The Exchanges

Q Dave, you are setting me up. I mean, this is T down on the fairway. I'm gonna swing for this one. Simplifiers. What does simplifiers mean, and, and how's that shown?

A Well, have you ever, I mean, you, I'm sure you have some people, there's people on your team where you're like, hey, I've got this idea, and it's gonna sound nutty. And I'm going to tell you, we're going to do this, that, or the other, you know, we're going to go to the moon next week. And there's the one person who, who starts and goes through a, an hour long, all of the things that are going to go wrong in very complicated ways of, of every little nuance that could happen of why that's the dumbest idea you've ever had in your life. And then there's the other person who's like, well, That's kind of crazy, but you know, this could work and that could work and that could work. This thing over here is going to be super hard. So we'd need to get somebody to figure that out. Like it's the difference between the people who find ways not to do things oftentimes and people who find ways to do things. They separate, you know, they separate the hard from the easy. Like almost all the problems that you think are too complicated to do are like Things that aren't too complicated to do, and 10% of the thing is. And they quickly shed the 90, and they know exactly what to go to, that, where the real innovation or the real hard piece lives. And that's where they spend all their time.

AI assessment note: “they quickly shed the 90, and they know exactly what to go to”

Q So my question to you is, how do you determine what to give them where when they don't achieve it, it won't mess up the business? Like, a lot of things actually, if not done right, will be problematic, and that is why people don't give them to them in the first place. How do you determine what you can give and mess up on versus not give?

A Well, some of it's a, you know, is this a everyday, you know, is this a fulfillment center and we're picking and packing boxes and there's a very clear defined process on how to do it. It needs to be done the same way every time and in order to be safe for the employee and high quality for the customer. Um, and you, you really don't want to like, you know, be going crazy experimentation on that every day and throwing big risk at that. The other is a big new project. You know, it's a thing that you want to try. It's a thing you want to build. It's a, uh, it's not existential to the today. It's a, uh, optimistic for the future. And those are great places to invest in people, right? Because, you know, that's a place where somebody can, you know, you just set a big audacious goal for what's possible and let them go off and run.

AI assessment note: “It's a, uh, it's not existential to the today.”

Q that kind of conversation rooted from. You made a very big decision to leave Amazon after 23 years. You didn't need to, respectfully, like you had such a great career at Amazon, and then you come home and say to your wife, you know what, I'm gonna move after 23 years, and I'm gonna be CEO of Flexport. What does she say, and what does that decision-making process look like?

A Uh, well, she said it's about time, uh, in all honesty. But it, it's a, you know, I, I, I consider it a sign I married the right woman, which is probably the most important decision I've ever made. But, um, you know, I was in a place where I just wasn't happy with what I was doing. You know, I, I love the people I was working with. It's an incredible problem, but I had moved into a role where I was like a, you know, mostly I was a bureaucrat in a lot of ways, you know, it was basically, you know, talking to government and PR and, you know, Managing my boss and, you know, and I was not in a place where I was spending my time building. You know, Amazon's still a builder, you know, oriented company, but I personally was not in a place where I was getting good to do that anymore. And, you know, I didn't start at Amazon with the intention of, you know, having a two million person workforce, you know, and running one of the largest companies in the world. It wasn't my plan. I like, I like working closely with the team and Getting into the creative work and building, and so I wanted to go do that again. That's where I get a lot of joy. I didn't want to stop working. I love, I love working. I just, you know, it was time to do something else.

AI assessment note: “she said it's about time, uh, in all honesty.”

Q So my question to you is, how do you determine what to give them where when they don't achieve it, it won't mess up the business? Like, a lot of things actually, if not done right, will be problematic, and that is why people don't give them to them in the first place. How do you determine what you can give and mess up on versus not give?

A Well, some of it's a, you know, is this a everyday, you know, is this a fulfillment center and we're picking and packing boxes and there's a very clear defined process on how to do it. It needs to be done the same way every time and in order to be safe for the employee and high quality for the customer. Um, and you, you really don't want to like, you know, be going crazy experimentation on that every day and throwing big risk at that. The other is a big new project. You know, it's a thing that you want to try. It's a thing you want to build. It's a, uh, it's not existential to the today. It's a, uh, optimistic for the future. And those are great places to invest in people, right? Because, you know, that's a place where somebody can, you know, you just set a big audacious goal for what's possible and let them go off and run.

