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.

EXCLUSIVE: The new-look Skydance is worth just $29B due to its huge debt pile, according to media analyst Evan Shapiro.

The former NBC, Participant Media and IFC exec, who now maps the media landscape through his ESHAP business, said the valuation was down to both the $81B debt that Skydance assumed on day one of trading and its links to major shareholder Oracle, which is has long-term debts of over $160B due to investments in AI.

Shapiro is talking at MIPCOM Cannes this week, where he will unveil the latest edition of his Media Universe Map, which will be the first that is interactive and allows users to compare entertainment and tech ecosystems of the past to 2026.

“One of the puzzles we needed to solve in making this map was figuring out what the name of Paramount/WBD would be and, more importantly, WTF Skydance is actually worth,” he said ahead of his talk. “No one in their right mind would buy the $81B in debt they are carrying and no one who isn’t high as a kite would buy Skydance for the $111B price that was just paid for WBD.

“One of the biggest reasons for that is that the fortunes of Skydance and Oracle are now intrinsically intertwined, and combined they have $240B of debt, a good portion of which is either junk or a millimeter above junk. To put that in perspective the Ellisons now carry more in debt than all of Disney is worth.”

Shapiro claimed this meant his team had to determine a net asset value for Skydance, which came in at just $29B, far below the value David Ellison’s Paramount paid for WBD.

We have reached out to Skydance for comment.

The latest Media Universe Map highlights the dominance of tech companies, with Nvidia’s value the largest at $5.3T, followed by Apple ($4.9T), Alphabet ($4.3T), Microsoft ($3.8T), Amazon ($2.8T) and Meta ($1.8T). Larry Ellison’s Oracle, which is a major shareholder in the American version of Chinese social platform business Bytedance, was valued at $429B.

Of the pureplay media and entertainment businesses, Netflix was the largest with a valuation of $293B, ahead of Disney ($187B). Comcast was at $73B, while Fox was just $25B, though this is set to almost double when it completes its deal for Roku, which is valued at $23B.

India’s Reliance, which houses Disney-backed streamer JioHotstar, was at $164B, Sony came in at $144B. Both companies have assets well beyond the media space.

Shapiro, who describes his role as a media cartographer, has been rolling out his media maps for six years and is unveiling the first interactive version this week in Cannes. As he has described in the past, he claims there had been a fundamental shift in media ownership in recent years, which the map demonstrates.

“The biggest change in the Media Universe since I started mapping it is the shift from an industry controlled by C-suites to an ecosystem controlled by the consumers,” he said. “We are now in the ‘user-centric era,’ so I felt it was only fitting to put control of my map in the hands of the users. This new Media Universe Map App does just that – allowing you to drive the map yourself, on desktop or mobile, and double click on anything and everything you want more of.”

He added that the functionality would allow users of his program to compare today’s landscape with those of yesteryear.

“One of the things I get asked for most in my map, is a way back machine to compare years past to today’s map,” he said. “This new user-driven map does just that – we’ve included a time machine to allow you to compare and contract the media universe from years and eras gone by to the latest landscape.”