Ryan Petersen: Building Flexport into a $3B Logistics Giant

Trump lost a lawsuit on the new tariffs and is appealing; oral arguments are scheduled for July 30 at the court level below the Supreme Court, with potential progression to the Supreme Court by year-end.

“Trump has lost the lawsuit on these new duty on these new tariffs. And they they is going to appeal. So, the oral arguments for that start on July 30th, next month. Is that at the Supreme Court level? No, it's the level below the Supreme Court.”

When Flexport over-applied workflow automation and task fragmentation (breaking shipment handling into 50 people each doing 1-2 tasks), quality suffered because freight forwarding is a service business full of exceptions requiring human judgment, unlike Amazon's fulfillment model where standardized tasks work.

“We took that that workflow system I was describing where you have like all these tasks that have to get completed and we had taken this idea of efficiency way too seriously to where an operator here would just do like one or two of these tasks and do those over and over again like a robot almost. What will happen? Then you have like 50 different people collaborating on one shipment...the quality really started to suffer and it's a really good lesson in business and I think most businesses like actually quality costs less. It's very counterintuitive. In logistics, like all the costs come from you making a mistake. Like like if you file a customs entry and you get the wrong classification code, you're going to spend weeks on doing that with the customs agencies”

Tariffs are a historical form of government revenue (primary funding source before income tax) and remain useful for protection of domestic industries and national security in sectors like steel, autos, and semiconductors.

“Tariffs, I think it's an Arabic word. It goes back a long time. Governments have always had tariffs thousands of years. Control their borders uh and make money. It used to be the primary source of revenue for most countries is tariff. Uh in the United States, that was for sure true. Uh the income tax wasn't introduced until Abraham Lincoln in the Civil War...a way to control protectionism for companies. That's been a major reason to use tariffs over the years is to protect US businesses from competition. In part just for employment reasons, in part for national security reasons like you want to have certain industries be successful. Steel has always been one of these and autos most comp most major countries like believe their auto industry is like important not just for jobs but for armaments. Like you make tanks. your Ford factory during a war etc.”

Paul Graham's critique of a founder stepping down is that it's like saying another man would be a better husband for your wife—it might be true, but you shouldn't act on it; if your company is your life's work, you must learn the skills where you're weak rather than abandon the company.

“Paul had this amazing line. He said, uh, that's like saying this other guy would be a better husband for your wife, might be true, but like don't act on it. Like this is your company. You need to stay in there.”

Peter Kaufman's 'go positive, go first' principle argues that assuming good faith and initiating positive interactions (e.g., saying hello to a stranger in an elevator) leads to reciprocal positive responses, and the small risk of negative response is outweighed by the gains from genuine connections.

“One of the things that I got from Peter...go positive, go first thing is just such an unlock in life...This example is from the elevator. You're stuck in an elevator with someone. Most people will say nothing, which is like kind of polite to not say anything, but if you say hello, they'll actually turns out most people will say hello back and be nice to you. And then we don't do it because like the 2% of people will sort of scallow at us.”

Asset ownership in logistics is toxic to customer centricity because the economics incentivize filling the asset rather than serving customer needs; when you own planes or ships, you push cargo toward your assets rather than finding the optimal solution for the customer.

“it kind of turns you against your customers in some ways that can be unhealthy. You have to really overcome that inner that because um your job when you have a plane or a ship is to fill the plane or the ship. It's not to serve the customer anymore. like if the customer's cargo needs to go to a different airport, you'll try to convince them to fly it where your plane is going and then truck it a long distance or you know it's like oh you just wait 3 days the plane's leaving in 3 days instead of going hey let me find you a different option.”

In logistics, quality costs less than trying to optimize for efficiency, because a single mistake (e.g., wrong customs classification code) cascades into weeks of rework with government agencies, instantly erasing months of efficiency gains from cost-cutting.

