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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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Ever wondered what it’s like to run a private club inside one of the most iconic hospitality brands in the world?
In this episode of The Private Club Radio Show, we go behind the scenes with Kevin O’Brien, General Manager of Hershey Country Club, to explore what it takes to lead a club that sits at the intersection of tradition, luxury, and the sweetest brand in America.
With over 13 years at Hershey Entertainment & Resorts, Kevin brings a rare perspective on:
- Leading a private club within a corporate hospitality structure
- Building a culture of internal growth and leadership development
- Balancing guest experience across resort and member expectations
- Managing multiple outlets, teams, and operations under one vision
- What makes the Hershey model unique — and what other clubs can learn from it
From food and beverage to full club operations, Kevin’s journey is a masterclass in consistency, adaptability, and sweet leadership.
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Chapters
1. Welcome And Episode Setup (00:00:00)
2. Meet Kevin O’Brien And Hershey CC (00:00:30)
3. The Hershey Ecosystem Explained (00:02:26)
4. Career Path Inside Hershey (00:06:16)
5. Operating Lessons From F&B To Parks (00:12:32)
6. Pace, Continuity, And Club Relationships (00:18:27)
7. Corporate-Owned Club And Courses (00:24:05)
8. Legacy, Founders Day, And Culture (00:27:55)
9. Human-Centered Leadership Habits (00:31:10)
10. Snowstorm Banquet And Two Left Shoes (00:37:15)
11. Brand Quirks, Chocolate Martinis, Requests (00:42:05)
12. Stadium Radio Mishap With Steve McNair (00:48:25)
13. Networking, Mentors, And Closing (00:53:20)
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