AI transcript
0:00:10 You see what’s happening in the world in an insane degree. I’ve been working on my own thing,
0:00:14 which became Flex for. Our goal is to be an asset-light technology platform for freight
0:00:19 forwarding. And you’re the most tech forward of all the companies. Kind of, we’re the only one.
0:00:23 I think most businesses, like, actually quality costs less. It’s very counterintuitive.
0:00:27 Go deeper on that. Well, in logistics, like, all the costs come from you make a mistake.
0:00:32 Like, if you file a customs entry and you get the wrong classification code,
0:00:37 you’re going to spend weeks on doing that. Hey, that’s the game. You know, it’s business. It’s not a
0:00:42 kind of socialist project. What did you learn from that? This is proprietary secret I’m going to let
0:00:47 you in on. We’re going to get into some of this. These tariffs have had the opposite impact that
0:00:50 Trump would like. I think his intention, there’s some validity to it all, like some of the things
0:00:54 I’ve said from national security and employment and other things. But the result has been…
0:01:06 Welcome to the Knowledge Project Podcast. I’m your host, Shane Parrish. In a world where knowledge
0:01:11 is power, this podcast is your toolkit for mastering the best of what other people have already figured
0:01:19 out. US Customs called Ryan Peterson with surprising news. Steve Jobs was furious. Ryan had just used
0:01:25 public shipping records to predict April’s secret iPhone launch. That same contrarian thinking would
0:01:33 build Flexport into a multi-billion dollar logistics company spanning 147 countries. But Ryan stepped down
0:01:39 as CEO. He was certain that somebody else would do a better job. His successor hired 900 engineers in 12
0:01:47 months and burned through cash. Customer satisfaction crashed from 70 to 17. Paul Graham’s response to Ryan’s
0:01:53 decision cut deep. That’s like saying this other guy would be a better husband for your wife. Ryan returned
0:01:59 to a company hemorrhaging cash. The turnaround forced him to embrace micromanagement. But he discovered it
0:02:06 was just attention to detail with bad PR. In logistics, one customs error destroys a month of efficiency gains.
0:02:12 Most critically, he learned that every operation has a bottleneck. You either choose it or it chooses you.
0:02:18 In this conversation, we explore stories you won’t hear anywhere else, like how he flew 500 million
0:02:24 mass to US hospitals in empty passenger plans, and how tariffs accidentally push American factories
0:02:29 overseas. We also explore the counterintuitive lessons he’s learned from Charlie Munger and Peter
0:02:35 Kaufman. Whether you’re scaling a startup or managing any complex system, Ryan’s journey will reshape how
0:02:41 you think about growth, confidence, and micromanagement. It’s time to listen and learn.
0:02:54 I love the idea of life’s work, and it seems like your interest in logistics started really young. Can
0:03:01 you tell me this story about your mom getting you to get soda? Oh, wow. Yeah, well, my mom’s a great
0:03:10 entrepreneur. Started and sold two companies in the biotech, biochemistry space in Washington, D.C.,
0:03:15 and so both my brother and I had this job. It was like our first job was delivering soda to her off. It
0:03:21 was like stacking the snacks cabinet and the sodas and stuff. So we basically just buy the stuff at
0:03:27 a giant, it’s like Safeway, and then mark it up 2X and so on. Put it in your little, like, cart?
0:03:32 Yeah. Yeah. In my dad’s minivan, we would stack up the back of the, you know, the trunk full of
0:03:38 cases of Coke and Diet Coke. And then my dad taught us to write software. He was a programmer, so we
0:03:43 wrote software to generate the invoices so we could, so she could submit the expenses to the IRS or whatever
0:03:48 and make sure she got the tax deduction on our allowance. You were motivated to do it because you
0:03:53 could just get paid for it. What was the kind of easy money? I mean, you buy this soda case for four and
0:03:57 sell it for nine, make five bucks on every case that I deliver. What were the dinner table
0:04:02 conversations like? Do you remember growing up? Well, two entrepreneurial parents. Yeah, super boring
0:04:06 because they were talking about biochemistry and food safety and regulations. I couldn’t understand
0:04:10 any of it. I think I’m still like a very fast eater as a result. I was trying to get out of there
0:04:17 as quickly as I could. Did you always know you wanted to do your own thing or? No. My brother was
0:04:23 much more an entrepreneur than me. Maybe still is. And when I graduated, I went to UC Berkeley when I
0:04:28 graduated from college. I was 2002. I didn’t, I was thinking I’d go into like international development
0:04:35 or something cool. I like to travel internationally and I traveled a lot in the third world because I
0:04:40 had no money. So I was like traveling places I could afford. And I was always very intrigued by like
0:04:46 why some countries were poor and some were rich. So I wanted to work in some aspect. I would try to get
0:04:51 job in microfinance or government or something. And no one, no one was hiring. I got it. I wasn’t
0:04:54 really, I didn’t have a lot of skills when I graduated college, but my brother was hiring and he was
0:04:57 running a startup. And so I started working for him and that’s how I got into entrepreneurship.
0:05:02 Which startup was that? Well, we didn’t really call ourselves a startup to be honest. We were like
0:05:09 buying motorcycles in China and selling them on the internet in the U S and sort of, uh, this would have
0:05:14 been, I graduated in 2002. He started it before that and we were, um, tech company, but we didn’t call
0:05:19 ourselves that. And we wrote all of our own software to do kind of like, it was pre Shopify, right? So
0:05:25 e-com checkout, inventory management, billing, all this stuff. Like if we’d have been smart,
0:05:29 like Toby was, we had to sell subscriptions to our little platform and maybe could have been Shopify,
0:05:35 but instead we just like bought motorcycles and sold them on eBay motors and actually, uh,
0:05:38 through live car auctions, our own website, et cetera.
0:05:43 So you’re arbitraging sort of buying in China and then selling everywhere else.
0:05:47 Yeah. Uh, buying in China, selling in the U S and you went to live in China. What was that like?
0:05:53 Well, I was very curious about the world and like, I had lived in South America. I speak Spanish and
0:05:56 Portuguese. I was like, Hey, you know, we were making money, not a lot of money, but we’re making
0:06:01 money in China. Didn’t have anyone. We had one employee actually in China, but we weren’t like really
0:06:09 deep in China. And I, it was very clear in 2002 that China was like just on a tear and that it would
0:06:15 be maybe the future. It was like really obvious to me. So I moved there thinking, okay, if anyone can
0:06:18 learn Chinese, I already learned Spanish and Portuguese. I could probably learn Chinese. Let’s
0:06:24 go for it. Uh, so I moved there, kept my work basically of like doing supply chain logistics,
0:06:30 e-com development, web development, uh, customer services, a heck of all trades for the startup
0:06:36 that we had. Um, and then also just like studied Chinese for three hours every day for a few years
0:06:42 while I lived in China. That’s intense. Yeah. It’s supposed to be one of the hardest languages to learn
0:06:49 as an adult. It isn’t, it isn’t. Um, it’s very hard, but the Chinese people, if you give any effort
0:06:55 at all or like, wow, they love it. They compliment you. They reinforce you. They make you want to do more
0:07:00 of it. So it actually, that part makes it kind of rewarding and easy. Whereas I feel like I’ve, I’ve tried to
0:07:04 go in French and I get the, I’m like way better at French than in Chinese, but nobody and everyone
0:07:08 in France is like, ah, you’re terrible. You shouldn’t even try. I’m like, all right, I won’t.
0:07:13 Yeah. They talked to me. I try to speak in French and they talk back in English. If you get like one
0:07:18 word wrong or like, yeah. The Chinese is the opposite of that. You know, you say hello and they’re like,
0:07:24 wow, your Chinese is amazing. So if we think of the beats between being in China and ending up in
0:07:28 Silicon Valley, what are they? What are the major sort of like, how did that happen?
0:07:34 We had this business, um, which we were a startup, but yeah, like I, that’s like, we call it that now
0:07:39 at the time we were just trying to make money, honestly. And it was, we were building tech in
0:07:43 the cloud. We were cutting edge in a lot of ways, like in the early two thousands that weren’t cloud,
0:07:47 you know, I think Salesforce and NetSuite. Well, NetSuite, I don’t even know if it was cloud,
0:07:51 probably it was. Yeah. We realized, and it was while I was living in China, we discovered that
0:07:57 shipping manifests for ocean freight or public record. And it has a lot of really interesting data on it.
0:08:02 The public record in the U S we’ve since learned in like over almost 20 countries that you can get
0:08:08 the shipping manifest data. So it tells you kind of like your plane ticket, your boat ticket for your
0:08:12 cargo. So it tells you which factory, who made the products, where’s it from, who bought it,
0:08:16 who sold it, the dates, the ports, a lot of interesting data. And so we realized this data
0:08:21 was incredibly useful for us in sourcing products for that company. We were always adding new products
0:08:25 to the line, like, cause you could find out who’s manufacturing the products.
0:08:30 Yeah. You could look up any product type and see who the factories are, look up any importers,
0:08:35 see who their factories are, et cetera. So we built, um, a search engine for that data called
0:08:38 import genius.com. Still a great business. So you still own it. So we started that business,
0:08:44 sell subscriptions. And that, that was like, again, bootstrap, not Silicon Valley. We started it in
0:08:50 Arizona, uh, where the motorcycle business was, but we very much like got into tech. Like it was a
0:08:57 SaaS business. I was started following, like trying to learn about SaaS. I wish we knew more the blogging
0:09:02 and podcast world. You can learn so much more about, uh, AI, whatever you can learn so much more now than
0:09:09 you could back 15 years ago, how to run a SaaS business. Um, but that got that, that’s what really
0:09:15 got us into the tech scene. We were still outsiders for sure. Uh, and then both my brother and I both
0:09:20 started new companies. At some point that, that business is a great business, but it’s kind of like
0:09:24 hit, it’s keeps growing actually, but it was, it, it was stopped being a rocket. So we had like a few years
0:09:29 of like runaway growth and then it kind of reached its place in the ecosystem. And it’s been like a steady
0:09:34 compounder for the last decade, but not, wasn’t enough for me to like stay engaged as, as I should
0:09:38 have been. And I came back to this idea of like, should be an online platform to help you with
0:09:42 your logistics, especially your customs clearances coming back to our motorcycle days.
0:09:48 I’m like, man, this, uh, it’s way too important to be this hard and this lack of tech. My brother
0:09:52 had gone in a different direction, which was his is like, what other public data sets are out there
0:09:56 that we could build valuable data sets and sell subscriptions or provide access to. And so he
0:10:02 started a company called build zoom in constructing construction data. So you’re building permits or public
0:10:07 record in most places and building like profile, rich profiles of contractors, or you can look up
0:10:14 any building and see who remodeled it, et cetera. So it’s kind of like both similar origin starting
0:10:19 points, but very different businesses, obviously. Um, and so he had, he did Y Combinator for that.
0:10:26 And that was 2012. He would have been 2013. And we were, and then I saw that I got jealous. I mean,
0:10:30 I’m like, uh, you’re moving from Arizona. I moved to Arizona. I’m not from there. I moved there for
0:10:36 KPX after, uh, before China, actually. No, after China, excuse me, both, um, before and after. So I had
0:10:43 moved there for this business for these businesses. And then I saw him leave to go to the Bay area where I
0:10:48 went to college at Berkeley to work, to do Y Combinator. I was like jealous. I followed him.
0:10:49 Like sleeping on the couch.
0:10:55 Literally. Yeah. Sleeping in the air mattress in the, you know, little apartment. And, and I would just go,
0:10:59 Y Combinator at that time did not have great security. So I would just go with him to all the
0:11:03 Y Combinator, uh, sessions and just said, like, acted like I was part of his company, even though
0:11:09 my kind of was. And then that inspired me to go, I’d been working on my own thing, which became
0:11:14 Flex for, inspired me to apply to Y Combinator and go through it as well. Okay. Let’s pause here for
0:11:19 a beat. I want to go back. Cause there’s the Steve jobs moment that we, we need to capture here with
0:11:25 the import genius. You want to tell us the story? Oh, so back in one of the early, we had built
0:11:32 import genius. It’s a great data set. Um, it’s really powerful and you can look up companies and see
0:11:37 what they’re shipping and who they’re buying up and stuff. And at that time, I guess still the big
0:11:42 thing was, when’s the new iPhone going to come out? I think we were just on that. There was the 3G
0:11:47 iPhone. Forget it. I think that’s just like the second iPhone ever. It was kind of crazy. Where
0:11:53 are we on 5G now? But it was the 3G iPhone. We had built this product and we had like no users for it.
0:11:56 It was a great example of like, if you build it, they will not come while you have to go get
0:12:01 customer. We had a couple of customers, but not really any. Um, so I knew we needed to get some
0:12:05 attention. People needed to know that this data is out here. And I, we had such interesting data
0:12:12 by companies. And so I was searching in the data set for Apple shipments and saw it’s public record.
