Exclusive: free agentThe podcast series, hosted by creative entrepreneur Kenny Annan-Jonathan, returns for its second season on TODAY.
In its first run, the pod became known for its high-profile guests, with names from the worlds of 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.
free agent Season two launches today with an episode featuring streetwear pioneer Jeff Staple.
Annan-Jonathan said of Staples, “Everyone knows Jeff as the ‘pigeon dunk guy,’ but his story goes much deeper than that.” “He’s a trailblazer and one of the forefathers of global streetwear. He’s celebrating 30 years of being a staple.”
Staples is one of the most influential designers and creative executives of his generation. He launched STAPLE, an independent streetwear brand, in 1997. Over its decades-long tenure, STAPLE has collaborated with companies like Nike, Google, New Balance, Timberland, PUMA and LVMH. 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 added: “The real crux of our conversation focused 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’s pursued, even when they’ve been rejected. was given, and what they had to do to make things work.”
free agent Episodes will once again drop to weekly. The guests are mainly high-profile individuals working within sports and the creative arts who rarely speak publicly, yet have wide influence in their industry.
“Season one was really good. I think it was a powerful introduction,” Annan-Jonathan said, adding that her goal is simply to “broaden the knowledge pool” and “carry on the conversations that happened before” in her second season.
“You can listen to Rich Kleiman and learn part of the story. Then, when you listen to one of his counterparts in the same space, you get a clearer picture of the broader ecosystem,” Annan-Jonathan explained.
“Then you can hear from someone in an adjacent business or on the brand side, and you can learn more about how brands work with law and legal teams. From there, you understand how talent managers and the people behind the business work.”
He added: “My goal is to cover the ecosystem of sports, entertainment and media from beginning to end, whatever that may be.”
Annan-Jonathan said that free agent The podcast also gives them the opportunity to celebrate important cultural figures who are rarely publicly supported for their work.
He said, “Season two is about continuing to stand on the shoulders of giants while celebrating people who do amazing work.” “I think people should be given their flowers.”
Annan-Jonathan is the founder of marketing and talent management agency The Mailroom and Media House Transmission. 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 the sports director at the Cannes Lions International Festival of Creativity.
free agent Podcast episodes drop weekly. jeff staple episode is live Now.