The Exchanges

Q so few things are one way door. Like we were talking before, we were talking beforehand about, you know, children and egg freezing, which will get taken out of this edited note to take out. But like kids are a one way door, but like so few is actually a one way door key hires, not, um, strategic systems in countries, not products, not, is there really one way doors?

A Well, uh, a one, Spending money, you can't get the money back. So picking you by capital allocation, making sure you don't blow the money. Uh, so things that cost a lot of money, that's the one way to work. Although we found a logistics that, uh, it's, I think general Patton said it's, it's not, not how high you climb. It's how high you bounce after you fall. And so a lot of our best customer relationships are people that we royally screwed up with five years ago, but it's how do you respond in that moment? Do I, does the CEO give them a call? And apologize and make things right. Do you take care of them? Do you, do you pay the extra money? You know, do you, that's, that's ultimately a value system because your values don't really count unless you're willing to give up money for it. Otherwise it's just word on the wall. If you don't show up and you don't really handle things well, that could be a one-way door. I mean, you can, I have people that I don't interact with anymore and I won't do business with because of the way they behave. There's still one-way doors out there, but I agree with you in general, like most things are two-way doors.

AI assessment note: “There's still one-way doors out there, but I agree with you”

Q Has agent investing changed how you are as a CEO?

A Yeah, I probably, it helped me a lot to understand the VC world and how it works. Probably helped me with some of our fundraising, having a little bit of perspective, being on the other side of the table, understanding the game, or being, being, having, you make friends with other investors and can learn more about the VC world and how to navigate it. Well, I think net net, no, I don't know if it has because it's also taking up time. I don't spend a lot of, I haven't spent a lot of time on it, but you know, it's inevitably going to take up some time. I do it not, not because it's going to help me. I actually quit angel investing a while ago, basically. I'll do it a little bit here and there if it's a friend of mine or something, but the reality is any time spent away from Plexport is probably net negative for Flexport. I mean, I spent all my time on Flexport if I want to make Flexport more successful. Hey, life is not all about money or one thing. Like I enjoy it. I like learning. I like making friends with other founders. I benefit from those relationships. In ways that are hard to predict, and certainly, 10 years ago, 12 years ago when I started Angel Invest, I had, I don't know, who knew what I was doing. I'm just trying to get out here and have fun.

AI assessment note: “it helped me a lot to understand the VC world and how it works”

Q When you, when you put on the ambassador hat, you're like big time tick. Um, on the flip side, What was the worst resource allocation decision? What was a mistake that you allocated resources to that you shouldn't? And how did that change your perspective?

A Oh, you know, the Flexport is over, over the last decade, capital raising came easy to Flexport. I mean, you had zero interest rate, Flexport's a really good bet. We get, we raised a lot of money. I think that that money in it, I've never seen a company and I've tried this and I've raised as much money as almost anybody. I've never seen a company successfully raise a bunch of money And not start spending it in ways that don't, that aren't actually very smart. It's the biggest risk to raising too much money is you just like lose discipline and you start spending money. This was true, um, by the way, from day one, we raised a twenty million dollar series A. The time it seemed like a ton of money. The next day or like within a week, we had a conference coming up like a, where we were exhibiting a trade show or something. And I immediately purchased a shipping container and transformed it into a booth and spent like 50,000 bucks on this thing. And like, I don't know if that was a good or bad decision, but like, I definitely wouldn't have made it two weeks prior when we didn't have the twenty million bucks in the bank. It's like the money wants to spend itself. And so that's the ultimate risk. And you can sit here and go, we're not going to spend it. We're going to pretend we didn't raise it, but you would be as a founder, the first person ever to succeed in that. Um, now I think my…

AI assessment note: “I immediately purchased a shipping container and transformed it into a booth and spent like 50,000 bucks”

Q Yeah. No, I have to say fizzy water doesn't quite cut it in that respect for me nowadays. Ryan, can I ask, because you look at the headlines, and you look at the valuation numbers, and was there any insecurities for you attached to the drinking, do you think?