“most businesses like actually quality costs less. It's very counterintuitive. In logistics, like all the costs come from you making a mistake. Like like if you file a customs entry and you get the wrong classification code, you're going to spend weeks on doing that with the customs agencies and like you might have license issues or regulatory problems. Like getting it right the first time costs way less than one mistake will undo all your efficiency gains for the month”

In a well-managed operation, the bottleneck should always be customer demand; if a bottleneck appears elsewhere, you're not running the operation—the operation is running you.

“Bottleneck is going to be, you know, the point, the choke point, the point at which the um the limiting factor. And I think you're in a in a company, your bottleneck should always be customer demand should never be like bottleneck. Oh, I can't...If you're bottlenecked in how much space, we've had a number of it...that's not right. like there should not be a bottleneck for I can't get cargo loaded on a ship and therefore I can't help the customer...It is a fact of the industry right now. But that um bottleneck shouldn't be in a warehouse environment.”

Tariff valuation and product classification are now critical business decisions where they previously didn't matter; if tariffs are 30% or higher, companies care deeply about exactly how products are valued and classified to minimize duty exposure.

“if before you didn't care about valuation, the value of the goods, if it was time zero, who cares? Yeah. But now all of a sudden if it's times 30% or whatever number you care a lot more of how is it valued.”

Peter Kaufman's 'competitive exclusion principle' from biology states that in an ecological niche, two species cannot occupy the exact same space; one must outcompete the other or adapt. In business, this means you should spread your competitive offerings so comprehensively that competitors have no remaining niche to survive in.

“Peter Kaufman...his um competitive exclusion principle what is that it's basically it comes from biology and it's this idea that um in a niche in an ecological niche ecosystem there's only a two two species can't occupy the same niche one of them must out compete the other one if they're like for life they're both occupying the exact same niche one will win the other will get pushed aside go extinct or have to adapt and so in business the way to apply that is like you should be able to do all the things that your competitor can do and you can't leave any room for them to exist because they can do something you can't do the opposite of this dogma that you should only do one thing and do it really really well.”

The kinetic energy formula (E = 1/2 × m × v²) illustrates that velocity has exponentially greater impact than mass because it's squared, explaining why small fast-moving startups outcompete large, slow incumbents and why agility matters more than resources.

“Peter's...the formula for kinetic energy is 1/2 of mass times velocity squared we use velocity as like our main word at flexport velocity go deeper on that because velocity matters more because it's it's power law right from the kinetic energy formula it's a square function and mass is only linear and so this is why um in football American football is hitting so are knocking. Often it seems like this little guy can just like create more way more energy. Well, they are. They're velocity. They're running really fast. Yeah. It's more important than how big you are. It's how fast you're moving. And now velocity is different from physics than speed. Velocity has a vector. So, you got to go in the right direction in business.”

Executives joining startups must approach with extreme humility because the founding team has spent years obsessing over problems and likely has thought deeper than any external hire could imagine—the odds that an outsider sees solutions the founders missed are low.

“You have to approach startups if you're an executive and you're joining a company you have to approach it with extreme humility. Like these are smart, really smart people. Like some of the smartest people I've ever met have worked come through the doors of Flexport or still work at Flexport. And we've been obsessed with the problems that we're working on for a decade. And like the idea that some big shots could come in here, this is no knock on any particular person. It's just like a classic like what are the odds that anyone could come in and know, you know, on day one do figure out problems that we couldn't think of or solutions that we couldn't think of.”

Investors rarely provide useful advice because they don't have deep domain knowledge; they can advise on people and high-level strategy or capital markets, but on business strategy they cannot know your business better than you if you obsess about it every waking hour.

“It's why like no investor ever gives me useful advice really because like I not sure they can't about people and some high level stuff for sure or capital markets but like business like strategy like how could they ever know my business better than me? I obsess about it like every waking hour.”

Peter Kaufman holds the view that a company should only do as many things as the founder can personally be involved in—an ideal that doesn't work for Flexport due to its global complexity but that Peterson aspires to approach.

“I think he says like if the company should only do as many things as the founder can be personally involved in. It's a nice ideal. It doesn't work at my company. We're like in all these different countries and all these different modes of transport that like one person can't actually keep it all in their head, but I try my hardest.”

