yeah, for people like that, money is just a way to measure how much smarter/slicker they are than their mark. it’s really about the grift. that $100k invested well in the 80s would have been an enormous portfolio in 30 years had he just been interested in a living.
Average house price in 1983 in the US was $62k. Assuming he's in a lower col area, and isn't going top of the market, he could have bought 2-3 houses outright, or put down payments on a solid 10 homes. Then renting them out and paying mortgages, that would be very lucrative.
Assuming he did his "invest in houses" plan as he said.