Convoy

Convoy was the "Uber for trucking," connecting shippers with truck drivers through a digital freight marketplace. Valued at $3.8B with backing from Jeff Bezos and Y Combinator, the company seemed unstoppable. But the freight market collapsed in 2022-2023 as post-pandemic demand normalized. Convoy's take rate compressed as competition intensified, while its cost structure—built for hypergrowth—couldn't adapt. The company abruptly shut down in October 2023, laying off all 500 employees with minimal notice. The $900M raised evaporated. The lesson: cyclical industries require conservative financial planning. Growing aggressively during a boom creates existential risk during the inevitable bust.