‘FREEAgent:’ Streetwear Pioneer Jeff Staple Among First Guests On Season Two Of Kenny Annan-Jonathan’s Podcast

EXCLUSIVE: FREEAgent, the podcast series hosted by creative entrepreneur Kenny Annan-Jonathan, returns today for its second season.

In its first run, the pod became known for its high-profile guests, with names across fashion, business, and sports joining Annan-Jonathan to discuss their careers. Guests included Naomi Osaka’s longtime agent Stuart Duguid and veteran executive Rich Kleiman.

FREEAgent season two launches today with an episode featuring streetwear pioneer Jeff Staple.

“Everyone knows Jeff as ‘the Pigeon Dunk guy,’ but his story is much deeper than that,” Annan-Jonathan said of Staple. “He’s a trailblazer and one of the forefathers of global streetwear. He’s celebrating 30 years of STAPLE.”

Staple is one of the most influential designers and creative execs of his generation. He launched STAPLE, an independent streetwear brand, in 1997. Over its decades-long run, STAPLE has collaborated with companies like Nike, Google, New Balance, Timberland, Puma, and LVMH. Staple is perhaps best known for creating the iconic Nike SB “Pigeon” Dunk — one of the most influential sneakers of all time. Staple is also the founder of Reed Art Department, an influential creative and marketing agency.

Annan-Jonathan continued: “The real substance of our conversation centres on his redesigned agency and what it means to bridge the gap between the corporate and creative worlds. He’s a cultural translator who understands both sides. Most creators are raw. They don’t always know how to convert their creativity into revenue or communicate their message commercially. Jeff’s story gives you details about the projects he pursued, the times he was turned down, and what he had to do to make things work.”

FREEAgent episodes will once again drop weekly. The guests are predominantly high-profile figures working between sports and creative arts who rarely speak publicly, yet still wield widespread influence in their industry.

“Season one was really good. I think it was a powerful introduction,” Annan-Jonathan said, adding that he is simply aiming to “widen the knowledge pool” and “build on the conversations that came before” in his second season.

“You might listen to Rich Kleiman and learn one part of the story. Then, when you hear one of his counterparts within the same space, you get a clearer picture of the wider ecosystem,” Annan-Jonathan explained.

“Then you can hear from someone in an adjacent business or on the brand side, and you gain more insight into how brands work with law and legal teams. From there, you understand how talent managers and the people behind the businesses work.”

He added: “My goal is to cover the ecosystem of sports, entertainment, and media—from the point of inception, whatever that may be, all the way to the end.”

Annan-Jonathan added that the FREEAgent podcast also gives him the opportunity to celebrate important cultural figures who are rarely championed publicly for their work.

“Season two is about continuing to stand on the shoulders of giants while celebrating people doing amazing things,” he said. “I think people should be given their flowers.”

Annan-Jonathan is the founder of the marketing and talent management agency The Mailroom and media house Trnsmission. In 2023, he was appointed Creative Director of English Premier League side Crystal Palace, the first such role established at a professional English club. He is also Sports Director at the Cannes Lions International Festival of Creativity.

FREEAgent podcast episodes drop weekly. The Jeff Staple episode is live now.