The Worst Advice I Ever Got

Jeff Hilimire was told to “dream big.” Sounds like great advice—until it nearly burned him out.

In this episode, Jeff shares how chasing massive goals led to overextension, failed ventures, and a lesson he now lives by: dream small. Focus on what matters. Build with purpose. And grow from there.

From launching startups to founding 48in48, Jeff’s story is a masterclass in scaling back to move forward.

In this episode of The Worst Advice I Ever Got, Jamie shares why traditional business plans can be a trap for creative entrepreneurs. From freelance life to launching multiple ventures, he talks about embracing uncertainty, staying agile, and why “figuring it out as you go” isn’t failure—it’s freedom.

Whether you’re a planner, a dreamer, or somewhere in between, this episode will make you rethink the way you start something new.

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In this episode, Anita shares how she rebuilt her business with a minimalist mindset—focusing on fewer, high-value clients instead of chasing constant growth. We talk about the cost of hustle culture, the power of clarity, and how success looks different when you're actually enjoying the life you're building.

In this episode of The Worst Advice I Ever Got, Evren shares how achieving the kind of success most people dream about left him feeling empty, addicted, and disconnected from what really mattered. It took one powerful moment with his son to change his life—and inspire a journey toward real meaning.

From corporate highs to completing a 100-mile ultra-marathon in the mountains of Turkey, Evren’s story is a lesson in what happens when we stop outsourcing happiness and start living with intention.

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.