A I didn't know when I go out in a social setting, I'm not like the most gregarious extroverted person. And so even though I sometimes come off that way, and I think I was using alcohol to kind of like help me settle my nerves and become like feel a little bit better in those settings. And like, by the way, as the CEO of a semi big company, you get invited to these things like four or five nights a week. And a lot of them are really interesting and you want to go. So the normal thing to do in these scenarios is to have a couple of drinks. So pretty soon, if you're not actually really conscious about it, You could be drinking a lot. And once I started to become conscious about it, I started realizing, whoa, I'm having to turn down alcohol really often. But one of the things I noticed was like, actually nobody cared. Really zero people cared whether I drank or not, especially at my age. And like with my friend group and the one or two people who did pressure me to drink, it was like a heat seeking map for like who I shouldn't be friends with. Cause they're probably like, why would you care if I drink? Like you drink, I don't, I don't drink. Like who gives it? And actually very, very few people care. It's all in your head. And you can do what you were talking about, have a lemonade, and nobody notices or cares. Really, people are not, they're much more obsessed with their own life t…

AI assessment note: “I think I was using alcohol to kind of like help me settle my nerves”

Q Your brother told me you're unemployable. Uh, no, uh, your, your, your wife, though, asked the question. You said there about kind of the, the mirage of entrepreneurship. Your wife said, what's the biggest misconception people have of Flexport today versus what it is really?

A Oh, well, there's been a lot of, uh, you know, Flexport's been in the news a while lately. Um, we had the CEO transition. The demand for scandal and drama is way higher than the supply. In this world, and the media has been really sensationalizing some stuff. There was a story about Flexport that I will not point people to because I don't want to give it any attention because there was other crap, but it was a whole article. Flexport delivered thirty-three million packages to consumers' homes. That's what we're on track to do this year. Then one package got lost, and they wrote this, all of this mainstream media publication wrote an entire story where the first four paragraphs are about a lady whose package got lost. I feel bad for her. I'm sorry. Like, we lost the package. We genuinely We screwed that up. We reimburse her in full, but like one out of thirty three million, I mean, that is like, you know, this is people trying to sensationalize and stir up drama or like that same article clean that one of our biggest customers was really unhappy with us. Literally the customer went on the record telling them that it's not true. We were very happy with Flexport and they didn't publish that. They wrote that we have sources saying that they're not happy, but like the source of the company told you that that's not true. So the media wants to drive these narratives about Flexport as …

AI assessment note: “the media wants to drive these narratives about Flexport as if we're a mess”

Q Do you know when you're going in the wrong direction? Do you know early? Is it apparent?

A Not always. Um, I think that's, that's like, that's the art of leadership, I suppose. You know, I really like Bezos' concept here of like the one-way door and the two-way door and being able to move very, very fast as long as it's easy to change direction and come back. That often that's the case and you should go really, really fast. Cause it's fine. Sometimes it's a one way door. You can't come back. And so then you better be real careful. Now it's okay to go the wrong direction as long as you can change courses and be nimble. Right. But if it's a one way door type, uh, type one decision, then you got it. That those are decisions that need to be made by senior people with a lot of judgment to avoid mistakes. Uh, otherwise it's fine to go fast and make mistakes.

AI assessment note: “Not always. Um, I think that's, that's like, that's the art of leadership”

Q A lot of what you just said is predicated on actually having the right people on board as well. You know, they have to want to learn. They have to bluntly be honest and genuine people. I again have made many hiring mistakes. What are some of the biggest hiring lessons you have that you wish you'd known when you started or in the earlier years?