0:12:17 You can look it up. Um, saw that they were importing a new product. They’d never imported
0:12:22 before called an electric computer, which is very interesting. All computers are electric. It was
0:12:29 like a silly name. Um, and it was a perfect storm, perfect moment. Everybody knew it was already
0:12:34 being rumored that the 3G iPhone was arriving. I don’t even know if it was right. I just put out
0:12:39 this blog post being like, Apple has this new thing. Maybe it’s the 3G iPhone. Um, and it went
0:12:48 very viral. We got within a week, we were doing like $50,000 in monthly revenue, like all of a sudden,
0:12:56 you know, from zero to 50,000 in a couple of weeks. And, um, and I got a call from us customs
0:13:02 at saying, Hey, we just talked to Steve jobs and he’s really pissed about this. You need to explain
0:13:06 where you got this data sort of like threatening to show us out. I’m like, so I showed him the letter.
0:13:11 We showed him the letter of the law explaining why this is public record in this public record. And then
0:13:16 he sent us a letter and email later saying, Hey, thank you so much. I had explained,
0:13:23 I shared that with Apple’s team. Thank you for taking the pressure off of us. Uh, but it was a
0:13:29 bit of the early days of like, you know, how do you get attention and traffic for a new product? That’s
0:13:33 pretty cool. It was kind of like a really viral marketing type thing, even though it was hindsight
0:13:38 kind of a couple of questions here. One, did Apple change the name going forward to make it more
0:13:42 sort of like, I don’t think electric computers there anymore. What are some of the lessons you
0:13:48 take away from import genius before we sort of move on to Flexport? Most important one is the user
0:13:52 retention company’s great. And the data set’s extremely valuable, but for a lot of users,
0:13:56 you don’t need to keep paying for it on an ongoing basis. You can get the data,
0:14:03 run your search, find the factory that you’re looking for or the data, uh, and you don’t need to
0:14:07 keep subscribing. So we had a relatively high churn rate, certain types of, we’ve eventually figured
0:14:12 out which types of customers like would pay every single month. Tended to be actually a freight,
0:14:17 a lot of freight forwarding companies. Oh, interesting. We use it at Flexport is for
0:14:21 list, list construction, lead gen, like finding who’s importing though. They have my sales team
0:14:28 call them and talk to them about their, their freight. Um, and hedge funds and analysts like
0:14:32 Wall Street types that want to see what’s going on. They’ll, they’ll pay and they’ll pay. They’re
0:14:36 not, they’re not that price sensitive and they’ll keep paying every month. So, but we weren’t that
0:14:45 excited and our, our, our signups were always pretty good, relatively consistent. Forgot the
0:14:49 numbers, but we would sign up a few hundred customers every month. And then, but eventually,
0:14:54 you know, you’re the, the size of your business is just simply the number of new signups that you get
0:14:59 divided by your churn rate and your churn rate. And that tells you how many customers you’re going to
0:15:04 get at state at equilibrium when those, cause those two lines will cross. Uh, and we got to that point.
0:15:08 And then from there, I tried everything I could to like, we tried everything we could. It wasn’t just
0:15:14 me, um, to bend that arc, either make the signups go up or the retention change. And like, we ended up
0:15:19 just adding a lot of costs to the business without, you know, we, we did some South that works, but it
0:15:23 really your, your scale of your business is very much limited by your churn rate. If you have any
0:15:28 churn at all, you have like a cap on how big you can be, unless you’re increasing the number of
0:15:33 customers you’re getting or the size of those customers. Like it’s very, it’s pretty simple
0:15:37 math. I teach a lot at Flexport. It’s like how important it is to retain customers.
0:15:43 Are there any other niche data sets that you came across while you were doing that, that are super
0:15:46 tiny, but would be highly valuable in the same way?
0:15:51 Yeah, I think so. My, well, my, that’s what my brother largely does is take data sets and build
0:15:53 businesses around them.
0:15:55 Oh, outside of construction too?
0:15:58 Yeah. So he’s now, he’s got that company builds in, but he has a few other
0:16:04 partners with, uh, great entrepreneurs. And so like for import genius, are these records like paper
0:16:06 and you go and like, you take a picture of them? Like how does that work?
0:16:10 We use Freedom of Information Act to access them from all the, from, from customs and border
0:16:15 protection and you get access to the, to the data. They, they make no effort whatsoever to make
0:16:18 it useful. You don’t have to do paper digitization, but they just give it like data dumps and they
0:16:19 won’t give you past data.
0:16:21 Oh, interesting.
0:16:28 And that’s just custom. That’s just us. We have data sets for Latin America, uh, mostly
0:16:30 Latin America, a couple other countries, India.
0:16:35 Okay. So let’s go back to Ycom and enter 2013. You’re there with your brother, 2014, you apply,
0:16:39 you get in, uh, at that point you have the idea for Flexport?
0:16:45 No, we’d already gotten licensed. Um, and that was the thing, like we had the idea of a debate
0:16:49 between me and my brother and our other partner who had the idea for Flexport. We all claim it.
0:16:56 but first email that I can find like discussing this was like in 2008 or nine, but it took a long
0:17:00 time to get licensed by a customs of border protection. I had to go through an FBI background
0:17:06 check, had to do a whole bunch of, yeah, it just takes two years. Um, so it was when we got the
0:17:12 license from CBP that I left, stepped down and started Flexport. And that was about six months
0:17:17 before YC started. I forgot the timeline of the application, but about six months before. So we
0:17:22 had, but we didn’t like, we had maybe a one customer. We really didn’t have any customers,
0:17:27 but we had a V1 of the software app, had the license, like had a bit of a strategy for what
0:17:28 we’re going to go do.
0:17:31 Take me through the, the Y Combinator experience.
0:17:37 It may have changed. This was already 10 years ago. Um, they do a Tuesday dinner.
0:17:42 PG used to cook it. I think it was really bad food.
0:17:47 You were the last batch where he was the, yeah, I’m really lucky that I, not only was the last
0:17:51 batch, but he announced it mid batch. So you didn’t take it for granted that you’re getting this time
0:17:52 with Paul.
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0:20:20 But for me, it was amazing because I’m not from, I hadn’t been living in the Silicon Valley ecosystem. I
0:20:26 wanted to have connections. And the Evernote CEO, Phil Libin, he was hilarious. Brian Chesky.
0:20:33 Yeah, kind of like somewhat eminent founders and investors. But they just come and give a
0:20:42 talk for a couple hours, do Q and A. So nothing amazing. But the real benefit of what I see, I think,
0:20:51 is the friends that I made. As an outsider, fair to call myself that back then, I didn’t have a lot of
0:20:56 entrepreneur friends. They were trying to find them online and stuff. So all of a sudden, I had all these
0:21:01 peers who were also building businesses. And I don’t know, that’s just super valuable from a life experience
0:21:04 standpoint. I don’t know how much it helped a business, but it just made my life better.
0:21:11 And then it also, I guess that kind of understates like YC, if you’re one of the top companies, I think
0:21:14 it’s very important to be a top company if you’re going to do Y Combinator. There’s a bit of a
0:21:18 competition. A lot of people don’t realize that. It’s like, at the end of the day, there’s only so
0:21:22 many hot companies that can come out each year. And you want to be, if you’re one of those, then it’s
0:21:27 tremendously valuable for you. Because fundraising, I put have raised money, I had built a successful,
0:21:32 profitable SaaS business, I’m sure I could have raised money. But I literally like tried at one point to
0:21:37 raise money. And I showed up in Silicon Valley on Sand Hill Road wearing a suit and tie. I just
0:21:42 didn’t know. I think people like just were like, who’s this guy, you know, and tried to raise money
0:21:48 for it. No, I didn’t try that hard. I did a couple pitches and they went nowhere. And then with YC,
0:21:52 it was a feeding frenzy. It turned it from an outbound sale, which is hard doing outbound kind
0:21:57 of cold calling to an inbound sale where everybody was like eager to invest. They heard about Flexport.
0:22:03 PG himself really liked and likes Flexport and was telling investors, you should invest in this
0:22:08 company, which kind of controversial, YC partners. I think they’re a little better about it now than
0:22:13 they used to be, but they would kind of choose favorites. And hey, that’s the game. You know,
0:22:18 it’s business. It’s not a socialist project. We’re here to like find the best businesses and back them.
0:22:22 Um, um, but it is, I, I, I, I try to tell every founder, like, you’re going to go into YC. It’s
0:22:27 not, you’re not there to have fun. You’re trying to be the best. And it is a competition. You first,
0:22:31 you sure make friends with them, but I’m sure Michael Phelps is friends with the other swimmers,
0:22:35 too. But like you’re trying to beat them on some level. What are some of the lessons that you learned
0:22:40 from Paul Graham that still resonate with you today? I know you still talk to him a lot.
0:22:44 His main thing is not, he doesn’t look at the downside and what could go wrong. He only looks at what
0:22:48 could go right. And like how big and awesome could this be in the best case scenario? And what
0:22:53 should you do to make that happen? He’s not, you’re not looking, and that’s like for a seed investor,
0:22:58 the obviously correct way, because the losers don’t matter. All that matters is you get the
0:23:02 power of all winners that do a hundred thousand X or whatever their best deals have done for them.
0:23:07 Again, I was really lucky because we were in his last batch and he announced like halfway through
0:23:11 the batch that he was stepping down and Sam was taking over, but he kept running the batch the whole way.
0:23:17 So then when it came to demo day, the preparation for a demo day for when you go pitch the investors,
0:23:21 um, I barely worked on my pitch. In fact, my pitch was pretty bad. I think
0:23:26 I’m like, not very good at reading a script and they only give you two minutes. So you kind of have
0:23:30 to have a script if you’re going to do a two minute pitch. But also I was kind of bad because I didn’t
0:23:37 practice very much. I had the opportunity to sit there. I’m in Picasso studio, you know,
0:23:42 watch Picasso paint, you know, he’s about to retire. So I got to sit there and watch PG critique other
0:23:46 people’s pitches instead of go, I don’t want to sit there and paint. Like, let me just watch Picasso
0:23:51 paint, you know? Um, um, so I sat next to him for 12 hours a day for like three days in a row,
0:23:54 watching him critique everyone else’s pitch.
0:23:56 what did you learn from that?
0:24:01 This is proprietary secret. I’m going to let you in on, you should tighten the aspect ratio on your graph
0:24:07 and it’ll make it, the curve looks deeper. I feel like he told everybody that, like,
0:24:14 just scratch your graphs and watch out. Your startup looks hotter. Uh, there’s something to that. You got
0:24:18 to appeal to investors greed. I don’t know if he taught me that or someone else, but it’s kind of the same
0:24:23 thing. You want to, there’s a feeling that goes to it really simplifying things. I mean,
0:24:27 one of the things that PG is really good at, if you read his writing and stuff is just like very
0:24:31 simple language. You won’t read like a PG sentence when you’re like, what is that word? I don’t
0:24:37 understand. He’s like very simple. It’s easy to understand. My favorite PG moment from that period
0:24:44 was one of my friends had us in the batch did a presentation and PG was like, this is terrible.
0:24:48 This is not good. And he rewrote the whole thing for me. He’s like, you should say this,
0:24:52 this, and this. And like, he just said all the things. And my friend just took down perfect notes,
0:24:55 probably does like you pitch for two minutes. Then he gives you like 10 minutes of feedback.
0:25:00 And then the next group comes and he just does that over and over again all day. So there’s a cue.
0:25:04 So if you pitch and you want to do it again to come back and try again, you got to wait like three
0:25:09 hours for your turn. So like three or four hours go by and my friend goes back up and presents the,
0:25:14 the pitch. And he says exactly word for word, everything that PG told him to say. And then
0:25:19 PG was like, that’s perfect. That’s the best pitch I’ve ever heard. He totally forgot. Cause he’s
0:25:23 doing too many pitches in a row. He totally forgot that. That was like, dude, you wrote that pitch.
0:25:28 That was amazing. I learned a lot from all his essays and stuff too. It’s hard to remember what I learned
0:25:35 from him personally versus reading all of his stuff. You get out of YC, uh, 2014. Walk me through the
0:25:41 major beats, uh, and milestones up until the soft bank investment, which was 2019.
0:25:45 There’s a lot. Um, actually one of the funniest things, one of our other investors is Ron Conway.
0:25:49 And he was, he saved Flexport at one point. I don’t know if I’ve ever told this story, but, um,
0:25:54 we had a license from customs and border protection, but it was issued oddly enough in the port of Houston,
0:25:58 which is like the whole story, but it was like, that’s where we got our license for.
0:26:04 And it’s fine. You have a national license. One of the things that made Flexport possible
0:26:14 was that in 2007, I think it was, the customs will change the rules to allow for electronic filing of
0:26:21 customs entries. And it used to be that you had to have a license at each port where you wanted to clear
0:26:25 goods. So a startup could not possibly enter unless you were just like a little mom and pop.
0:26:28 help the local companies, but like, there’s no point in doing an internet company
0:26:35 to serve one port. Um, and so that changed in 2007. We started applying for licenses in
0:26:41 like 09 or something markets aren’t totally efficient, but kind of, um, and okay, so we had this license,
0:26:47 but it was in Houston and we wanted to be in San Francisco after YC. And in order to transfer it,
0:26:52 it’s just an administrative process, but you have to have a business license from the city of San
0:26:58 San Francisco. Simple, right? It’s just a business license. Well, the city of San Francisco had an IT
0:27:04 problem and was unable to issue business licenses. And this was in 2014. They worked, they had not been
0:27:10 issuing business licenses for several years. They could issue a letter that says you have a business
0:27:17 business license, but customers wouldn’t accept that. They wanted the license and they printer
0:27:22 problem. I don’t know what the IT problem was. They wouldn’t accept a letter on city letterhead saying,
0:27:26 yes, this company has a license on file with us. They wanted to see the actual license. It was
0:27:32 kind of like Kafka ass at some point where you just weren’t going to be able to operate.
