Restaurant Owners Uncorked - By Schedulefly

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 c