Dave Clark: Lessons from Leading 1M Employees w/ Jeff Bezos at Amazon to CEO of Flexport | E1036

1. 0:00 – 4:50

   From Amazon to Flexport - Dave Clark’s Journey

   1. DCDave Clark0:00

      You know, when you're in the shit, you often don't realize that you're in the shit. You know, if you're just, you know, if you work until 11:00 at night, you don't, you kinda don't even recognize that you're doing it to a degree, or that you don't recognize that you're not engaging, you know. You don't, because you're in the shit. (instrumental music)

   2. HSHarry Stebbings0:15

      Dave, I am so excited for this. I heard so many great things from many different people, from Ryan Peterson to your friend Oli beforehand. So thank you so much for joining me today.

   3. DCDave Clark0:24

      Glad to be here. Thanks for having me.

   4. HSHarry Stebbings0:26

      Not at all. Listen, 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?

   5. DCDave Clark0:47

      Yeah. It was 23 years. Uh, you know, I came straight out of grad school, and then worked up from that to be CEO of the consumer business. Was a hell of a ride. In Amazon years, it's like, uh, 150 years or something. So it's like a normal, a normal time, you know. (laughs) 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 it 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 mean, when I think about the, the career I had, um, much of why I had it is 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.

   6. HSHarry Stebbings1:53

      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?

   7. DCDave Clark2:13

      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, it's not existential to the today, it's uh, 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.

   8. HSHarry Stebbings3:02

      Can 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-

   9. DCDave Clark3:14

      Yeah.

   10. HSHarry Stebbings3:15

       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?

   11. DCDave Clark3:25

       Well, I, I think what I would tell you is, uh, w- one, uh, I measure on progression. So I look at it as, uh, how far down the path did we get? Al- almost no matter where ... You know, you're gonna miss a number of goals, almost no matter what you set them up. Like if you say, "I wanna go 100 yards," you know, you, you most of the time, at least some percentage of the time, 10, 15, five, you're going to come short of a hundred. Uh, if you say, "We're gonna go 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 100% over 100 yards. Right? 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, 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, in my experience, has been that people you 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 150. Like they go further than even, you know, they exceed what you thought was even the stretch goal.

2. 4:50 – 8:39

   What Makes a Great Hire

   1. DCDave Clark4:50

   2. HSHarry Stebbings4:50

      Can I, can I ask you, when you look at the people that exceeded the 150 or met the 150 stretch goal, when you review those hires, do they have things in common that were obvious in the interview process? Like don't laugh, but for me, my best hires were the most boring in the interview process.

   3. DCDave Clark5:08

      (laughs)

   4. HSHarry Stebbings5:09

      Like specifically, the ones where I was like, "I would be bored working with you," they turn out not to be boring and brilliant.

   5. DCDave Clark5:17

      Uh, I don't know I've ever had the boring, uh, a- anecdote. That's interesting. Uh, I don't ... I ... What I find to be most consistent is that, um, the three biggest traits, um-

   6. HSHarry Stebbings5:31

      Mm-hmm.

   7. DCDave Clark5:31

      And, and maybe in order, they're simplifiers, uh, they have great grit, and they're smart.

   8. HSHarry Stebbings5:40

      Dave, you are setting me up. I mean, th- this is tee down on the fairway, I'm gonna swing for this one. Simplifiers. What does simplifiers mean, and, and how is that shown?

   9. DCDave Clark5:51

      Well, have you ever ... I mean, y- you can ... 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 gonna tell you, we're gonna 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 the things that are going to go wrong in very complicated ways, uh, 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 gonna be super hard, so we'd need to get somebody to figure that out." Like, it's the difference between the people who find, uh, ways not to do things oftentimes and the people who find ways to do things. They separate, you know, they, they separate the hard from the easy. Like, almost all the problems that you think are too complicated to do are like 90% 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.

   10. HSHarry Stebbings7:07

       How do you test for grit?

   11. DCDave Clark7:10

       Uh, you put them under load and see what happens.

   12. HSHarry Stebbings7:15

       (laughs) Go ahead, you-

   13. DCDave Clark7:16

       Like, there's no, there's not a, there's no, uh, simulation for it. You just have to like, you know, you put somebody into, you know, it, it's like increasing pressure, you know? Like it's a, you, you know, you, you basically start at, at one level load and if you can handle it, then you get more, and then you get more, you know, you, and, and find out where it breaks.

   14. HSHarry Stebbings7:36

       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?

   15. DCDave Clark7:49

       Uh, probably that I- 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 most, the hires I feel best about are the ones I feel the most nervous about being additive to helping them. Like, you know, like, oh, uh, that, I'm gonna have to work harder (laughs) . Like, this person is going to make me have to work harder because they're, you, they're going to be challenging. 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 them now, and what I want is somebody who's going to fill the job that's going to 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

3. 8:39 – 10:17

   What Makes Jeff Bezos Greats

   1. DCDave Clark8:39

      basis.

