What is the most foolish thing you’ve done with your money? The first investment I made, at 15, was buying 10 shares of Chrysler. It was trading at $50-something. Later on, when I needed money—I was a father, and I was 19 and got married—I sold it at $10. Good thing it was only $400 I lost. But at the time, $400 was a lot of money to me.

What’s your next move? I need to figure out what I want to do with the rest of my life. Right now, I want to learn to speak Italian and play the piano. If I really want there to be a third career, I’ll make that decision later. I tell my family I’m gonna become a bourbon-swilling, blues-singing, slow-dancing man.

Where are you putting your money these days? A handful of financial companies and homebuilders. Three to five years from now, I think we’ll look back and say, “Can you believe we could have gotten these companies for those prices?”

Making money’s great, but does ­anything match laying a guy out flat? I loved being a linebacker and stopping somebody on third and one. But the reality is that 30 seconds later, you’re going to have to make another hit, and nobody cares that you made the hit the last time. It’s a short-term euphoria. In business, it’s more prolonged.

Are short-sellers really ruining the world? Short-sellers have the right to be short-sellers. But to short blindly and not have to borrow the stock you’re shorting, that might be irresponsible. If they’re doing that with their own money, it’s one thing. But if it’s my money or other people’s money, I want to understand what the leverage is and what the philosophy is.

For a guy from a rough neighborhood in New York, you’ve had quite a run. What’s been your biggest challenge? I grew up with a pretty severe stutter. As a coach, if I had to give a 10-minute presentation, I’d practice for three to four hours in front of the mirror, practicing moving my mouth. I’ve gotten pretty good at it, but to this day, I have this tremendous fear of not being able to speak.

Who’s the best C.E.O. ever? Jack Welch.

The worst? I don’t know. You got anyone you want me to go after?