Charlie Munger told Ryan that Flexport succeeds because it faces 'dumb competition'—competitors who aren't as smart as Flexport's team—and that competing against AI geniuses (like in AI startups) is a nightmare, so entrepreneurs should apply smart technology to less-competitive domains.

“One of my favorite things that Charlie told me at one of these dinners at his house was uh when I told him about Flexport, he was like, 'Oh, you had a great business because the key to success is dumb competition.' which that's kind of insulting. We have some really smart competitors, but I I always say that to people who are like building AI companies. It's just like what a nightmare. Your your competitors are literally AI geniuses. Like you should find a way to apply AI in some other domain. So you're not competing with the smartest people on planet Earth because like the odd it's like trying to be a boxer. like you're going to you might beat all the people in your local gym, but at some point you're going to run into uh somebody bigger, stronger, faster, Jon Jones or somebody's going to kick your ass.”

Amazon's strategy for warehouse operations is to make the bottleneck the most capital-intensive step (e.g., sorting machines), then overinvest in that step with excess capacity so that labor or other constraints never limit throughput.

“the way that Amazon does this, as I understand it, is they they try to make the bottleneck the most capital intensive piece and then they overstack it so that there's plenty of capacity on that whatever the machine is probably that is capital intensive, that requires a lot of capital, have like lots and lots of that machine. So that that way they're never it just keeps flowing the goods the you don't hit the bottleneck.”

Amazon's unloading dock strategy pushes the bottleneck to the outbound side, creating endless lines of trucks unable to get unloading appointments, which is inefficient because it forces the constraint onto trucking partners rather than managing throughput internally.

“I'm not sure that they do it right. Like one of the things that they do that pisses off their merchants is they have this endless line of trucks at the warehouse. They can't unload. They've pushed the bottleneck often to the unload piece. the loading docks and truckers and can't get appointments and stuff. So, I think that'd be wrong in that framework that like they should allow the goods to flow through.”

If Trump loses the tariff lawsuit at the Supreme Court, everyone will be owed refunds on duties paid, creating massive processing burden, fraud risk, and years-long payment delays as the government processes millions of claims simultaneously.

“If they lose again, everybody gets a refund on all their duties, but it won't they won't just refund it. You're then going to have to file paperwork, of course. Yeah. They're not going to like here's a magic check in the mail. Yeah. So, it's going to be And then it's already takes like about a year when you get one of these refunds from the government. Takes about a year to get your check. Yeah. When every single company in the country applies for a refund, you probably won't see the check for like three years. There's going to be so much fraud.”

Buffett uses intermodal rail volume as a leading economic indicator; Ryan is skeptical of macro indicators generally and finds tariff-driven noise makes logistics data unreliable for economic forecasting, unlike actual consumer sales and inventory data.

“one of the things that Buffett has always said is he looks at intermodal rail volume as a leading indicator for the economy. I'm curious like given your aperture into everything. I've never been like a macro person. I'm not an investor like that. So, it doesn't matter to me that much. I guess it's I mean Buffett is right like the logistics, but it's the international stuff is so um seasonality. There's a lot of weirdness in lately in this tariff data that is just like I don't know if that means you want to know what the consumers are doing ultimately. What are they buying and selling and a lot there's just a huge amount of noise like they didn't ship that much less or more because of consumer demand. That was like you know cost and inventory forecasting and so I don't it's probably if I had my access to any data it would be the consumer you know sales data from all the customers and inventory levels.”

Peter Kaufman's view on inventory is contrarian: while business school teaches that excess inventory is evil due to working capital costs, in practice (especially in aviation), excess inventory of critical parts enables premium pricing and customer satisfaction when they face downtime.

“he also had an inventory of extra rooms just in case somebody needed one. Actually, walk me through that. Why why does he love inventory? Well, because everyone else hates it. I There's a contrarian element to it. Everybody went to business school and learned that extra inventory is uh evil and carries working capital costs, etc. But he's in his business, which is airline airport airplane parts, avi aviation parts, uh having excess inventory means you can provide the part on demand. Any part you have it, no one else does. So people are willing to pay a real premium if you're especially in aviation if your line is down or your plane's not flying.”