   2. HSHarry Stebbings8:39

      Speaking of amazing people around you, there are very common traits, sayings about Jeff Bezos. You worked with him for 23 years. Uh, you have un- 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?

   3. DCDave Clark8:58

      I think the world tends to think of Jeff as like, you know, it's like Moses coming down from the mountain with the Ten Commandments and is like, "Shazam! Here is what we shall..." And, and it's not like that. I think, uh, what Jeff is good, is particularly skilled at, well, I mean, he's brilliant, you know, I mean, just 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 simplifier I've ever met, which is he can, he can context shift incredibly well. He could 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 mo- mode in the moment, which a lot of people have trouble doing, and he can quickly sort out the 90% that isn't hard, and is sort of, he doesn't need to worry about because 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 senior level of intellect to figure out how to solve and what's most important. And so he's hyper efficient with the time that he spends because he doesn't waste time on the stuff that's easy.

   4. HSHarry Stebbings10:16

      That's a decision that

4. 10:17 – 17:47

   Decision Making Framework

   1. HSHarry Stebbings10:17

      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?

   2. DCDave Clark10:31

      You know, that'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 the subject because I don't kn- I, I don't know that I have a particular like, you know, because some people have these really robust like acronym decision trees that they go through and I don't know, I don't have that. Um, I sort of just approach every document, like every document I review with, I have a, I hold a lot of important views on things, so just, uh, particularly in the spaces I've occupied because I have a lot of experience in those places. And then I just approach it with a lot of curiosity and try to dig in, you know, and to understand what, again, what's the most important things? What's hard? Wh- wh- where's the real innovation? What's the separation? Uh, what makes us better than the other? Uh, but I don't have a... Sadly, you know, I feel like I need to, 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, because I get asked it a lot and it always sounds-

   3. HSHarry Stebbings11:31

      I, I do two, I, I do two things. I do two lists. One, what will lose me the most money, and two, what will let down the most or the most meaningful people or persons, and if they align-

   4. DCDave Clark11:40

      I think I have a similar top level framework to that, which is, uh, I do, first, I do the things that will get me fired, and second, I do the things that get me promoted.

   5. HSHarry Stebbings11:48

      Correct.

   6. DCDave Clark11:48

      So like I do, on a, on a straight up prioritization mechanism, I have a similar structure to that. You know, but I have a more Amazon one where, what's going to get me fired or what's going to get me promoted? Like it's narrow set. Do the promotion list last, fire list first.

   7. HSHarry Stebbings12:02

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

   8. DCDave Clark12:08

      I've made lots of wrong decisions over time. I, I think my batting average is pretty good. But I certainly struck out plenty of times at the plate. And no, I personally don't mind any of the, like, mistakes I've made. The ones I've, the on- uh, 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 had, I had, you know, my gut was, "We should've 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, a decent amount of that was probably all me in sort of looking at the cost and the, you know, there's really not, there's not a great feasible, there's not a real feasible, like, one-hour delivery profitable model, uh, you know, de- despite, you know, all the efforts, you know, all, all the, uh, 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 gonna make it." But the piece I didn't have conte- 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 think I held us back from that. We launched, you know, Prime Now, you know, I don't know, however many years ago now, but, uh, and we launched it super fast, I was really proud of what the team did there, but we were late to it, I think, because, in part because I was conservative on, like, this isn't gonna work long term, and we should do it anyway.

   9. HSHarry Stebbings14:02

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

   10. DCDave Clark14:06

       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 know, have a perception of speed about you as a company. And there was a period of time there where, you know, I mean, two-day was like the, you know, you could get anything you want in the world basically in two days or less, and th- like nobody was really competitive with that. And then all of a sudden there were all these companies who were like, "Well, two-day is for, you know, boomers." Like this is, "I'm gonna get it to you in, you know, 15 minutes." Uh, and that was where all the VC money went, it's where all the eyeballs went, and because of that, it made two-day, the impression of two-day 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 e- we weren't on the cutting edge anymore.

   11. HSHarry Stebbings15:04

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

   12. DCDave Clark15:14

       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 ad.

   13. HSHarry Stebbings15:23

       Mm-hmm.

   14. DCDave Clark15:25

       You know what I mean? You really, you're not gonna, like just product COGS and margin with delivery cost, it's very hard to get the density you need. If you're net averaging $20 to $25 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.

   15. HSHarry Stebbings15:52

       Yeah.

   16. DCDave Clark15:53

       And that takes a lot of, it takes a lot of scale, 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, 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 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 'cause of cost.

   17. HSHarry Stebbings16:25

       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?

   18. DCDave Clark16:33

       I think it's gonna vary by company, and it's gonna kind of depend, um, but I, I think unless you're a m- unless you've got a lot of s- the n- people who will make it will have tremendous scale, and have customers who are sort of inelastic in 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 the, they actually put a financial value on their time, and they've done some sort of trade-off. Uh, and the people without scale just won't, won't make it. They'll go away.

