Asking 70 Year Old Billionaires If They Have Any Regrets

Regrets and Satisfaction in Selling a Business

Some business people regret selling their businesses and wonder if it was worth it.
One founder expresses that being in business is about the money and that he was never emotionally attached. He is happy with his decision to sell.
The founder of Kinko’s expresses satisfaction with the success of his business.

“I don’t regret anything. It sounds like Frank Sinatra, as I did it my way, and I have no regrets.”

The speaker reflects on a time when they were solely focused on paying bills and feeling internal pressure.
They describe feeling physically and mentally strained, with sleeping issues and physical discomfort.
The speaker contrasts this with their current state, where they have less stress, better sleep, and improved physical well-being.

“I sleep like a baby and my neck doesn’t hurt.”

The speaker shares that they have no regrets about selling their business.
They explain that the business was growing rapidly, but they lacked the financial knowledge to forecast production requirements.
At a certain point, around $15 million, the speaker recognized the need to find someone who could effectively manage and run the business.

“I got to find somebody who can really take this and run with it because if I hadn’t tried to hold on to it… I would have failed miserably.”

The speaker responds to a question about whether they would have worked less or done anything differently.
They explain that they couldn’t have worked less because the work needed to get done.
While they acknowledge being busy, the overall experience was enjoyable and rewarding.

“I was always busy, my mind never switched off… overall it was really enjoyable.”

The speaker expresses a desire to be remembered as someone who had an interesting life and was the head of their family.
They emphasize the importance of having a warm family and being the leader.

“I want to be remembered for being the head of my family and having a warm family.”

The speaker shares that the most common compliment they receive is about being genuine and real.
They express the desire to be remembered as someone who is authentic and relatable.
The speaker believes that they are doing a good job in that regard.

“The highest compliment that I get… ‘oh my God, you’re so real.’ That, I think, is how I want to be remembered.”

The speaker reflects on what makes a great life and defines success as having adult children who want to spend time with you.
They express that having children who choose to be with you is a measure of true success.

“Success is when your children want to be with you when they’re adults.”

The speaker comments on being called “dad” throughout their life and considers it the coolest thing they have been called.