A Penchant for Entrepreneurship
By Joey lee
The Delta, and all of north Mississippi for that matter, could not wish for a better advocate than it has in the Flatland Development Group, a dynamic enterprise founded and led by visionary entrepreneur, Andy O’Bryan.
O’Bryan’s roots run deep in the Delta soil. Having grown up around Greenwood, his affinity for the area is deeply personal. His journey as an entrepreneur began as he was pursuing his degree at Ole Miss.
Completely unintentionally, he says he fell into his role of being a serial entrepreneur. “I never intended on doing this, it just happened. In my early 20s, I started a company and a larger one looking to enter the market called wanting to buy it. I never start a company with the intention of selling it, but it seems to happen organically.”
With his penchant for entrepreneurship, O’Bryan has embarked on a remarkable journey of founding and nurturing businesses across north Mississippi, primarily in the hospitality industry. His ventures continue to leave an indelible mark on the state’s culinary and entertainment landscape, from restaurants to breweries to luxury cigar lounges and wine boutiques.
The Flatland Group owns six active companies throughout the region. O’Bryan explained that over the past two years, they expanded into consulting. “Universally, restaurants have one of the highest fail rates. So clients come to us to help fix their business. We can consult or we can come in and run it completely for them,” he said.
At this time, they are working with several establishments. Most notable is Giardina’s Restaurant in the Alluvian Hotel. They also oversee the food and beverage service at the Greenwood Country Club.
Flatland is driven by a desire to revitalize forgotten corners of the Delta and foster economic growth. With a focus on Greenwood, O’Bryan hopes to create more investment and development in one of his favorite cities.
“There are certain areas of the state that are receiving a lot of development dollars; unfortunately, the Delta isn’t one of them,” he says. “I feel like the Delta has almost become a forgotten quadrant of the state and there’s such a cool vibe and so much potential here.”
He has two projects moving forward in downtown Greenwood, a restaurant and a cigar lounge. Both will likely begin construction in the next few months. Long-term, Andy hopes to open a blues hall/juke joint in the downtown area, wanting to bring live blues music back to Greenwood.
Plans just outside the Delta include transforming the Yalabusha Brewing Company into a brewpub in Oxford.
Flatland has approximately twelve employees with several management-level positions open. Additionally, the restaurants owned and run by the company employ hundreds more.
O’Bryan says that entrepreneurship is not just a profession but a way of life—one marked by unpredictability, challenges and endless opportunities.
“I like to have a lot of plates spinning. Having a lot of different businesses makes for a life that’s never boring,” he said. “There’s a new challenge for me every day when I wake up. After doing this for 20-plus years, I can say this is what I’m supposed to be doing, this is 100% the life for me.”
Under the leadership of Andy O’Bryan, the company is working to provide opportunities throughout north Mississippi. O’Bryan hopes his development efforts will help lead to a brighter, more prosperous future for the region.
“I’m very proud to be back working in the Mississippi Delta again. I love this place and I’m proud to be working and creating jobs here,” says O’Bryan.