0:27:37 I mean, we were like operating remotely in Houston and it just wasn’t going to work. And customs was
0:27:42 kind of clear. Like you need to, you can, you can only transmit entries physically sitting in Houston.
0:27:50 So I told Ron Conway about this situation and he emailed the late Ed Lee, who was our mayor.
0:27:56 And Ron was like one of his big donors and friends. And we got the license within six hours. They like
0:28:00 went down. I don’t know what happened at city hall. They got the license printed and we,
0:28:03 you know, sent it to customs and all got moved. But like, there was a moment there where like
0:28:10 Flexport was not going to be able to operate in San Francisco. And it was just crazy. Can’t issue a
0:28:15 license. That’s insane. So anyways, that was very early days. Many things happened. I would say,
0:28:21 like those summary of it all is we had product market fit just like insane from the get go to
0:28:25 the point of it being a problem, like more demand than we could keep up with asking us to do more
0:28:30 things than we were capable of doing just sort of run away. It was not all success, lots of mistakes
0:28:37 and bumps in the road. But, um, I guess the big, a couple of big milestones on there. One is we started
0:28:41 out when we went through why Combinator Flexport was just a customs brokerage. We didn’t do freight
0:28:44 forwarding and we said, Hey, we’re going to do freight forwarding someday, but we wanted to just
0:28:48 focus. The kind of dogma in startups is like, be really good at one thing,
0:28:54 really focus. You’ve written about this, like the need to focus. We also, the other dogma is talk,
0:28:59 you know, why Combinator talk to users and make something people want. And when we were just doing
0:29:05 customs, we get customers, but like we get the worst kind, we get a lot of rough types of customers.
0:29:10 One of the first things we ever imported was, uh, a tuk tuk, which is like, uh, from Cambodia.
0:29:15 Some guy went to Cambodia and bought like one of those little, uh, jeepney, uh, kind of scooters
0:29:20 with the seats in the back. Like Berkeley professor wanted it for the nudist parade in Berkeley.
0:29:25 Uh, this is not, he was only going to do one of those in his life. Not a great customer.
0:29:30 So we had like a lot, a lot of customers for a customs brokerage, but like rough customers doing
0:29:34 things that they were amateurs. They know what they were doing. They weren’t probably going to recur.
0:29:40 Some guy bought like a bouncy house for his kid’s birthday party in China. Cause he was too cheap
0:29:44 to buy one locally, like stuff like that. Is that because people want to deal with one,
0:29:48 one interaction from a freight forwarding and customs brokerage point of view?
0:29:52 Exactly. And so like when, whenever we talk to real companies that were doing repeat transactions,
0:29:56 they’re like, we didn’t want to separate customs from the freight. And if they did,
0:30:00 they were going to give the customs to like the best customs brokerage in the world
0:30:05 with the best reputation for compliance. And like, we were not to the startup.
0:30:09 Now we actually have a lot of big companies that use Flexport for customs only,
0:30:13 uh, because we’ve built our brand and our reputation and our technology systems to actually,
0:30:16 we can say, Hey, we’re the best. If you want to separate your customs from freight,
0:30:20 and there are good reasons to do so. Like it’s a hub for your compliance data. You don’t want to
0:30:23 shop it out there, you know, and have all this compliance records living in
0:30:28 10 different freight forwarder systems, right? People are much more likely to have a single
0:30:32 customs broker and many forwarders that move the freight. But when we were starting out,
0:30:37 like that wasn’t us. So we’d, and when we only did customs, we were not getting like
0:30:42 the legitimate companies that we wanted to build a business around. So that was the first, um,
0:30:47 kind of, it’s not really a pivot. We always knew we’d go into freight, but we went there much faster
0:30:53 than we wanted to. And the moment we did that, it was again, like back to couldn’t keep up with the
0:30:57 demand. And it became a much harder problem. Like customs, like, okay, cool. I self-contained,
0:31:02 there’s a contained environment here. I got to collect the data, got to transmit it to us customs.
0:31:06 Freight forwarding all of a sudden, I’m like unconstrained. I’m out here in the freaking wild,
0:31:07 giant round world.
0:31:14 You’re dealing with multiple parties, different interfaces to each party, because you’re trying
0:31:19 to computerize things at this point. And I don’t imagine there’s API. Like, how does that even work?
0:31:26 Right. There’s, there were no APIs, still very few APIs. Um, a lot of manual work, a lot of like,
0:31:32 we’ve built like automation and software interfaces and wherever there are systems,
0:31:38 like a lot of integration layers into different IT systems of all the vendors. But yeah, we opened
0:31:43 up a can of worms. Like we got unlimited demand, but like problems much harder and hard to keep up.
0:31:46 And as I said, it’s been like this race to like build the capabilities,
0:31:53 tech people, geographic footprint infrastructure around the world to match the demand. Um, but we went
0:31:59 from, but I forget the metrics at the moment of the first soft bank investment, but, um,
0:32:07 one point Inc magazine rated Flexport the second fastest growing company in the world. They did this in
0:32:14 the Inc 5000. We were in, we were second place, but the first place company was started before us and was
0:32:19 smaller than us. Okay. So like the math says we grew faster than they did. I don’t know how they
0:32:22 did their math, but they were wrong. We should have been number one that year. It wasn’t weighted.
0:32:26 I don’t remember who it was, but, um, but we should anyways, we were very fast growing company.
0:32:30 And a lot of times, yeah, that, that can kind of like cover up a lot of problems that we had.
0:32:36 Were you doing things manually and trying to computerize it as you go or trying to do it
0:32:37 computerized from the get go?
0:32:42 Yeah. We were doing a lot of stuff manually. We’re still open to do, we do a lot with people. Um,
0:32:51 but with this, we’re not satisfied with that. We’re like constantly figuring, okay, we’ll just do it.
0:32:57 That’s the secret to our success. We’re willing to do what the customer needs with humans as needed. Um,
0:33:03 but constantly say, this is not good. What are we going to do software wise to take this and structure
0:33:10 the workflow and put it into a automation. So we’re now on like a freight, just a standard plain vanilla
0:33:17 ocean container from any port in Asia to anywhere in the U S inland, all the way to destination.
0:33:26 We break it down about 108 steps that have to be completed. And 92% of those are done either by
0:33:35 software automation or sent out to like a third party BPO processing entity. And so that gets our costs down.
0:33:38 And the quality is really good because everything’s measurable and precise. So we’ve got
0:33:43 that piece is like really, um, took us a long time to build. It wasn’t like that in the beginning.
0:33:49 In the beginning, it was people, uh, people picking up the phone and sending a freight email forwarding,
0:33:53 I call it, but that’s the way every other freight forwarder in the world does it too. So we’re like,
0:33:59 okay, build a better interface for the customer, drive demand, and then have this,
0:34:02 we are not satisfied with the way the industry works. What are we going to do to, you know,
0:34:07 structure? In fact, in many cases, the car costs that be higher because if you don’t structure the data,
0:34:11 you, you just forward the email, the PDF, like that could be cheaper than like being like,
0:34:17 oh, I got to structure that, put it into our database. Um, and so your costs can be higher,
0:34:21 especially if you’re just doing one shipment, one time, like, well, I bother structuring the data.
0:34:25 The whole point is that the second time you ship the same thing, your costs are really low.
0:34:27 Cause you just go, yeah, do that again.
0:34:33 Yeah. So that leads to the SoftBank investment, which was, I think they gave you a billion in cash.
0:34:35 Yeah. 2019.
0:34:37 They and other investors in the round did. Yeah.
0:34:42 So what happened with that? Like you get this money and are you like, we can put the pedal to
0:34:47 the metal here. Cause didn’t something happen right after that? Somebody went bankrupt or something.
0:34:52 Oh, that was even before Hanjin was the big ocean carrier. They went bankrupt in 2016.
0:34:56 Oh, it was 2016. 2016 was very interesting year for, for freight forwarding that everyone’s
0:34:59 forgotten about. Cause we all keep talking about expensive freight and all the chaos and problems
0:35:05 in supply chain. Now tariffs, but COVID a whole bunch of other things, the, the Red Sea crisis,
0:35:08 like wars, but we’re going to get into some of that stuff.
0:35:13 Yeah, I’m sure we will. But in 2016, it’s kind of the opposite. There was so much capacity. It was so
0:35:20 cheap. You can ship a container from China, the U S for our cost was like $600. Uh, normal long run
0:35:24 average about 2000 today. I didn’t check the price this morning, but it was probably four or 5,000
0:35:30 right now. Um, and the peak COVID was, you know, famously got to like 20,000. So it was 600 bucks
0:35:37 that year. And that was an early year. We did YC in 2014. And in 2016, we took those cheap prices and
0:35:43 just pass them through to customers. And it led to crazy growth for us. Um, a good lesson, actually,
0:35:47 we don’t want to be able to play that strategy, pass through low costs and you’ll grow really fast.
0:35:50 So it was 2019 when you started to look for a COO?
0:35:56 2019, we got the funding from SoftBank and then we did, we, I hired a CTO that year.
0:35:57 Okay.
0:36:03 I really upgraded, go invest in our tech. We hired a CTO from Amazon logistics and he was, he helped us
0:36:08 build like some of that workflow software that I just described. It was like kind of the architect for
0:36:14 that. And then COVID hit. And that’s where I say Flexport looked really great. Like we were,
0:36:19 we turned profitable in 2022. Our revenue peaked at 3.8 billion because the price of freight was so high.
0:36:25 But pause, like you knew COVID was going to hit in February before it actually hit.
0:36:29 January even. Yeah. I mean, well, it was, it was in the newspaper, but we have a group called
0:36:35 flexport.org. We do shipping for humanitarian causes like refugee camps and hospitals, non-profits at
0:36:41 cost, uh, sometimes below cost. We had been part, we’re partnered with a lot of great groups,
0:36:46 like international aid groups and things like this. And, um, COVID it was in the newspaper,
0:36:52 it would hit in Wuhan. And we actually got a ton of demand to ship masks to China for the doctors in
0:37:00 China. And so in January of that year, we shipped about 300,000 N95s from the U S to China, which then
0:37:06 like two months later when there were no N95s masks in the U S were like, uh, whoops. Like, um, so yeah,
0:37:13 we saw that pretty early. And then the other thing that came out in that period was people,
0:37:18 about 50% of the world’s air freight travel. We do air freight too, not ocean freight. Um,
0:37:22 and about 50% of the world’s air freight flies in the belly of passenger planes.
0:37:26 And those all got grounded because of COVID, there was no reason to, you know,
0:37:32 I think they’re actually grounded legally. Um, and so we saw, we were at the heart of
0:37:41 kind of bringing masks, bringing PPE generally in for U S hospital networks from mostly produced in
0:37:48 China. And so we saw this insane demand for air freight and there were no ships, no planes to move
0:37:54 it. And the ships are too slow. Like hospitals are running out of masks. So we saw that and got
0:38:00 pretty active. Like, well, you can kind of see the solution to that problem is in the problem itself.
0:38:06 It was like, well, all of the passenger planes are grounded. So we can’t ship any mass. We’re
0:38:11 like, wait, the passenger planes are all grounded. Uh, and so with some of our connections, we got
0:38:16 in touch with all the major passenger airlines and we got 80 plane or 80 passenger aircraft and flew them
0:38:17 to China.
0:38:19 Cause cargo planes are allowed to travel internet.
0:38:22 Yeah. Well, passenger planes could travel too, just not with passengers.
0:38:22 Right.
0:38:27 So we got the airplane, uh, the airlines to give us great deals.
0:38:29 Cause otherwise the planes are just idle.
0:38:32 We’re just sitting there in the desert and still just sitting at the airport. So we got all of this,
0:38:40 we got 80, we did 88, I think it was 87, 88, um, passenger planes, full of masks in the overhead
0:38:46 compartments and every seat, obviously the belly. And we just, we flew 500 million masks and other object,
0:38:50 other PPE items in for us hospital network in March and April of 2020.
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0:40:12 It was crazy. It was like one of the most meaningful parts of my career and everyone at Flexpora. It was
0:40:18 great because we were like, not in a, none of us in the world was in a good place, but it all of a sudden
0:40:23 totally distracted us from whatever problems we trade fell off a cliff. It was really bad for business in
0:40:28 the first month or two. We’re like, who cares? Like we get a hospitals, like there’s civilizational
0:40:32 collapse. If the hospitals don’t show it, the doctors don’t show up for work and became friendly
0:40:39 friends with, um, the guy who runs UCSF, Sam Haga. He’s a chancellor of UCSF, our local hospital.