Many companies are cheating on tariffs by letting factories undervalue goods or misclassify their tariff codes; this is rampant in the industry, particularly through shell companies set up in offshore jurisdictions that import goods and then disappear if caught.

“one of the temptations that a lot of people are falling into right now is letting your factory import the goods for you and then buying it from them in the US and then not turning a blind eye if the factory cheats on the value of the goods or their classification. That's kind of rampant in the industry right now. That's just a matter of time before I would imagine who regulates that Customs and Border Protection um and DOJ...the factories will do is set up a shell company, not in the US...they just register with CBP with customs. They import the goods into the US from abroad. If they cheat, they just disappear. And C customs doesn't have agents in China to go chase it down.”

Flexport's goal is to be an asset-light technology platform for freight forwarding, allowing the company to remain agnostic about which carriers it uses and customer-centric rather than asset-optimization-centric.

“Our goal is to be an asset light technology platform for freight forwarding”

In 2014, San Francisco's city government had an IT system failure that prevented issuing business licenses for several years; they could issue a letter claiming the license existed but Customs would not accept it, nearly preventing Flexport from operating in San Francisco until Ron Conway intervened with the Mayor to get a physical license printed.

“the city of San Francisco had an IT problem and was unable to issue business licenses. And this was in 2014. They were they had not been issuing business licenses for several years. They could issue a letter that says you have a business license, but customs wouldn't accept that. They wanted the license and they printer problem. I don't know what the IT problem was. They wouldn't accept a letter on city letterhead saying yes, this company has a license on file with us. They wanted to see the actual license. It was a kind of like Kafka-es. At some point we just weren't going to be able to operate in San we were like operating remotely in Houston and and it just wasn't going to work and customs was kind of clear like you need to you can you can only transmit entries physically sitting in Houston. So, I told Ron Conway about this situation and he emailed the late Ed Lee who was our mayor and I Ron was like one of his big uh donors and friends and we got the license within six hours.”

Flexport initially struggled with customer acquisition for customs brokerage services because it attracted low-quality one-time customers (e.g., Berkeley professors buying custom scooters, people buying single bouncy houses) rather than repeat businesses; adding freight forwarding services solved this by attracting companies doing recurring shipments.

“when we were just doing customs we get customers but like we get the worst kind we get a lot of rough types of customers one of the first things we ever imported was a a tuk tuk which is like a from Cambodia Some guy went to Cambodia and bought like one of those little uh jeep knee uh kind of scooters with the cool seats in the back. Like Berkeley professor wanted it for the nudest parade in Berkeley. Uh not he was only going to do one of those in his life. Not a great customer. So we had like a lot a lot of customers for customs brokerage but like rough customers doing things that they were amateurs...And so like when whenever we talked to real companies that were doing repeat transactions, they're like, 'We didn't want to separate customs from the freight.'”

Flexport went from operating in a contained customs-only environment to an unconstrained global freight forwarding problem that required building technology, people, geographic footprint, and infrastructure across 147 countries to match customer demand.

“customs like, 'Okay, cool. I self-contain. This is a contained environment here. I got to collect the data, got to transmit it to US customs. Freight forwarding. All of a sudden, I'm like unconstrained. I'm out here in the freaking wild giant round world. You're dealing with multiple parties, different interfaces to each party cuz you're trying to computerize things at this point.”

By breaking down a standard ocean container shipment from Asia to US inland destination into 108 sequential steps, Flexport has automated or outsourced 92% of those steps, dramatically reducing costs and improving measurable quality.

“we're now on like a freight just a standard plain vanilla ocean container from any port in Asia to anywhere in the US inland all the way to destination. We break it down to about 108 steps that have to be completed and 92% of those are done either by software automation or sent out to like a third party BO processing entity. Um so that gets our cost down and the quality is really good because everything's measurable and precise.”

Most major global companies founded before the invention of the web browser are not fundamentally tech companies; Flexport is the only company in the top 100 global logistics firms founded after the web browser was invented, giving it a structural tech advantage.

