By Valerie Wilson | Special to The Times
At first glance, some may ask what a comedian and actor brings to a conference centered on business and ownership. The answer, according to Roy Wood Jr.’s career, is everything.
“I realized comedy was a business when I started selling CDs,” he explained. “Just learning the art of how to sell merchandise and how to market yourself.”
The Birmingham native will return to the Magic City as a featured guest speaker at the 2026 A.G. Gaston Conference on Feb. 18 at the Red Mountain Theatre Company. While the conference is known for highlighting business leaders, innovators, and entrepreneurs, Wood’s presence underscores an important truth: entrepreneurship does not always look like a storefront or a boardroom. Sometimes, it looks like a microphone, a stage, and a well-timed punchline.
“You know the difference between most entrepreneurs and me is that I am the brick and mortar,” says Woods. From printing headshots to investing in promotional materials, Wood learned early that success required constant reinvestment and self-marketing. According to him, “you really have to market yourself”.
Raised on Birmingham’s west side from the third grade, Wood is a graduate of Ramsay High School and Florida A&M University, where he earned a degree in broadcast journalism in 2001. His early ambitions blended storytelling, media, and humor; skills that would later define his entrepreneurial approach to entertainment.
Wood recalls one of his earliest turning points, which occurred while he was still at Florida A&M University, when he had an opportunity to open for comedian Tommy Davidson. The opportunity came during midterms, and he failed a class because of it. At the time, Wood thought the moment would be his big break, imagining himself heading back to Los Angeles as a newly famous comedian. Instead, it became an early lesson in risk, sacrifice, and long-term vision.
Many Birmingham residents remember Wood as a local comedian and radio personality, entertaining listeners each morning on the “Buckwilde Morning Show.” After taking a temporary leave from radio, he gained national attention on “Last Comic Standing,” finishing third and quickly becoming a fan favorite. He returned to Birmingham to host his own radio show but eventually felt the pull of larger opportunities.
That pull led him to Los Angeles, where he pursued acting on the sitcom “Sullivan & Son” for three seasons, as well as appearances on ESPN. From there, Wood made another strategic move. This time, he took his talents to New York, landing a correspondent role on “The Daily Show,” where his work earned him an Emmy nomination.
“It was a really good opportunity, and the perfect blending of both of my skill sets in journalism and standup,” Wood said of his time on the show. “I learned about political satire and the art of it from people who all studied under Jon Stewart, and I got to go on that journey with Trevor Noah.”
Today, Wood continues to forge his own path in entertainment. Audiences can now catch him on CNN’s “Have I Got News For You,” further cementing his role as both a cultural commentator and a media entrepreneur.
Like many entrepreneurs, Wood admits that some of his earliest business decisions came with hard lessons. “I’ve made a few mistakes in hiring the wrong people, and it hurts,” he shared. “You have to judge people on their skill sets and not necessarily their relationship to you or their price.”
Betting on himself has been a recurring theme throughout his career. “Periodically, you have to take a chance on yourself and bet on yourself,” Wood said. “Even moving to Los Angeles was a huge dice roll.”
That willingness to take risks extends to how he approaches the business side of comedy today. “You have to know your audience,” he said. “There is way too much data to not know your audience. You have to know where you are loved, where people are indifferent, and price your tickets accordingly.”
Marketing, consistency, and adaptability are key pillars of his strategy. Wood emphasizes learning broadly, understanding trends, and staying competitive. “The best people you know in comedy are consistent,” he said, pointing to creators like Druski as an example.
Financially and creatively, Wood has repeatedly reinvested in himself. “I took every penny that I made early on and re-invested in myself,” he said. “If it were safe to do all this stuff, everybody would have their own business and be successful.”
He also learned when to prioritize opportunity over immediate income. “You have to know when to work for opportunity versus when to work for cash,” Wood explained. Working unpaid on sports shows eventually led to ESPN, which caught the attention of “The Daily Show” producers. “After eight years, I walked right across the street to CNN.”
That long-term vision aligns closely with the legacy celebrated at the A.G. Gaston Conference; one rooted in ownership, perseverance, and building something that lasts.
“Try to do things just a little bit differently,” Wood said. “When I got to ‘The Daily Show,’ I tried to be the correspondent that didn’t repeat the views and angles of anyone who preceded me.” Wood has navigated spaces where he was rarely the first choice.
“Everything I’ve ever gotten, I was never anybody’s first choice, but I’ve proven myself to be the right choice,” he said. He also recognizes the importance of representation, adding, “I stand on their shoulders. I am thankful to show that Blackness is not monolithic.”
Now, with a well-established brand, Wood feels a responsibility to give back. “My goal is to try to create as many opportunities as possible to bring back to Birmingham,” for him, coming home is both personal and purposeful. “It is still fun to come home. It is an inspiration; maybe an inspiration to someone else,” Wood said. He credits seeing figures like Rickey Smiley for helping him believe success was possible.
If A.G. Gaston were sitting in the audience today, Wood believes he would recognize his dedication to Birmingham. “Mr. Gaston would recognize my time and dedication to the city and doing what I can, and my endeavors outside the city to bring opportunity and hope back to the people within it.”
As Roy Wood Jr. takes the stage at this year’s A.G. Gaston Conference, he brings more than humor. He brings a masterclass in entrepreneurship; one built on risk, reinvestment, consistency, and vision. And while his career continues to evolve, one thing is certain: he is still rolling the dice, and Birmingham is part of the bet.