A Don't hire outside people. I rather much, I don't hire senior executives. I think in almost all, I'm not, look, that's not a blanket rule. We've hired a lot of great senior executives at Flexport over the years, and a lot of them are doing amazing work for us, but it's so much higher risk. Then promoting from within. Um, and, and so much better get to know people. You get to really get bought in that they believe deeply in your mission. They build credibility and respect and stretch people and promote people from within. I think that I didn't do enough of that over the years. I think, uh, trying to pursue in blind pursuit of growth and, and, and hitting our goals and being global and taking over the world and bringing our vision to life. You need help. And you turn externally instead of going, Hey, I'm a, I've actually got amazing people at Flexport. Like we have ex Flexport people who are in key roles, like way more senior at amazing companies than, than they were doing at Flexport. And we didn't promote them and they left and do better things somewhere else. And like, so I, I think, uh, spending more time with your customers and more time in the presence of your people and more time with the front lines, So you can identify like the key job of leadership is identifying talent within your company. And certainly yes, but like, it's so much better if you can get internal folks a…

AI assessment note: “Don't hire outside people... it's so much higher risk. Then promoting from within.”

Q Do you know when you're going in the wrong direction? Do you know early? Is it apparent?

A Not always. Um, I think that's, that's like, that's the art of leadership, I suppose. You know, I really like Bezos' concept here of like the one-way door and the two-way door and being able to move very, very fast as long as it's easy to change direction and come back. That often that's the case and you should go really, really fast. Cause it's fine. Sometimes it's a one way door. You can't come back. And so then you better be real careful. Now it's okay to go the wrong direction as long as you can change courses and be nimble. Right. But if it's a one way door type, uh, type one decision, then you got it. That those are decisions that need to be made by senior people with a lot of judgment to avoid mistakes. Uh, otherwise it's fine to go fast and make mistakes.

AI assessment note: “Not always. Um, I think that's, that's like, that's the art of leadership”

Q Is it better than kind of, and this could apply to just complex technical issues and complex companies. Is it better just to find investors then who get it? Maybe those who've narrow demographic VCs who've had past experience in freight and in shipping and in transport. Is that the best solution?

A Yes, if possible, right? Um, we found that to be very hard, very, very hard. We were the very few investors that had it, uh, for our, in our case, it was fine investors. I think the best conversation we had were people who had been involved in real world businesses before either running them, investing in them, et cetera, and just understood like, oh yeah, freight, we spent five percent of our revenue on freight. Like that's pretty normal, right? And it was broken. We saw that. And so if you get investors to understand the problem pretty well, you get much further. The other thing that we did, I mean, we were, our series B was Done almost entirely by insiders, by people who had been in the series A and even, and a lot of the money came from people who were in our seed round. And so there, they've had years to get to know us, understand what we do, see that we actually hit our projections that always, like, we don't make projections we're not going to hit. And so building, the other thing is build a relationship. It's so time consuming though. I think relationships are overrated, but if you, you know, once you have existing investors, hopefully they keep backing you through over time.

AI assessment note: “Yes, if possible, right? Um, we found that to be very hard”

Q CEO hates HR, and like a complete dick that I am, I thought I'd front run his show and take every great CEO hates HR, and I'd tweet it myself. Oh my god, I got killed By everyone for this tweet, which was essentially Adam's words, which I agree with, and I think he's right, and in credit to Adam, he's amazing. Do you agree every great CEO hates HR?

A You probably go through these phases, right? I mean, I think the thing that you cannot have is them being like union representatives of your employees. They're not. They're there to represent the company, and therefore the CEO, and so if there's, if you don't have that as a CEO, like a trusted HR Leader and you feel like the HR leader is more on the side of the employees than on the side of the company, then there's a problem. There have been periods in my company's history and like the industry in general where you're like, didn't have the right HR leadership that wasn't focused on the business outcome. Um, and, but the employees are the company and the company is the employee. Everything else is a fiction. We're just like, just a fake brand name here with a bunch of people that are building the company or serving the customer. So The, the word HR is kind of wrong because they're not, humans are not a resource that you can mine and take out of the earth, like you have to give back to the employees and have a two-way relationship.

AI assessment note: “You probably go through these phases, right?”