0:40:45 And, um, I remember years later, I met his wife dinner and she was like, it was, well, when,
0:40:50 when I saw this zoom call of you talking to Sam was the first moment when I realized everything’s
0:40:54 going to be okay. Cause you guys really touched me. It was like, I saw you guys are highly
0:41:00 competent. People are going to get mass delivered, you know, the day before they run out. Uh, now,
0:41:07 another thing that came out of that was in April of 2020, same problem statement. The passenger
0:41:12 planes weren’t very economic. They were giving us great deals because we were serving hospitals and
0:41:18 it was all like kind of pro bono, not for profit work. They were giving us great deals. It was,
0:41:24 I remember once we, one of the planes, the one I remember was a Dreamliner won’t charge us $200,000
0:41:28 to fly a Dreamliner to China and back. Oh, wow. It’s like, if you, anyone’s ever flown private,
0:41:32 that would be like a Dreamliner. I mean, this is many millions of dollars, probably round trip,
0:41:36 a couple of million, like a million, probably 500k. I’m not sure. So it gave us a great deal.
0:41:41 We saw lots of things like that, but it wasn’t sustainable for the business side of things.
0:41:45 Now we had a lot of ongoing demand for air freight, but all the passenger planes are grounded.
0:41:52 So we signed a long-term deal for three 747s from Atlas Airlines, the biggest cargo airline in the
0:41:57 world, dedicated to Flexport. And it was in that response to that, like, hey, the passenger plane,
0:42:02 we had this vision, this view, this perspective that air freight is going to be very expensive
0:42:09 because all the capacity is grounded and stuff still needs to move. People still need to ship stuff.
0:42:16 So we signed a deal with the airline, with that airline at a great rate. And I think they were,
0:42:21 their stock, Atlas was in, is in these airline indices. Because actually, if we were smarter,
0:42:25 we’d have just bought their stock because they were a public company and they were in these public,
0:42:31 these indices for airlines. And those tanked. But the cargo airline, the price should have gone to the
0:42:34 roof because they’re still, the price of air freight is going to go crazy. I think,
0:42:38 I probably haven’t really talked to them about why they signed the deal with us, but we got a good
0:42:43 deal as a result of that moment where there was this, this location. I assume that their stock price
0:42:48 going down was like part of the, their anxiety to like get these things signed off with us. So we got
0:42:55 a good deal. It, but it did kind of turn Flexport into a cargo airline. And we’ve had those planes ever
0:43:01 since. So it’s not our, it was more of a tactic than a strategy. Like our goal is to be an asset
0:43:06 light technology platform for freight forwarding and work, be like more neutral and agnostic and move
0:43:08 the cargo on anybody’s planes. But we, we saw that.
0:43:15 Has that moment, has that helped you in other ways, not from a business point of view, but like learning
0:43:17 and being more responsive to customers.
0:43:20 I mean, it really helped us during those few years of COVID when there’s tight capacity,
0:43:24 we can serve people and no one else could. It really an education about asset ownership
0:43:29 and logistics in, in that it kind of turns you against your customers in some ways that can be
0:43:35 unhealthy. You have to really overcome that inner that because, um, your job when you have a plane
0:43:39 or a ship is to fill the plane or the ship. It’s not to serve the customer anymore.
0:43:44 Like if the customer’s cargo needs to go to a different airport, you’ll try to convince them
0:43:49 to fly it where your plane is going and then truck it a long distance. Or, you know, it was like,
0:43:52 all right, you just wait three days. The plane’s leaving in three days instead of going, Hey,
0:43:58 let me find you a different option. So you have to overcome that culturally. Like if you’re an asset
0:44:03 owner, it’s pretty hard to be customer centric because your job is like fill the asset or you don’t make
0:44:07 money. Which is interesting because later on you get warehouses, but we’ll get to this.
0:44:12 Uh, and okay. So fast forward a couple of years and you’re looking for a COO,
0:44:19 what was the thought behind that? Yeah. So COVID, it did some interesting things for us. It made us
0:44:23 kind of famous in part because of the hospital stuff and some other things that we did during that time
0:44:29 when, when supply chains got dislocated. Um, but it, uh, so it helped the business and the profile of
0:44:36 the business. It financially was, we turned profitable, but it really exposed some flaws in our operations.
0:44:43 And we were, we were remote for way too long. Um, work from home, which just doesn’t work in our
0:44:48 industry, maybe in any industry, but certainly not in logistics. You need to be like in person,
0:44:52 collaborating, partnering on the, with the assets, et cetera. Um, really exposed some flaws. Like
0:44:57 when you, we would just prior to COVID, just send a truck to the port, pick up the container.
0:45:02 Yeah. And you take it for granted. But during that time, you couldn’t get appointments. You
0:45:08 couldn’t get trailers, the chassis to go to hold the containers. There’s not enough capacity. It was
0:45:15 like it, uh, the operation was really failing in a lot of ways. Um, we, by the way, same for all of
0:45:20 our peers and other freight forwarders, everyone was kind of in the same boat, but that’s not how,
0:45:24 that’s not an excuse. We want to be the best. And we didn’t feel like we were winning for a period
0:45:28 there operationally and like how we serve customers. Our net promoter score, like was
0:45:33 always in the seventies, which is a great, good metric for customer satisfaction. And that like
0:45:39 collapsed. I forgot how it got to like 17 at one point. It was pretty bad. So had a lot of operational
0:45:45 problems and I’m, um, much more of a creative type than I am. And operators like do the same
0:45:50 thing every single day and a little bit better measure every detail. And that, that it’s not like,
0:45:54 I’ve gotten good at that, but that’s not like naturally who I am. What my background is. I’m
0:46:00 more just like a freewheeling entrepreneur. So we’re looking for a partner to kind of take that on for
0:46:06 me and help Flexport mature and grow. So yeah, that was in, that would have been in 2022 when we really
0:46:13 like kind of launched in earnest search for a business partner, helping out the operation side of things.
0:46:20 And then you end up meeting Dave Clark, who would go on to take over as CEO for a period of time.
0:46:25 Uh, but he was originally where you think you were thinking COO?
0:46:30 I was trying to hire COO and met Dave Clark. He was the CEO of amazon.com. He’d run Amazon’s logistics
0:46:36 and supply chain for many years. Um, so it seemed like great fit tech and logistics. It was actually
0:46:43 in many ways. And you had the good Amazon hire in 2019, the CTO. Yeah. Um, and a lot of people I hired
0:46:47 from Amazon, we hired a lot of great people. We still have a lot of good people who worked at Amazon
0:46:53 logistics and tech. Like they’re probably the best. I think we’re the best now, but I think that, uh,
0:46:58 I don’t think I could always say that. I think we keep getting better, but, um, yeah, Amazon logistics
0:47:03 and tech, that’s what they’re known for. Right. So it seemed like a perfect fit. Walk me through how
0:47:08 we get from that moment of hiring to you stepping down as CEO. Uh, well, it’s kind of an orderly
0:47:12 transition when we hired him. I was like, Hey, let’s have a path for you to become a CEO. It became
0:47:15 pretty clear that like, I don’t know. It’s hard for me to picture. Like, what am I gonna be better
0:47:19 at today? He’s run this big company. And was that a confidence thing for you? Yeah. I mean,
0:47:24 I feel a lot more confident now. I haven’t seen, uh, done a much better job, uh, in the last 18 months
0:47:29 than we ever did before. So yeah, Dave, he was only the, he was with us for years. The CEO,
0:47:34 he’s just CEO first. We were co-CEOs and then CEO by himself for six months while I became chairman
0:47:41 of the board and work out. I think these hires are really hard in hindsight. What was the first
0:47:48 sort of sign or first moment you realized, oh shit. There are a lot of things that was building up. I
0:47:51 mean, honestly, it was the P and L at the end of the day. Like we just started burning too much money.
0:47:57 Some of that was market forces turned against us. Like we, we over-hired. I approved all those hires.
0:48:04 Like we wanted to go big on tech and just dominate. We kind of read the market. It was just like trying
0:48:09 to be contrarious. So we had a really strong balance sheet. Um, I had like 1.6 billion in the bank
0:48:19 and everybody was cutting tech hiring in 23. And we felt like, let’s go lean in, put the pedal to the
0:48:25 metal and go hire a bunch of engineers. I think we added 900 software engineers in 12, in like 12 months.
0:48:34 Oh wow. And turned out they’re all in the U S or almost all in the U S Seattle. Mostly it was like
0:48:39 very expensive people had a lot of senior execs. So we just like over invested in the business.
0:48:45 And at the same moment, like the freight markets were collapsing. Capital markets got ugly. It
0:48:48 like became clear, like, Hey, you’re not going to go raise. We’d already raised too much money.
0:48:53 Like we don’t need to raise, can’t raise more money. And so it was just like kind of a perfect storm
0:48:57 of bad decisions of which I was like, you know, sign off on all of them. So I don’t blame Dave
0:49:02 for that, but it became clear. We got to change courses here, change course here. And our customer,
0:49:09 one of the mistakes that we made during that period was we took that workflow system I was describing,
0:49:16 where you have like all these tasks that have to get completed. And we had taken this idea of efficiency
0:49:22 way too seriously to where an operator would just do like one or two of these tasks.
0:49:29 and do those over and over and over again, like a robot almost what will happen. Then you have like
0:49:33 50 different people collaborating on one shipment. That’s how fulfillment works. If you go to a
0:49:36 fulfillment center, it’s the only way it could work. You’re like, you’re not going to have the
0:49:42 same person like, yeah, unload the truck, put away the goods, take the good bout, put it in the box.
0:49:45 Like you break it into stages. Right. And so that’s where the Amazon
0:49:51 background and Flexport background really came in conflict actually, because they break it apart into
0:49:54 a simple task and have the same person do it over and over again. And like kind of robot,
0:50:00 human robots, almost like, or literal robots. And at forwarding, it’s much more of a service
0:50:03 business. There’s a lot more exceptions that can go wrong. You’re out there in a messy world.
0:50:07 You don’t own all the assets. You don’t control all the things that are happening. You need to like
0:50:12 oversee these things. And, oh, the trucker didn’t pick it up. Like better call a different trucker.
0:50:16 Like, oh, they’re not responding on the API. Okay. Pick up the phone, you know,
0:50:20 go there. Lost the cargo. All right. Drive to the airport. Like, you know, I mean, it’s a service
0:50:25 business for, and it’s B2B. You spend a lot of time with the customer. So, but especially that,
0:50:31 that piece, um, the quality really started to suffer. And it’s a really good lesson in business.
0:50:35 And I think most businesses, like actually quality costs less. It’s very counterintuitive.
0:50:40 Go deeper on that. But well, in logistics, like all the costs come from, you make a mistake.
0:50:46 Like if you file a customs entry and you get the wrong classification code,
0:50:51 you’re going to spend weeks on doing that with the customs agencies.
0:50:55 And like, you might have license issues or regulatory problems. Like
0:51:02 getting it right that first time costs way less than one mistake, undo all your efficiency gains for
0:51:06 the month, you know, and logistics. So I had to learn that the hard way. Our customer NPS really
0:51:10 started to suffer. So the board was looking at it and going like, okay, you’re burning too much money.
0:51:14 You’re going to have to cut costs. And that means cutting head down. Like that’s where most of the
0:51:21 costs at. So you got to cut costs and you got to improve your quality. That’s a kind of a hard
0:51:27 thing to do. And our culture had been suffering. We brought in all these new leaders and like the
0:51:32 core core people that built the business were like, we grew an insane leaving. We had grown. It’s a
0:51:37 really hard business. Cause it’s so global. Like we shipped to and from 147 countries. We got to have,
0:51:42 we got people all over the world. Like, and so the board kind of looked at this problem and said,
0:51:46 like, this is a problem for the founder of the business. Like you need to come back.
0:51:51 Nothing against Dave per se, but it was like very clear. Like, okay, you’re going to cut people and
0:51:56 tell them you care about the culture and tell them I need you to work harder to solve like customer
0:52:01 problems and do a giant reorg back to the way we’d always been organized that led to all the growth,
0:52:06 which was operator would take a shipment end to end and own all the tasks, own, own that.
0:52:12 And those just like the board was like, Ryan, we need, you know, you, you got to come back and step in
0:52:18 and do this. And I had already taken a job at Founders Fund as a partner. So it was a little,
0:52:21 it was, it’s still embarrassing for me. Like, I’m like, I just took this job and I got to go back.
0:52:25 Like, what am I doing? I got to follow through on my commitments, but it was obviously like I’m
0:52:30 honor bound to, to make Flexport work, make it successful. So I was very happy and excited to come
0:52:35 back. What happened when you told PG you were stepping down? I didn’t tell him until later.
0:52:42 I forget when, but like after I’d, I was the chairman. So I think I was already at Founders Fund.
0:52:46 He was pissed because he thought I should go be a partner at Y Combinator instead of
0:52:50 Founders Fund first off, but I went for a walk with him when he came back to Palo Alto
0:52:55 at one time. And he, um, he asked me why he did it, why I stepped down. I said, well,
0:52:59 I thought, I think Dave’s going to be better at the job than I am. There’s a genuinely true.
