Building a Supply-Chain Company

On 7 February 2022 Flexport, a San Francisco freight forwarder that was not yet nine years old, announced that it had raised $935 million in a Series E round co-led by Andreessen Horowitz and MSD Partners, at a post-money valuation reported at about $8 billion (reported). Its founder, Ryan Petersen, had started it in 2013 on the bet that a forwarder built as a software company, with one database for every shipment and customs document, could serve importers at lower cost per shipment than incumbents running on email and spreadsheets. Flexport did not sell software to forwarders; it became one, with the licences, the carrier contracts and the same spread as everyone else. SoftBank's Vision Fund had led a $1 billion round in February 2019 at a reported valuation of about $3.2 billion. When the investors of 2022 bought in, Flexport said its 2021 revenue had more than doubled, to about $3.2 billion, and that it had made an operating profit for the first time (company claims). The revenue was gross: it included the ocean and air freight Flexport bought and resold, in a year when a container from Shanghai to Los Angeles cost many times its 2019 price.

Petersen had become the industry's best-known commentator, whose thread about container-yard rules in October 2021 preceded Long Beach's decision to relax them (Chapter 3). In September 2022 Flexport hired Dave Clark, who had built much of Amazon's logistics network and run its consumer business, as co-chief executive; he became sole chief executive in March 2023, with Petersen as executive chairman. By then rates had collapsed. Flexport cut about 20% of its staff, about 640 people, in January 2023; took over Shopify's logistics business, including Deliverr, for stock in a deal announced on 4 May 2023 that gave Shopify about 13% of Flexport; and on 6 September 2023 announced that Clark had resigned and that Petersen would return as chief executive. FreightWaves, citing people familiar with the matter, reported that the board had decided to remove him; Clark described the decision as mutual (reported). A second round of layoffs of about 20% followed in October, about 1,300 jobs across the two rounds, and on 1 November Flexport said it had acquired the technology of Convoy, the digital broker that had shut down two weeks earlier (Chapter 18).

The repair took longer than the boom. Flexport missed its target of profitability by the end of 2024; it sold the Convoy Platform to DAT Freight & Analytics in a deal announced on 28 July 2025, and its 2025 profit was reported to have come from the one-time gain on that sale rather than from operations; and in February 2026 Petersen said the restructuring was complete, that he expected revenue to grow about 30% in 2026 with "very nicely profitable" results, and that an initial public offering was possible within five years (reported). Its tariff-refund tools of January and February 2026 were winning customs work as the paperwork of trade policy grew faster than freight (Chapter 19). This chapter explains the paths by which supply-chain companies are built, why the order in which a founder proves the factors matters more than the amount raised, and why a boom is the worst time to learn what a business costs.