Entertainment · TV & Streaming · 9 hrs ago
Jeff Staple Opens Season Two of Kenny Annan-Jonathan’s FREEAgent Podcast
Kenny Annan-Jonathan’s podcast FREEAgent has started its second season with an episode featuring designer Jeff Staple.
Staple founded the independent streetwear brand STAPLE in 1997, and the brand has worked with companies including Nike, Google and New Balance.
He is also known for creating Nike’s “Pigeon” Dunk sneaker and for founding the creative agency Reed Art Department.
The conversation looks at his agency and how he connects creative work with business.
The podcast features influential people working across sports, entertainment, media and creative industries.
New episodes are scheduled to come out weekly.
Kenny Annan-Jonathan’s FREEAgent podcast returned for its second season on October 12, 2026, with an episode featuring streetwear designer Jeff Staple.
The podcast’s episodes are set to be released weekly.
Staple launched his independent streetwear brand STAPLE in 1997.
STAPLE has collaborated with Nike, Google, New Balance, Timberland, Puma and LVMH.
Annan-Jonathan said the season aims to explore the connections between sports, entertainment, media, brands and creative work.
- Who
- Podcast host Kenny Annan-Jonathan and guest Jeff Staple.
- What
- FREEAgent launched its second season with an episode featuring Staple.
- When
- October 12, 2026.
- Where
- The episode is available to watch on Deadline.
- Why
- Annan-Jonathan said the podcast aims to explore the wider ecosystem of sports, entertainment and media, and to celebrate influential cultural figures.
This story does not have two clearly opposing sides.
Jeff Staple launched the independent streetwear brand STAPLE.
FREEAgent returned for its second season with an episode featuring Staple.
Episodes of the second season are scheduled to be released.
- Host
- Kenny Annan-Jonathan
- Season two launch guest
- Jeff Staple
- Brand founded
- STAPLE, 1997
- STAPLE collaborators
- Nike, Google, New Balance, Timberland, Puma and LVMH
- Release schedule
- Weekly
What people are saying
Everyone knows Jeff as ‘the Pigeon Dunk guy,’ but his story is much deeper than that
He’s a trailblazer and one of the forefathers of global streetwear.
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.
I think people should be given their flowers.
Sources
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