The educators who bought a bar business

By day, Sean Connor is a guidance director at Cooper River Center for Advanced Studies, where he helps students Plan, Prepare, and Pursue their next moves, whether it’s college, military, or joining the workforce. But on the weekends, he and his wife, Cassie, who is also in the education system, are running a mobile bar business, Charleston Cheers, pouring drinks and creating “good times” for events around town.

From cheers to career counseling

I moved here from New York in 2006 to open a sports pub, Mad River Bar & Grille. I transitioned out of the restaurant business in 2010 to go back to school. I obtained my Master’s in School Counseling from The Citadel.

On starting a business

I’ve always been a worker bee. Back in 2012, I was a school counselor, and I wanted to do something different to earn extra money. I saw a wood-fired oven trailer back in New York and thought it was a great idea, so my partner and I started a mobile pizza business, Towin’ the Dough. We quickly realized there was a big need for food trucks for weddings, and the business exploded. We were doing two to four weddings a month.

On making a hard choice

The decision to close Towin’ the Dough was the opposite reason you see businesses closing. We closed because we were too busy. My son, Sammy, was 11 and getting into travel baseball. The weddings were on the weekends—the same time as his tournaments. I was missing too many games. I realized that if we kept going, I was going to blink, and that amazing time of a family’s life was going to be gone.

On the perfect partnership

In 2021, I met Dave, the owner of Charleston Cheers and we hit it off. I was able to see how he was able to grow Charleston Cheers, and see the process of wedding bartending out of a beautifully restored donkey trailer.

On taking the leap

Cassie and I had been talking to Dave for a while about eventually taking over the business, but we thought it was a couple of years away. About a month ago, he was ready to transition it to us fully, but he still wanted to be involved, so we hired him as our ‘Chief Good Times Operator.’ He handles all the contracts and initial communications, which allows us to be quick in our responses to potential clients. With Cassie and me in education full time, we’ve assembled an amazing bar staff over the years that keeps Charleston Cheers rolling smoothly.

The vision for Charleston Cheers

The big thing for us right now is making more meaningful connections with the amazing vendors here in Charleston. We’ve worked with many of them before as bartenders, but now that we’re owners, we need to build those deeper relationships with wedding planners, venue managers, florists, and caterers. Our goal is for them to feel comfortable recommending us as a premier bar service. As for the big picture, we’re not trying to do this full-time. We love working in schools—that’s our passion. We’d like to continue running Charleston Cheers and eventually pass it on to our kids when they are old enough to take it over.

The best tip

My best life tip was from my cousin, a math teacher at my high school. He saw I was hanging with some kids that didn’t have the greatest reputations, and he would constantly pull me aside and tell me to ‘make good decisions.’ I try to live by that and stress it to my own kids and students. The same goes for the business. As an entrepreneur, you have to be prepared to work hard.

Fast Facts
Ages: Sean is 46, and Cassie is 45.
Status: Married with two kids, Sammy (14) and Amelia (10).
Hometowns: Sean is from New York, and Cassie is from Connecticut.
Favorite drink: A Paloma.
Favorite restaurants: Basil and EVOO in Park Circle, Coast Bar and Grille, Hugh Baby’s, and Lewis BBQ.
Hobbies: Watching what our kids love to do – Amelia is a Level 3 Acro and Tumbler and Sammy played Varsity Baseball as an 8th grader last year.
Website: charlestoncheers.com