   19. HSHarry Stebbings17:10

       Can I ask you, it's

   20. NANarrator17:10

       It's hard-

   21. DCDave Clark17:10

       I don't expect a lot of acquisition 'cause there's not a lot of value in acquisition for them.

   22. HSHarry Stebbings17:15

       Why d- why do you think not? Just because the local networks don't carry much value?

   23. DCDave Clark17:19

       Exactly. I think the customers aren't portable necessarily to the new venture. You're not really buying customers, you're not really buying process, the drivers work on almost all the platforms today, or on many of the platforms today, so you're not really picking up capacity, uh, you also don't really pick up customers because the customers will just move to the new service on most of those cases. Again, it can vary by company, but I, I don't, I wouldn't expect

5. 17:47 – 21:15

   Why Dave Left Amazon After 23 Years

   1. DCDave Clark17:47

      to see a tremendous amount of acquisition.

   2. HSHarry Stebbings17:49

      We, we mentioned kind of decisions there, and that's where that kind of conversation rooted from. You made a very big decision to leave Amazon after 23 years. You didn't need to. Respectfully, (laughs) 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?

   3. DCDave Clark18:13

      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, uh, which is probably the most important decision I've ever made. But, uh, you know, I was at 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, uh, I was not in a place where I was spending my time building. You know, A- Amazon's still a builder, you know, oriented company, but m- I personally was not in a place where I was getting to, 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 large- 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. Uh, I didn't wanna stop working. I love, I love working. I just, uh, it, you know, it was time to do something else.

   4. HSHarry Stebbings19:25

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

   5. DCDave Clark19:31

      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, uh, on fulfillment and ops. So you can, you can go back and look at the square footage ramps, you know, this sort of 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. Uh, 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 then 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, it's kind of, you know, that journey of, you know, decade or so from 2011 to 2023 of building that for Amazon, uh, is, is what excited me about Flexport. You know, it was really this, you know, we'd built that at Amazon for Amazon and for sellers who were part of Amazon's, uh, 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 environment to pull carbon, you know, to improve carbon utilization, to pull waste out of the, the processes, uh, and they need it to be competitive, you know, with small business to be competitive with the largest businesses in the world. So I'm a supply chain guy,

6. 21:15 – 24:34

   Differences Between Amazon and Flexport

   1. DCDave Clark21:15

      so I, I just wanted to go do it again.

   2. HSHarry Stebbings21:17

      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 wanna do again?

   3. DCDave Clark21:31

      Yeah. I, I mean, I l- I love so much about Amazon. I, I sort of view myself as, uh, somebody who helped establish parts of the culture at Amazon over, over that time period. And I, I d- what I loved is the, most is the customer centricity, you know, this place of, like, uh, you really do make a decision for the customer. You know, a lot of people say they do, uh, and they really do well up until the point to where it's a trade-off between the money and the customer, you know? (laughs) Like, it, 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 gonna 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 the culture.

   4. HSHarry Stebbings22:25

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

   5. DCDave Clark22:30

      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 a, uh, for many customers, uh, right now if you get an item you say is damaged, w- you know, as soon as you

   6. NANarrator22:44

      (clicks tongue)

   7. DCDave Clark22:45

      ... as soon as it registers that you printed the label and sent it back, we're giving you your money back. That's expensive, and there's fraud in that, and, uh, and, but it's super positive for the customer to, you know, f- from an Amazon perspective be able to drive that efficiently. From a Flexport 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 gonna send you the 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 gonna bill the 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 gonna cost you money.

   8. HSHarry Stebbings23:45

      What have you not taken to Flexport that either did or didn't work?

   9. DCDave Clark23:48

      You know, I think, you know, when I look at, you know, cultural history for me, it's, uh, um, I think, I mean, Amazon's a fairly intense place, you know, and it's a, um, you know, Amazon, I think you kind of, uh, you know ... It's very, you know, you're as good as you w- what you did yesterday kind of thing. There's not a lot of longitudinal, um, stickiness in that way. And I'd like to think that what we're bringing is the intensity for customer, the intensity for process, um, with a, a more-... a little more empathetic, uh, and a little more, uh, collaborative in a type of approach to engaging together, and a little more long-term

7. 24:34 – 27:33

   On Leadership and Trust

   1. DCDave Clark24:34

      engagement success.

   2. HSHarry Stebbings24:36

      Speaking of that intensity, I spoke to Ollie before the show, and he told me a mantra of yours, "Make tough promises and keep them." What did he mean by this? 'Cause he didn't expand on it. And how does it impact your thinking?

