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Entrepreneurs: What Was the Biggest Risk You Took and Did it Pay Off or Not?

Entrepreneurs: What Was the Biggest Risk You Took and Did it Pay Off or Not?

Update: 2025-07-22
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What does it really take to break away from the expected path and build something extraordinary? In this segment of "Your New Business Journey" on Passage to Profit Show, three entrepreneurs reveal the biggest gambles they took to chase their visions—from launching a tech radio show with zero experience, to ditching college and crossing continents to pursue a beauty empire, to failing multiple times before finally hitting entrepreneurial gold. Their stories are raw, unexpected, and full of the kind of insight you won’t find in a business book.


 


Richard Gearhart and Elizabeth Gearhart, co-hosts of Passage to Profit Show have this discussion with podcasting and digital media expert Rob Greenlee, global beauty specialist Tania Crawford and Michael Tomao from Service Level Advisors.


 


Whether you're a seasoned entrepreneur, a startup, an inventor, an innovator, a small business or just starting your entrepreneurial journey, tune into Passage to Profit Show for compelling discussions, real-life examples, and expert advice on entrepreneurship, intellectual property, trademarks and more. Visit https://passagetoprofitshow.com/ for the latest updates and episodes.

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Entrepreneurs: What Was the Biggest Risk You Took and Did it Pay Off or Not?

Entrepreneurs: What Was the Biggest Risk You Took and Did it Pay Off or Not?

Richard and Elizabeth Gearhart