Kobe Bryant. Alex Gallardo/AP

In case there were ever any doubts about how Kobe Bryant plans to approach his retirement, a recent anecdote from billionaire investor and "Shark Tank" personality Chris Sacca illustrates pretty definitively that it will be with the same obsessive competitiveness that defined his basketball career.

Appearing on Bill Simmons' podcast to discuss a slew of topics, Sacca shared a terrific story about his interactions with Bryant.

Sacca said that a few years back, he reluctantly took a meeting with Bryant because the basketball star wanted to discuss some business ventures and the startup world. Sacca told Simmons that he was skeptical about Bryant not only because he wasn't a basketball fan, but because he had witnessed many professional athletes treat business like tourism, barely dipping their toes into the world and learning how it works.

Not surprisingly, Bryant was slightly different.

From Sacca:

So I said, "Look, if you're serious about this, then prove it to me." I said, "I'm going to send you a bunch of stuff that you should read, a bunch of TED Talks and other videos you should watch, and if you do your homework then I'll talk to you about investing." It was funny because I didn't think he was going to do it. I thought it was kind of a nice way to let him off easy.

Bryant did not balk at the homework assignment:

So, sure enough, for the next few months my phone never stops buzzing in the middle of the night. It's Kobe, reading this article, checking out this tweet, following this guy, diving into this Ted Talk, diving into the Y Combinator Demo Day stuff. And I'm getting these texts, literally two or three in the morning, and my wife is like, "Are you having an affair with Kobe Bryant? What is happening here?"

In the end, Sacca became just as fascinated with Bryant as Bryant was with the world of Silicon Valley:

It was just at all hours, and the guy was serious! He was bringing the same obsessive work ethic to learning about startups that he does to training, to rehab, to his thousand makes a day, to everything. I was fascinated by it. So I ended up becoming really enthralled by him because this is a very unique personality type that I only kind of see in some of our very best entrepreneurs.

Kobe Bryant is currently an untested rookie when it comes to entrepreneurship, but his obsessive competitiveness certainly suggests that he could be in for a prolific career.