In this episode of Unconventional Wisdom About Conventional Wisdom, host Kim Miller-Hershon sits down with serial entrepreneur and real estate leader Betsy Pepine to unpack what it really means to chart your own path—and why breaking the mold can lead to your most authentic success.
From walking away from a preordained path in medicine to launching a multifaceted real estate empire, Betsy shares candid stories of risk, reinvention, and the mindset shifts that fueled her growth. We dive into the unexpected loneliness of leadership, how to turn failure into feedback, and why building meaningful relationships—not just making sales—is the true key to business longevity.


Along the way, you'll hear about:
How Betsy pivoted from pharma to real estate at age 37
The myth of “safe” careers—and what true security really means
Why authenticity and ownership matter more than having all the answers
A fresh perspective on service-driven sales
The value of asking: “How can I make this right?” or “What could I have done better?”


Plus, Betsy opens up about writing her first book, Breaking Boxes, and the imposter syndrome that came with it—offering a vulnerable and inspiring reminder that growth comes from stepping into the unknown.
If you're tired of conventional paths and ready to embrace your own version of success, this episode is for you.
🎧 Listen, subscribe, and leave a review to help others discover the power of unconventional thinking.
📘 Get Betsy’s book Breaking Boxes and learn more at: https://www.betsypepine.com/
📱 Follow Betsy on social: @BetsyPepine
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