0:53:02 That’s why I did it. It wasn’t because I was burnt out or something. I just thought he would be better
0:53:06 for the company. I thought we needed to mature. It’d be better at operations and better at building
0:53:11 tech than we were. And I thought he’d be better at that. Um, and Paul had this amazing line.
0:53:15 He said, uh, that’s like saying this other guy would be a better husband for your wife.
0:53:20 Might be true, but like, don’t act on it. Like this is your company. You need to stay in there.
0:53:25 I thought that was super hilarious. And he then told me, okay, if he’s better than you at these
0:53:30 things. And he asked me, is this your life work? I heard you say that earlier. Is this your life’s
0:53:34 work? Is Flexport your life’s work? I was like, yeah, it is. He’s like, well, then you need to figure
0:53:39 out all the things that he’s better than you at and go learn them. Go learn them from him,
0:53:42 learn them from other people. Like figure out what are these things that you think he’s better than
0:53:48 you. So you can be the next CEO after he steps back. Like Larry Page did, uh, after he came back,
0:53:51 you know, he hired Eric Schmidt for a decade and then came back. He’s like, you need to go
0:53:58 learn those skill sets. But it happened much faster than, uh, PG and I could imagine on that walk.
0:54:01 Did you go and learn those? Was there a conscious effort on your part?
0:54:06 I don’t know. It all happened so fast, but really, uh, I’ve learned plenty of lessons along
0:54:13 the way. Yeah. Walk me through some of those. Well, the number one thing I think is, um, I learned from
0:54:21 Toby from Shopify and Brian Chesky who’ve been good advisors for me. The micromanagement is not a bad
0:54:26 word. It’s a good word. You gotta like stay involved in all the details. And that’s very hard in my
0:54:31 company. We’re like big and sprawling and do a lot of stuff, but need to be way more hands-on.
0:54:37 Do lots of skip levels. Don’t trust, don’t like hire big executives and then just trust them,
0:54:40 like treat them like a black box. Like I had, when I heard him say this, I was like, Oh my God,
0:54:43 I just committed the sin at the highest possible level. Right. But like, don’t do that at any level.
0:54:49 Like it’s all my company, audit everything, inspect everything. It’s, you can’t just like
0:54:54 give people too much leash to run things their way. And if they disagree with me, like
0:54:59 sure. I want to, I want to debate it. I want to hear from them. But like at the end of the day,
0:55:03 I know I’m going to still work at Flexport in 10 years. And I don’t know if that’s true about anyone
0:55:08 else. And that, that’s, that’s how they heard from Chesky. And I was like, you know, it’s like,
0:55:12 it’s probably true. Like, I hope that my team stays and I got the team for 10 years, but I’m positive
0:55:16 that I’ll be here. And so if they really don’t like the way I want to do something like, okay,
0:55:21 no problem, but it’s my company. And like, they can move on. And like, that’s the level of confidence
0:55:22 that I didn’t have prior.
0:55:29 I heard from people that we have in common that you, when you came back, uh, you were a different
0:55:33 CEO and you were like founder mode before it became founder mode.
0:55:40 Yeah. I mean, Chesky’s like way more hardcore. I think I try, uh, learn, but, but I didn’t have as
0:55:44 many frameworks for it. I was just like, Oh, I got to do what I have to do, you know? And there was a
0:55:49 lot of stuff that I really didn’t understand about the company. I had way too much committed all these
0:55:54 sins of just like, okay, there’s a problem in some department, hire a big exec, let them,
0:55:59 and then don’t get in their way. Like that is the kind of the corporate way that most people teach
0:56:03 or like most people expect, like, this is how a company should be run. Micromanagement is a bad
0:56:06 word. Toby’s the first person I ever heard that from that. Like, it’s not a bad, it’s like a great
0:56:12 thing. Get involved. You know, why would you ever want like micromanagement and attention to detail,
0:56:15 same two words for the same thing, right? Attention to details. Great. Like your boss is involved
0:56:18 in your stuff. Like that’s only a problem. If your boss is an idiot,
0:56:23 and out of touch and making bad decisions. But like, if your boss, like genuinely cares
0:56:27 about your work is involved in tune, knows what you’re doing, has good judgment. Like,
0:56:32 why would you not want them looking over your shoulder and participating with you and what
0:56:37 you’re doing? So, but Flashboard is a much, I don’t know. I don’t know. I’ve never worked at
0:56:43 another company really, but it’s, um, compared to other businesses, I think far more complex.
0:56:48 So it’s hard. It’s really actually quite hard for me to live up to Chesky’s ideal of like,
0:56:52 I think he says like, if the company should only do as many things as the founder can be personally
0:56:58 involved in, it’s a nice ideal. It doesn’t work at my company. We’re like in all these different
0:57:03 countries and all these different modes of transport that like one person can’t actually keep it all in
0:57:09 their head, but I try my hardest. How do you hire differently? What do you look for differently?
0:57:14 And then how do you integrate people differently now as a result of these experiences?
0:57:20 I just like only promote from within except for very rare cases where just like really can’t find
0:57:29 the person. Uh, and then I spend a lot more time with the new hire. I’ve only hired one person actually
0:57:34 from external in the last couple of years. And I spent just like loads of time with him. And I told
0:57:38 him he’s not allowed to make any decisions for 90 days. How did that play out?
0:57:43 It was perfect, honestly. And he even told me like, maybe I should have done more time
0:57:50 because I remember he told me at like day 88, but no, he told me day 91 that if I had let him,
0:57:54 if I told him 80 days, he would have made different decisions than he made. And like,
0:57:59 even those last 10 days, there was still like learning and taking things in. You have to approach startups.
0:58:02 If you’re an executive and you’re joining a company, you have to approach it with extreme humility.
0:58:08 Like these are smart, really smart people. Like some of the smartest people I’ve ever
0:58:12 may have worked come through the doors of Flexport or still work at Flexport. And we’ve been obsessed
0:58:17 with the problems that we’re working on for a decade. And like the idea that some big shots could
0:58:21 have come in here, this is no knock on any particular person. It’s just like a class. Like what are the
0:58:28 odds that anyone could come in and know, you know, on day one, do figure out problems that we couldn’t
0:58:34 think of or solutions that we can think of. It’s why I like no investor ever gives me useful advice,
0:58:40 really. Because like, I’m not sure they can about people and some high level stuff for sure,
0:58:45 capital markets, but like business, like strategy, like how could they ever know my business better
0:58:51 than me? I obsess about it. Like every waking hour. I’m always skeptical of people who run businesses
0:58:55 or even government and they contract things out to consultants. And it’s like, well,
0:58:59 how is that consultant know your business better? That scares me.
0:59:03 Yeah. PG wrote about that in his founder mode thing. It’s like, well, if you’re a professional
0:59:10 manager, your mindset is that you can run any companies, how you go in and, and in that world,
0:59:13 you shouldn’t be too involved in all the things. Cause like, Hey, you know, you don’t,
0:59:18 you don’t know about that particular domain, that industry. So just trust the people that are already
0:59:26 there that your job is kind of babysitting at all. But that’s not like founder, founder mode,
0:59:30 as they come to be called is like, you should know all the stuff. Like more or less.
0:59:35 You were at that talk. What did you, were you inspired by that? What did you take away from it?
0:59:38 What was the moment that really like solidified things for you?
0:59:43 He was like, I wish I could, I wish it was recorded. He went on a rant like four out of
0:59:48 three hours. Just like, he’s a very intense guy. I took like four or five pages of notes. I was
0:59:54 definitely like enthralled in the back and like a lot of stuff deeply resonated, but I’m already,
0:59:59 um, yeah, I’ve shared already some of the specific things. A lot of it is like, yeah,
1:00:04 just be way more involved in the day to day. And if the people don’t, and do a lot more skip levels,
1:00:08 like meet the people who report, don’t trust the managers. Not a bad way. Hey, like, you know,
1:00:14 I’m here to help. Like actually I’ll, when I go skip level, meaning like go talk to the people who
1:00:19 work for, I talked to anyone. I’ve, I’ve talked to 40 or 50 people every day on Slack or text or phone,
1:00:24 um, at Flexport. And if I talked to somebody who works for you, I’m not like trying to undermine
1:00:27 you. I’m going to come back to you and be like, here’s what they said. Like, here’s what I think we
1:00:31 need to do. And if the person asks me to keep it confidential, I’ll do my best. But, um,
1:00:36 ultimately I try to solve problems together with my exec. So, you know, and if people have a problem
1:00:39 thus far, they haven’t, but if somebody had a problem with that, I’d be like, well, it’s probably
1:00:42 not a fix. This is my company. I’m going to talk to anyone I want in this company.
1:00:46 I find it interesting. Cause you remember that telephone game in like preschool where you sit
1:00:51 in a circle and there’s like 10 of you and the teacher like passes a message to some kid on the
1:00:55 right. And then it goes through 10 kids. And by the time it gets back to the teacher,
1:01:00 it’s like this completely different sentence and meeting and organizations sort of filter this
1:01:06 way unconsciously. Nobody’s trying to make a mistake. Uh, but people just filter information
1:01:10 differently. And what’s important to somebody on the front line might be different to the manager,
1:01:15 to the team leader, to all the way up to you. And so by the time you get it, it’s like,
1:01:16 how accurate is this information?
1:01:21 And vice versa. Like he’s just like, how, what are the odd that people don’t know what I want.
1:01:27 Exactly. And so the other way just as well, right. It’s an interesting way to think about it.
1:01:32 Yeah. They’re leaning, like leaning way more than I realized in the communications and enablement
1:01:40 training. Like we’ve been doing the last year, huge amount of like strategy sessions and teaching and
1:01:45 like traveling the world and doing these like little, almost like a little music festival.
1:01:50 It’s the wrong analogy, but like, you know, music festival, I give you like multiple tracks that
1:01:53 you can, you know, you go to see different acts. Like we have that. We’ll come to different offices
1:01:56 and have different tracks that learn about different things. I think it’s very important that the people
1:02:01 have agency. You show up in an office and you’re like, okay, we’re going to do a half a day of training.
1:02:05 You have to sit through like four talks in a row. You lose your mind. But if I give you a menu and
1:02:09 you’re like, Hey, there’s like four talks happening right now. And there’s 16 talks,
1:02:12 right? For the next four hours, you can just choose your own adventure. Which talk would
1:02:16 you want to go to people all of a sudden like, this is amazing. I get to go learn about it.
1:02:21 And our business is super interesting. So geographically we’re in all the different
1:02:26 countries and, um, almost all the countries, we, different modes of transport, different
1:02:30 technologies. There’s like, it’s actually an incredible thing. So if you give people agencies,
1:02:36 so we try to do that to like overcome this problem of, I just realized I, I, we haven’t
1:02:41 really, I think we’re a pretty well-run company. We have everybody writing teams like write these
1:02:45 documents of what their strategy is. What happened this month? Like these six pager kind of,
1:02:50 we took this from Amazon years ago before we ever heard Dick Clark, um, the six pagers that you would
1:02:56 write about updates. Well, I read them all. I get access to all of them, but no one else does.
1:03:00 A couple other people on the team. We’re not that secretive, but just like,
1:03:08 it’s not part of the, the structure is like, they don’t disseminate. Uh, so I was just realizing
1:03:12 like no one else has such incredible things happening at this company, but nobody knows
1:03:16 about it or like not enough people know. So we started, I’m trying to work on that problem
1:03:19 more. It was kind of to overcome this telephone problems. Like I just realized, oh, like no one
1:03:25 else has the access. I do. What’s the cadence and frequency of those six page updates monthly.
1:03:31 There’s about 26 teams that do an MBR monthly business review and a six pager. And then that’s
1:03:35 just like, it doesn’t, uh, I think we cap it at six, but it’s the six isn’t that important. It’s mostly,
1:03:43 um, honestly, I actually think the six pager is sort of maybe wrong. Uh, I’m not sure, but it’s more how
1:03:48 much time it takes to read. Right. You know, what’s Twain say? Like, uh, it’s harder to write
1:03:52 a six pager than it is to write a 12 pager for a lot of businesses. And so you’re like,
1:03:55 if you had more empathy for the people who are working hard, you’d let them write the 12 pager
1:04:02 and spend more time reading it. Uh, but it turns out you, that six pages seems fine. Um, so we have,
1:04:07 I think 25 or 26 teams that write those monthly, and then they do an annual plan, uh, two year
1:04:14 rolling, but once a year update. Okay. Uh, Chesky does his twice a year update. Okay.
1:04:18 I don’t know if that’s secret, but, uh, I haven’t moved to that yet.
1:04:23 You mentioned the word obsessed. I want to talk about that for a beat before we move on to tariffs.
1:04:27 What does that mean? Do you? Oh, it’s just like, I can’t stop thinking about Flexport.
1:04:32 It’s just all the time. It’s like consuming the problem. It’s very addictive industry.
1:04:38 It turns out it’s always on. It’s always different. Every day is unique. You have a
1:04:42 front row seat, your backstage pass, you see what’s happening in the world in an insane degree.
1:04:48 And there’s infinite problems to solve ours and our customers and our vendors. Like, I mean,
1:04:54 it’s just like a crazy landscape of problems to solve. So yeah, it’s a, it’s a pretty awesome
1:04:57 industry. And I think one of the things that we’ve done well is show people that actually this thing
1:05:02 that looks boring, you don’t think about it actually a really interesting place to build a career.