   3. DCDave Clark24:50

      Well, look, uh, you know, you, you don't, you earn trust, right? I mean, you, you earn trust in people, and you earn trust in customers. And, uh, you know, it's, it's easy to make an easy promise. Like, you know, it's easy to, you know, you know, to say something and, you know, or to make a promise and not live up to them sometimes. And I, I think we, as a company, are making... Like, Flexport right now has got a very aggressive roadmap of products we're building for 20, late '23 and '24, and we're going out. We haven't always historically delivered on them, uh, but we've put the pieces in place. And we're going out and telling customers, "This product is coming in '23 and '24. And if you'll sign up to be part of this, uh, and be part of helping us develop it, you're gonna get this." Those are hard promises because they're a lot of work and there's a lot of dependencies between here and there. Uh, but if you deliver on it, you earn an immense amount of trust. Like, it, you get a lot of credit for committing to deliver something that they know is not... that they know requires a lot of work, and then when you actually do it. Just following through on, you know, doing what you mean and meaning what you say, you know, is where trust is built. And the more you're willing to lean out on that for people and for customers, the more trust you build.

   4. HSHarry Stebbings26:13

      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?

   5. DCDave Clark26:22

      Well, as a trust as a person, you 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. Um, on the other side, it's less... I, 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, w- w- 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 a... You know, by the way, is like, uh, among the most trusting things you can do, uh, 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. Uh, 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

8. 27:33 – 31:50

   How to Recruit Talent

   1. DCDave Clark27:33

      my job is to help you be successful.

   2. HSHarry Stebbings27:35

      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?

   3. DCDave Clark27:46

      Yeah. It's, uh, yeah, I mean, it's a gift, you know, for one. I mean, it's like, uh, I'm extremely grateful that these people, uh, 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 gonna come in and do the things you need to do to deliver in the company. And you're placing a bet that I'm gonna support you and that I'm gonna live up to my end of the deal with help and support and resources and, uh, and guidance and whatever's needed to enable you to be successful in your role. And it's a two-way street, especially at a senior level, because the, you know, those are big, big... Those are marriages that might be much le- you know, they aren't really... You know, those aren't short-term hires, right? I mean, you're hiring somebody for, you know, that's gonna decide who these big teams are for the company for the next 10 years.

   4. HSHarry Stebbings28:56

      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?

   5. DCDave Clark29:08

      Well, I mean, I, I, I am far from perfect, uh, for sure. Uh, I, I can't think of a specific example per se. I mean, I think especially younger in my career, I don't... Uh, you know, I think I was less patient maybe. You know, I, I didn't have enough appreciation for... Sometimes we didn't have enough appreciation for sort of the impact of broader life on people's, 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... Uh, l- 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-

   6. HSHarry Stebbings29:50

      How do you, how, how do you accept them without creating a culture of acceptability of failure? 'Cause it's really tough when people go, "Oh, well, this happened in my personal life," and you're like, "I get it. That's tough. I'm sorry." But it's like, but, I'm sorry, we're a business. We, we do this stuff to keep moving, and sometimes people can use it and abuse it.

   7. DCDave Clark30:10

      Well, I think that's it. I mean, it's pretty clear usually where somebody is using it and abusing it and when they're not, you know? And, yeah, if they're using and abusing it, then you handle, you know, you treat it differently. That's not really... That, what you've learned about them is a bit of a... And that's a trust loss, right? You know, because, you know, that's somebody basically...... being deceptive about why they're, you know, like, feeling challenged, versus the... There are people with real, you know, legitimate things happening in a moment in their life, and they need your support to get through this. They're fantastic people, but for the next six months, they're not gonna be fantastic. And, you know, you have to decide whether that's okay or not. And, you know, for most of the time, that's okay.

   8. HSHarry Stebbings30:49

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

   9. DCDave Clark30:57

      Yeah, I don't think companies are families, you know? I, I, it's a... You know, I think these people who, like... People have very differing relationships. Like, uh, you know, there are people I've worked with for 20 years that 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 r-... 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, y- 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. Uh, it just means that it's not... You know, you, you... Family is family. There's no getting, no getting out of your family, right? 'Cause that... It's permanent.

9. 31:50 – 34:35

   Hiring Internally vs Externally

   1. DCDave Clark31:50

      Uh, jobs aren't permanent.

   2. HSHarry Stebbings31:52

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

   3. DCDave Clark32:09

      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, uh, then, you know, 99 times out of 100, I would rather hire internal. Uh, but in fast growth environments, like I was in at Amazon and like we're in at Flexport, 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... Uh, it, it, it's really... Uh, the way I think about external talent is, uh, 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.

   4. HSHarry Stebbings33:13

      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 transferrable?

   5. DCDave Clark33:26

      Uh, I think I understand what you mean with that. And, uh, I like to hire entry-level jobs out, right out of college as an example, 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, w- where we have opportunities to do it, I really like hiring people who are, like, day one in their career, uh, because it, you know... You, you have more attrition in that, 'cause people are still f- you know, discovering themselves and discovering what they wanna 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... If they're here for 10 years, that's, that, they're, you know, tried and true Flexport employee, and they know the culture, or they're part of building it. You know, there's no better evangelist for it. And they learn what we're all about, be 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

10. 34:35 – 37:12

    Details on Acquisition of Shopify Logistics

    1. DCDave Clark34:35

       in the right kind of role.

