Roger Sherman, Pitmaster and Owner of The District Pit

Alfred Duncan

Roger Sherman’s reputation as a grill master is growing.

Not only was he cooking turkeys for family members during the holidays, Sherman was starting to pick up business from the friends of those family members as well.

The first time that someone asked the Washington, D.C.-based Pitmaster if he catered, Sherman enthusiastically shouted an optimistic “yes” before he could say a realistic “no”.

“Even though we didn’t cater at the time I figured we could. At the time I really didn’t know what I was getting myself into, but I was willing to give it a shot,” said Sherman, the first-place winner of the second Black Men’s Ventures Black Founders Pitch Competition.

“One day, a friend of mine had a need. He asked me to cater for 100 people. It sounded daunting but I thought I was up to the challenge. That was actually five years ago this week. It took us 20 hours to cook three meats and three sides. We were up the entire night. I was pretty sure my wife was going to ask for a divorce at the end of that. I got lucky and she opted to say.”

Sherman, who now can cook for 100 people in his sleep, had a simple business strategy: make a plate so delicious that he would leave each catering job with his next catering date booked.

“If you’re lucky, every event you do someone else will ask you do to an event,” Sherman said. “That gets you to the next one. Before we knew it, we were doing a catering event a month. After that, two catering events a month. It just kind of grew slowly over time.”

Sherman is average height, and his early morning workout routine has helped him retain much of his wrestling physique. He started grappling as a youth and continued to complete up until the start of the pandemic when he finally hung up his shoes.

His scalp is cleanly shaven, and only remnants are left from his full-length beard. It was a casualty of the global pandemic. With a pediatrician for a mom, his mask had to fit his face just perfectly or face her scorn.

Much like his beard, his catering business was brought to a halt by the global pandemic. The District Pit’s Pitmaster switched strategies to compensate.

“Serving customers outside of catering events was not something that we did prior to the pandemic,” Sherman said. “When the pandemic started in March of 2020 we had events signed all the way through June. All of that was canceled. Believe me when I say that was devastating. We were faced with an option. Do nothing, or do something. We opted to do something. We were forced to try a new business model and started selling individual plates. Not something I thought I’d ever do, but It worked. We would put out an offer at the beginning of the week and take orders until Thursday. On Saturday, we’d have a pick-up. We did that every weekend for the rest of the year.”

Sherman is a Christmas baby. The year he was born, mom never got around to making the Christmas turkey. The joke inside the family for years was that Sherman owed the family a holiday turkey. As an adult, he finally got around to smoking that turkey.

By the second bird, Sherman knew he was on to something.

And now much of the nation’s capital knows that The District Pit Pitmaster is on to something, too.

His next business initiative is pairing good food with good drinks.

More specifically, he’s creating a partnership with local wineries and the historic and prestigious Museum in the Mansion on O St to create an Urban Winery.

“What we have in mind now is the marriage of those catering events-slash-individual platters with the wineries in the Washington, D.C. area,” Sherman said. “There’s a huge wine culture in Washington, D.C. that we can tap into. They love going to the wineries in Virginia and Maryland, but you can get here (O Street) on the metro. I love the Virginia wineries, but you have to travel an hour to 90 minutes from DC to get to there. We just want to make it easier for residents of the District of Columbia to get the best food and drink.”

Just about the same time that Sherman was thinking about a third business model for the District Pit – bringing in wineries and The Mansion on O Street – he found about the Black Men Ventures Black Founders Pitch Competition.

Sherman won first place with an amazing pitch.

“I’m excited that I had the opportunity to compete in it, and I’m excited that I won it,” Sherman said. “It was a fun process. You get a chance to get out there and pitch your product to a panel of experts who are going to ask you tough questions about your business model.“

Sherman loves feeding the diverse population of Washington, D.C. His customer base is anyone with a good taste bud palate.

However, being supported by other Black men has a special significance to Sherman.

“I’m proud to be part of it,” he said. “Any time you have small Black businesses being supported by Black individuals willing to invest in our product, we’ll do better. To have Black men supporting Black men is important to me. I’m a Black man. I’m an inner-city kid. I’m from Washington, D.C. If you have Black role models to look up to, you’re going to believe in yourself a little more. Maybe you’ll be able to take yourself a little bit further. That’s all we want. To make it just a little further. Now I’m a part of the Black Men Ventures family, I can help the next group coming along.”