Entrepreneurship as Art 

Art begins with vision. The artist sources materials, refines techniques, and iterates until the final piece comes to life. Great artists also know when to scrap an idea and hit the drawing board again. Swap “artist” for “entrepreneur,” and Garrett James’ process is the same.

During the COVID-19 pandemic, many of us had no idea how to handle our sudden increase in free time. As a previous businessman but without prior experience in fashion, Garrett James decided his time would be spent undertaking a new venture: creating a luxury athletic brand. James realized that “selling the perfect pair of shorts over the internet that people would fall in love with” could be the perfect morale boost for stir-crazy athletes missing their sports seasons, streetwear enthusiasts, and active, stylish individuals stuck at home. Reflecting on his journey, he told us, “I didn’t grow up in the fashion industry, I didn’t go to fashion school—I’ve just always been really entrepreneurial.” Much like a no-look pass or game-winning fadeaway, the launch of Ryoko Rain was instinctive rather than formulaic. Conversion KPI’s? Supply chain logistics? The intimidating jargon of the fashion industry and manufacturing nuances never dimmed James’ intuition that the world needed his vision.

After instinct and vision comes execution.

The utter isolation during quarantine was difficult for both seasoned business owners and those just starting out, but James persevered. Without the ability to network in person or lean on industry connections, he had no choice but to teach himself—everything. “It was all self-taught for me,” he says. “(I had to) meet with a bunch of different vendors and sewing shops in Orange County, and until I found the perfect one that aligned with me and taught me everything, I had to just be there myself. I had to source my own fabric, draw cords, elastic—taking my time until about a year where I was happy with what I had.”

Like a player refining his shot mechanics through relentless practice, James treated entrepreneurship as an art: one that demanded patience, intuition, and obsessive attention to detail. He says that in order to be passionate enough to dive into an industry, “you have to be obsessive over it… everyone’s in streetwear, so how can you do it better?”

Once his business foundation was strong, James had to evolve into a two-way player, balancing creative direction with business strategy. “I wear all the hats,” he admits. “If you’re starting from the ground up, you have to be both.” When the brand took off, he realized that sustainable growth meant knowing when to pass the ball. James advises that “it’s most important to surround yourself with smart people so you can (trust in) taking certain tasks off your plate, allowing yourself to spread out to doing what’s most beneficial to the brand.”

He says the balance between being an artist and a businessman is “probably 50/50.” One doesn’t function without the other. The art fuels the vision, but the execution makes it real.

Storytelling as Art

Beginning with its name, Ryoko Rain has intentionally injected significance into every aspect of the brand. The brand proves, like the great designer Paul Rand used to exclaim, that “everything is design!”. Garrett James named the brand after the middle names of his two daughters at the time, Ryoko and Rain. Later, when he had a third daughter, he introduced a secondary logo featuring a girl chasing butterflies—an illustration of his youngest daughter, Poet. The butterfly itself as a logo (two R’s for Ryoko and Rain, side-by-side) holds deep personal significance. As children, James' daughters would raise caterpillars in their grandparents' garden, watching them transform into butterflies. That tradition became a metaphor for his family’s journey, and, ultimately, for his brand.

Just as the butterfly represents transformation and growth, James is using Ryoko Rain to help push forward a long-overdue shift in sports and fashion. His focus on women's sports is intentional. As a father of three daughters, he designed Ryoko Rain to be gender-neutral and embraced by athletes across all sports. “My clothes are unisex, so I purposely like to target women's sports,” he said. “We just did a collaboration with ATHLOS, the first all-women’s track event. And then we just launched the collaboration with Angel City FC a month or two ago.” This approach directly counters the long-standing industry pattern where women's sports have historically received less visibility, fewer endorsement deals, and lower media coverage compared to men's leagues. Even fashion, being one of the most visible industries in the world, was slow to embrace female athletes as style icons, only recently amplifying WNBA and NWSL players on major platforms like @leaguefits. Ryoko Rain is part of this positive shift. It’s been worn by elite female athletes like WNBA stars A’ja Wilson, Kelsey Plum, Paige Bueckers, and Cameron Brink, helping to allow the crossover between women’s sports and streetwear to grow wings and take flight.

The same authenticity that grounds Ryoko Rain also fuels a self-sustaining community built on word-of-mouth. Unlike most clothing brands, Ryoko Rain doesn’t pay athletes or celebrities to wear its pieces—it doesn’t have to. James built the brand through direct outreach, personally messaging athletes to get the gear in their hands. “People ask me that all the time—how do you get all these athletes? Did you know people before? I knew a couple, but really, it was cold calling. I’d be putting my kid to sleep at night, laying in bed, just (sending out) messages in an obsessive way,” he said. “And then it worked.” James’ consistent efforts paid off, with Ryoko Rain being worn in NBA and WNBA tunnel walks, warmups, NFL events, and beyond—not because of paid deals but because athletes genuinely like the product and the founding behind it. Word spreads quickly when players can finally get their hands on trendy, luxury fabrics in athlete-friendly styles—something far beyond the usual rotation of generic team-issued gear and endless Nike Tech sets. It’s not only superstars wearing the product (although you might spot the shorts on Paul George or Angel Reese). Children and adults everywhere—whether streetwear aficionados or aspiring pros—are drawn to the same message that first caught these superstars’ eyes. Athlete or not, celebrity or not, everyone knows it’s unequivocally cool to rock Ryoko’s horror film work jackets or the electric flame shorts (seen on our model Oliver).

Athletics as Art

Ryoko Rain’s meteoric rise from a pandemic-born startup to a luxury streetwear powerhouse is a testament to both resourcefulness and persistence. Beyond the product, Ryoko Rain thrives because it resonates with athletes at every level. That was clear in our Forward studio, where basketball players Tessa and Ty, women’s rugby players Hannah and Lauren, and men’s volleyball players Lee and Oliver modeled the brand. For student-athletes, their lives are that same artistically arranged balance of training, studying, and competing that define both athletics and artistry. Whether on the court, in the classroom, or shaping their own post-grad careers, these athlete-artists, like former student-athlete James, are proof that art and sport have never been separate. J. Cole went from hip-hop icon to pro basketball player. Former NFL tight end Vernon Davis became a seasoned painter. Flo-Jo designed her own iconic track uniforms. Shaquille O’Neal built a second career as a DJ. The best athletes have always been artists in their own right, and Garrett James—whether he’s on the court as director of Ironmen Basketball, working on financials for Ryoko Rain, or behind the creative direction of the brand—is proof that you can be both.