November 2025

Hot Dog!

Bill Dempsey retired in 2016 and quickly got bored, recalls Sean. The family soon launched their side hustle, Dempsey’s Proper Hot Dog Co. —a hot dog cart. Proper took on 35-50 events per summer, serving up gourmet viennas. “We almost have a cult-like following,” described Sean. “We do a Hot Dog of the Week (#HDOW) , along with four to five varieties ( Chicago , Coney , Warsaw , and Cincy .—a lot of regionals from different areas.”

With six years of Proper under their belts, Sean says he doesn’t plan on stopping now. “I joke people aren’t going to remember me as the pizza guy,” he said, “they're gonna remember me as the ‘Hot Dog King of South Dakota.’ ”

Check out Dempsey’s Proper Hot Dog Co. mid April through mid August.

LÉ RED BARON

64 | 605MAGAZINE.COM

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