“kind of we're the only one founded only one in the top hundred in the world founded after the web browser was invented. A lot of good companies, but they're not tech companies fundamentally.”

Aircraft on ground (AOG) logistics is a specialized market where customers will pay essentially any price for expedited delivery of replacement parts because a grounded aircraft or plane represents massive daily financial losses.

“We have a whole branch of logistics called air aircraft on ground logistic AOG aircraft on ground. People will pay any price. I once um flew an this is not what Flexport does, but I know this guy's a billionaire and his plane, his G650 Gulfream uh private jet broke down in Antarctica or uh in southern Chile, like right next to Antarctica. Somebody crashed it uh like a tractor into the wing and he called me. He's like, 'Can you get me a I need this? I have the wing. I need to fly it to Chile. I will pay any price.' like connect you with this guy and he told us like 10 times like if there's a way to pay more to get this there faster we will do it.”

Flexport is obsessed with problems and trying to solve them; the logistics industry is addictive because it's always on, always different, with infinite problems to solve across customers, vendors, and internal operations.

“It's a very addictive industry. It's always on. It's always different. Every day is unique. You see what's happening in the world in an insane degree...There's infinite problems to solve. Ours and our customers and our vendors, like I mean, it's just like a crazy landscape of problems to solve. So, yeah, it's a it's a pretty awesome industry.”

Success for Ryan is being worldly wise and continuously learning; his number one value is learning, with love (for family) a close second.

“I'd like to be worldly wise. I try to keep learning. I'm lucky to have that learn that value early on in my life that learning is the most important thing. I mean, now I've got kids, so it's love, but learning is right there as a close second for what my number one value is.”

Inventory of perishable goods with shelf life (like PPE and masks) cannot be pre-positioned strategically because they expire; this creates a healthcare preparedness problem: just-in-time supply chains are inadequate for crisis, but stockpiling expiring goods is wasteful.

“the problem I think becomes that these the PPE the mass and stuff has a shelf life and expiration load so you can't just build a warehouse full of this stuff and let it sit there you only need to pull it out 20 years yeah it won't work so it's a hard problem similar with like military like how much artillery do you want to just produce and just have sitting around just in case there's a war but like you want some when there's a war you you don't want to start your production then”

Ryan only promotes leaders from within Flexport except in rare cases where he cannot find internal talent, and he requires new external hires to have a 90-day period where they cannot make independent decisions.

“I just like only promote from within except for very rare cases where just like really can't find the person. Uh and then I spend a lot more time with new hire. I've only hired one person actually from external in the last couple years and I spent just like loads of time with him and I told him he's not allowed to make any decisions for 90 days.”

A new external hire told Ryan on day 91 (after his 90-day observation period) that if Ryan had set the restriction at 80 days instead of 90, the hire would have made different decisions, showing that learning continued throughout the entire observation period.

“It was perfect honestly. And he even told me like maybe I should have done more time because I remember he told me at like day 88 but no he told me day 91 that if I had let him if I had told him 80 days he would have made different decisions than he made and like even those last 10 days there was still like learning and taking things in.”

Flexport's organizational model evolved to have teams doing quarterly six-page written business reviews (MBRs) covering strategy, progress, and plans; approximately 25-26 teams do this monthly, with annual two-year rolling planning updates once per year.

“There's about 26 teams that do an MBR monthly business review and a six pager and then that's just like it doesn't I think we cap it at six but it's the six isn't that important. It's mostly um honestly I actually think the six pager is sort of maybe wrong. Uh, I'm not sure, but it's more how much time it takes to read, right? You know what's Twain say? Like, uh, it's harder to write a six-pager than it is to write a 12-pager. Yeah. For a lot of businesses.”

Flexport offers a 'product library' technology that tracks all subcomponents of products and their origin, allowing customers to calculate precise tariff exposure at the subcomponent level rather than being charged duty on the entire product.

“we call it a product library uh which flexboard offers this technology product. So you you want to be able to track all these things at the subcomponent level. Where's every item made? And then there's all these new regulations that have been coming out for many many years.”