Q really consider myself a founder, but I, you know, I am alone in, in kind of founding what I, what I do, and, and I do find it difficult sometimes. I'm intrigued as to hear when times have been tough, how have you dealt with those hard times when there's no one to pick you up, when, when I'm not there to give you a hug and a mojito? Yeah.

A That, that I, I, dang, that was going to be my answer. I call Harry to get a hug. Um, well, I would say this starting a company solo is very good. The number one reason that companies fail is that the founders split up like early stage, right? So you eliminate that risk right away. If you do a great job, you get some traction, you get progress, you build, you know, you start really doing something, especially you raise some money. Now, all of a sudden you can go recruit your co-founders. And so that's what I did basically was One, I had my brother as like my emotional, spiritual co-founder. I can bring all my problems to him and talk about, but two is I went out and actually recruited co-founders. And in that case, I got better people because I had demonstrated some progress. I had de-risked it to an extent and I got better people and for less equity, right? Like if they were my original partners, we would all just split everything, right? 50, 50 or whatever the, whatever the number of people is. And in this case, I gave them something less than that, right? So it worked out better for me. And now I, they really are like, Co-founders in all but name. Like they, they're my partners in running the business for sure.

AI assessment note: “One, I had my brother as like my emotional, spiritual co-founder.”

Q I think you learn a lot from wins and losses, right? When you look at your resource allocation decisions, the investments you've deliberately chose to make, what have been your best resource allocation decision and what's been your worst? And what were the takeaways when you reflect on them?

A I think it was part of resource allocations. We've raised, uh, we've raised capital twice where we did very large rounds of capital at what felt like the peak of a bull market and wanting to put money in the bank so that we can ride out and have a fortress balance sheet to ride out any storm that comes. So we did that. The first time, uh, was in 2019 and it turned out the bull market continued and, uh, and you know, you can't predict these things, but we raised a billion dollars in 2019 and then in 2022, we raised nine hundred eighty four million dollars. That turned out to be true. Like that we were kind of at the peak of the bull market and that balance sheet serves us very well today that we have a billion dollars in cash and we're in a place to execute and not be too concerned, overly concerned about the, you know, there's a recession in freight right now and capital markets for tech companies have come Down quite a bit since then. And we have a fortress balance sheet to protect us and insulate us from those problems. But if you call that resource allocation, I sort of do it because you're now in a place to protect the company and have cash that you can continue to allocate through the cycle. We've done a limited amount of M&A. We apply, we acquire Shopify logistics. Um, I'm very, very proud of that deal. I think it's incredibly powerful to now be able to go end to end all …

AI assessment note: “We've done a limited amount of M&A. We apply, we acquire Shopify logistics.”

Q 2500 employees. Can you tell me, how do you still be a great father and be CEO of a 2500 person company? What do you know now that you wish you'd known when you had kids?

A Well, love is the, you know, when most important value. So I love my children so much that I want to get home and make sure I get time to spend time with them before bedtime and hang out with them every night, uh, and see them in the morning too. So I've had a three-year-old and a one-year-old, uh, my, especially my older daughter, my one-year-old, like, you know, started learning how to talk or anything yet, but my three-year-old is like, it was a little ball of energy. So I love playing with her and I make time for that. And, um, yeah, and then I worked more in the evenings after she goes to bed and I, Get up early and work and that's fine. I mean, I think I can work, I work as hard now as I ever worked in my life and I just have to deprioritize some other stuff.

AI assessment note: “I worked more in the evenings after she goes to bed and I, Get up early”

Q Well, pause. Why is marketing in HR the hardest to hire for?

