His insurance won’t cover him in an accident
Are you sure he hasn’t taken the proper precautions of just getting commercial insurance and filing taxes 4x a year (assuming US based)? Like yeah, you shouldn’t just go get in your car and go to a bar and offer people rides for money but if this guy has regular customers I wouldn’t be surprised if he also knows how to look into his own rights
I mean, I would assume that someone who doesn’t get a new enough car doesn’t have enough money to pay for commercial insurance. Also offering people rides on the street is a bad idea (because you can get robbed) and possibly illegal. This is just running an unlicensed taxi service. Gypsy cabs have been around for hundreds of years. It’s not a good idea.