I have to be optimistic. Otherwise I'll stop. And I think that when you're doing this kind of job, you have to keep yourself optimistic. You always have to find openings and entry points and try to see what you can work with and where you can create some opportunity to have a conversation that results in some concrete outcome.

Discretion and good cheer.

Their responsibility to the friendship.

Being able to share a confidence.

I’ll get half way through a book and then jump to another.

I create offbeat advice; I don't follow it. I rarely take third-party advice on my investments.

The Guinness Book of Records credits Cuban with the "largest single e-commerce transaction" after purchasing a Gulfstream V jet for $40 million over the internet in October 1999.

I try to find leverage points. Sure, I give to charities and those in need. But for me, I try to help people create and grow their companies, and build a future for people. The hope is that they can become self-sustaining and grow to be a pillar of their community. That’s what I love to do and think has the most impact.

I was never a big risk taker. When I started my first businesses, I really had nothing to lose. I was sleeping on the floor. I had five roommates in a three-bedroom apartment. My car was a junker. I had absolutely nothing to lose when I started MicroSolutions, so it really was never a risk.

Winning, absorbing the journey and the destination. When all of it comes together, whether it’s something you started or took over, you get to look at yourself and everyone around you.