After working for months on creative projects for clients like Virgil Abloh and Chris Gibbs, Reginald Jolley, better known as Reggieknow, is barely getting any sleep these days. When I dialed into Reggieknow’s world via Zoom, he spoke to me from a dimly lit office in his Los Angeles duplex. He’s so sleep-deprived from a project he worked on with Abloh that his head is slumping into a cardigan draped over his office chair, which happens to be the same sweater Paul Michael Glaser wore in Starsky & Hutch. But after falling asleep on Zoom, he springs himself awake and is able to answer my question in full. Although it’s hard to make out what his workspace looks like, Reggieknow says he likes decorating his rooms with objects that inspire him—things like Vaughn Bode characters, original ’90s Polo Stadium pieces, and anime toys. The room he’s currently speaking from is modeled after the office of Noble Drew Ali, who founded America’s first Black Muslim organization, the Moorish Science Temple of America. Similar to Ali’s space, an American flag flipped sideways with 48 stars hangs above Reggieknow’s head during our Zoom chats, and it’s all I see whenever his head starts to plop down to his chest. 

“My sleeping pattern is so horrible right now; it’s crossing the line into being unhealthy,” says Reggieknow. “I’m getting it where I can, but I sleep better at my desk than I do in my bed. I have to trick myself into bed because my brain is always spinning, and it won't quiet down.” 

It’s been a busy year for Reggieknow, short for “Reggie knows best.” Before the pandemic, he flew out to Wyoming on a private jet with Kanye West to chop it up about the creative direction of the Yeezy apparel line. He’s been working with Gibbs on Union’s Air Jordan IV campaign, which was centered on a hip-hop anime Reggieknow’s been building for over a decade. And he’s had long Zoom calls with Abloh to talk about Black creativity and hip-hop. 

“Well, what's funny is I'm pretty boring,” says Reggieknow with a smile. “My day-to-day is just a lot of creative problem solving, and I've always said the life of creative ideas really depends on who is on the other side of the desk. By chance it’s the decision maker who has a vision, then everything is great.”