    2. HSHarry Stebbings34:36

       Speaking of bringing in talent, uh, you also made some acquisitions that were very strategic. What was the thought process behind the acquisitions? Specifically, I guess, with Shopify Logistics, which also includes Deliverr.

    3. DCDave Clark34:48

       I mean, it was a great opportunistic, um, moment, I think. You know, we, we have been, uh... We had a plan to b-... We wanted to be end-to-end. So we wanna be, you know, we're, uh... We wanna be an R now, end-to-end 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 end this year, and so we were gonna start a team later in 2023 to build that, when we started having conversations with Shopify about the idea of... you know, that they were gonna s- sell, or they were looking to potentially sell Shopify Logistics and Deliverr, b-

    4. HSHarry Stebbings35:37

       How did that actually look, Dave? I'm so sorry for being base, but like-

    5. DCDave Clark35:40

       Yeah. (laughs)

    6. HSHarry Stebbings35:40

       ... does Toby drop you a WhatsApp and say, "Hey, Dave, got time to jump on a FaceTime?" Like... (laughs) What, what... Uh-

    7. DCDave Clark35:46

       It, it, it went something like that. Uh, you know, Toby that knows Ryan, 'cause they, uh, 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. You know, 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. Uh, 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, that, uh, they had a really good product. And, uh, they had a product that would work for us. And, uh, the build versus buy on what they had and where they were at, uh, made a ton of sense for us to acquire. Company felt a lot like the culture of, um, Flexport.And so, it also doesn't need to integrate super heavily. It can 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, 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, wi- wi- you know, is a great thing for us as a company, and, uh, gives us, you know, just that much more access to help,

11. 37:12 – 39:29

    Mergers and Acquisition Mistakes

    1. DCDave Clark37:12

       uh, merchants and sellers even faster than we had planned.

    2. HSHarry Stebbings37:15

       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 Deliverr and Here. That's a big one. What are the biggest mistakes that you were very wary of?

    3. DCDave Clark37:27

       You know, in my own experience, the, the, the thing that, you know, is waiting too long to, to hit the ground running, and to just make the moves to integrate. Uh, you know, make... you know, like, the H- 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 gonna 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, 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 them 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 know, a- and, and try to be overly sensitive about everything, you know, when the only thing that really matters is we need to go build stuff for customers.

    4. HSHarry Stebbings38:25

       So you're like, "Hey, you're all Flexporters now. This is the kind of, this is the state of play. Let's go do this." And for anyone that doesn't kind of get excited, it's like, "Hey, maybe not for you, and like, good luck." Is that kind of it?

    5. DCDave Clark38:39

       Yeah.

    6. HSHarry Stebbings38:39

       Or do you kind of try and softly, softly it?

    7. DCDave Clark38:42

       Uh, well, I mean, we want everybody to stay. So, you know, it, y- we try to convince people that it's the right thing, and here's why it's a good thing, and ... But if it's not for you, that's okay. No hard feelings. Uh, I mean, not everything is for everybody. There's a, uh, uh ... There are lots, and lots, and lots of places to work in the world. And you should find the one that makes you happy. And if it's not us, that's okay.

    8. HSHarry Stebbings39:06

       Can I ask you, Dave, when you, when you say that, I, uh, I actually think about relationships a little bit. I listen to, uh, many kind of romance and love philosophers, which is probably, uh, why I have the woeful state of love affairs that I have. I'll, I'll send you a playlist afterwards. It's gonna be incredible. But you don't need it. You've got a fantastic wife. I've, I've listened to your commencement speech. Loved it. Fantastic. But you said it was like the best decision, or

12. 39:29 – 46:37

    How do you make marriage work while being CEO?

    1. HSHarry Stebbings39:29

       one of the most important decisions of your life. Can I ask you, Dave, how do you make it work? I know it's a really obvious one. But you're a CEO of like a multi-thousand person company. How do you make it work, and be a good partner at the same time?

    2. DCDave Clark39:48

       Well, I wish I could say I've always done that. Uh, but, you know, I don't, I don't think that's true. You know, there's certainly been moments where I've been out of balance on that. Uh, you know, uh, first and f-

    3. HSHarry Stebbings39:59

       And how, how, how do you get through those moments, actually? When you're out of balance, how do you get through them?

