In his early 20s, Rich Kleiman was a college dropout running an illegal sports gambling operation in New York City with more than 100 clients. It wasn't glamorous, and didn't earn Kleiman much money--but it taught him how to network.

That skill helped him become a high-flying, celebrity-representing executive who left a cushy vice president job at rapper Jay-Z's entertainment agency Roc Nation, to co-found VC firm Thirty Five Ventures with NBA superstar Kevin Durant in 2017.

"I got a little complacent," says Kleiman about his time at Roc Nation. While he was making a good salary and partying with celebrities he'd "always dreamed about being around," he wanted to build something of his own. "I started to understand the difference between being entrepreneurial and doing work, and starting something." 

Breaking out of that complacency, walking away from a high-powered job, starting a new career, and launching a new venture takes courage and self-evaluation. That's one of the key takeaways from this week's episode of Inc.'s What I Know podcast, featuring Kleiman. 

Listen for this and more in the player below, or wherever you get your podcasts. And please subscribe to What I Know, our new podcast in which entrepreneurs and visionaries recount how they've gotten where they are--and what they've discovered that has helped them along the way.