AI assessment note: “The other is a big new project... It's not existential to the today.”

Q Speaking of amazing people around you, there are very common traits, sayings about Jeff Bezos. You've worked with him for 23 years. Uh, you have an unparalleled insight into how he works. What's one or two of the biggest lessons from working alongside Jeff that you don't think the world really sees?

A I think the world tends to think of Jeff as like, you know, it's like Moses coming down from the mountain with the 10 Commandments and is like, Shazam, here is what we shall, and it's not like that. I think what Jeff is good is particularly skilled at. Well, I mean, he's brilliant. Table stakes is like, he's sort of just a brilliant guy. Uh, but he is one of the best simplifiers, if not the best simplifiers I've ever met, which is he can, he can context shift incredibly well. You have a meeting, you know, this hour on AWS, the next hour on the consumer business, the next hour on labor, and be perfectly, uh, in the mode in the moment, which a lot of people have trouble doing. And he can quickly sort out the 90% that isn't hard in this sort of, he doesn't need to worry about cause somebody will figure out and he can very quickly narrow down to the 10% or whatever it is, the, the small slice that requires sort of his level of intellect or a senior level intellect to figure out how to solve and what's most important. And so he's hyper efficient with the time and That he spends, because he doesn't waste time on the stuff that's easy.

AI assessment note: “he is one of the best simplifiers, if not the best simplifiers I've ever met”

Q Dave, can I ask, can you take me to a wrong decision that you've made and how did that change your mindset?

A I've made lots of wrong decisions over time. I think my batting average is pretty good. But I've certainly struck out plenty of times. And no, I personally don't mind any of the, like, mistakes I've made. The ones I've The one of where we did something and screwed it up. The ones that linger with me are the ones where we didn't do it. Like where I, I, you know, my gut was we should have done this thing and now I was overthought it or I was too cautious and I didn't do it. It's the errors of omission to me ring much louder than the ones where I did it wrong. And if I think about the ones that, you know, Like things that we omitted, like I think we were late getting to the, um, ultra fast shipping piece when we were at Amazon. And I think some of that was, you know, a decent amount of that was probably on me and sort of Looking at the cost and the, you know, it's really not, there's not a great feasible, there's not a real feasible, like one hour delivery profitable model. Yeah. Despite, you know, all the efforts, you know, all the subsidized, you know, funding processes to the contrary, there's not a lot of great profitable models for that. And so I was always like, well, this isn't going to make it, but the piece I didn't have content that I didn't put enough weight in was how much doing the effort actually sent a message to customers about the company and velocity. And so I, I…

AI assessment note: “I think we were late getting to the, um, ultra fast shipping piece”

Q that kind of conversation rooted from. You made a very big decision to leave Amazon after 23 years. You didn't need to, respectfully, like you had such a great career at Amazon, and then you come home and say to your wife, you know what, I'm gonna move after 23 years, and I'm gonna be CEO of Flexport. What does she say, and what does that decision-making process look like?

A Uh, well, she said it's about time, uh, in all honesty. But it, it's a, you know, I, I, I consider it a sign I married the right woman, which is probably the most important decision I've ever made. But, um, you know, I was in a place where I just wasn't happy with what I was doing. You know, I, I love the people I was working with. It's an incredible problem, but I had moved into a role where I was like a, you know, mostly I was a bureaucrat in a lot of ways, you know, it was basically, you know, talking to government and PR and, you know, Managing my boss and, you know, and I was not in a place where I was spending my time building. You know, Amazon's still a builder, you know, oriented company, but I personally was not in a place where I was getting good to do that anymore. And, you know, I didn't start at Amazon with the intention of, you know, having a two million person workforce, you know, and running one of the largest companies in the world. It wasn't my plan. I like, I like working closely with the team and Getting into the creative work and building, and so I wanted to go do that again. That's where I get a lot of joy. I didn't want to stop working. I love, I love working. I just, you know, it was time to do something else.

AI assessment note: “she said it's about time, uh, in all honesty.”

Q When you have a new employee start, it could be C-suite, it could be anyone, do you start from a position of full trust, or is trust there to be built as well?