A In enterprise marketing. The moment something works, it stops working because the competitors will copy it. And so it's like, it's all about creativity and originality and like, how do you get creativity and originality in B to B enterprise marketing? Like, and it's, and if you are creative, like you probably kind of become a founder if you can do good storytelling and creative idea, ideation in the marketing storytelling angle. So it's, it's, if you find a good marketer in B to B, you really want to lock them in, uh, and get a great. So it's been, it's been a, that's a hard one to hire for, Um, and also to do that, to do like successful B to B marketing and stand out, like it's one thing. Oh, I just make good sales decks for the team and like, okay, fine. Like that's some baseline stuff, but you're not going to differentiate or move that bend the curve on a start on a company success. You have to be doing kind of crazy stuff. Most crazy ideas are bad ideas. So you're, it's like being an investor. Like you want to do crazy things that happen to also be good ideas. Like it's that narrow intersection.

AI assessment note: “In enterprise marketing. The moment something works, it stops working because the competitors will copy it.”

Q My honest reflection on people management is like being CEO is the worst thing ever because great people you're permanently worried will be leaving because they're so good. Average people you permanently worry that they're not good enough and bad people you permanently worry that you should have got rid of them last week. Do you agree with that?

A I think it's a, it's an incredible job being the CEO of a company. If you believe in the mission and you love what you're doing, you know, and you're executing against It's an incredible job. Uh, but it's not an easy job and it's not necessarily fun. I mean, it's people look from the outside and think like, oh, I'll be an entrepreneur. I'll be the CEO. And like, it's, it's really tough, man. I mean, it is not an easy thing to do for, for the reasons that you said and many others, but hey, that's, that's why you, you know, that's why we do it because we want to, we believe deeply in what we're trying to achieve. And I don't know, I'm kind of unemployable. I don't want to work for somebody else. I want to go build stuff.

AI assessment note: “it is not an easy thing to do for, for the reasons that you said”

Q My honest reflection on people management is like being CEO is the worst thing ever because great people you're permanently worried will be leaving because they're so good. Average people you permanently worry that they're not good enough and bad people you permanently worry that you should have got rid of them last week. Do you agree with that?

A I think it's a, it's an incredible job being the CEO of a company. If you believe in the mission and you love what you're doing, you know, and you're executing against It's an incredible job. Uh, but it's not an easy job and it's not necessarily fun. I mean, it's people look from the outside and think like, oh, I'll be an entrepreneur. I'll be the CEO. And like, it's, it's really tough, man. I mean, it is not an easy thing to do for, for the reasons that you said and many others, but hey, that's, that's why you, you know, that's why we do it because we want to, we believe deeply in what we're trying to achieve. And I don't know, I'm kind of unemployable. I don't want to work for somebody else. I want to go build stuff.

AI assessment note: “it is not an easy thing to do for, for the reasons that you said”

Q I think you learn a lot from wins and losses, right? When you look at your resource allocation decisions, the investments you've deliberately chose to make, what have been your best resource allocation decision and what's been your worst? And what were the takeaways when you reflect on them?

A I think it was part of resource allocations. We've raised, uh, we've raised capital twice where we did very large rounds of capital at what felt like the peak of a bull market and wanting to put money in the bank so that we can ride out and have a fortress balance sheet to ride out any storm that comes. So we did that. The first time, uh, was in 2019 and it turned out the bull market continued and, uh, and you know, you can't predict these things, but we raised a billion dollars in 2019 and then in 2022, we raised nine hundred eighty four million dollars. That turned out to be true. Like that we were kind of at the peak of the bull market and that balance sheet serves us very well today that we have a billion dollars in cash and we're in a place to execute and not be too concerned, overly concerned about the, you know, there's a recession in freight right now and capital markets for tech companies have come Down quite a bit since then. And we have a fortress balance sheet to protect us and insulate us from those problems. But if you call that resource allocation, I sort of do it because you're now in a place to protect the company and have cash that you can continue to allocate through the cycle. We've done a limited amount of M&A. We apply, we acquire Shopify logistics. Um, I'm very, very proud of that deal. I think it's incredibly powerful to now be able to go end to end all …

AI assessment note: “we've raised capital twice where we did very large rounds of capital”

Q Has managing teams got harder with the rise of woke society?