1:05:06 Well, let’s talk about what’s going on in the world and let’s start with tariffs a little
1:05:11 bit. And I think it would just help orient people for the conversation. What are tariffs? When do they
1:05:15 apply? Is this a simple question or is this not?
1:05:20 Dariffs. I think it’s an Arabic word. It goes back a long time. Governments have always had
1:05:24 tariffs, thousands of years, control their borders and make money. It used to be the primary source
1:05:31 of revenue for most countries is the tariff. In the United States, that was for sure true. The income tax wasn’t
1:05:37 introduced until Abraham Lincoln in the Civil War. And it has a percent of the value of the goods that
1:05:41 are imported that you have to pay to the U.S. Treasury. Primary reason for it, I guess there’s
1:05:48 a few. Revenue is real. In fact, Trump’s chief economic advisor right now, the chairman of the
1:05:51 council, I don’t know if he’s the chief advisor, but the chairman of the council of economic advisors
1:05:56 is a guy named Stephen Moran. And he, in his current administration, he said
1:06:05 that in the Trump one, first term, that the tariffs on China paid for one third of the tax cuts that
1:06:11 Trump did. So it’s pretty meaningful. I mean, it’s an, it’s an interesting alternative way to fund the
1:06:16 government via tariffs instead of income tax. Like, I’m not sure. I hate that idea. I don’t know what
1:06:21 would happen. So it’s a source of revenues, very, very important and valuable to the government.
1:06:28 It’s a way to control protectionism for companies. That’s been a major reason to use tariffs over the
1:06:34 years is to protect U.S. businesses from competition. In part, just for employment reasons, in part for
1:06:39 national security reasons, like you want to have certain industries be successful. Steel has always
1:06:45 been one of these and autos. Most, most major countries like believe their auto industry is
1:06:51 like so important, not just for jobs, but for armaments. Like you make tanks out of your Ford
1:06:56 factory during a war, et cetera. So yeah, those are legitimate reasons for tariffs.
1:07:01 Why do they matter in the context of like the global politics?
1:07:05 Obviously, it increases the cost for companies that are sourcing goods. And we’ve become
1:07:10 so globalized. Our economy is just like the supply chains are unfathomably complex and
1:07:16 interdependent. And they’re full of independent actors making their own decisions about how they
1:07:22 want to do things. And there’s these component, subcomponent ecosystems of supply, moving goods all
1:07:26 over the world and doing assembly and production in different countries and bringing things together.
1:07:32 So introducing massive changes on short notice to the tariffs has caused borderline chaos,
1:07:37 certainly a lot of disorder in global supply chains, which ultimately affects all the stuff
1:07:42 that we buy. It’s not true that America doesn’t make anything anymore, but like a lot of the kind
1:07:46 of consumer goods that are all made over, a lot of them are made overseas, obviously.
1:07:51 I mean, you talk to a lot of customers, are people on-shoring or are they just sort of accepting or
1:07:52 what’s happening?
1:07:58 Well, that’s the thing. And then you have to judge policies, not by their intention, but by their outcome.
1:08:02 Like they, one of the mistakes that a lot of people make is like, well, it was good intention.
1:08:07 So therefore the policy is fine. And that’s not right. And these tariffs have had the opposite
1:08:10 impact that Trump would like. I think there’s intention. There’s some doubt, some validity to
1:08:14 it all. Like some of the things I said from national security and employment, other things, but the, um,
1:08:20 the result has been thus far, and it’s pretty early in the cycle. We’re only a couple months since the
1:08:25 liberation day or whatever, but the, um, I’ve met way more. I’ve been infinitely more. I haven’t
1:08:28 met anyone who said, Oh, because of these tariffs, I’m going to start doing production in the U S
1:08:31 I’ve read some headlines on it and they’ve done some white house announcements and things,
1:08:37 but like, those aren’t my customer base and my customer base met at least a half a dozen companies
1:08:41 that said stop production in the U S because of the cost of the components coming in.
1:08:42 Oh, interesting.
1:08:49 And there’s kind of like three categories of these two or three. Uh, one is people, for example,
1:08:55 we have a bicycle company that makes bicycles in the U S kids bikes. And for some reason,
1:08:59 they made an exemption for importing bikes. They’re duty-free, but not bike components.
1:09:03 So their costs went way up and their competitors from overseas didn’t
1:09:09 said they are cheaper to manufacture overseas. So they’re moving their factory that like has been a
1:09:14 well-known brand, reasonably well-known brand known for being made in America. And they’re like,
1:09:20 it doesn’t work anymore. So that’s one example. Um, two is if you’re doing it for export,
1:09:25 you’re exporting goods, you’re paying your costs have gone up on the import of the goods of the
1:09:30 components doing assembly in the U S and then exporting. You’re better off setting up that factory
1:09:36 now somewhere else where you don’t have the costs on the imported components. Third would be machinery
1:09:41 costs. So like fact, a friend of mine was setting up a line for a fab, like a semiconductor fab.
1:09:48 Um, and just like the machines are made in Germany for that particular line. And the cost was going
1:09:52 to go up 30%. It’s like, oh, all right, I’ll just build this line somewhere else in another country.
1:09:57 And there’s all sorts of like hedges and ways around this. Like one would, I think a bonded
1:10:02 warehouse is you don’t actually technically pay the tariff until you take it out of. So it’s landed
1:10:05 in the United States, but you don’t pay the tariff until it comes out of the bonded.
1:10:08 Yeah. And it’s temporary though. You’re still going to pay the tariff. So it doesn’t really work
1:10:13 for like changing their nature, but a bonded warehouse will let you make a bet that tariffs
1:10:18 are going to come down. So when tariffs were at 145 on China, we helped a lot of companies move into
1:10:23 bonded warehouses because we all predicted that it would come down from there. So you’re better off
1:10:28 waiting and only enter the goods, only exit them out of the building, but enter them into the U S
1:10:33 commerce after they’ve, after the tariffs have come down. So there’s some, there’s some hacks
1:10:38 around the edges. There’s a lot that you need to do if before you didn’t care about valuation,
1:10:43 the value of the goods, if it was times zero, who cares? Yeah. But now all of a sudden, if it’s times
1:10:49 30% or whatever number you care a lot more of, how is it valued? Um, and there are all kinds of legal
1:10:56 ways and you need to get really great advice on legal advice or, uh, advise trade advisory on how
1:11:01 to do this, but there are ways tracking that, um, you want to be able to really track every single
1:11:08 component of the product. Where is it made? Uh, and what is its stuff? What is, what is its cost? So
1:11:12 like if you have a cow, there’s steel and aluminum duties right now that are really high. I forget the
1:11:19 exact number, but they’re quite high. I think 50% or more, um, on, on Chinese made steel and aluminum,
1:11:23 maybe I should know all this details is very complex. Um, but if you have a couch that has
1:11:28 steel and aluminum, you don’t want to pay that 50%. You don’t want to pay that high duty on the entire
1:11:33 couch. You want to only pay it on the portion that’s steel and aluminum. So you really have to build this
1:11:38 great, we call it a product library, uh, which Flexport offers this technology product. So you,
1:11:42 you want to be able to track all these things at the subcomponent level. Where’s every item made?
1:11:46 And then there’s all these new regulations have been coming out for many, many years.
1:11:51 There’s one called the Uyghur forced labor protection act requires you to track the cotton,
1:11:56 anything cotton, where was it made? Uh, specifically like wet down. And then
1:12:00 the EU has a new ones very similar, but any forestry, any wood product,
1:12:05 you’d be able to show where the wood was grown anywhere in the world. Track that.
1:12:07 This is insanely complex.
1:12:12 Yeah. Carbon. They want to know the carbon border adjustment.
1:12:15 factor. I think it’s called that they want to know all the input,
1:12:20 all the carbon inputs of every single subcomponent of every product in the world,
1:12:25 how much carbon went into making it. So they can measure the carbon footprint.
1:12:29 Um, and then the U coming soon, um, you’re going to have to provide a,
1:12:34 like a QR code on every item that you can scan and it’ll tell you the carbon footprint.
1:12:39 footprint. So the world just keeps getting more and more complex, which plays into the hands of
1:12:44 customs company and companies like Flexport, because you’re like, oh, you need technology to track all
1:12:50 this stuff. Um, kind of classic regulatory capture types of, we’re not lobbying for any of these things,
1:12:54 But, uh, and you’re the most tech forward of all the companies kind of, we’re the only one
1:12:59 founded only one in the top 100 in the world founded after the web browser was invented.
1:13:02 There’s a lot of good companies, but they’re not tech companies fundamentally. So we have to, uh,
1:13:06 we have the, the world is our oyster. We should win it all.
1:13:11 Are there any sort of creative strategies you’ve seen any of your customers use that you’re like,
1:13:16 Oh, that’s novel or interesting. You have to be careful. There’s, um,
1:13:19 there’s some illegal stuff that I see and not so much of our customers. We talk them out of this,
1:13:24 but, um, one of the temptations that a lot of people are falling into right now is
1:13:30 letting your factory import the goods for you and then buying it from them in the U S
1:13:38 and then not turning a blind eye of the factory cheats on the value of the goods or their
1:13:41 classification. That’s kind of rampant in the industry right now.
1:13:46 That’s just a matter of time before I would imagine who regulates that.
1:13:51 Customs and border protection. Um, and DOJ there, uh, the problem is
1:13:56 what the factories will do is set up a shell company, not in the U S you don’t have to have
1:13:59 a U S entity to import goods into the U S. Oh, interesting.
1:14:02 You can just, or Canada or most of Western Europe. So you can just,
1:14:06 they set up the shell company in whatever country, it could be China, it could be anywhere. Um,
1:14:13 that company registers, not as an LLC or any kind of legal entity, but they just register with CBP,
1:14:20 with customs. They import the goods into the U S from abroad. If they cheat, they just disappear and
1:14:27 customs doesn’t have agents in China to go chase it down. So then they just do again under a different
1:14:32 shell company. And that’s a huge amount of what gets sold on Amazon. It’s not not,
1:14:35 not, I’m not saying it’s fraudulent, but is these foreign registered companies.
1:14:38 It’s definitely like a gray area. Do you think they’ll bring that back?
1:14:41 I think they’re going to crack down on that. I think they’re going to shut down that, um,
1:14:43 and make it. So you have to be a U S entity to import.
1:14:47 That’s a great LLC. It can be foreign owned LLC, but you’ll have to have like an LLC that can be held
1:14:53 accountable. Uh, but it’s very unclear exactly how it will be, or should be structured. Like,
1:14:57 does it need to have employees who could face jail time? Like what’s the, you know,
1:15:02 what does it need to have a certain amount of cash in the bank that can be taken if there’s fraud?
1:15:05 There’s a lot of ways, but I have no idea what’s going to pass. There’s a couple,
1:15:10 I understand there’s a few bills like looming, but I haven’t read the text of them yet. Um,
1:15:14 in Washington that would shut down the ability for foreign companies to import or put in new
1:15:19 requirements for it. So that’s like one creative thing that will happen is you get offered as an
1:15:23 importer. You’ve been buying these goods from your factory and then all of a sudden they offer
1:15:27 them to you for way cheaper than the duty alone. You’re like, yeah, that’s not my problem. I just
1:15:33 bought it in the U S guarantee you, like you are reliable for that. Like as a warning, look at the
1:15:38 camera. You have CBP DOJ has announced this. Their number two priority in white collar crime division of
1:15:42 the department of justice is, um, customs fraud after healthcare fraud is number one, and then
1:15:46 customs fraud number two. Are there any other creative strategies we can sort of put out there in the
1:15:50 the world today that you’ve seen not your customers use? Yeah. Well, the good strategies,
1:15:53 let’s not talk about the illegal ones anymore. I mean, but be careful, make sure you’re getting
1:15:59 good advice. Um, is have that database, know all the sub components. There’s a few things like
1:16:05 valuation. You can’t, there’s a thing called first sale. I won’t bore you all with the technicalities
1:16:10 of it, but there’s, it’s called first sale, which basically says that you pay, um, the value of the
1:16:16 goods based on the first time it was sold, not the price that you paid at import. So there’s legal
1:16:19 ways to do that. If you bought it, like there was a middleman or an agent that bought it in
1:16:24 China, marked it up to you. You can actually import the goods at the price they paid, not the price you
1:16:29 paid. You can deduct the Porsche. If you file it all correctly, and don’t quote me on this because
1:16:33 you want to get good legal advice, including from Flexport’s team, but you, uh, you can deduct the
1:16:38 portion that’s us made, but you have to, you don’t just get to automatically do that. You have to like
1:16:42 file all the right paperwork and stuff. And then importantly, if you import something,
1:16:46 you pay duties and then you later export a product with the same classification,
1:16:49 you’re owed a refund on the first pass.
1:16:53 Okay. You get your import back, the import duties you pay.
