Jackson, like he did in the early 2000s on Grounds and as he does now in Hollywood, doesn’t mind betting on himself.
It’s proven to be a successful approach.
The McIntire School of Commerce graduate is the creator of “Grand Crew,” a sitcom based on a group of friends who discuss all of life’s challenges at a wine bar. The show, which features an all-Black cast, recently wrapped its second season on NBC.
Jackson, 39, says he’s just hitting his stride as a professional. That’s saying a lot for someone who’s already worked on several other remarkable shows, produced his own music and once had a high-level position at a New York City-based advertising agency.
“I’ve just always followed the fun,” Jackson said. “I follow the things that I wake up excited to do and not the things I feel like I’m supposed to do, which was a temptation when I got out of school.”
Jackson made the most of his time at UVA. Beyond classroom excellence, the Yardley, Pennsylvania, native was active around the University. He played sax for the Black Voices gospel choir, was involved in the “Grounds for Discussion” theatrical production that’s put on each year for first-year students, and ran his record label, “Oluponya,” first out of his dorm room and later in some office space in Newcomb Hall.
Oluponya, which is now known as University Records, recorded and cut CDs for UVA-based singers such as the Virginia Glee Club and Black Voices. It grew to hosting outdoor musical festivals and concerts, something the organization still does now in its 20th year on Grounds.
“At UVA,” Jackson said, “the extracurricular scene is so robust that I felt like, with all my interests, I had to take advantage of it. I’m so glad I did. I think it just showed that I liked managing. I like putting things together. I like organizing groups of people with shared interests and creating things.”
It was a loaded schedule for Jackson back then, but it prepared him for life after graduation when he worked in New York for the advertising agency Publicis during the day and took improv classes at night.
Janette Martin, a since-retired McIntire professor who taught Jackson in a couple of her courses, met with him in New York when her former student was contemplating a major change.
Even as he climbed the corporate ladder from junior strategic planner at Publicis to vice president of strategy in just four years, Jackson knew deep down his passion resided in the entertainment industry.
“He had this dream job that our [McIntire] students would wish for,” Martin said, “but it was becoming more and more difficult for him because he always had his eye on something more creative.”
Adhering to his own motto, Jackson followed the fun. He eventually made enough connections – and showed enough promise – on the acting scene to catch his big break as a writer for “Key & Peele,” a sketch series starring Keegan Michael-Kay and Jordan Peele that ran for five seasons on Comedy Central.
At 30, Jackson moved to Los Angeles and began his second career.
“I was on a great path in advertising,” Jackson admitted, “but success in a field doesn’t necessarily mean it’s your end destination.”
In addition to “Key & Peele,” Jackson has now worked as a story editor for Starz’s “Survivor’s Remorse,” and as a supervising producer for FOX’s “Brooklyn Nine-Nine” and co-executive producer for HBO’s “Insecure.” In 2020, he released “The Redondo Tape,” an extended-play record of six songs he wrote and performed.
“Grand Crew,” Jackson’s crown achievement to this point, was a staple of NBC’s Friday night programming this spring. Fellow UVA alumnus Jarrett Lee Conaway, Jackson’s resident adviser as a first-year student, directed an episode in each of “Grand Crew’s” first two seasons.
Jackson, who lived as a fourth-year student in West Lawn No. 11, credits a chunk of his Hollywood rise to his UVA experience.
“In hindsight, I’m just thankful to have gone to a university where I could explore all these different interests while also getting my education,” Jackson said. “I really got both out of UVA. I got a marketing degree and I had an advertising job for 7 1/2 years, but I also was acting and doing music and writing stuff there. And now I’m doing that.”
Jackson counts Martin as one of the McIntire professors he “really rocked with.”