A Managing teams is always hard dealing with people who are not focused on the company's mission and have their own missions that are separate from a company's mission. Is incredibly frustrating because there's a million organizations in this world, one for every possible topic that you want to drive. And so finding people at Flexport who are focused on anything other than making Flexport successful at work, It's like really, really frustrating. I don't care what you want to focus on outside of work at all, what your politics are, what your cause is. I think that's awesome. People should have passion to do stuff, but like, that's not what Flexport's all about at the company during the day. Like, let's just talk about our problems are hard enough. We got to make global commerce easy. We got to ship cargo in every corner of the world. Like this is hard enough. We don't, we can't solve other people's challenges outside of that.

AI assessment note: “Managing teams is always hard dealing with people who are not focused”

Q What have been the biggest lessons for you in where those interlinkages break, where the cross functions don't work?

A Well, I, I can't speak to every, uh, every kind of company. There's so many unique businesses out there, but it, but it is, you know, in our business, it's an end to end offering. So what the way that Flexport works is Companies come onto our platform. They place orders to their factories. They reflect for it by purchase orders, buying goods. Those factories become users. The average importer of goods is onboarding, 18 factories. And then those factories become users. They place bookings. They say, okay, the cargo is ready on this date. Uh, we send a truck out there and across a hundred, over a hundred countries, send a truck, pick it up, export, clear it out of that country, put it on a ship. So we've got to have contracts, all the ocean carriers and airlines across the world, clear it through customs. Truck picks it up at the airport or the port, either direct delivers it directly to the customer, puts it on. Sometimes we put it on a train actually and skip the truck. Sometimes we do a barge and you're up a lot of barge shipping in China to go up the Rhine river. Uh, sometimes we'll bring it to a warehouse, unload the container, put it on a dry van on a regular truck and deliver it, bring it to another warehouse. We then deconsolidate it and ship it to customer stores or into retail stores. So it's an incredible amount of complexity, as you can imagine. I haven't even mention…

AI assessment note: “So if you try to run this where all each leg is just only thinking”

Q But a lot of founders are sitting in the seat today going, man, I want to bring it back. I want in person. I know the value of in person, but I don't want a revolt when I say I'm sorry. What advice would you have to them?

A Yeah, I just gotta do what you want to do. I mean, I think that all the bad things that have happened at Flexport were when I didn't do what I wanted to do and was trying to, like, you don't want to ever be afraid of your employees, first of all. Like, the employees don't want that either. They want a leader who's gonna, like, go in the direction that they believe in. Even if they disagree, like, they want to follow a good leader. And if they opt out, like, that's fine. They can opt out. Like, not everyone, you know, and There's a lot of good jobs. I, I think that, um, also the, the, the idea that work from home is going to benefit highly paid employees is sort of a total fantasy. Like, work from home done correctly, you should be hiring the world's greatest geniuses. There should be a labor arbitrage here, where you're finding really, really smart people who make a lot less money because of the, the, um, the way that our economy is structured, where some countries just have a lower purchasing power.

AI assessment note: “I just gotta do what you want to do.”

Q Can I wear one before we just discuss parenting, which I do have to discuss because I think it's fascinating and helpful for me. Question, would you be long China? China have so many problems from, you know, population decline, manufacturing decline, reversion away from urbanization. Would you be long China or short?

A Yeah, it's very hard for me to do macro type stuff like that. I think that Chinese China has a few advantages that we take that we don't have Chinese China believes in China. Chinese people believe in China. Half of Americans hate America. I think that's a huge advantage to have as a civilization to believe that what you're doing is that you're part of something that's bigger than yourself and trying to support your country. You know, we lack that these days in America. Um, and that's a huge advantage to have. They're incredibly, Industrious people. They're working. They are hungry. They want success. They work six days a week. A lot of people don't realize that. I lived in China for two years. They work Saturdays. We don't work Saturdays. You know, that's a bit extreme, but most Chinese people work six days a week. How much more productive would you be? Work an extra 20%. You know, they're industrious. They're hardworking. They're intelligent. They have a lot going for them. Their leadership is incredibly smart. They have some demographic challenges that are beyond my scope to understand because, you know, people are like, the population's declining. China's not the worst in this by any means. There's, uh, there's Western countries, Italy and Korea, uh, Other countries that are declining faster, but I always think like, well, but isn't it better if you have to your people to s…

AI assessment note: “it's very hard for me to do macro type stuff like that.”

