During a stretch of heavy layoffs I noticed how many people were moving into rideshare and delivery work, and a friend explained the business of leasing cars for exactly that. We started doing it. Then the manual fleet management started eating every evening.
Workhorse Vehicles is what I built instead. It takes a driver from their first visit to the website all the way to a signed lease with automated weekly autopay: apply, get screened, get approved, sign, pay, collect the car. The happy path needs nobody in the loop.
Underneath it is a quiet orchestra of other people's APIs, each doing exactly one job, Checkr for screening, DocuSign for the lease, Stripe for deposits and weekly billing, Samsara for vehicle tracking. Delinquency workflows, late fees, tolls and violations and full audit trails all run themselves, with every action logged: who, what, when and why. It is the least glamorous system I have built and one of the ones I am most pleased with.
It began as a side hustle renting cars to rideshare and delivery drivers. The business worked; the operations did not. Running it by hand alongside a full-time job was unsustainable, so I built the system that made it manageable, and in one week, because that was the time I had.
Non-payment, handled safely. Taking payments is easy; the hard question is what happens when someone stops. After a grace period the driver gets a notification. If the vehicle is parked when that period expires, it is immobilised and they are notified again, parked only, never in motion, and they can clear it themselves through the driver portal, at which point the system releases the vehicle automatically. I get notified at every step. In the life of the business we have had to use it once.
Live and quietly running the business day to day.