He started out as a Catholic school teacher, started a painting contracting service, and has kept it debt-free by buying equipment and vehicles at liquidation sales as his competitors went out of business. He began investing his profits in real estate and other businesses (I honestly don’t know what they all are). Then in the 2006-2007 real estate crash, he was the only painting contractor left standing, and is now the dominant company in a county larger than the state of Massachusetts, among his other businesses.

The 55-and-older investment properties (think Del Webb’s Sun City developments) cater to the fastest-growing sector of our society, so those houses or duplexes literally stay on the rental market 24 hours before a qualified tenant shows up. Older folks pay their bills on time, and aren’t likely to move often, or at all. He’s in the construction business, so he renovates them at his cost, far below what it costs individual home owners.