    4. DCDave Clark40:04

       Well, first and foremost, I think it's, um ... For me, it's been about, uh ... Like, Leanne and I want the ... you know, we're, we're 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're, we're 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, 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've got to figure out, how do you balance the time and 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's different for every person. Uh, I've always said I could only be good at two things. And, you know, that's work and my family. And, you know, sometimes I'm not even good at two things, uh, you know, 'cause one takes place over the other. Uh, the key I've 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, the only thing of true value I have is time. And so I've become much more protective of it than I was, you know, a decade ago. And as a result, I, I reserve, you know, e- structurally reserve in my calendar and with my assistant, like, making sure that I have, you know, a more structural basis for spending the time in the places that matter to me and that can have the most impact. It's like the simplicity thing. I now have to spend my ... I don't ... I only have a limited amount of time, so I want to spend it on the 10% that gets the maximum impact, you know, between my job, my kids, and my wife. And, uh, and hopefully, you know, all those things make me happy too at the same time.

    5. HSHarry Stebbings41:57

       When was it most out of kilter? When was the debt to family highest?

    6. DCDave Clark42:03

       Out of COVID. I mean, it had to have been. I mean, I think the, uh ... When I think about the 2020 and '21 of ... I mean, we doubled the size, basically, of the entire operating footprint for Amazon in, like, 18 months. And, you know, the, um ... Everything was happening with employees, and sort of trying to keep people safe. And, I, I, I mean, I can't ... I mean, that two years of COVID, I think for everybody that was in operations at Amazon was like, you know, a decade. It was like ... It's like a, a weird sadistic blur at this point, you know? (laughs)

    7. HSHarry Stebbings42:37

       And so, you say to your wife, "This is a time-bounded period where I will not be here, and I will not be what you need from a partner."Please bear with me.

    8. DCDave Clark42:48

       I, I wish that I was that sophisticated in my thought and language in those moments, but it is more I, I think, uh, you know, look, in hindsight those are the kind of conversations you have, but in the moment, you know, you're, you're trying to just make the best choices you can make. And, you know, I think it, it, it's a, uh... For me, it's just always been try to be as open in communication as we can be, and accept that I, I, you know, I screw up a lot, and, you know, we're heading on the same journey. It's like everything else, you just try to be committed and try to make it better tomorrow than it was yesterday. You know, I don't, I don't know that there's any magic there. I wish it was like that clear, but you know, when you're in the shit, you often don't realize that you're in the shit. You know, you're so, you know, like, you, you know, if you're just, even if you're working to the level I'm talking about, you don't, you kind of don't even recognize that you're doing it to a degree, or that you don't recognize that you're not engaging, you know? You don't, because you're in the shit.

    9. HSHarry Stebbings43:48

       Dave, you, you are fantastic. When you're in the shit, you often don't recognize you're in the shit. That is a title for a podcast in the making. I love that. That's fantastic. (laughs) Um, no, I, I agree with you totally. Can I ask one fear that I have, is like you go to date night with your wife, which is fantastic, or you go home for dinner, that is time that you could be spent working, and like, you know, I have a wonderful other half now, but respectfully, sure we want the same things, but it is time away from work, and I am better at work and achieve more when I work harder. Can you alleviate my fears? 'Cause I'm worried that I'm gonna become less good with a partner.

    10. DCDave Clark44:29

        Well, this has really turned into a therapy session for you. I, it's good. I like it. Let me, let me see if I can help you.

    11. HSHarry Stebbings44:34

        Nice. (laughs)

    12. DCDave Clark44:36

        Uh, you know, here's the way I would put it. I'm a better leader and partner to my teams when, uh, I'm balanced, and when I'm, when I'm at full patience and where I have clarity of thought and, and bandwidth to, to go deeper on things. And I am in that condition best when my home life is also in balance, in, in at, at least a respectably good way. And so, if the choice is that the company and the team can have me, you know, and I'm unwilling to sacrifice my family. I, you know, like it's too important to me. I, it's, it's a piece that I view as a requirement for me being happy. And so it becomes a decision, which is does the company want me in that capacity? You get this much of me, and you get me in a healthy, happy state, and then my family gets the other part, or you can have none of me. And the some of me, I think is better than the none of me, and I suspect the same is true for you, that, uh, in a well-rounded you state, you're better than when maniacally focused. I suspect that, uh, I suspect that it's true that the company and the people you work with would be better off with some of you than none of you, uh, and that some of you is still better than the replacement. Right? 'Cause I also view it as like, "Well, who would do this if I didn't do it?" And would they be better than me right now, uh, with what time I spend, I mean, I think, still think I spend a lot of time, uh, with, with what time I spend, would they be better than me? And if they would, then I should go. Then they should take that job. And I would do that and feel fine about it. Uh, but I don't think that's true today. So, I, I feel very imbalanced on that. But I suspect it's similar for you.

    13. HSHarry Stebbings46:31

        I hope so. Uh, o- otherwise, I can just stop and retire, and then someone else

13. 46:37 – 55:18

    How Having Kids Changes Life

    1. HSHarry Stebbings46:37

       can take my place. (laughs) Um, but, a, a big change is when you have kids.

    2. DCDave Clark46:42

       Yeah.

