really only know if you're customer-centric in a very, very hard moment where you're faced with doing something that the customer would like, but it's going to cost you a lot of money that you really, really, really don't want to spend. Uh, and that's when you discover whether you're customer centric, and Amazon was that, or is that, and, uh, we're gonna make Flexport that. That's who we, that's how we operate today, and that's our, that's how we're gonna build a culture.

AI assessment note: “Amazon was that, or is that, and, uh, we're gonna make Flexport that.”

Q What did you learn at Amazon then that you've not taken to Flexport, and what did you learn at Amazon that you have taken to Flexport? Like, what worked that is replicable, and what worked that isn't? Or what didn't work that you don't want to do again?

A Yeah, I, I mean, I, I love so much about Amazon. I sort of view myself as, uh, somebody who helped establish parts of the culture on Amazon over, over that time period. And I, what I would love is that most is the customer centricity, you know, this place of like, and I really do make a decision for a customer. You know, a lot of people say they do, and they really do, relative to the point where it's a trade-off between money and the customer. You know, like, you know, you really only know if you're customer-centric in a very, very hard moment where you're faced with doing something that the customer would like, but it's going to cost you a lot of money that you really, really, really don't want to spend. Uh, and that's when you discover whether you're customer centric, and Amazon was that, or is that, and, uh, we're gonna make Flexport that. That's who we, that's how we operate today, and that's our, that's how we're gonna build a culture.

AI assessment note: “Amazon was that, or is that, and, uh, we're gonna make Flexport that.”

Q Have you ever let someone down when they've joined in that way? I think I've let people down before in terms of setting them up for success, and it's changed a lot of how I think. Have you, and how did you do that?

A Well, I mean, I, I am far from perfect for sure. Yeah. I can't think of a specific example per se. I mean, I think especially younger in my career, I don't, you know, I think I was less patient. Maybe, you know, I didn't have enough appreciation for something. We didn't have enough appreciation for sort of the impact of broader life on peoples, you know, in the moment, what was, you know, the, the whole person and not just who they were at work. Uh, you know, early in my career, I think there was, you know, learning to understand who people were as a whole person, uh, in and out of the office and how those things interplay with, uh, their performance was important, you know, especially.

AI assessment note: “I can't think of a specific example per se. I mean, I think”

Q Have you ever let someone down when they've joined in that way? I think I've let people down before in terms of setting them up for success, and it's changed a lot of how I think. Have you, and how did you do that?

A Well, I mean, I, I am far from perfect for sure. Yeah. I can't think of a specific example per se. I mean, I think especially younger in my career, I don't, you know, I think I was less patient. Maybe, you know, I didn't have enough appreciation for something. We didn't have enough appreciation for sort of the impact of broader life on peoples, you know, in the moment, what was, you know, the, the whole person and not just who they were at work. Uh, you know, early in my career, I think there was, you know, learning to understand who people were as a whole person, uh, in and out of the office and how those things interplay with, uh, their performance was important, you know, especially.

AI assessment note: “I can't think of a specific example per se.”