Flexport has invested heavily in communication and training, running strategy sessions globally with multiple tracks offering 'choose your own adventure' learning so people feel agency rather than forcing everyone to sit through mandatory training.

“they're lean like lean in way more than I realized into communications and enablement training like we've and doing the last year huge amount of like strategy sessions and teaching and like traveling the world and doing these like little almost like a little music festival. It's the wrong analogy but like you know music festival they give you like multiple tracks that you could you know you go to see different acts like we have that we'll come to different offices and have different tracks to learn about different things. I think it's very important that the people have agency. You show up in an office and you're like, 'Okay, we're going to do a half a day of training.' You have to sit through like four talks in a row, you lose your mind. But if I give you a menu and you're like, 'Hey, there's like four talks happening right now and there's 16 talks, right? For the next four hours, you can just choose your own adventure. Which talk would you want to go to?' People all of a sudden like, 'This is amazing.'”

The most recent tariffs caused shipping volumes from China to collapse 60% when they hit on April 9th; the volumes stayed depressed for 5 weeks, then when Trump relaxed the tariffs from 145% to 30%, shipping volumes surged to 80% above pre-tariff levels for two weeks before settling back down to above pre-tariff levels.

“volumes from China collapsed 60% down when on April 9th the day the duties hit stayed down for 5 weeks what and then as soon as he relaxed as soon as they the Trump administration relaxed the duties on China to 30% instead of 145 it surged to 80% above pre-tariff levels that lasted for two weeks and then it came down it's still above pre-tariff levels”

Instead of hiring big executives and trusting them as black boxes, Peterson now skips levels, talks directly to people who report to executives, and uses skip-level conversations to gather information and surface problems rather than relying on filtered reporting from layers of management.

“don't trust don't like hire big executives and then just trust them. Like treat them like a black box. Like I had when I heard him say this, I was like, 'Oh my god, I committed this sin at the highest possible level, right?' But like don't do that at any level. Like it's all my company. Audit everything. Inspect everything.”

A semiconductor fabrication equipment manufacturer was going to build a fab line in the US using machines made in Germany, but tariffs raising machinery costs by 30% made locating the fab outside the US cheaper than absorbing the tariff.

“Third would be machinery costs. So like fact a friend of mine was setting up a a line for a fab like a semiconductor fab um and just like the machines are made in Germany for that particular line and the cost was going to go up 30%. He's like, 'All right, I'll just build this line somewhere else in another country.'”

Customer NPS (net promoter score) at Flexport dropped from 70 to 17 during the period of operational chaos and remote-first management (COVID period and Dave Clark tenure), indicating a massive quality and service degradation.

“Our net promoter score like was always in the 70s, which is a great good metric for customer satisfaction. And that like collapsed. I forgot how got to like 17 at one point. It was pretty bad.”

Peter Kaufman introduced Ryan to Charlie Munger and they became friends; Ryan was at Munger's 99th birthday party before Munger passed away, and Kaufman has been a significant advisor and influence on Ryan's thinking.

“I got to become friendly with Mer towards the with Charlie towards the end of his life. I went to his 99th birthday party late last year actually um before he passed. I got lucky. I got really in fact his um the person I'm closer with is Peter Kaufman who's the author of Poor Charlie's Almanac and that's like one of my favorite books.”

Flexport hired 900 software engineers in 12 months (mostly from Seattle, mostly senior) in 2023 while other tech companies were cutting; this was a conscious contrarian bet that backfired when freight markets collapsed and capital markets tightened, creating unsustainable cash burn.

“I think we added 900 software engineers in in like 12 months. Oh wow. And turned out they're all in the US or almost all in the US, Seattle mostly. It was like very expensive. People had a lot of senior exeacts. So we just like overinvested in the business and at the same moment like the freight markets were collapsing.”

Ryan's early motivation for entrepreneurship came from his parents: mother was a biotech entrepreneur who sold two companies, father taught him software; they modeled both business and technical thinking.

