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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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The Outer Banks market is shifting—so how do you stay ahead? In this episode, Randy sits down with returning guest Jonathan St. Ledger, an investor, developer, and builder, to unpack what's really happening with rentals, construction, and investment opportunities in 2025.
Jonathan shares how he balances buying and selling in today's climate, why tax benefits like bonus depreciation matter more than ever, and the creative ways he adds serious value to his properties (rooftop pools and dive-in movie theaters, anyone?).
Key takeaways include:
- Why short-term rental demand is evolving, not disappearing
- How to leverage tax incentives for smarter investing
- The little details that turn a rental into an experience
If you're curious about the future of real estate on the Outer Banks—or just love hearing how creative investments come to life—this conversation will inspire you to think bigger and smarter.
42 episodes
