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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this powerful and deeply moving episode of TheUPside with Theresa Flood, we sit down with powerhouse real estate leader and entrepreneur Sarah Layson of The Layson Group. From running a four-location business and raising two young children, to serving as the primary caregiver for her father in his final months, Sarah opens up about the raw, real, and often unseen side of leadership and loss.
Together, we explore:
Sarah’s unconventional path from Six Flags sales to a multimillion-dollar real estate empire- What it really takes to lead through personal crisis without losing yourself—or your business
- How grief reshapes your values, time, identity, and legacy
- Practical tools for staying grounded: faith, family, discipline, and radical prioritization
- Why success isn’t about the scoreboard, but how you show up when it matters most
This episode isn’t just about real estate or entrepreneurship—it’s about resilience, grace, and the kind of fierce love that shows up every day, even when life is at its hardest.
Whether you’re navigating your own personal storm or simply want to lead with deeper integrity, this is a story you need to hear.
42 episodes
