I cover creators at Like & Subscribe, a standalone Ankler Media newsletter that’s being sampled today for paid subscribers to The Ankler. I scooped the details on Giggly Squad’s SiriusXM deal and interviewed Jake Paul about his $180M venture fund. I’m natalie@theankler.com
In Hollywood, firing your manager or agent is a dramatic but not uncommon move. It’s much more rare that a star decides to go nuclear on their former reps. Today, the story of a popular podcaster who’s done just that.
The Why Files host A.J. Gentile is very unhappy with the team at Night Media that was previously managing his business. So unhappy, in fact, that he filed a complaint with the California Labor Commissioner’s office, as Tatiana Siegel reported Tuesday morning for Page Six Hollywood. But Gentile didn’t stop there. As I reported exclusively yesterday over at Like & Subscribe, a tongue-in-cheek video he made calling out Night’s practices has been circulating around town in recent weeks.
I’ve watched the unlisted video (it’s linked below), and I’ll share more about what it alleges for paid subscribers to Like & Subscribe. Keep reading for the full story, then stick around for a jam-packed newsletter that includes:
- My scoop: Netflix is looking for an exec to lead its podcast business
- Exclusive details about an election-season team-up between Lemonada and news and culture podcast The Moment LIVE
- An interview with The Tonight Show Starring Jimmy Fallon head writer A.D. Miles about the team’s embrace of microdramas
Why Files Nukes Night Media
As host of The Why Files — a top 50 podcast that details conspiracies about UFOs, mysteries of the Vatican and myths like the lost island of Atlantis — Gentile is accustomed to asking the questions no one else will ask.
Now he’s asking whether his former managers at Night Media have been screwing over clients.
Siegel reports that Gentile is accusing Night — a management firm run by Reed Duchscher that represents some heavy hitters of the creator world, including Kai Cenat, Hasan Piker and the Kalogeras Sisters — of violating the Talent Agencies Act, which stipulates that only companies registered as agencies in the state of California can procure and negotiate employment for clients, including brand deals and sponsorships. Night is not registered as an agency, according to this database operated by the Association of Talent Agents.
In the complaint, which Page Six Hollywood obtained, Gentile says Night, which began repping him in 2023, owes him $743,988 in commission for one year. Gentile reportedly parted ways with the reps in April and filed the complaint last month.
I’ve learned that just a few weeks ago, Gentile posted an unlisted video to the Why Files YouTube channel — where he has nearly 6 million subscribers — titled “Call 76-BAD-NIGHT to learn about the Talent Agencies Act.” I’ve obtained the video.
Don’t stop here
Get the rest of this story — and the scoops and intelligence Hollywood reads first.
Already a subscriber?
Netflix ISO Podcast Master
It’s been just about a year since Netflix moved aggressively into the podcast business, inking dozens of licensing deals and adding a handful of original video podcasts to its programming lineup. Now multiple sources tell me that the streamer is looking to hire someone to lead its podcast efforts.
The details? The job is not formally posted, but I have learned a few things.
Don’t stop here
Get the rest of this story — and the scoops and intelligence Hollywood reads first.
Already a subscriber?
The Moment Before Midterms
As midterm elections coverage heats up over the coming month, there’s another race worth watching: which online voices will emerge as the most influential in swaying national political sentiment. The field appears wide open, after the Wall Street Journal reported last week that conservative podcasters who helped drive President Trump to his second victory in 2024 have largely stopped talking about him. (According to the report, mentions of Trump’s name per hour on conservative pods dropped 70 percent from their peak ahead of the presidential election.)
Podcast network Lemonada Media clearly senses the opportunity, striking a deal with The Moment LIVE, a live multiplatform show that blends pop culture and news and politics commentary. Lemonada will work with The Moment LIVE and its hosts, journalist Rebecca Sananès and creator Meredith Lynch, on distribution and ad sales.
Launched in 2025 on TikTok, The Moment LIVE is a twice-weekly live show that now broadcasts across multiple platforms, including YouTube and Instagram Live. It has an audience of around 500,000 followers.
During an hourlong broadcast, Sananès and Lynch are just as likely to debate whether Nara Smith is a tradwife as they are to unpack concerns over mass surveillance via Flock cameras, or what Sananès calls “the politics of culture and the culture of politics.” They’ve interviewed politicians like Sens. Chris Murphy and Ed Markey, activists like Erin Brockovich and celebrities like Margaret Cho and Jodie Sweetin.
Sananès, a veteran public radio journalist who previously produced Kara Swisher and Scott Galloway’s Pivot and led audio for Prince Harry and Meghan Markle’s Archewell, first connected with comedian and creator Lynch — who has more than 348,000 followers on TikTok — in the comments section of a Whitney Cummings video. They started going live on TikTok — their first guest was Rep. Ro Khanna.
As with a lot of live shows, the audience that actually tunes in to The Moment is small but engaged. This spring, an interview with Rep. Joaquin Castro about Texas’ Dilley Immigration Processing Center — where detained families have described poor conditions, including a lack of clean drinking water — struck a chord with viewers, including Ms. Rachel. Lynch and Sananès then launched a fundraiser that raised more than $100,000.