A Well, as a trust, as a person, you can get full, you get full trust from me as a person, like integrity and things on day one. Like, you know, I mean, I, it's not, you know, that's yours to lose. Um, and to earn, you know, deeper relationships on that front. And on the other side, it's less, I, I think people like emotionalize it too much. It's less about trust and more about, uh, ramping up on knowledge and experience. You know, it just becomes a bit of like, Hey, we've been doing this for a long time. You've been doing this for now two days. You know, where is it? If you don't have all the keys to the car and the house yet, it's just because you've been here for two days. It's not a, we, we, we hired you, which is, you know, by the way, it is like among the most trusting things you can do is to hire somebody and give them a big role. Uh, and You know, sometimes people conflate ramping into things with trust, and I think that's just a bad sort of misnomer. Yeah, but for me, you know, you, whoever starts on my team starts with trust. You know, I, I assume you're gonna be great, and I assume you're gonna have all positive intent in what you do, and, uh, and my job is to help you be successful.

AI assessment note: “you get full trust from me as a person, like integrity and things on day one”

Q Doug Leone says that, like, companies are teams, they're not families. Do you agree with that?

A Yeah, I don't think companies are families. You know, I, it's a, you know, I think these people who, like, People have very different relationships. I got, you know, there are people I've worked with for 20 years who I'm, uh, who I work with and I'm also friends with, and then there are people I've worked with for six months that, uh, you know, I consider this great working relationship, but you know, we don't have like a, we don't, you know, I don't know six layers of their family kind of thing. Uh, but we're not a family because we're all here to do a job and we have a set, a set of roles and responsibilities and You know, you have to deliver on performance. You know, it is a team. I think that's a much better way of framing it than, than a family. It doesn't mean that you don't have personal relationships with people. And it just means that it's not, you know, you, you, family's family. There's no getting, no getting out of your family. Right. It's permanent. Yeah. Jobs aren't permanent.

AI assessment note: “Yeah, I don't think companies are families.”

Q They're not permanent. Can I ask you, you have a very hard decision when you bring in senior leaders, because you have internal talent who often wants to be promoted. How do you manage the balance of internal promotion versus bringing in external talent? It's something many managers struggle with.

A I mean, my preference, you know, is to hire internally. You know, if you, you can, if you can do it, if the talent is available and matches the need, then, you know, 99 times out of a hundred, I would rather hire internally. Uh, but in fast growth environments, like I was at Amazon and like we're in it flexed work, uh, you often have to intersperse more senior external talent because the business, the people who grew up internally, they haven't, don't have exposure to the business you're becoming. And so you need to hire some people from the outside who understand the business you're becoming. To help teach everybody that's being developed underneath. So it's not, it's really, the way I think about external talent is external talent is really coming in to teach the people who are developing internally something that they, that the, the fastest path to learn is by having somebody who's already seen it be present to, to model that behavior and help give them guidance on how to, how to lead in that new way.

AI assessment note: “my preference, you know, is to hire internally... but in fast growth environments”

Q How does that actually look, Dave? I'm so sorry for being based, but like, Does Toby drop you a WhatsApp and say, hey Dave, got time to jump on a FaceTime? Like, what?

A It, it, it went something like that. Uh, Toby knows Ryan because they invested in our round, uh, in early 22, uh, and so Ryan and Toby have a relationship, and so he reached out and said, hey, we're thinking about this, uh, we think you, you all might be an interested party in this, would you be? Ryan and I talked and agreed we would be, and we started engaging in conversation. Yeah. But it was pretty clear after I got to know Harish and we did some technical deep dives on their software and what they had built, but they had a really good product and they had a product that would work for us in the build versus buy on what they had and where they were at. And it made a ton of sense for us to acquire. Company felt a lot like the culture of, um, Flex Fort. And so it also doesn't need to integrate super heavily, kind of drop in as a business unit in many ways. And so it all kind of lined up to make for a pretty effective, um, we viewed it as a, it would be a pretty effective, uh, acquisition and accelerant to our overall plan and getting to be Shopify's, you know, um, Preferred logistics provider, or official logistics provider, and provider for Shop Promise, uh, with, you know, is a great thing for us as a company, and, uh, gives us, you know, just that much more access to help, uh, merchants and sellers even faster than you'd plant.