1:16:57 Yeah. And so every year in the United States, seven billion goes unclaimed. And that was pre
1:17:03 these new tariffs. So it’s presumably much higher. Yeah. So we, we help companies with that. We’ve
1:17:07 been getting people like big checks back that haven’t, and you can go back five years in time. So that’s
1:17:10 like a really important one. If you haven’t done it, it’s called duty drawback. If you haven’t done
1:17:14 that and other countries offer this to most countries. So yeah, there’s a lot of strategies.
1:17:19 In fact, the one thing that people should really know is your data on all your past transactions with
1:17:24 the U S government are with U S customs are your, it’s your data. You have the right to it under the
1:17:31 freedom of information act. So you can pull your last five years of transactions from CBP. Now they won’t,
1:17:36 they give it to you, uh, in a very unusable format. I think like giant CSV dump, basically,
1:17:42 maybe even on CDs, I forget, but they give you like, not, not useful. It is still your data. So it’s
1:17:46 useful, but you have to know how to clean it up. So we’ve built this interface that like visualizes
1:17:50 all of this for you and shows you every transaction you’ve done in and out of the country. And then our
1:17:54 experts kind of walk you through and be like, okay, here’s our checklist. This is ways that we think
1:18:00 we could maybe get you a refund. Now, Trump has lost the lawsuit on these new duty on these new
1:18:08 tariffs. Um, they, they, it’s going to appeal to the oral arguments for that start on July 30th
1:18:13 next month. Is that at the Supreme court level? No, it’s the level below the Supreme court. So
1:18:17 presumably if he, if he loses again, it’ll get appealed again to the Supreme court. So that’s
1:18:21 probably, I don’t know enough how this works, but towards the end of the year is my imagination. Um,
1:18:25 is my guess that it would go to the Supreme court either way. It’ll probably end up there.
1:18:31 Probably it ends at the Supreme court. Yeah. Um, that will be in really an interesting case. If they
1:18:35 lose again, everybody gets a refund on all their duties, but it won’t, they won’t just refund it.
1:18:38 You’re good. Then you’re going to have to file paperwork. Of course. Yeah. They’re not going to
1:18:43 like, here’s a magic check in the middle. Yeah. So it’s going to be, uh, and then it’s already
1:18:47 takes like about a year when you get one of these refunds from the government takes about a year to get your
1:18:52 check. Yeah. When every single company in the country applies for a refund, you probably won’t
1:18:56 see the check for like three years. There’s going to be so much fraud. Oh man. It’s going to be kind
1:19:03 of a total mess. If they lose that lawsuit, where’s traffic now, is it back to normal? Is it down? Is it
1:19:11 volumes from China collapsed 60% down when on April 9th, the day the duties hit stayed down for five
1:19:16 weeks? What? And then as soon as he relaxed, as soon as they, the Trump administration relaxed the
1:19:24 duties on China to 30% instead of one 45, it surged to 80% above pre tariff levels that lasted for two
1:19:31 weeks. And then it’s came down. It’s still above pre tariff levels. I haven’t studied enough that market
1:19:36 data. And now I’m looking at Flexport data and we have got 30% growth over last year.
1:19:42 So then I start to figure we’re actually up again from the drop. Like it came down and now we’re back
1:19:49 up. But I think that’s a Flexport thing. I think the market’s shrinking again from the peak that we hit
1:19:54 post COVID, but, uh, our own volumes were like 30% year over year growth. So what are the markers you
1:19:59 look for that are like public information or that you have as proprietary information that are sort of
1:20:04 indicators? Like the economy is really good. Oh, we’re going to hit some trouble. You know,
1:20:09 one of the things that Buffett has always said, as he looks at intermodal rail volume as a leading
1:20:14 indicator for the economy, I’m curious, like given your aperture into everything.
1:20:19 I’ve never been like a macro person. I’m not an investor like that, so it doesn’t matter to me
1:20:24 that much. I guess it’s, I mean, Buffett’s right. Like the logistics say, but it’s the international
1:20:31 stuff is so, um, less easy. There’s a lot of weirdness and lately in this tariffs data that is
1:20:35 just like, I don’t know if that means you want to know what the consumers are doing ultimately,
1:20:40 what are they buying and selling? And a lot of, there’s just a huge amount of noise. Like they didn’t
1:20:45 ship that much less or more because of consumer demand. That was like, you know, cost and inventory
1:20:52 forecasting. And so I don’t, it’s probably, if I had my access to any data, it would be the consumers,
1:20:59 the sales data from all the customers and inventory levels. I just don’t know. I, the sales data final,
1:21:03 like public companies report on their sales inventory data. I I’ve never understood like
1:21:09 the U S government publishes these inventory, um, metrics every month. I, I, where do they get that?
1:21:14 I have no idea. Um, I haven’t gotten any good economists to answer that. Look how they run
1:21:18 a survey. I’m like, yeah. Interesting. Is that valid data? Is that accurate? I know how hard it is to get
1:21:22 accurate data out of my own company. So the idea of the government economists getting accurate data
1:21:26 about all of the companies, I’m like always very skeptical on these things. It’s a hundred percent
1:21:33 correct. I’m so skeptical. I’m like big government data sets. One of the things that you said that I came
1:21:38 across that really stood out for me was when you’re designing an operation, you’re choosing your
1:21:44 bottleneck. If the bottleneck appears somewhere, you didn’t choose it. You aren’t running an operation.
1:21:47 It’s running you double click on that for a moment.
1:21:54 Bottleneck is going to be, you know, the point, the choke point, the point at which the, um, the limiting
1:22:00 factor. And I think you’re in a, in a company, your bottleneck should always be customer demand should
1:22:04 never be like bottleneck. Oh, I can’t right now. We’re bottlenecked in our customs team, our trade
1:22:09 advisory team, the people that are helping solve these problems that I was describing around how
1:22:14 much dues you owe and how to minimize it, how to be compliant. That team is super bottlenecked. We
1:22:20 didn’t plan for a world that would require this much money, this much expert head count. And it’s
1:22:23 hard to find these types of people that really know the space. So we’re bottlenecked in a place that we
1:22:29 didn’t plan. The bottleneck should be, I don’t have enough customers wanting my thing. Uh, you’d like
1:22:33 that to be in a B2B environment. That should be the bottleneck. But if it shows up somewhere else,
1:22:36 yeah, I’m not in control right now. It feels very uncomfortable. I’m like,
1:22:41 though I want, I don’t want to just hire more people, especially if it’s not, if it’s a temporary
1:22:48 surge. So what, uh, it feels out of control as it, um, and we need to get, get our handle on that. And I,
1:22:53 I hate that. I want my problem always to be like, oh, I need to be more creative in my marketing and sales and
1:22:59 like work on the pitch and the user experience and the things there. Uh, so yeah, if you’re bottlenecked
1:23:03 in how much space we’ve had a number of it, this has, um, been, we’ve had bottlenecks move all over the
1:23:08 place during COVID and, and since, um, how much space there is on ships, there’s been a bottleneck for us
1:23:14 even as recently as last couple of weeks with this huge surge of new bookings following the relax,
1:23:21 relaxation of the terrace. Um, that’s not right. Like there should not be a bottleneck for, I can’t get
1:23:25 cargo loaded on a ship and therefore I can’t help the customer or the customers getting this huge delay
1:23:28 and getting loaded and getting their cargo delivered. It’s a, it is a fact of the industry
1:23:35 right now, but that, um, bottleneck shouldn’t be in a warehouse environment. You know, you’ve got
1:23:41 picture of this flow of goods at the loading dock. You can choose where to put the bottleneck on in the,
1:23:51 in the flow of those goods. So loading dock, unload, put away, pick pack outbound, you know, and ship again.
1:23:59 Um, and the, the way that Amazon does this, as I understand it is they, they try to make the
1:24:05 bottleneck the most capital intensive piece, and then they over stack it so that there’s plenty of
1:24:09 capacity on that. Whatever the machine is probably that is capital intensive. It requires a lot of
1:24:16 capital and have like lots and lots of that machine so that that way they’re never, it just keeps flowing.
1:24:20 The goods, the, the, you don’t hit the bottleneck. You don’t actually hit it. And if you do, it’s because,
1:24:27 oh, okay. Didn’t nothing I could do. There is like more capital needed rather than if it’s labor, you’re
1:24:30 like, cool, just throw more labor at it. That should never be the bottleneck. It’s only where, oh, I need
1:24:36 a lot more capital here, even than I planned. And then they over-invest in CapEx so they don’t hit the bottleneck.
1:24:41 Because you want the most asset intense part sweating just nonstop.
1:24:44 Yeah. The asset intense part should be always, should be operating. No, but you should have
1:24:50 excess capacity there. That way you don’t get stuck with this machine holding you back. Like you have
1:24:56 an extra machine, but it’s, it’s a, um, that’s a strategy for people with a lot of CapEx. That’s
1:25:02 Amazon’s model, but plenty of CapEx. Uh, and I’m not sure that they do it right. Like one of the things
1:25:06 that they do that pisses off their merchants is they have this endless line of trucks at the
1:25:09 warehouse. They can’t unload. They’ve pushed the bottleneck off into the unload piece,
1:25:15 the loading docks and truckers and can’t get appointments and stuff. So I think that’d be
1:25:21 wrong in that framework that like, they should allow the goods to float through. It’s a, it’s
1:25:27 fascinating world of like, uh, you know, W.E. Deming is the, um, kind of business philosopher of
1:25:35 quality. He’s written a lot on, um, statistical process control and creating even flow through
1:25:41 a system that you don’t want to have these spikes and, uh, of, of flow. Cause it makes planning really
1:25:47 hard and labor and assets or people become idle. You don’t want any variance. Yeah. Eliminating
1:25:52 variance is like lean six Sigma type stuff. I’m it’s one of these things that doesn’t come naturally to
1:25:56 me. So I’m like trying to study it and take an interest in it, but it’s not my, uh, natural
1:26:02 forte to go deep on this area. I do find it quite, um, intellectually stimulating, but it hasn’t,
1:26:06 it’s not like my training and background. Is that like the whole Toyota production system
1:26:11 thing? It is. Yeah. Do you guys use that? A little bit. Yeah. I mean the Toyota production
1:26:16 system, I think there’s like two companies that have taken it really, really seriously and advanced
1:26:21 it in the United States. One is, one is Amazon and one is a Donaher manufacturing company.
1:26:26 The idea is a couple of things. One is one things that we do that is very Toyota production
1:26:30 system work like is in the Toyota production system. And I’ve never been to Toyota. I got a
1:26:34 proper tour of this. I’m a bit of a chauffeur knowledge, like repeating what I’ve heard and
1:26:39 learned a little bit from a distance, but is, um, the, the worker, the, the line worker follows the
1:26:45 part down the line and does many of the steps operate several of the, or many of the machines
1:26:53 instead of like in a U S production, Toyota auto production, each guy does one job and kind of more
1:26:58 robotic. Like I was describing earlier. And, you know, our models are similar to the Toyota one in
1:27:03 that sense. They were like the same worker follows this shipment down the line as it were doing all the
1:27:10 tasks until it’s complete. Um, that, that I think Toyota kind of pioneered that, that piece of it
1:27:13 better for the worker, for sure. Or you like have more agency, you’re more involved, you know,
1:27:17 more of the details. You’re like, your career is more interesting. You’re learning all the steps.
1:27:21 Um, but they really, the other thing that Toyota really does is empower the workers to like elevate
1:27:25 problems. It’s like, right. They famously had the rope they can pull to shut down the whole line.
1:27:30 Uh, if things aren’t right and take quality super seriously, quality costs less. I think that comes
1:27:36 from W.E. Deming. So it’s all, it’s all a very interesting area, uh, that we tried to apply.
1:27:41 And this is where I needed help at some point. He’s not like a natural on these things.
1:27:46 You mentioned chauffeur knowledge, which is, uh, such a tell that you’re a Charlie Munger,
1:27:53 uh, devotee. I would love to hear some of the lessons you took away from, uh, reading him or
1:27:57 interacting with him. I got to become friendly with Munger towards that, with Charlie, towards
1:28:01 the end of his life. I went to his 99th birthday party last year, actually, um, before he passed.
1:28:08 I got lucky. I got really, in fact, his, um, the person I’m closer with is Peter Kaufman,
1:28:12 who’s the author of, uh, poor Charlie’s Almanac. And that’s like one of my favorite books.
1:28:16 And when I lived in China, I’ve got a copy of that book.
1:28:21 And really love it. It’s like a coffee table, but Stripe just re-released a copy of it. It’s
1:28:26 now available in print again. It used to be kind of out of print. And I had that book and I loved it.
1:28:30 It really inspired me. Munger has this really wonderful essay, which I actually discovered
1:28:35 on the Y Combinator website, um, called the art of worldly wisdom or something to that effect.
1:28:39 If you Google Munger worldly wisdom, you’ll find it. Um, and it’s a US,
1:28:44 it’s a speech of that he gave at USC. It’s like a graduation speech.
1:28:45 We’ll link to it in the show.
1:28:48 Yeah, you should link to it. It’s wonderful. And it’s about this idea
1:28:56 that there’s like 300 domains in the world of knowledge, 300. It’s kind of an arbitrary,
1:29:00 I don’t remember if he says 300 or not, but there’s some number of limited quantity of domains.
