...I should have taken my poker winnings at the time and invested in his company Winmark.
Wow!! You sure should have. I looked at their financial reports and revenue didn't grow much over the last 3 years but profits really surged. I don't know what they did, don't understand their business, but impressive.
I once saw profit genius in action: I worked for a geophysical firm that did seismic surveys. Big crews, lots of capital equipment. Downtime was horrendously expensive. When a slowdown happened in the oil industry, all seismic companies took a very big hit that broke half of them.
But at Western Geophysical, the CEO decided to keep the crews working, collecting a vast library of seismic data. Then instead of it being the property of, say, Exxon, we sold it for less money non-exclusively. So we could sell it to Exxon for half of what they would normally pay, and in exchange they'd let us also sell it to Shell, Conoco, BP, etc. It would take two sales for us to make what we had made with one.
The thing is we averaged selling it 12 times for most surveys and printed money. It was embarrassing how much money we made while everyone else was laying off and folding. It was genius and guts in action.