AI assessment note: “It, it, it went something like that. Uh, Toby knows Ryan because they invested”

Q do you know now that you wish you'd known when your first child was born? What do you wish you could tell yourself about parenting, about how you are in the room, about how you are with them, about how you are with your wife? If you could have that conversation with yourself now with the 11 and nine year old that you have, what would you say to yourself?

A Mostly I'm like super happy with the choices I made in my life, but if I didn't go back and do anything, it would just, I would be more present wherever I was. Whenever I was there, uh, over time. And, you know, cause I think it's very easy to fool yourself that you are present when you're not, you know, and kids become good truth tellers at that. They're like, dad, you've been on your phone the whole time you've been sitting here. Yeah. You, you, you, you start to, you start to recognize things you're doing that you didn't realize you're doing. So I think, uh, presence is so important to people, whether it's people at work or people at home or your kids. And I think learning to be, I wish I had learned to be more present with everyone I was with in the moment earlier.

AI assessment note: “I would be more present wherever I was. Whenever I was there”

Q When you have a new employee start, it could be C-suite, it could be anyone, do you start from a position of full trust, or is trust there to be built as well?

A Well, as a trust, as a person, you can get full, you get full trust from me as a person, like integrity and things on day one. Like, you know, I mean, I, it's not, you know, that's yours to lose. Um, and to earn, you know, deeper relationships on that front. And on the other side, it's less, I, I think people like emotionalize it too much. It's less about trust and more about, uh, ramping up on knowledge and experience. You know, it just becomes a bit of like, Hey, we've been doing this for a long time. You've been doing this for now two days. You know, where is it? If you don't have all the keys to the car and the house yet, it's just because you've been here for two days. It's not a, we, we, we hired you, which is, you know, by the way, it is like among the most trusting things you can do is to hire somebody and give them a big role. Uh, and You know, sometimes people conflate ramping into things with trust, and I think that's just a bad sort of misnomer. Yeah, but for me, you know, you, whoever starts on my team starts with trust. You know, I, I assume you're gonna be great, and I assume you're gonna have all positive intent in what you do, and, uh, and my job is to help you be successful.

AI assessment note: “you get full trust from me as a person, like integrity and things on day one”

Q Strange one, Dave. What do you think makes you so good at hiring? You've hired hundreds and hundreds, if not thousands of people. What do you think have been your biggest lessons on talent acquisition?

A Uh, probably that I, my favorite hires, I'm a little afraid that they're going to be way better than me. Like, you know, I, I feel the most that hires I feel best about are the ones I feel the most nervous about being additive to helping them. Like, you know, like, uh, uh, I'm glad to work harder. Like this person is going to make me ever work harder because they're, you know, they're going to be challenged. Uh, and I think too many people look for somebody who's going to do what they're told. Like, you know, they want somebody who's going to fill the job of the now. And what I want is somebody who's gonna fill the job that's gonna be the job three years from now, or five years from now, and that is going to be, you know, very unhappy if their world is just me telling them what to do on a regular basis.

AI assessment note: “I'm a little afraid that they're going to be way better than me.”

Q Dave, the joy of this show is, um, the natural discussion. Have a generation of VCs just lost money on last mile delivery companies?

A Uh, in my personal opinion, yes. The place, the closest I think it gets to working as a model is if you can get to subscription and add. Yeah. I mean, you really, you knock a like just product cogs and margin with delivery costs. It's very hard to get the density you need. If you're net averaging 20, 25 dollars an hour for, you know, a delivery or an hour for somebody who's doing deliveries in the US. You know, you really need to net You know, five or six deliveries an hour to get good scaled costs there. And that takes a lot of, it takes a lot of scale. It takes a lot of density to make that happen. Um, and so in order to economically make it work, you have to do, you know, there's companies who do it, right? But they do, there's a lot of ads. There's a tremendous amount of fees. I mean, my, my kids love Chick-fil-A and you know, they, they get, you know, their 30 dollar Chick-fil-A sandwich and fries on a regular basis. By the time you pay the fees and the delivery fees and the tip, um, you know, and so it's an expensive proposition just because cost.

AI assessment note: “Uh, in my personal opinion, yes.”

Q What's an example of how Amazon is that, just for people to resonate with and understand?