“Well, my mom's a great entrepreneur. sold two started and sold two companies uh in the biotech biochemistry space in in Washington DC. And so I um both my brother and I had this job...my dad's a programmer. So, we wrote software to generate the invoices”

Ryan uses founder mode: he talks to 40-50 people at Flexport daily via Slack, text, or phone; he does extensive skip-level meetings and information gathering that some might call micromanagement; he is transparent that this is his prerogative as founder and owner.

“I talk to anyone. I've I've talked to 40 or 50 people every day on Slack or text or phone um at Flexport. And if I talk to somebody who works for you, I'm not like trying to undermine you. I'm going to come back to you and be like, 'Here's what they said. Like, here's what I think we need to do.' And if the person asked me to keep it confidential, I'll do my best. But, um ultimately, I'm trying to solve problems together with my exact. So, you know, if people have a problem, thus far, they haven't. But if someone had a problem with that, I'll be like, 'Well, it's probably not a fix. This is my company. I'm going to talk to anyone I want in this company.'”

Flexport's vision is to be the number one global logistics company by far, operating in all countries, enabling companies to ship anything anywhere with technology, and reducing global shipping costs by 5-10%, which would have massive positive economic impact.

“In the business context for Flexport, we want to be the number one logistics company in the world by far. And we think there's real scale economies in this industry that you can unlock, but we're pretty far from that. We're only about 0.1% of global trade uh in the containeriz in the world in the domain in which we play. So I we got 20 30 years of just like building going global...I actually think we can lower the cost of shipping anything by 5 to 10%. And I think it could have just like a massive impact on the world economy.”

Customs brokers are among the few professionals that operate in the highest-touch, most expertise-dependent parts of the supply chain where errors have cascading consequences, making the need for experienced talent non-negotiable, particularly during tariff uncertainty.

“Right now, we're bottlenecked in our customs team. Our trade advisory team, the people that are helping solve these problems that I was describing around how much dues you owe and how to minimize it, how to be compliant. That team is super bottlenecked. We didn't plan for a world that would require this much money, this much expert headcount. And it's hard to find these types of people that really know the space.”

Ryan moved to China in early 2000s believing China was 'on a tear' and would be the future, with intention to learn Chinese (3 hours/day for years) and position himself for China's growth.

“it was very clear in 2002 that China was like just on a tear and that it would be maybe the future. It was like really obvious to me. So, I moved there thinking, okay, if anyone could learn Chinese, I already learn Spanish and Portuguese. I can probably learn Chinese. Let's go for it. Uh so I moved there, kept my work basically of like doing supply chain logistics, ecom development, web development, uh customer service, just attack of all trades for the startup that we had. And and then also just like study Chinese for three hours every day for a few years while I lived in China.”

Ryan reads all six-pager reports from Flexport's 26 teams but no one else besides a couple other people has access; he realized this information asymmetry is a problem because amazing things are happening at the company that most people don't know about.

“I just realized I I we have an I think we're a pretty well-run company. We have everybody writing teams like write these documents of what their strategy is, what happened this month, like these six pager kind of we took this from Amazon years ago before we ever heard Dick Clark. um the six pagers that you would write about updates. Well, I read them all. I get access to all of them, but no one else does...I just realized oh like no one else has the access I do. There's such incredible things happening at this company, but nobody knows about it or like not enough people know.”

Y Combinator partners at that time (2014) had 'favorites' they actively promoted to investors in a way that created competitive advantage for top companies; Ryan acknowledges this is exclusionary but argues it's appropriate because 'it's business, not a socialist project.'

“PG himself really like liked and likes Flexport and was telling investors, you should invest in this company, which kind of controversial YC partners. I think they're a little better about it now than they used to be, but they would kind of p choose favorites. And hey, that's the game, you know? It's business. It's not a it's not a socialist project. We're here to like find the best businesses and back them.”

Import-export data from Flexport shows 30% year-over-year growth currently, though the market overall appears to be shrinking from the post-COVID peak; Flexport is gaining market share during the contraction.

“I think the market's shrinking again from the peak that we hit postcoid but uh our own volumes were like 30% year-over-year growth.”