1:29:05 And that in each of these, there are two or three big ideas that carry all the 80% of the freight,
1:29:10 as he said. Uh, and so if you were to go and learn those two or three big ideas from each of the
1:29:13 disciplines that up your alley, I’m sure you’ve written about this before. You have all these
1:29:19 mental models and you have lots of stuff to hang things on. Uh, and then also a lot of the innovation
1:29:25 in the world comes from taking an idea from one domain and applying it elsewhere, a mental model from
1:29:29 one and applying it elsewhere. So I learned about this when I was like 25 or so living in China.
1:29:35 And that really set me off on a lifetime journey of like trying to read because like learn as many of
1:29:43 these domains as I could just try to be worldly wise. Um, and so I, I, I loved that. It really inspired me.
1:29:47 And then one day I was at a party at a house in Silicon Valley, not like a fun party, but like, you know,
1:29:55 gathering a cocktail event or something. And, um, I didn’t know anybody. And I, this older guy’s older
1:29:59 gentleman was there and I struck up, he struck up a conversation. He saw me not talking to anyone
1:30:03 or something. We started talking to each other. And he, at some point asked me what my favorite
1:30:07 book was. I told him, Oh, it’s poor Charlie’s almanac. And because he’s like, why do you like
1:30:10 that book? And I told him all this and he’s like, well, I know that book really well, actually.
1:30:17 I’m the author of that book, uh, Peter Kaufman. And so he’s like one of Munger’s really good friends.
1:30:24 Uh, for many, many years. And he’s the one that put together this almanac. So he just thought that
1:30:27 was so funny that he started bringing me to Charlie’s house and like, tell Charlie the story.
1:30:33 One of my favorite things that Charlie told me at one of these dinners at his house was, uh,
1:30:37 when I told him about Flexport, he was like, Oh, you had a great business because the key to success
1:30:43 is dumb competition, which that’s kind of insulting. We have some really smart competitors, but I always
1:30:49 say that to people who are like building AI companies. It’s just like, what a nightmare.
1:30:54 Your, your competitors are literally AI geniuses. Like you should find a way to apply AI and some
1:30:58 other domain. So you’re not competing with the smartest people on planet earth. Cause like the
1:31:02 odd, it’s like trying to be a boxer. Like you’re gonna, you might beat all the people in your local
1:31:07 gym, but at some point you’re going to run into, uh, somebody bigger, stronger, faster,
1:31:11 John Jones or somebody you’re going to kick your ass. Yeah. I don’t think we’re the smartest people
1:31:16 in the world, but within our little old school industry, we can, we can do some damage.
1:31:22 Funny story about Peter before, uh, he’s a mutual friend years and mine. And the way that I met him,
1:31:28 I was at a Berkshire Hathaway meeting and I had went up to the, uh, the hotel, you know,
1:31:32 naively, this is my first meeting ever, you know, I just show up and I’m like, can I get a hotel room?
1:31:38 And the person behind the counter starts laughing. And I was like, Oh, no problem. I’ll just sleep in
1:31:44 my car, you know, whatever. And Peter walks up to me and he’s like, I hear you, you need a hotel room.
1:31:49 And he ends up giving me, he had a block of rooms and he ends up giving me one of his rooms.
1:31:51 That’s amazing. Which is the perfect Peter room.
1:31:56 It is totally. And it’s the most perfect embodiment of one of his phrases, which is go positive and go
1:32:02 first. Yeah. And he, we ended up striking up a conversation. Uh, we had a mutual friend who joined
1:32:07 us in that, which was Peter Bevelin. And we just ended up chatting for a long time. And he’s like,
1:32:12 if you’re ever in California, you know, come see me. And I was like, Oh, it just so happened to be
1:32:16 there next week. I had no plans to be there at all. Right. But if you’ve ever gone there,
1:32:20 Oh yeah, totally. And, uh, that struck out my friendship with him, which has been,
1:32:24 he’s been an incredible influence. Yeah. Yeah. Okay. That makes sense. That’s hilarious. Cause he loves
1:32:29 inventory. Yeah. And he had, he also had an inventory of extra rooms just in case somebody
1:32:34 needed money. Actually walk me through that. Why does he love inventory? Well, because everyone else hates it.
1:32:37 And I think it was a contrarian element too. And everybody went to business school
1:32:42 and learned that extra inventory is a evil and carries working capital costs, et cetera,
1:32:46 but he’s in his business, which is airline airport, airplane parts, aviation, aviation parts. Uh,
1:32:52 having excess inventory means you can provide the part on demand, any part you have it. No one else
1:32:58 does. So people are willing to pay a real premium. If you’re especially in aviation, if your line is
1:33:03 down or your plane’s not flying, we have a whole branch of logistics called air aircraft on ground,
1:33:08 logistic AOG aircraft on ground. People will pay any price. I once, um,
1:33:14 fluid, this is not what Flexport does, but I know this guy’s a billionaire and his plane,
1:33:21 his G6 50 cold stream, uh, private jet broke down in Antarctica or, uh, in Southern Chile,
1:33:26 like right next to Antarctica, somebody crashed, uh, like a tractor into the wing.
1:33:31 And he called me and said, can you get me a, I need this. I have the wing. I need to fly it to
1:33:39 Chile. I will pay any price. Like this guy told us like 10 times, like, if there’s a way to pay more
1:33:44 to get this there faster, we will do it. And so being the guy with all the parts, uh, for that type of
1:33:49 customer, you think of it, you have this, like in some cases, you know, 10 million to
1:33:56 $200 million plane or more sitting grounded from a like thousand dollar part, or it could be 10,000.
1:34:00 You could charge a hundred K for that part and then you’d be like, no problem.
1:34:05 Yeah. And the inventory, I mean, inventory should be not that expensive to keep around,
1:34:09 but it depends if it’s perishable. Like the COVID was a great example. Like people at the hospitals
1:34:13 didn’t have enough inventories all run just in time, which is just a ridiculous way to run a
1:34:16 healthcare network just in time because in a crisis, so you better have some inventory.
1:34:21 But the problem I think becomes that these, the PPE, the mass and stuff has a shelf life
1:34:25 and expiration. So you can’t just build a warehouse totally full of this stuff and let it sit there.
1:34:29 You only needed to pull it out in 20 years. Yeah. It won’t work. So it’s a hard problem.
1:34:35 Similar with like military, like how much artillery do you want to just produce and just have sitting
1:34:39 around just in case there’s a war, but like you want some when there’s a war, you’re not,
1:34:42 you don’t want to start your production. Then are there any
1:34:45 other Peter Kaufman lessons that stand out?
1:34:48 So many. I don’t know if, uh, you know, hopefully he publishes more books at some
1:34:53 point. He’s written a lot of stuff that he keeps offline. I really like his competitive exclusion
1:34:54 principle. What is that?
1:35:00 It’s basically, it comes from biology and it’s this idea that, um, in a niche, in an ecological
1:35:06 niche ecosystem, there’s only, uh, two, two species can’t occupy the same niche. One of them must
1:35:10 outcompete the other one. If they’re like for life, they’re both occupying the exact same
1:35:15 niche. One will win. The other will get pushed aside and go extinct or have to adapt. And so
1:35:20 in business, the way to apply that is like, you should be able to do all the things that your
1:35:27 competitor can do. And you can’t leave any room for them to exist because they can do something
1:35:31 you can’t do the opposite of this dog. Whether you should only do one thing and do it really,
1:35:35 really well. It’s like, actually you should spread out and make sure there’s no room for the other guy
1:35:39 to stick around and maintain a relationship with your customer just because you’re not able to do that
1:35:45 thing. And we still have some of these, I mean, we very hard to do everything, but he calls it, it’s a,
1:35:48 there’s a Wikipedia article about it. The competitive exclusion principle. I think that’s pretty
1:35:53 interesting. I learned from actually just generally Peter’s whole thing is, um, is the worldly wisdom
1:36:00 ideas, taking the ideas from biology and physics. And I, what’s his other one is the, um, formula for
1:36:07 kinetic energy is one half of mass times velocity squared. We use velocity as like our main word of
1:36:14 flexible velocity. Go deeper on that. Cause velocity matters more because it’s, it’s power log, right?
1:36:20 From the kinetic energy formula, it’s a square function and mass is only a linear. And so this is
1:36:26 why, um, in football, American football is hitting so hard, knocking often. It seems like this little
1:36:30 guy can just like create more, way more energy. Well, they are, they, their velocity,
1:36:33 they’re running really fast. Yeah. It’s more important than how big you are is how fast you’re
1:36:40 moving. And now velocity is different from physics than speed of velocity has a vector. So you got to
1:36:45 go in the right direction in business, but it also, it’s kind of an explanation for why startups out
1:36:51 compete. Big companies have way more mass, but they start to become slow and bureaucratic and three guys
1:36:58 in the garage can often out compete. It’s interesting to sort of visualize as like the incumbent being fat
1:37:04 and you being, you know, skinny and quick and agile, and you kind of want to run upstairs and it sucks
1:37:08 for you, but it really sucks for them. Yeah. That’s how I sort of think about that. Yeah.
1:37:14 Like how do you, how can you cause pain in a way that like, it’s going to suck for you, but it sucks
1:37:19 more for them. What are some things that you got from Peter? Well, the go positive, go first thing is
1:37:24 just such an unlock in life and the demonstration, like I had never talked to him or, or sort of like
1:37:29 had any conversations with him at that point. And it’s just stuck with me. This example is from the
1:37:33 elevator. You’re stuck in an elevator with someone, most people will say nothing, which is like kind
1:37:37 of polite to not say anything. But if you say hello, they’ll actually, turns out most people will say
1:37:41 hello back and be nice to you. And then we don’t do it because like the 2% of people will sort of
1:37:45 scowl at us. I mean, I don’t really want to talk to me about all the meters either, but I get that.
1:37:51 Yeah. I mean, it’s an interesting point. Well, now everybody’s on their phone. It’s a different world.
1:37:56 Ryan, we always end these interviews with the exact same question, which is what is success for you?
1:38:01 I like to be worldly wise. I try to keep learning. I’m lucky to have that, learn that value early on in
1:38:06 my life. That learning is the most important thing. I mean, now I’ve got kids, so it’s love, but learning
1:38:11 is right there as a close second for what my number one value is. That’s why I like flex sports so much. It’s like
1:38:17 a really incredible vehicle to learn. And the best way to learn is to solve, you know, be really engaged
1:38:21 and do things and solve problems for people. In the business context for Flexport, we want to be
1:38:27 the number one logistics company in the world by far. And we think there’s real scale economies
1:38:35 in this industry that you can unlock, but we’re pretty far from that. We’re only about 0.1% of global trade
1:38:43 in the containerized, in the world, in the domain in which we play. So we got 20, 30 years of just
1:38:49 like building, going global. We got Flexport employees in 18 countries. I want to be in
1:38:55 all the world’s countries, be like a true network business or ship anything anywhere,
1:39:01 I think it’s super easy with tech. Actually, we think we can lower the cost of shipping anything
1:39:07 by five to 10%. And I think it could have just like a massive impact on the world economy.
1:39:12 So all those things, all those things are like part of the success path, but we’re trying to enjoy the
1:39:17 journey, like learn every day. We help our customers on that, on that path.
1:39:23 I’m looking forward to rooting for you from the sidelines. Thanks for listening and learning with
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1:39:59 really like us, sharing with a friend is the best way to grow this community. Until next time.
Ryan Petersen is the founder and CEO of Flexport, the platform that coordinates global logistics from factory floor to customer door.
In this conversation, he’s refreshingly transparent about the mistakes and painful lessons he’s learned building several companies. He opens up about stepping down as CEO, his struggles with self-confidence, and what happened when he was forced to step in and save his own company.Along the way, we explore why micromanagement might be the secret to better leadership, how Trump-era tariffs reveal the hidden complexity of global trade, and what it takes to scale a company without losing control.
There are stories and lessons here you won’t find anywhere else, from a data leak that triggered a call from Steve Jobs to flying 500 million masks into the U.S. during a global shutdown.
Thanks to our sponsors for this episode:
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Approximate Timestamps:
(2:49) Early Life
(4:58) First “Start Up”
(5:38) Living Abroad in China
(10:19) Y Combinator
(11:13) Steve Jobs & the iPhone 3G Launch
(13:41) Lessons from Import Genius
(22:33) Lessons from Paul Graham, Billionaire Investor
(25:31) Flexport Early Days
(36:08) COVID-Era Flexport
(40:06) COVID-Era Flexport – Continued
(44:09) Hiring Flexport’s First COO
(47:02) Stepping Down as CEO of Flexport
(51:07) Cutting Cost & Improving Quality
(53:57) Lessons from Other CEOs
(57:05) How to Hire the Best Employees
(59:31) Paul Graham’s Closed-Door Talk
(1:03:21) The Value of a 6-Page Monthly Business Review
(1:06:57) Why Do Tariffs Matter?
(1:09:52) Tricks for Dealing with Tariffs
(1:15:43) Other Creative Strategies for Tariffs
(1:21:30) Dealing with Operational Bottlenecks
(1:27:41) Lessons from Charlie Munger
(1:30:12) Lessons from Peter Kaufman
(1:37:50) What Is Success for You?
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