Brendan Kelly '90 - Risk & Reward

“There is never a good day to become an entrepreneur,” says Brendan Kelly ’90. “If you’re going to do it, do it.” That attitude is what led Brendan to take a chance on what he believed to be an up-and-coming industry 20 years ago. No one could have anticipated just how considerably that hunch would pay off.

The 11th of 12 children in an Irish-Catholic family, Brendan is by no means the first entrepreneur of the bunch. After immigrating to the United States, Brendan’s father earned his high school diploma and worked as a union electrician for many years. When he was 52 years old, he launched Kelly Electric. Now, all six of Brendan’s brothers and one of his sisters own their own companies.

After college, Brendan began working for his brother John at Kelly Generator. When he started selling generators to a telecommunications company, the entire trajectory of his career changed. “The first cell site I ever saw was at Wintergreen Ski Resort in 1997,” Brendan explains. “I went back to my brothers and said, ‘We need to get into this wireless cell site industry.’ At the time, there was just a big bag phone you carried in your car and never used. People said, ‘That’s never going to work. Who needs to use their phone in the car?’ And, here we are today.”

From voice to push-to-talk to black and white text messaging to the groundbreaking advent of the iPhone and the thousands of apps that were quick to follow, the telecommunications industry has experienced exponential growth and undreamed-of innovation. Brendan and his company, Smartlink, have been along for the ride for 20 years now. As a national talent solutions and telecommunications services company, Smartlink works with all the major network providers, recruiting qualified professionals and managing the development, engineering, and maintenance of new and existing communications infrastructures.

Over the years, Brendan’s entrepreneurial spirit and aptitude for predicting rising industries has led him on several other successful ventures. In 2007, a need for reliable drivers to transport Smartlink candidates to and from the airport led to the inception of a company called Driven, which has evolved into a luxury car service that today chauffeurs 175 members.

Brendan also founded the Chesapeake Sports & Entertainment Group (CSEG) in 2016. CSEG houses three brands: Legendary Sports Group, a sports and entertainment company specializing in event management; six-time Major League Lacrosse champions, the Chesapeake Bayhawks; and Chesapeake Park, a 1,700-acre development in the works that will offer 24 sport grass fields for use by both professional and youth sports and an indoor 10,000 seat arena, as well as retail, office, and living space.

While Brendan has celebrated many accomplishments in business over the last 20 years, he is most proud of his wife and five children. “Everything else can be rebuilt,” he says. And, when it comes to work, it is also the relationships he has developed there that matter most to him. “The most rewarding part of being an entrepreneur is when you see people working for you for as long as they have for me, you get to see them go from young adults to getting married to having kids to watching their careers blossom,” he reflects. “When you take a breath and step back for a minute, you realize how many people are building homes and moving their lives along because of a chance you took 20 years ago.”

Mount Saint Joseph High School

Mount Saint Joseph is a Catholic, college preparatory school for young men sponsored by the Xaverian Brothers.