Capital Cycles, Booms and Busts

On Wednesday 18 October 2023 the shippers who used Convoy, a Seattle digital freight broker, found that their loads had been cancelled. The next day the company stopped operating. Dan Lewis, its chief executive and co-founder, told staff in a memo that a massive freight recession and a contraction in the capital markets had left it without a way forward (reported paraphrase). About 500 people lost their jobs that week, down from a peak of about 1,500 (reported), and former employees filed a class action within days alleging that they had not received the notice that federal law requires before a mass layoff (reported; outcome not confirmed). There was no buyer for the business. On 1 November Flexport announced that it had acquired Convoy's technology and some of its staff, but not the company or its liabilities, for an undisclosed sum.

Convoy had been founded in 2015 by two former Amazon employees, Lewis and Grant Goodale, on an idea that drew a generation of start-ups into American trucking. The market was huge, fragmented and run by telephone; software would price loads automatically, offer them to small carriers through an app, chain one load to the next so that trucks ran empty less often, and pay carriers quickly. Investors from outside freight bought the idea, including, reportedly, Jeff Bezos and Bill Gates. Convoy raised about $400 million at a valuation of about $2.75 billion in 2019 and, in April 2022, a package of $260 million: $160 million of preferred equity led by funds of Baillie Gifford and T. Rowe Price, and $100 million of venture debt from Hercules Capital, alongside a separate $150 million credit line from J.P. Morgan (reported). Its valuation that spring was reported at about $3.8 billion in deal-data summaries, a figure widely repeated but not found in a primary source. In all it reportedly raised more than $1 billion.

The money arrived at the top of the cycle and was spent in the trough. Convoy grew fastest in 2020–21, when spot truckload rates were high and a broker's spread between what a shipper pays and what a carrier is paid was at its thinnest (Chapter 13). From mid-2022 spot rates fell below contract rates, shippers rebid their lanes, volumes fell, and the large incumbents cut prices to hold share. Convoy cut staff in three rounds between June 2022 and February 2023 and a fourth later in 2023, and sale talks failed (reported). The technology outlived the company. Flexport relaunched it as the Convoy Platform in early 2024 and announced on 28 July 2025 that it had sold it to DAT Freight & Analytics, the load-board company, for an undisclosed price (company).