He did well off real estate during his life.
He also believes in long term investments. Never chasing stocks that are on the rise. He’s been saying for about a decade the market is to expensive right now. The average total market value to GDP of the U.S. averages out to 85%. Then he plays the market like counting cards. When the market value is below that 85% he buys long term investments. When it’s above, he sits on his current investments and rides them unless he is forced to make a move.
So what you will see is in 2012, we were below market average, so he advised people to be making purchases/investments. Especially since the housing market collapsed in 2008 and people were running out of ways to pay their mortgage so they were foreclosing left and right.