The $2 Billion Long Haul

KeepTruckin brought much-needed innovation to the trucking industry and achieved a valuation in the billions. But to keep growing, the company must rethink a core part of itself.

- By Liz Brody

Susan Rockey loved trucking. What she hated was compliance.

Lured by the call of the open road after years of working as an ER tech and running group homes for emotionally disturbed kids, she took a job in 2015 at Conner Logistics. Mostly she drove an 18-wheeler, a reefer—meaning ree-frigerated, as she's had to explain way too often—hauling meat and produce across America. But half the time, she was rooting around in the truck for a pencil and her three-ringed binder to enter her hours on the required gridded paper. She needed a ruler, too, and often had to fax the logs in from the next truck stop. All drivers had to do some version of this; no one liked the rigamarole. “There was a lot of noncompliance, a lot of cheating,” she says.

One day, she found an app called KeepTruckin. The name wasn’t fancy. It was free. It solved her problem.

The app also solved a problem for the guy who made it, Shoaib Makani, who was for many reasons an unusual figure in trucking at the time. An immigrant from Pakistan, he’d become a tech-focused venture capitalist and was doing well at it in 2013. But while his peers were falling all over themselves for crypto and AI, Makani saw white space in tar, tires, and 80,000-pound semis. The industry was almost untouched by outsiders in Silicon Valley. He just needed a way in.