    3. HSHarry Stebbings46:42

       This is like the ultimate inflection point.

    4. DCDave Clark46:45

       Right.

    5. HSHarry Stebbings46:45

       How did having kids change how you think?

    6. DCDave Clark46:49

       Mostly, it just made me more patient. You know, I think you, you, yeah, in the sense that, well, 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? Uh, and so, you see some stuff and you're like, "Oh, shit 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, it, 'cause you can't with their kids. Like, what are you gonna do? Uh, it's also very humbling. You keep, nothing keeps you humbler than like wiping somebody's butt. Like, if, you know, I wiped a lot of butt. Keeps me... I got two boys. They're 11 and eight.A lot of poop in my house. So like, I have, 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 n- 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 cause, come in and out of challenges and good stuff, and I, I think I just have a deeper appreciation of the whole person having now have kids.

    7. HSHarry Stebbings47:59

       Yeah. Dave, what was 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?

    8. DCDave Clark48:13

       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, it, you know, it helps, at least for me, it helped soften me, I think, in a bunch of ways, and help 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 know. When something goes bad with your- ... 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.

    9. HSHarry Stebbings49:11

       Can I ask you, what 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-

    10. DCDave Clark49:26

        Yeah.

    11. HSHarry Stebbings49:26

        ... now, with the, you know, 11 and 9-year-old that you have, what would you say to yourself?

    12. DCDave Clark49:32

        Mostly, I'm, like, super happy with the choices I've made in my life, but if I could 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 you, 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." You know. You know. Uh, you, you, you start to, you start to recognize things you're doing that you didn't realize you were doing. And so, I think, uh, presence is so important to people, whether it's people at work or people at home or your kids, and, uh, I think learning to be ... Uh, I wish I had learned to be more present with everyone I was with in the moment, early.

    13. HSHarry Stebbings50:21

        Is there anything you do to be more present? Put your phone away, turn off your phone entirely? Uh, we have very different lives, but we're both, I'm sure, addicted to devices in many ways. Is there anything you do to be more present for them?

    14. DCDave Clark50:35

        Uh, look, most of the distractions are the ph- like, the phone is, like, the worst.

    15. HSHarry Stebbings50:39

        Hmm.

    16. DCDave Clark50:40

        Yeah. And so largely, it's, like, trying to be very conscious of, what am I doing with my phone at this moment while I'm engaging with this person? Kind of, you know, putting it away. Uh, I, I had an Apple Watch for a while I was trying to wear 'cause I was trying to do sleep tracking and stuff. And I realized that, uh, like, it was making me not present because I would- it would engage me in, like, lots of very different ways. Uh, and so I just stopped wearing it 'cause it was, like, a distraction.

    17. HSHarry Stebbings51:08

        I'm going to 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, you know, affluent environment. I speak to many very, very successful founders. I asked Tobi 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?

    18. DCDave Clark51:31

        You know, we talk about it a lot. Uh, you know, my, my wife and I both come from backgrounds that, you know, certainly they look nothing like the lives we have today. And, and it's a challenge. Uh, our number one rule is, uh, we have two, two rules in our house, yeah, 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 30. Like, I, 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 or not ... Like, I was a terrible student in life. Man, I hated school. School was the most boring, pedestrian, like, check the box. I hated it. And 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, yeah, 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 wanna 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.

    19. HSHarry Stebbings52:51

        What about flying private? (laughs)

    20. DCDave Clark52:56

        Well ...

    21. HSHarry Stebbings52:57

        Sometimes. (laughs)

    22. DCDave Clark52:58

        They better, they better like Southwest.

    23. HSHarry Stebbings53:00

        (laughs)

    24. DCDave Clark53:00

        Like, I, I ... You know, look, I, I don't ... I ... Uh, there is a lot of people who sort of say, uh, they sacrifice their own, like ... I view it as I work really hard. And I'm not flying coach so that my kids can learn to re- respect coach. Like, that's ... But they've got to, you know, they're gonna have to ... They've got to learn to have societal responsibility and they do things, you know, with school and other things to help and to learn those skills. Uh, I don't think you can, like ... I mean, if you're very wealthy and flying coach, your kids still know you're very wealthy. It's not a, it's not-

    25. HSHarry Stebbings53:40

        Because I, I, I ... With total respect, and I, I don't think there's, like, um ... I think you're, you're absolutely right. You know what some of the hardest working children in the world are? The Arnaults. Bernard Arnault's children.

    26. DCDave Clark53:50

        Yeah.

    27. HSHarry Stebbings53:51

        They are the wealthiest family in the world. And I'm sure they went in every private jet in the world, and they were also told that, "You have to work your fricking ass off for it, and you are the ones who are gonna be doing it too." And they are amazing.

    28. DCDave Clark54:03

        Yeah. My kids are fully aware that, uh, if they, if they want to enjoy this lifestyle after they leave the house, they're go- they're gonna have to figure out how to work.

