A married 66 year-old with three children owned a $25 million oil and gas company and was looking to get top dollar when he sold sometime within the next 5-10 years. The company was structured as a C Corporation, and he didn’t realize there was a high likelihood of paying double tax on the sale. He also had no idea how much money he would need after-tax to maintain his current lifestyle for the rest of his and his wife’s lives.