Episode 634: On Our Shoulders: Carrying a Community Through Hospitality with Uptown Hospitality Owner Keith Benjamin

Keith Benjamin, co-founder of Uptown Hospitality Group in Charleston, tells the story of how throwing massive Penn State tailgates set him on a 20-year path from NYC bartender to operator of six concepts—while raising three kids under five. After buying small equity stakes in New York bars and becoming an operating partner at 29, he felt pulled to Charleston and went all-in on a $5M buildout of Uptown Social, a 10,000 sq. ft. sports bar and nightlife hub inside a 1915 building. He recalls surviving COVID—shutting down 48 hours after his wedding—then creating Bodega, a New York-style breakfast sandwich brand that grew from a parking-lot pop-up to multiple locations. Uptown Hospitality later added Share House, the upscale tavern By the Way (with partners from Southern Charm), and The Waverly, a wedding venue. Through rapid growth, thin margins, seasonality, and crushing liquor liability laws, Keith stays centered on preparation, service, and his belief that restaurants and bars are the emotional backbone of a community—and that operators carry that responsibility on their shoulders.

10 Takeaways

1. Hospitality people “run into the fire.”
   You’re either wired for the chaos and unpredictability of restaurant ownership or it will spit you out.
   
   
2. Preparation beats the playbook.
   Every shift changes at minute one; the only constant is how ready your team is for the unexpected.
   
   
3. Tailgates were the training ground.
   Running $40K-per-season Penn State tailgates taught Keith energy management, leadership, and crowd control.
   
   
4. From golden handcuffs to ownership.
   High-earning NYC bartending could have trapped him, but he insisted on a path to management and equity.
   
   
5. Charleston was the “chips all in” leap.
   With no collateral, Keith borrowed from friends and family to take on a 25-year lease and rebuild a 1915 building.
   
   
6. COVID nearly crushed the dream—but sparked Bodega.
   Forced shutdowns led to launching a breakfast-sandwich concept that quickly exploded in popularity.
   
   
7. Growth exposed growing pains.
   Opening multiple concepts while having three young kids humbled him and revealed how thin the margins can be.
   
   
8. Food-heavy concepts are a different math.
   Booze-driven venues thrive; a full-service breakfast-and-lunch model did not, leading to a fast pivot to QSR.
   
   
9. Liquor liability laws threaten the industry.
   South Carolina’s rules once assigned 100% blame to anyone who served one drink to someone later in a wreck, pushing insurance premiums into the stratosphere.
   
   
10. Service and community are the lasting moats.
    With heavy competition and rising closures, the only real differentiator is how you make people feel—because restaurants are the heart of every community.