'FREEAgent:' Street Fashion Pioneer Jeff Staple Among First Guests of Season Two of Kenny Annan-Jonathan's Podcast

Exclusive: FREEAgent, the podcast hosted by creative entrepreneur Kenny Annan-Jonathan, returns today for its second season. In its debut, the show was known for high-profile guests, with names from fashion, business and sports joining Annan-Jonathan to discuss their careers. Guests included Stuart Duguid, former agent of Naomi Osaka, and veteran executive Rich Kleiman. […]

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

In its first run, the pod was recognized for its high-profile guests, with names from fashion, business and sports joining Annan Jonathan to discuss their careers. Guests included Naomi Osaka's longtime agent Stuart Duguid and veteran executive Rich Kleeman.

The second season of FREEAgent launches today with an episode featuring streetwear pioneer Jeff Staple.

"Everyone knows Jeff as the 'Pigeon Dunk Man,' but his story goes much deeper than that," Jonathan Annan said of Staples. He is a pioneer and one of the forerunners of global streetwear. He celebrates 30 years of STAPLE. Watch Deadline News Kenny Annan-Jonathan on the merger of the world of sports and culture with UK-based independent production house and media channel Trnsmission News "FREEAgent:" Naomi Osaka, Stuart Duguid, the first guest on Kenny Annan-Jonathan's sports and culture podcast

Staple is one of the most influential designers and creative directors of his generation. He launched STAPLE, an independent streetwear brand, in 1997. STAPLE has collaborated with companies such as Nike, Google, New Balance, Timberland, Puma and LVMH during its decades of operation. Staples is perhaps best known for creating the iconic Nike SB "Pigeon" dunk - one of the most influential sneakers of all time. Staples is also the founder of Reed Art Department, an influential creative and marketing agency.

Annan Jonathan continued: "The real content of our conversation focused on his redesigned agency and what it means to bridge the gap between the corporate world and the creative world. He is a cultural translator who understands both sides. Most creators are raw. They don't always know how to turn their creativity into revenue or communicate their message commercially. Bottom, and what he had to do to make it all work."

FREEAgent episodes will once again drop weekly. The guests are mostly high-profile figures who work between sports and the creative arts and rarely speak publicly, but still have a wide influence in their industry.

Annan Jonathan said: “Season one was really good. I think it was a powerful introduction."

"You might listen to Rich Kleeman and learn part of the story," explained Annan Jonathan. Then, when you hear one of his peers in the same space, you get a clearer picture of the broader ecosystem."

You can then hear from someone in an adjacent business or on the brand side, gaining more insight into how brands work with legal and legal teams. From there, you understand how the talent managers and the people behind the business work."

He added: My goal is to cover the ecosystem of sports, entertainment and media from the starting point, whatever it is, to the end.

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

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

Annan Jonathan is the founder of marketing and talent management agency The Mailroom and media house Trnsmission. In 2023, he was appointed creative director of Crystal Palace in the English Premier League, the first role created at an English professional club. He is also the sports director of the Cannes Lions International Festival of Creativity.

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

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