He owned and operated a convenience store. Hated it. Sold it for a premium, found some other properties, and bought some (via loans, so he has debt). Over time, he took the cash flow and rolled it into new loans and bought more properties, etc.
He loves the shuttle job and makes good money— I tipped him well, for example.
I ended up grilling him about his commercial properties and how he did it, and it checks out. I know the town where he operates pretty well, and a familiar enough with the business he’s in to see that he knew his stuff.
He hates the single family homes. Way more hassle. So, he’s looking to exit that. The commercial properties are net leases with pretty long lease periods. No hassle at all: just cash flow.
He’s got a convenience store, a restaurant, a church, a strip mall, and I forget what else.
Anyway, I know a handful of people like him who are for a fact millionaires, with lots of cash flowing businesses (such as storage units) but who still hold down jobs that might surprise you.
¯\_(ツ)_/¯