In 2025, when trade chaos in the United States and the rush to implement artificial intelligence in industry are weighing on companies, there are few executives in higher demand than Flexport’s founder and CEO, Ryan Petersen. Flexport, founded in 2013, builds technology for logistics: freight forwarding, supply chains, customs brokerage, and even fulfillment of small packages to American homes. If it moves from country to country, Flexport has a technology product to help you move it. And for Petersen himself, it has been a whirlwind few years, too — and not just globetrotting.

In September 2022, Petersen and Flexport announced that he would become Executive Chairman, and that Dave Clark, who built Amazon’s logistics business, would become Flexport’s CEO. For six months, the two served as co-CEOs. They hired hundreds of new employees — the headcount peaked at around 3400 — including new executives. They bought Shopify’s logistics business for $1.3 billion. Clark served as the sole CEO for six months, and Petersen as chairman. Then, on September 7, 2023, it was announced that Petersen would return as CEO. He and the rest of the board had ousted Clark. What exactly the causes or merits were, will we ever know for sure? The board cited mismanagement of one kind or another. Clark insisted that he was tasked with fixing a broken organization.

Nobody needs your humble correspondent’s opinion on that dispute. But in a way, I think they could both be right: Flexport was broken, but Clark was the wrong person to fix it. That task belonged to one man, who’d stepped back for only a few months after a decade leading the company. “Ryan was really called back to Flexport,” said Ben Braverman, Flexport’s former Chief Revenue Officer and, as it happens, its first investor. Braverman built Flexport’s sales organization and now runs a venture firm, Saga Ventures.

On the day Petersen resumed his post as CEO in 2023, he tweeted: “Strategic Plan, Day 1: Make better decisions!”

Now, in September 2025 — three years after Clark joined, two years after he left — Flexport is firing on all cylinders amid the greatest trade policy upheaval in generations. “It’s one of the craziest turnarounds in the history of business. I am so grateful that Ryan ran toward the fire,” Braverman said of his longtime colleague and friend. Arena visited Flexport’s San Francisco office to talk with the man himself.

(Clark, after apparently considering a run for Governor in Texas, then started his own logistics business with a focus on defense and government. Auger has now raised $100 million.)

Flexport has global offices in, alphabetically: Amsterdam, Atlanta, Bangkok, Barcelona, Bellevue, Bangalore, Chicago, Copenhagen, Dallas, Frankfurt, Hamburg, Ho Chi Minh City, Hanoi, Hong Kong, Kuala Lumpur, London, Los Angeles, Manchester, Miami, Milan, Mumbai, New York, San Francisco, Seoul, Shanghai, Shenzhen, Singapore, Taipei, Toronto, and Vancouver. Besides the two dozen offices, Flexport has a handful of major warehouses and two Boeing 747 cargo aircraft. Petersen has a 747 model in his office. Contrary to what some might think, Flexport doesn’t actually operate cargo ships.

The Flexport San Francisco office is full of other curios from the world of logistics. The hallways are decorated with posters that Ryan Petersen himself generated by ChatGPT, showing off the flavors of its offices around the world.

Below a whiteboard on the engineering floor is a cardboard model of the Ever Given, the Taiwanese ship that ran aground in the Suez Canal in 2021. The Ever Given was stuck for six days, eventually freed by a Dutch company. Petersen actually published a children’s book about the Suez fiasco, “The Big Ship and the Little Digger.” With 4.6 stars on Amazon, it tells the story of how the ship was refloated by excavators and tugboats.

In the office’s lobby, beneath the Flexport wordmark, is a stuffed penguin, a reference to President Donald Trump’s “Liberation Day” tariff chart announcing 10% tariffs on goods from the Heard and McDonald Islands. The islands are an Australian territory in the far south of the Indian Ocean, over two thousand miles from the coast of Western Australia. The punchline is that the only inhabitants of Heard and McDonald Islands are penguins — a seven-figure herd. The alleged US trade deficit with the penguins was based on… well, nothing. For good measure, Petersen made a “Flexport Heard and McDonald Island” poster and posted on X that Flexport was “canceling all scheduled cargo flights and container vessel sailings” to the islands. “The penguins will have to revert to subsistence fishing.”

International logistics has always been a drama, but the last decade will live in the history books as a doozy. The United Kingdom voted to leave the European Union and by extension, its customs union. Donald Trump became President of the United States, and challenged for the first time in a century the long march toward full free trade with the world. The COVID-19 pandemic caused chaos and freight volumes collapsed. The post-COVID inflationary cycle caused chaos in the upward direction; the cost of freight soared. Houthi terrorists in the Red Sea and the Gulf of Aden attacked merchant ships. And then, Donald Trump got elected again, and in April unleashed a tariff whirlwind.

“I'm anti-taxes in all their forms, with tariffs being one of many kinds of taxes,” Petersen told me. “But tariffs are pretty central to the Trump administration's agenda, so I don't expect them to change course because of me.” And for Flexport’s business, trade chaos isn’t exactly bad news.

“A lot of our customers, especially from Europe or Canada, are facing duty payments for the first time.” Flexport’s customs brokerage division, which helps businesses deal with customs paperwork, is booming. According to Petersen, they’ve helped customers claim almost a billion dollars in refunds from overpaid duties.

The other Flexport business most positively affected by tariffmania is its US fulfillment business. Dave Clark had orchestrated the purchase of that business from Shopify. And when the US eliminated the “de minimis” tariff exemption for small packages — many of which are shipped by air from Chinese firms like SHEIN and TEMU — demand surged. “We were the only people dumb enough to have extra real estate space like that, so we were able to onboard everybody really quickly, while our competitors were telling people it’d be three months.”