Q What have been the biggest lessons for you in where those interlinkages break, where the cross functions don't work?

A Well, I, I can't speak to every, uh, every kind of company. There's so many unique businesses out there, but it, but it is, you know, in our business, it's an end to end offering. So what the way that Flexport works is Companies come onto our platform. They place orders to their factories. They reflect for it by purchase orders, buying goods. Those factories become users. The average importer of goods is onboarding, 18 factories. And then those factories become users. They place bookings. They say, okay, the cargo is ready on this date. Uh, we send a truck out there and across a hundred, over a hundred countries, send a truck, pick it up, export, clear it out of that country, put it on a ship. So we've got to have contracts, all the ocean carriers and airlines across the world, clear it through customs. Truck picks it up at the airport or the port, either direct delivers it directly to the customer, puts it on. Sometimes we put it on a train actually and skip the truck. Sometimes we do a barge and you're up a lot of barge shipping in China to go up the Rhine river. Uh, sometimes we'll bring it to a warehouse, unload the container, put it on a dry van on a regular truck and deliver it, bring it to another warehouse. We then deconsolidate it and ship it to customer stores or into retail stores. So it's an incredible amount of complexity, as you can imagine. I haven't even mention…

AI assessment note: “I can't speak to every kind of company... in our business, it's an end to end offering”

Q CEO hates HR, and like a complete dick that I am, I thought I'd front run his show and take every great CEO hates HR, and I'd tweet it myself. Oh my god, I got killed By everyone for this tweet, which was essentially Adam's words, which I agree with, and I think he's right, and in credit to Adam, he's amazing. Do you agree every great CEO hates HR?

A You probably go through these phases, right? I mean, I think the thing that you cannot have is them being like union representatives of your employees. They're not. They're there to represent the company, and therefore the CEO, and so if there's, if you don't have that as a CEO, like a trusted HR Leader and you feel like the HR leader is more on the side of the employees than on the side of the company, then there's a problem. There have been periods in my company's history and like the industry in general where you're like, didn't have the right HR leadership that wasn't focused on the business outcome. Um, and, but the employees are the company and the company is the employee. Everything else is a fiction. We're just like, just a fake brand name here with a bunch of people that are building the company or serving the customer. So The, the word HR is kind of wrong because they're not, humans are not a resource that you can mine and take out of the earth, like you have to give back to the employees and have a two-way relationship.

AI assessment note: “if you feel like the HR leader is more on the side of the employees”

Q Can I ask you, you know, you have CEO hat, you have father hat, you have husband hat, the husband hat as well. You got to keep up. How do you retain romance and retain prioritization of relationship when you're managing 2500 people, reading Curious George, holding one year old?

A Well, I have the greatest wife in the world. My wife is, uh, kind of the chief of staff of my life. Uh, she's been an incredible advisor for me on all things. And by the way, I was criticizing the media before, but my wife's a former reporter, so I'm, like, well in tune with how the media works. And, uh, she's a great, like, communications director, helping them, you know, understand how to behave. How to get the media to like, well, I was building Flexport well before I met her. And she's always known that Flexport's my baby and that, you know, serious priority for me. And that I'm very fortunate to find a woman who wanted it, like knew that and signed up for it and wants to help me in every way. And I, I don't know. I'm sorry. I never take it for granted.

AI assessment note: “Flexport's my baby and that, you know, serious priority for me.”

Q Can I wear one before we just discuss parenting, which I do have to discuss because I think it's fascinating and helpful for me. Question, would you be long China? China have so many problems from, you know, population decline, manufacturing decline, reversion away from urbanization. Would you be long China or short?

