Keith Benjamin

Charleston, SC is one of my favorite cities. It has so much charm, liveliness, and an amazing selection of restaurants and bars. If you’re a foodie like myself, Charleston is one of the best cities to eat and drink in (in my opinion). So, when my cousin told me he was friends with the owner of one of my favorite spots to visit, Uptown Social, I knew I had to hear more about the guy behind the awesome business. He also happens to be from the northeast, starting his career in the Big Apple! So, let’s meet Keith Benjamin, learn more about his entrepreneurial path, and how he created three of the most popular spots in Charleston, SC.

---

Tell us about yourself, your background and how it got you to where you are today.
I graduated from Penn State with a broadcast journalism degree in the spring of 2006 with no real idea of what I wanted to do for a living.  I was living with my mom in North Jersey about 20 minutes away from NYC and knew I needed to do everything in my power to earn enough money to live on my own in the Big Apple!  I quickly picked up a  job as a barback at Off the Wagon in Greenwich Village and by the end of the summer I was bartending full time.  I was absolutely hooked right from the start! 

Graduating from a big school like Penn State, throwing parties was practically in my DNA.  My parents met when my dad was bartending and my mom was serving; I like to think I was destined to be doing what I am today.  After 2 years at Off the Wagon, I moved up to the Upper East Side to help Eat, Drink, and be Merry Hospitality open The Stumble Inn as one of the opening bartenders.  Shortly thereafter, I was asked to manage and by the beginning of 2011, I was a small partner in The Stumble Inn!  It was right around that time that we signed a lease for Hair of the Dog on the Lower East Side where I got my first big shot to run a location as one of the lead partners on my own.  Hair of the Dog came on to the scene in October of 2012 as one of the hottest spots in New York City and we haven’t looked back since.

After about 4 years running Hair of the Dog, I got the itch to move out of the city and open something bigger in Charleston, South Carolina.  I took a trip with my partners in April of 2016 and it was at that point that we laid our eyes on the building that is now Uptown Social for the very first time.  We had a letter of intent signed a week after we saw the space and opened for business exactly 2 years later!  

What are your businesses and how did the idea for each of them come about?
We opened Uptown Social on April 6, 2018 after pounding the pavement all around Charleston for the previous 2 years.  It was my goal to ingratiate myself in the community and get to know as many people as I could.  I knew that there would be a huge learning curve coming from NYC and really wanted to learn from the locals that had built Charleston into the hospitality mecca that it is today.  When we opened in April of 2018, I felt like the work we put in yielded great results and we were fortunate enough to be super busy right from day 1!  Uptown (as it is now known by the locals) has become an institution of sorts in CHS.  We are a 10,000 square foot entertainment complex serving Jersey style bar pizzas, featuring an unbelievable social media moment with our “Social Butterfly” on the rooftop, and some of the best DJ’s and bands anywhere in the entire nation.  Uptown Social truly provides something for everyone.  

Right before the pandemic hit, we put our heads together to figure out what might be our next step in terms of expansion.  We looked at an old train depot (dating back to 1849) formerly known as Camden Depot and knew we found our next spot…actually next 2 spots!  23 Ann Street, only 5 blocks south of Uptown Social, is now the home of Share House and Bodega!  We launched Bodega as a pop-up out of Uptown Social during the pandemic to help build the brand and grow awareness for our “New York Style” sandwiches that are a sight to be seen on every level!  We always say 1 sandwich can feed 2 people, maybe even 3!  The pop up was a huge success allowing us to feel confident in our next step of opening a brick and mortar location.  Bodega takes up ⅓ of the old train depot with Share House taking up the rest of the railroad style building.

Share House has Uptown vibes in some ways while really leaning into our coastal location geographically.  We’ve got all sorts of bright/energetic IG moments throughout the space with some of the best bites in town courtesy of Executive Chef/Partner Alec Gropman who heads up the kitchens for all 3 concepts.  A customer may stop by for a bite and our famous Orange Crush cocktail only to end up staying for a raucous night of dancing!  Having opened Share House and Bodega in February of 2022, I couldn’t be more proud of where we are only 7 months later!

Who or what was your biggest influence in becoming an entrepreneur?
I always kind of beat to my own drum growing up.  I didn’t have many “real jobs” or internships in college and instead worked as a camp counselor for 7 summers until I graduated from Penn State.  Many of my parents’ friends would ask them why they didn’t force me to get an internship and they always responded with “we need to let Keith be Keith, he’ll find his way!”  I credit my parents for always pushing me to be my best but never pushing me to do anything I didn’t want to do.  It is that freedom and encouragement that allowed me to grow into the entrepreneur that I am today.

What motivates you and helps you generate new ideas?
Being the best motivates me, period.  Nike came out with a Kobe Bryant commercial a little while back with Kobe quoted over and over saying “just be better.”  I hold on to this mantra each and every day.  No matter how much success any of us have, there is always room for improvement.  I challenge myself and my team to constantly think outside the box and to push ourselves in ways we never thought possible.  

I’ve also had similar moments with my mom who has been fighting pancreatic cancer over the past year.  She has seen Share House and Bodega under construction but not since we opened due to her compromised immune system.  I know how proud she is from afar and I can’t wait for her to see it all in action.

What advice do you have for young entrepreneurs? 
Roll up your sleeves, roll the dice, and take chances.  No successful entrepreneur has ever taken the safe way out.  You need to be aggressive in every way and have faith in yourself and your vision.  It won’t come easy but if you stick with it, your time will come!

What is next? Where do you see yourself and your business in 10 years?
I see our business growing in the next 10 years in a way that our group could have never imagined.  I see us dreaming up new concepts while also growing the brands we have already established over the past 5 years.  I see us opening in new cities and rewarding many of our managers by making them partners and allowing them to grow the same way I have.  I strongly believe in paying it forward and rewarding those that bust their butts to grow the business.  More than anything, I can’t wait to raise my family (soon to be 2 kids under 18 months) and share all of the great things in life with my wife Stevie.