“That business went from burning money to breaking even overnight, basically.”

But at the same time, the de minimis change and others drove down the price of air freight, which directly affects Flexport’s ability to make money. Earlier this year, the price of air freight went below cost.

“The price of freight has a big impact on Flexport because our revenue is price times quantity. So if the price is going like this” — he’s gesturing an up-down wave with his hand — “it makes our revenue move all over the place.”

At one point, volume from China to the US had declined by 60%. It has since recovered, and Petersen said that from Flexport’s vantage point, global volumes to the US are up about 40% year-over-year. (This interview was conducted in late July).

The vertigo in the freight market in 2025 would be a daunting challenge for any company. For Flexport, with a motivated, product-oriented engineering team and a media-savvy CEO, it’s been a big energy boost. Whether it is helping companies claim tariff refunds for the first time, or help them rapidly scale up US fulfillment, there is always another product bubbling up on the roadmap.

Ben Braverman, no longer at Flexport but a careful observer, quipped, “When it takes a competitor six months to come up with a solution for a crisis, and Ryan is on television with his plan within 24 hours, it’s got to be demoralizing for them.”

Though Flexport is well-equipped to help customers navigate the new tariff world, Petersen is not convinced that it will turn out well, especially vis-a-vis the US versus China. “The fundamental question,” he says, “is can you centrally plan an economy or not? What's lost in this rivalry between the U.S. and China is that we’re now saying we can out-central plan the Chinese.”

“There’s been a lot of embarrassment for me going through this,” said Petersen of the last few years of leadership drama at Flexport. He recounted a few episodes.

“Dave and I just played the wrong strategy. We thought we were being contrarian, when everyone else was cutting end-to-end headcount, to say, ‘let's build out our team.’ So we quadrupled the size of our engineering team in 2023. And that was just crazy. You can't do that culturally or financially.”

“It’s very embarrassing to hire all those people and then let them go 12 months later.” That included a number of people who’d joined the executive team. Petersen is clear about not passing any buck on those decisions. He remained the chairman of Flexport throughout Dave Clark’s time as CEO. “But when I came back, I had to rein all that in.”

“We did the thing that we should have done in 2023, which was to get really lean. We did that in 2024,” Petersen said. Flexport’s headcount today is around 1,900 people. At its peak, it was 3,400. “And by the way, our tech velocity is higher. Our sales, our customer service... Everything's better. Our net promoter score is better than it ever was.

Another: “Taking the Founders Fund job and then unwinding that after two months was also personally embarrassing to me.”

“I changed a lot during that time. I came back and recognized that I needed to be infinitely more hands-on, dive way deeper, meet with way more customers, get way more involved, and manage in a different style.”

Petersen says that today, he ignores the formal org chart within Flexport more than he did before. “Instead of managing through a series of layers, like senior leaders, it's my right to go to whoever I want to in the company whenever I want, which is every day, and talk to the people doing the work.”

“All the metrics are up and to the right except for the headcount.”

One of the biggest obstacles for Flexport to go public, Petersen says, is that “it’s such a volatile freight market, so it's hard to make projections.” He points out that comparable public companies have declined to provide revenue guidance for decades. But he wants Flexport to figure it out. “We're going to be nicely profitable next year, we're going to end this year profitable,” he said. “But the biggest blocker to going public is getting to the level of certainty that Wall Street wants.”

I asked Ryan, “What has Flexport been from its founding until today, and how does that compare to how the next decade and beyond will look?"

“Up until now, we've been the best tech-enabled freight forwarding company, making it easier to ship cargo from where it's made to where it's delivered. Freight forwarding is a massive market. I think we could be the best.” He corrects himself: “I think we are the best.”

“What Flexport is evolving toward is a system of record for your products. We will be to products and product data what Salesforce is to customer data, or what Workday is to people data,” he said. “Where is this thing made? Where is it sold? Everything that goes into getting it between here and there and planning how many to buy, when to buy them.”

In that type of system of record, Flexport would be totally agnostic as to how exactly goods are shipped. “The goods will be produced, and we'll place the booking on whatever freight contract you want. Someone else can move the cargo. We don't care. We’ll be the hub for all that data: compliance data, ordering data, replenishment, everything else.”

“Ryan is very much a student of history, and of business,” said Ben Braverman. “He gets to go learn from the executive teams of all the coolest businesses in the world about how they operate.”

He recently took Flexport’s sales team on a trip to the Panama Canal, and he has been all over Europe and Asia, often boarding one of Flexport’s cargo flights.

It isn’t just companies that Petersen gets to learn about. There are countries to study, too. With a few dozen offices, Flexport has mostly focused on the most relevant trade routes for goods coming to the US. A large office in Vietnam has about 75 staff, and it’s taken years to cultivate. Even for a company that leans heavily on technology, the various locations have differ non-technical challenges to success. In Petersen’s vision, Flexport should “be everywhere to everywhere.” Vietnam to Latin America? Why not.

As for how Flexport chooses these new places, I was curious. “We basically look at the U.N. Corruption Index. I want to be really good in all the places at the top that are not corrupt.”

“When Starbucks goes to a country in Africa, they have to do business in these places because that's where they grow their coffee. They don't want to work with the local guy who maybe is better because they can pay bribes and get stuff through the paperwork faster. Legit companies want nothing to do with that. They want to work with someone who’s above board.”

“We aspire to be the best company that doesn't pay bribes in all these countries.”

“Have you ever felt in physical danger as CEO of Flexport, on the road?” I asked him.

“Yeah,” Petersen replied, without missing a beat. “Mostly here in San Francisco.” He grinned and then turned toward the window, gesturing at Market Street below.