#126

Josh, Mike, and Matt sits down with Keith Benjamin, nightlife operator and co-founder behind Uptown Social, Share House, Bodega, By The Way, and The Waverly, for a conversation about betting big, building brands, and turning hospitality into a true long game. Keith shares how his journey started with Penn State tailgates, fraternity social life, and bartending in New York before evolving into ownership in iconic Manhattan watering holes like Stumble Inn and Hair of the Dog. From there, he opens up about the leap to Charleston, why he saw an opening in the market, and how Uptown Social became the kind of unicorn venue most operators only dream about.

The conversation then shifts into the realities of nightlife economics, including the now-infamous $9 Modelo debate, how serious operators actually think about pricing, and why beverage-first businesses can be so attractive compared to labor-heavy food concepts. Keith, Josh, Matthew, and Michael dig into frequency, guest behavior, hospitality, and the brutal cost structure of modern restaurants, all while reflecting on what makes certain places worth returning to. Along the way, Keith talks about entrepreneurship, ADHD, risk-taking, and the compulsion to keep building, offering a clear look at the mindset behind one of Charleston’s most successful hospitality operators.

Links and resources 📌

Visit meez: https://www.getmeez.com

Follow meez on Instagram: https://www.instagram.com/getmeez

Follow Josh on Instagram: https://www.instagram.com/joshlsharkey/?hl=en

Follow Josh on LinkedIn: https://www.linkedin.com/in/joshua-sharkey-406965b/

Follow Keith on LinkedIn: https://www.linkedin.com/in/keith-benjamin-4bba57396/

Follow Keith: @keithbenjamin

Follow Bodega on Instagram: @eatdrinkbodega

Follow Uptown Hospitality Group on Instagram: @uptownhospitalityevents

Follow Michael: @michaeljacober

Follow Matthew: @conbeazie

Timestamps

03:13 Michael Jacober Introduces One Of His Oldest Friends

05:37 From Penn State Tailgates To Bartending In New York

10:03 The Stumble Inn Era, Golden Handcuffs, And First Ownership

16:39 Why Keith Left New York And Bet On Charleston

19:44 Opening Uptown Social And Building A Nightlife Unicorn

23:41 Bodega, Share House, By The Way, And The Waverly

30:10 The $9 Modelo Debate And The True Cost Of Doing Business

54:22 Beverage-First Concepts, Margins, And Why Frequency Matters

01:14:06 Why Hospitality Economics Are Reaching A Tipping Point