    29. HSHarry Stebbings54:12

        Totally.

    30. DCDave Clark54:12

        Because ...
14. 55:18 – 1:00:37

    Quick-Fire Round

    1. HSHarry Stebbings55:18

       give me your immediate thoughts. Does that sound okay?

    2. DCDave Clark55:21

       Okay.

    3. HSHarry Stebbings55:21

       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?

    4. DCDave Clark55:31

       In high, and so I, 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 Burt Creswell, was a big leadership guy, and there was a, this band guy, Tim Lutzenheiser or something was his name, and he did leadership books, and we did every year these big leadership sessions where you like l- l- you know, learned how to be a leader in high school, and it was a gift. And I remember, uh, one of the exercises he did, and this is so corny and cheesy, but I remember it like it was friggin' yesterday, he, he had this, like, pink heart, so you gotta imagine like 200 high school kids looking at this pink heart, and he's like, he'd fold it in half and he's like, "You're a jerk. You know, you're ugly. You're a bul," like, and 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 it was 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 apologetically, after you've done it, it's still never the same. So you best not do it in the first place.

    5. HSHarry Stebbings56:42

       I like that. What's the single biggest bet you've taken, Dave?

    6. DCDave Clark56:46

       It's probably, uh, where I went to school, 'cause I didn't know where Auburn was when I went there, uh, moving to Delaware with my later-to-be wife, uh, from Campbellsville, and, uh, and then, you know, maybe leaving Amazon, you know, a year ago.

    7. HSHarry Stebbings57:04

       What-

    8. DCDave Clark57:04

       And I, I always feel good about them though still after I take 'em.

    9. HSHarry Stebbings57:07

       What's the kindest thing anyone's ever done for you?

    10. DCDave Clark57:11

        Honestly, I think coming to work for me.

    11. HSHarry Stebbings57:15

        Hmm.

    12. DCDave Clark57:15

        You know, uh, it is a, uh, I view it as a gift. You know, I mean, the people on my team right now could be anywhere on the planet, like, they could all, most all of them could be running their own company if they wanted to be. They're brilliant, creative, fun people, and you know, they took a leap to come and, you know, do this crazy ride with me, and to, like, you know, there's not much more they, you know, there's not much more they could give me than that, and I take it as a gift, and I have, view it as a lot of responsibility as a result.

    13. HSHarry Stebbings57:47

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

    14. DCDave Clark57:52

        You know, I burned a lot of money over time, and I don't regret too much, uh, I, you know, 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 I don't really, it was very, I mean, it was very painful to lose your parents early, uh, but I don't think I would be who I am had I not gone through that. Like, I got shot out of a cannon after those, like, you know, like I realized I was fine without them there, it was on my own. I tell my kids a lot, I hope I don't need to die for them to feel the need to be really successful over time, but, uh, it is a, uh, it was very painful, uh, but transformative in a way that I think, um, shaped my independence and self-reliance and desire to succeed, uh, in a very powerful way early in life.

    15. HSHarry Stebbings59:00

        Dave, if you can be CEO of any company other than Flexport for a day, what would it be CEO of?

    16. DCDave Clark59:06

        I think I'd like to do it at like, one of the, like, Lockheed Martin, or like some weird defense, I wanna go to a defense contractor where I, where I can get into all the deep, most secret government files and access, and just go crazy for a little while.

    17. HSHarry Stebbings59:21

        (laughs) James Bond in disguise. Um, listen, next, fi- uh, final one for you, next five years for you, what's the plan ahead? Where are we if we sit down in 2028?

    18. DCDave Clark59:33

        Uh, well, I think we're gonna be sitting down in 2028 saying, uh, talking about how Flex, you know, n- you know, a massive portion of the world's goods move on Flexport's technology stack, and that there's been a massive amount of waste taken out of the environmental footprint of the world, and how small business is growing faster than it's ever grown before because, uh, it has the ability to be competitive in ways, at costs, that it's never been able to be competitive. And how many people are part of the Flexport universe today.

    19. HSHarry Stebbings1:00:07

        Dave, I'm not sure I've had quite such a varying show. From the personal...

    20. DCDave Clark1:00:12

        (laughs) .

    21. HSHarry Stebbings1:00:12

        ... to the professional, to the leadership, to the hiring, to the, you know, the supply chain and logistics. You've been patient, uh, wise. Thank you so much for doing this with me.

    22. DCDave Clark1:00:23

        Happy to do it. If you need some follow-up on your relationship advice, I'm, I'm, I'm happy to have follow-up sessions with you for a nominal price.

    23. HSHarry Stebbings1:00:30

        Well, this is an ongoing podcast series, actually, that you didn't know we were doing. (laughs) Dave, thank you so much for that.

    24. DCDave Clark1:00:37

        (laughs) .

    25. HSHarry Stebbings1:00:37

        You were fantastic.

Episode duration: 1:00:38