Jeff Staple Joins Season Two Premiere of Kenny Annan-Jonathan's FREEAgent Podcast
The FREEAgent podcast hosted by Kenny Annan-Jonathan has returned for a second season. Its opening episode features streetwear pioneer Jeff Staple, who is marking 30 years of his STAPLE brand. The first season included guests from fashion, business, and sports, such as agent Stuart Duguid and executive Rich Kleiman.
Kenny Annan-Jonathan, a creative entrepreneur, hosts FREEAgent. The show’s first season drew notable figures from fashion, business, and sports, including Stuart Duguid, Naomi Osaka’s longtime agent, and Rich Kleiman, a veteran executive. It returns today for season two.
The premiere centers on Jeff Staple, a streetwear pioneer. Annan-Jonathan says his influence goes beyond a single well-known sneaker association, calling him a trailblazer and a forefather of global streetwear. Staple is also marking 30 years of his STAPLE brand.
The second season may give fashion and streetwear audiences deeper access to career stories from creative and sports-adjacent figures. Listeners interested in entrepreneurship, design, and culture could find inspiration in Jeff Staple’s 30-year brand journey. The episode may also raise FREEAgent’s profile, potentially drawing new audiences to independent fashion media and highlighting how streetwear’s history connects with broader entertainment and business conversations.