A You know, think about it as a, uh, a damage or a return. You know, there's so many times, um, like if you're, for many customers, uh, right now, if you get an item, you say it's damaged, Well, you know, as soon as it registers that you printed the labels to the back, we're getting your money back. That's expensive, and there's fraud in that, and, and, but it's super positive for the customer to, you know, from an Amazon perspective to be able to drive that efficiently. From a flexible standpoint, we've had the same thing like, you know, Hey, uh, this trailer got held up at the port, you know, for some duration of time. Uh, you know, a typical forwarder would say, well, it doesn't matter why or how we're going to send you a bill for that. You know, we're looking at that and saying, Hey, You know, these days of this, you know, we really should have gotten it out that we're not going to build a customer for that. That's, you know, that's on us. That's an operational defect we need to resolve going forward. It's really these tension points to where you could choose, and the customer probably wouldn't know the difference, or it would be equal to what competitors do, but you know you can do something substantively better for the customer, but it's going to cost you money.

AI assessment note: “do something substantively better for the customer, but it's going to cost you money”

Q What are the biggest mistakes companies make with acquisitions and M&A, do you think, Dave? You've seen many from Amazon. You're then doing one now with Deliver and here. It's a big one. What are the biggest mistakes that you are very wary of?

A You know, in my own experience, the, the, the thing that, You know, he's waiting too long to, to hit the ground running and to just make the moves to integrate. Uh, you know, make, you like, the Harish and team are a great group. And, and the team from Shopify is a great group. But they're Flexport people now, you know, and it's, you know, we're all going to be one team and I'd rather, I want to get through that quickly. And if, and I think folks should be excited about the journey we're going to be on and part of the new company they're part of, but if they're not, it's okay. Like it's, it's fine. I'd rather than decide that sooner rather than later. And I'd rather more quickly all become part of one team than, than drag it out and try to be like overly You know, tiptoe around which companies what, and you, and try to be overly sensitive about everything. You know, when the only thing that really matters is you need to go build stuff for customers.

AI assessment note: “waiting too long to, to hit the ground running and to just make the moves”

Q So what single piece of content has had the most impact on you? Book, movie, song, you name it. What has really stuck with you?

A In, so I can't remember the name of the, uh, of the book right now, but it was in, when I was in high school, I was in band, and I was really fortunate that my high school band director, this guy named Bert Creswell, was a big leadership guy, and there was a This band got Tim Lutzenheiser or something with his name, and he did leadership books. And we did every year these big leadership sessions where you like, you know, learn how to be a leader in high school. And it was a gift. And I remember in one of the exercises he did, and this is so corny and cheesy, but I remember it like it was frigging yesterday. He, he had this like pink heart. So you gotta imagine like 200 high school kids through his pink heart. And he's like, he folds it in half, and he's like, you're a jerk, you know, you're ugly, you're, like, he pulls off all these pieces of it, and then, you know, he starts apologizing and taping it all back together, and he holds it up, and he's like, it's back, it's a heart still, but it's not the same. And so, like, there's a lot of leadership training, and then this moment of realizing that, like, you can say all the things you want and do all the things you want, but after you've done it, it's still never the same. So, you best not do it in the first place.

AI assessment note: “I can't remember the name of the, uh, of the book right now”

Q I ask you, I, I love to hear it, but Dave, I manage many people today. They don't hit the goals that I set, and I give them stretch goals, and they don't meet them. Um, I guess my question is, I've lost faith in a lot of people and a lot of teams, because so rarely do they hit the goals that I set. What would you advise me?

A Well, I think what I would tell you is, uh, one, I measure on progression. So I look at it as, uh, how far down the path did we get? Almost no matter where you're going to miss a number of goals, almost no matter what you set them up. If you say, I want to go a hundred yards, you know, you, you, most of the time, at least some percentage of the time, 1015, five, you're going to come short of a hundred. Uh, if you say we're gonna go a 150 yards, you may miss the 150 yards by, you know, 30%, you know, 30% of the time, or even 40% of the time, but you're far more likely to have a hundred percent over a hundred yards. Like your, your net gain of stretching farther is much better than setting something you think is a more realistic target. The key is you, you can't beat everybody, you know, you can't beat everybody up over, you know, not achieving those big hairy goals. Now, if you set a 150 yard goal and you go 50, then that's different, but that's not usually, you know, usually the people you take bets on. Uh, my experience has been that people take bets on get much closer to that unless something really goes sideways, and probably at least half the time they go further than the one 50. Like, they go further than even, you know, they exceed what you thought was even the stretch goal.

