If you own a business for 15 years, and sell it for a $50k profit, then whether or not it was profitable (as an investment), will depend on the cumulative gains or loses over the 15 years of ownership. As long as the losses amount to less than the $50k profit on selling, it WAS a profitable "investment"...whether or not it was a profitable "business" depends on what you expected to get out of it. If a profitable business to you, is one that makes money every year...then it probably wasn't. If a profitable business to you is one where the good years more than make up for the thin years, then it probably was. Using this framework...I think the NBA owners are pretty much all holding teams that would be good "investments" if they were to sell them.