In this episode, DePriest shares how generational expectations shaped his early career path, why he eventually walked away from corporate success, and how he found purpose in nonprofit leadership. From the weight of bad advice to the freedom of finding your “why,” this conversation is about more than just work—it’s about redefining what success really means.

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Honestly seems like sage advice. But it was the worst Stephen Ochs, founder of Fetch, ever got. Listen to his story. 

Sean and JB talk about why we're making a podcast in the first place, what we've learned so far and what we can look forward to this season on The Worst Advice I Ever Got.

After a very successful college track and field career, Matt Hemingway decided he was going to try to make the olympic team. It didn't happen the first time and then it didn't happen the second time. Now 10 years later, he decides he's going to try for a third time. Anyone who knew anything about the sport told him "you're too old to make an olympic team." That turned out to be the worst advice he's ever got.

When your father only gives you one piece of advice your whole life at the age of 10, thats apt to stick with you. It made Ryan a two time olympic skiier, the president of a private equity firm at 32 and a multi-milllionaire by 40. But on a flight back from Orlando before his 41st birthday, he realized that was the worst advice he ever got. 

When Paul was starting out in advertising, it was the golden age of analytic data so he was told that when it comes to selling a product or service, "brand doesn't matter." He believed it, and worked for 20 years pushing that data is the only thing that matters to sell your audience. After some pretty big changes in his life, he realized, that was the worst advice he's ever got. 

When Jon was told to join the military, he thought that would be a spring board to where he really wanted to be. Turns out, that was the worst advice he ever got.

When her professor told her "you're not cut out for business" after her very first test in college, Claudia took it to heart. How does hearing something like that effect someone's career path?

King Of Pops Co-Founder Steve Carse created a wildly successful pop brand. But when it was time to exand, he was told that frnchising would mean he would lose what was special about his brand. That was the worst advice he's ever got. 

When a reporter asked him how it felt not to have to worry about money anymore after winning the FedeX Cup in 2011, Bill Haas didn't know how to answer that question. And now that he thinks about it, that was the worst advice he's ever got.