A Yeah, it's very hard for me to do macro type stuff like that. I think that Chinese China has a few advantages that we take that we don't have Chinese China believes in China. Chinese people believe in China. Half of Americans hate America. I think that's a huge advantage to have as a civilization to believe that what you're doing is that you're part of something that's bigger than yourself and trying to support your country. You know, we lack that these days in America. Um, and that's a huge advantage to have. They're incredibly, Industrious people. They're working. They are hungry. They want success. They work six days a week. A lot of people don't realize that. I lived in China for two years. They work Saturdays. We don't work Saturdays. You know, that's a bit extreme, but most Chinese people work six days a week. How much more productive would you be? Work an extra 20%. You know, they're industrious. They're hardworking. They're intelligent. They have a lot going for them. Their leadership is incredibly smart. They have some demographic challenges that are beyond my scope to understand because, you know, people are like, the population's declining. China's not the worst in this by any means. There's, uh, there's Western countries, Italy and Korea, uh, Other countries that are declining faster, but I always think like, well, but isn't it better if you have to your people to s…

AI assessment note: “it's very hard for me to do macro type stuff like that”

Q Can I ask you, you know, you have CEO hat, you have father hat, you have husband hat, the husband hat as well. You got to keep up. How do you retain romance and retain prioritization of relationship when you're managing 2500 people, reading Curious George, holding one year old?

A Well, I have the greatest wife in the world. My wife is, uh, kind of the chief of staff of my life. Uh, she's been an incredible advisor for me on all things. And by the way, I was criticizing the media before, but my wife's a former reporter, so I'm, like, well in tune with how the media works. And, uh, she's a great, like, communications director, helping them, you know, understand how to behave. How to get the media to like, well, I was building Flexport well before I met her. And she's always known that Flexport's my baby and that, you know, serious priority for me. And that I'm very fortunate to find a woman who wanted it, like knew that and signed up for it and wants to help me in every way. And I, I don't know. I'm sorry. I never take it for granted.

AI assessment note: “she's always known that Flexport's my baby and that, you know, serious priority for me”

Q Do you think you should under price on IPO day so you have the pop? Or are you like, you should price to perfection?

A People focus so much on this, like, I, I don't understand it, like, on, not on, of course you're gonna focus on your price and whatever, but people, there's this concept of like an IPO window that investment bankers and founders talk about. It's like, ah, the window's closed, you can't go public, or like, cause the price won't be there or something, but you're like, well, what if you went public and then your price went down? Like, is that better? I mean, it's the same thing, isn't it? Um, so I don't quite understand that dynamic, like, I think you just run, I'm an operator, run a good business, like make it super profitable, have it grow. And like, don't compare yourself too much to Anthropic or these AI companies that are for 15 years, and there's companies that are getting to our revenue in 18 months, and you're like, I think envy is a very bad, uh, Is it one of the seven deadly sins? Like you certainly should avoid it.

AI assessment note: “I don't quite understand that dynamic, like, I think you just run, I'm an operator”

Q Do you think you should under price on IPO day so you have the pop? Or are you like, you should price to perfection?

A People focus so much on this, like, I, I don't understand it, like, on, not on, of course you're gonna focus on your price and whatever, but people, there's this concept of like an IPO window that investment bankers and founders talk about. It's like, ah, the window's closed, you can't go public, or like, cause the price won't be there or something, but you're like, well, what if you went public and then your price went down? Like, is that better? I mean, it's the same thing, isn't it? Um, so I don't quite understand that dynamic, like, I think you just run, I'm an operator, run a good business, like make it super profitable, have it grow. And like, don't compare yourself too much to Anthropic or these AI companies that are for 15 years, and there's companies that are getting to our revenue in 18 months, and you're like, I think envy is a very bad, uh, Is it one of the seven deadly sins? Like you certainly should avoid it.

AI assessment note: “People focus so much on this, like, I, I don't understand it”