[Warren Buffet says private equity is a scam. So many stories of struggling chains going Chapter 11 soon after going private due to high debt repayment. Only the suits and lawyers make out in the deals.]
Running money is like doing one night stands. Running a company is like getting married. This mindsets and skills required are very different.
I think he bought K-Mart and Sears for the real estate, but by the time he ran the stores into the ground as planned, the commercial real estate market went bust and he was left holding too much worthless property.