That's what my brother used to do. And ever since his car passed the threshold for being "too old" by Uber's standards it's actually made things easier. He goes to bars near closing time and offers people rides so they don't have to take an Uber since he can charge less and still make more money than he ever did with Uber. It's gotten to the point that he has regular customers to keep him busy almost year round.
I wasn't saying it was a good idea. But being broke as shit your entire life kinda shifts your standards of what's a good idea or not when you're just trying to get food on the table.
Also, he still has his CDL and pays extra for the right insurance.
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
Uber's insurance is pretty bad. Many get the additional coverage from their regular insurer anyway because of this. That coverage also (usually) applies to this situation as well.
Dude tried doing that at the Dallas airport recently as well. I do believe they should be getting a larger cut but it's sketchy as hell to not have anything backing the ride.