AI assessment note: “I measure on progression. So I look at it as, uh, how far down the path”

Q Strange one, Dave. What do you think makes you so good at hiring? You've hired hundreds and hundreds, if not thousands of people. What do you think have been your biggest lessons on talent acquisition?

A Uh, probably that I, my favorite hires, I'm a little afraid that they're going to be way better than me. Like, you know, I, I feel the most that hires I feel best about are the ones I feel the most nervous about being additive to helping them. Like, you know, like, uh, uh, I'm glad to work harder. Like this person is going to make me ever work harder because they're, you know, they're going to be challenged. Uh, and I think too many people look for somebody who's going to do what they're told. Like, you know, they want somebody who's going to fill the job of the now. And what I want is somebody who's gonna fill the job that's gonna be the job three years from now, or five years from now, and that is going to be, you know, very unhappy if their world is just me telling them what to do on a regular basis.

AI assessment note: “my favorite hires, I'm a little afraid that they're going to be way better”

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

Q It totally is. How do you feel like the next few years shake out then? Do these companies get bought? Do they get shut down?

A I think it's going to vary by company. It's going to kind of depend. Um, but I, I think unless you're, unless you've got a lot of people who will make it will have tremendous scale and have customers who are sort of inelastic and spend, uh, and can eat the fees and the subscription fees. And the convenience and time are worth more than the other, than their money. Or they actually value that they actually put a financial value on their time, and they've done some sort of trade-off. And the people without scale just won't, won't make it. They'll go away. I don't expect a lot of acquisition, because there's not a lot of value in acquisition for those.

AI assessment note: “And the people without scale just won't, won't make it. They'll go away.”

Q What's an example of how Amazon is that, just for people to resonate with and understand?

A You know, think about it as a, uh, a damage or a return. You know, there's so many times, um, like if you're, for many customers, uh, right now, if you get an item, you say it's damaged, Well, you know, as soon as it registers that you printed the labels to the back, we're getting your money back. That's expensive, and there's fraud in that, and, and, but it's super positive for the customer to, you know, from an Amazon perspective to be able to drive that efficiently. From a flexible standpoint, we've had the same thing like, you know, Hey, uh, this trailer got held up at the port, you know, for some duration of time. Uh, you know, a typical forwarder would say, well, it doesn't matter why or how we're going to send you a bill for that. You know, we're looking at that and saying, Hey, You know, these days of this, you know, we really should have gotten it out that we're not going to build a customer for that. That's, you know, that's on us. That's an operational defect we need to resolve going forward. It's really these tension points to where you could choose, and the customer probably wouldn't know the difference, or it would be equal to what competitors do, but you know you can do something substantively better for the customer, but it's going to cost you money.

AI assessment note: “think about it as a, uh, a damage or a return.”

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... except distribution and fulfillment.”

Q What are the biggest mistakes companies make with acquisitions and M&A, do you think, Dave? You've seen many from Amazon. You're then doing one now with Deliver and here. It's a big one. What are the biggest mistakes that you are very wary of?

A You know, in my own experience, the, the, the thing that, You know, he's waiting too long to, to hit the ground running and to just make the moves to integrate. Uh, you know, make, you like, the Harish and team are a great group. And, and the team from Shopify is a great group. But they're Flexport people now, you know, and it's, you know, we're all going to be one team and I'd rather, I want to get through that quickly. And if, and I think folks should be excited about the journey we're going to be on and part of the new company they're part of, but if they're not, it's okay. Like it's, it's fine. I'd rather than decide that sooner rather than later. And I'd rather more quickly all become part of one team than, than drag it out and try to be like overly You know, tiptoe around which companies what, and you, and try to be overly sensitive about everything. You know, when the only thing that really matters is you need to go build stuff for customers.

AI assessment note: “waiting too long to, to hit the ground running and to just make the moves to integrate”

Q Doug Leone says that, like, companies are teams, they're not families. Do you agree with that?

