In my earliest days on the trucking beat, it seemed to me that there was a massive showdown brewing. On one side, I saw stodgy freight brokerages headquartered in places like Northwest Arkansas and Cincinnati. Their opponents: Sleek startups, based in Seattle and San Francisco, who pledged to change trucking. They would transform the freight brokerage process from phone calls and fax machines to automated pairing of drivers and loads, thanks to big bucks from genius venture capitalists and tech gods.

As it turns out, though, the business case for swapping out humans for computers in the freight brokerage world is shaky. It’s also not as easy to fix trucking as a slide deck might make it seem. The recent shutdown of Convoy, a digital freight brokerage established in 2015, shows that.

Convoy enjoyed all the trappings of a runaway tech success. Its two co-founders, Dan Lewis and Grant Goodale, had Amazon and Ivy League credentials. Convoy counted Jeff Bezos, Bill Gates and (bizarrely) Bono among its investors. Convoy had more than 1,000 employees at its peak. Just 18 months ago, the Seattle-based startup was valued at $3.8 billion. But maybe more importantly than cash and caché, Convoy seemed keen on making trucking better – more efficient and more just.