Lynch tells me she and Sananès connected with Lemonada over the effort and will look to do more in the future. Teaming up with Lemonada — which focuses on female-oriented podcasts like Julia Louis-Dreyfus-hosted Wiser Than Me — will allow them to experiment with brand partnerships that can live across the live show as well as clips and their Substack, where they publish episodes in full alongside show notes.
“There are so many more places to work with brands creatively that isn’t just advertising in the traditional sense,” says Sananès.
With the midterms on the horizon, Lynch and Sananès are lining up guests like Dr. Abdul El-Sayed, who is running to represent Michigan in the U.S. Senate, but they’re already thinking beyond Nov. 3.
“I think we’re going to see a really interesting shift in people going all in talking about 2028,” says Lynch, “and we want to be at the front of that conversation.”
Fallon Helps Microdramas Go Mass
In the 15 months since my Ankler Media colleague Elaine Low and I first began covering the burgeoning business of microdramas, the medium has exploded as major media companies, tech giants and Hollywood veterans have invested significant resources into capturing their piece of a $150 billion industry. But in spite of all the time, money and conversation devoted to verticals, one key milestone has remained elusive. The format is still waiting for its Serial moment — when a show breaks through with audiences in such a major way that the entire medium goes mainstream.
What if a 72-year-old legacy TV institution is the one to crack the code?
On Sunday night, The Tonight Show Starring Jimmy Fallon debuted the second season of its experimental vertical series, Who Billionaire? Me Billionaire, after the first season had more than 27 million views across digital platforms. In a sign of how confident NBC is in the project, episode one appeared in The Tonight Show’s first post-Sunday Night Football episode of the season.
Who Billionaire? Me Billionaire is the brainchild of Tonight Show head writer A.D. Miles, who tells me he pitched Fallon on the idea of making their own microdrama after he got hooked on the format — he especially liked tropes about billionaire mafia boyfriends and werewolf romances. “We all love soap operas, and drama for comedy is catnip to comedy writers,” says Miles, pointing to past Tonight Show parodies like Downton Sixbey (a 2012 Downton Abbey spoof). “It’s just so fun to write.”
For Who Billionaire? Me Billionaire, Miles penned an affectionate send-up of the format. In season one of his story — which began airing this summer — two wealthy couples are celebrating an engagement when their party is crashed by a mysterious stranger. Season two picks up after the mysterious stranger reveals himself to be (spoiler alert!) a secret billionaire and breaks up one of the couples.
“At first, I have to admit, I was a little intimidated about the idea of how do you try to generate a cliffhanger every 90 seconds,” Miles says. “But once you get used to it, it becomes a natural cadence. And I found it to be, as a comedy writer, super fun to look for these cliffhangers and just invent them where maybe they wouldn’t exist.”
Who Billionaire? Me Billionaire plays into the over-the-top vibe of microdramas, but elevates the form through casting. Fallon stars as Chaiston, an entitled billionaire with a gambling problem, alongside John Stamos as Doug, the mysterious outsider. Rounding out the cast are comedian and TikTok star Delaney Rowe, Tonight Show writer Rose Kelso and microdrama vet Kasey Esser, whom Miles calls “an absolute pro.” Season two is packed with cameos, including Alix Earle and Dakota Johnson. Even Miles shows up in character for some of the action.
Though two episodes of Who Billionaire? Me Billionaire aired during episodes of The Tonight Show, the show is meant to be watched in binges online. Both seasons are available in full on The Tonight Show’s YouTube channel and TikTok page, and on Peacock.
Miles tells me this won’t be the last time The Tonight Show plays with the format. “I’ve got half a dozen, at least, more titles and ideas that I would absolutely love to keep going,” he says, teasing that the plan would be to roll out a new season every few months. “I’ll keep coming up with them until they tell me to stop.”
In the meantime, he’s been hearing from viewers he’s converted into microdrama fans. He says they’ll tell him, “I just found out about these verticals from your show, and now I’m watching My Billionaire’s Werewolf’s Cousin, or whatever.”
CNN has teamed up with Jubilee Media to host a town hall with Texas Senate candidate James Talarico. Erin Burnett will moderate the town hall, which will air live on CNN and stream later on Jubilee’s YouTube channel, which has more than 11 million subscribers.
What happens when a tennis influencer breaks up with her professional tennis player boyfriend? Hard Court went deep on the evolution of Morgan Riddle’s brand.
Creators are flocking to New York City — and bringing transplants and tourists with them.
Guy Raz has taken full ownership of podcast How I Built This and partnered with Vox Media as he launches video episodes of the 10-year-old show.
Druski told Diary of a CEO host Steven Bartlett that Netflix, Amazon and FX all rejected his ideas for longform projects. After making them himself, “now it’s a bidding war” to work with him.
Comments
Only Ankler All Access subscribers can comment
Already a subscriber?