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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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Some management companies build hotels. Olympia Hospitality builds identity.
I spoke with Sara Masterson (President) and John Schultzel (Chief Growth Officer) about how Olympia blends independent spirit, strong brand partnerships, and mission-driven hospitality across destinations like Nantucket, Boston, Winter Park, the White Mountains, and beyond.
On #NoVacancyNews, Sara and John explain how they combine boutique creativity with brand-backed consistency, how they think about technology adoption, and why community connection is becoming the core differentiator in both luxury and branded hotels.
A big thanks to Actabl — Actabl gives you the power to profit. Visit Actabl.com.
What we cover:🏨 How Olympia mixes brand standards with independent personality 🌎 Why "place-based design" beats cookie-cutter hotel experiences 🎨 How to create a hotel that could only exist in one community ⚙️ Why fast-moving tech adoption matters more for younger teams 📈 How owners think about character, authenticity, and long-term performance ❤️ The Alfond Inn and Boone Tavern: hotels that literally fund education 💡 Why short-term bumps shouldn't scare hoteliers from long-term vision
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