In 1962, future Pulitzer Prize–winning author Alex Haley sat down with jazz musician Miles Davis for what would become an institution of American journalism—the Playboy Interview. To celebrate the Interview’s 50th anniversary, Playboy has culled 50 of its most (in)famous Interviews and will publish them over the course of 50 weekdays (from September 4, 2012 to November 12, 2012) via Amazon’s Kindle Direct platform. Here, a glimpse at our conversation with business magnate Mark Cuban from the January 2006 issue.

“All the rules, the conventional wisdom, all the things that people said had to be done a certain way, I would test. Every chance I had and everyplace I went, I would put a toe in the water to see if those things were real. It taught me that just because something is the way everybody says it’s supposed to be doesn’t mean it shouldn’t be questioned. More often than not, something is there, but most people simply take the path of least resistance.”

“In any business you should have an understanding of what your optimal productivity is. In sales and marketing, in everything down to customer satisfaction and how fast tickets are processed and hot dogs are served, optimal productivity should be your goal. You need to figure out how close to your goal you can get this season if you work your ass off and everyone does his job. Those are called your benchmarks. In most businesses, if you exceed your benchmarks, you get rewarded. If you come close, you keep your job. If you fail, you’re gone.”

“A mutual friend suggested Trump invite me to his office to talk about Internet stuff. I went. It was a normal business meeting, uneventful except for one thing. Now, I figure the over under on office pictures of yourself and your family is four or five. In his office, every inch of every wall was covered with pictures of himself. And I’m like, Note to self: If you ever make it big, don’t ever be like this.

After the TV show was canceled, Trump sent me a letter, which I framed, by the way. It says, ‘I told you, you never should have done the show. I could have told you it would fail.’ Totally low-rent, right? But I had pissed him off by saying in one of the show’s promos that I could write a bigger check than Donald Trump and not know it was missing. He threatened to sue me. The point was not net worth but cash. Most of my money’s in cash. If everything comes crashing down, I have cash. I have no debt. I told my lawyer, ‘Let’s pray to God he does sue,’ because how much fun would that be? He would have to disclose everything. It was ‘I’ll show you mine; you show me yours.’”

To read the interview in its entirety on your Kindle App, Kindle Fire or Kindle Touch, click below.

*Or read the interview with access to all Playboy interviews on iPlayboy.*