Back in the early 2000s I remember reading an interview with Ted Turner, who founded CNN and later sold it. He wasn’t happy with how it was being run so the reporter asked him why he didn’t buy it back.
He explained that he had only a few billion dollars, which meant he wasn’t “in the game” anymore. People mocked him for it, since to a normal person that’s more money than they could ever use, but he was right. He had sold, and now he couldn’t re-buy; prices for key assets like CNN had gone up.