A Yeah, I don't think companies are families. You know, I, it's a, you know, I think these people who, like, People have very different relationships. I got, you know, there are people I've worked with for 20 years who I'm, uh, who I work with and I'm also friends with, and then there are people I've worked with for six months that, uh, you know, I consider this great working relationship, but you know, we don't have like a, we don't, you know, I don't know six layers of their family kind of thing. Uh, but we're not a family because we're all here to do a job and we have a set, a set of roles and responsibilities and You know, you have to deliver on performance. You know, it is a team. I think that's a much better way of framing it than, than a family. It doesn't mean that you don't have personal relationships with people. And it just means that it's not, you know, you, you, family's family. There's no getting, no getting out of your family. Right. It's permanent. Yeah. Jobs aren't permanent.

AI assessment note: “Yeah, I don't think companies are families.”

Q I hope so. Uh, otherwise I can just stop and retire and then someone else can take my place. Um, but a big change is when you have kids. This is like the ultimate inflection point. How did having kids change how you think?

A Mostly it just made me more patient. You know, I think you, you, uh, in the sense that one, I think you see yourself in your kids. Like you see your behaviors in your children, like, you know, they don't fall far from the tree, you know? Yeah. And so you see some stuff and you're like, oh, you said, that's annoying. Like I should stop doing that. That that's, that's really frustrating. And, and you just learn to be patient with people, you know, I mean, it, cause you can't, but they're kids. Like, what are you going to do? Uh, it's also very humbling. Nothing keeps you humbling, like wiping somebody's butt. Like if you, I wiped a lot of butt. I got two boys that are 11 and eight. Lot of poop in my house. So like, I've, I've done a lot. It keeps you humble. And that's helpful. You know, I mean, it just keeps you connected to the real, real world. Right. You know, like people, people are a composition of everything in their life, their kids, their family, you know, their work and All those things make them great, and come in and out of challenges and good stuff, and I think I just have a deeper appreciation of the whole person having now have kids.

AI assessment note: “Mostly it just made me more patient.”

Q I hope so. Uh, otherwise I can just stop and retire and then someone else can take my place. Um, but a big change is when you have kids. This is like the ultimate inflection point. How did having kids change how you think?

A Mostly it just made me more patient. You know, I think you, you, uh, in the sense that one, I think you see yourself in your kids. Like you see your behaviors in your children, like, you know, they don't fall far from the tree, you know? Yeah. And so you see some stuff and you're like, oh, you said, that's annoying. Like I should stop doing that. That that's, that's really frustrating. And, and you just learn to be patient with people, you know, I mean, it, cause you can't, but they're kids. Like, what are you going to do? Uh, it's also very humbling. Nothing keeps you humbling, like wiping somebody's butt. Like if you, I wiped a lot of butt. I got two boys that are 11 and eight. Lot of poop in my house. So like, I've, I've done a lot. It keeps you humble. And that's helpful. You know, I mean, it just keeps you connected to the real, real world. Right. You know, like people, people are a composition of everything in their life, their kids, their family, you know, their work and All those things make them great, and come in and out of challenges and good stuff, and I think I just have a deeper appreciation of the whole person having now have kids.

AI assessment note: “Mostly it just made me more patient.”

Q I was first struck when I saw that you spent 23 years at Amazon. Now this is loyalty that we don't see today, and I just thought that there were so many incredible learnings to unpack. So when we start there, what are one to two of the biggest lessons that are maybe non-obvious that you took from your time at Amazon and how they've impacted you as a leader?

A Yeah, it was two, three years. Uh, you know, I came straight out of grad school and, uh, worked up from that to be CEO of the consumer business was a hell of a ride in Amazon years. It's like a 150 years or something. So it's like a normal, of normal time. Yeah. So, uh, it was a fun ride and I did, I learned a lot. And, uh, you know, when I think about the things that, you know, a lot of has been published about Amazon and about Um, the way Amazon operates and runs its business. Uh, but I think, you know, some of the things that I think have been really important to me over time is this idea of, you know, giving people an opportunity to stretch beyond what they think is possible. You know, I, I, when I think about the, the career I had, uh, much of why I handled this because people, you know, let me do things that I had no business doing and had a high probability of failing at, but then I ended up finding a way to be successful. And, you know, I think people too often, uh, put limits on what they think their people are capable of out of fear of overstretching them in some way.

AI assessment note: “giving people an opportunity to stretch beyond what they think is possible”

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.”