For fans of business and sports, it doesn't get much better than that. The event was hosted by Brandon Steiner and produced by his well-known sports memorabilia company, Steiner Sports.
While Cuban, the business titan, and Jeter, the baseball legend, come from different industries (though Cuban does own the Dallas Mavericks basketball team) the men were in agreement on a number of things. Namely, the idea that, to be successful in business, you have to be hungry, passionate and willing to work your ass off to accomplish your goals.
Here are some highlights from the discussion:
Get up and hustle.
Steiner asked Cuban about what it takes to be a success. "Find something you love, be great at it," Cuban said. "No one quits something they're good at."
In true, profanity-laden Cuban fashion, he expanded on what it takes to eat and sleep your business, and get your hustle on:
Crush the competition.
Being the professional athlete, you might think Jeter would be the first to speak up about competition and doing everything it takes to win. Not when he's in the room with Cuban, who is notorious for his opinions about dominating in business.
"Business is the ultimate sport," Cuban said. "Unlike sports, you often don't even know who your competitors are. ... Your character is really tested when you're challenged ... when someone is chasing you, when someone's fighting you.
"You come into my industry, I'm gonna kick your ass," Cuban added. Of course.
Be prepared and be willing to do the hard work.
To launch a business and take on your competitors, entrepreneurs need to do everything it takes to be prepared. On the field and off, Jeter said his biggest fear is not being prepared.
"Just because you want it doesnt mean it's going to happen," Cuban said. "You always need to learn. You need to do the work. ... The minute you slow down, someone will pass you by."
Be passionate about what you do.
Keep your team motivated.
Not every one of your employees will share all the same passions as you. The trick is twofold: Hire people who are passionate and driven, then have a mutual understanding -- for each individual -- about what each of you wants to accomplish, Cuban said.
"It takes time to get to know the people you lead," Jeter said. "Treat everyone fairly, but you have to get to know everyone separately. Its about the right chemistry."
"I'm close with my family," Jeter said. "Even at this age, I still never want to do anything to disappoint my family."