Alex Cooper has built a career defined by eye-popping deals, and the numbers keep getting larger.
In 2021, Cooper exited Barstool Sports and took her hit podcast, “Call Her Daddy,” to Spotify in a landmark $60 million agreement. By 2024, she had moved into an even richer chapter, signing a SiriusXM deal reportedly worth up to $125 million. Now, a new figure is being tied to her expanding media operation: $500 million.
Unwell, the media company Cooper launched with her husband, producer Matt Kaplan, has secured its first outside investment in a transaction that values the business at $500 million before the new capital is added. The funding comes from WTSL, a media, entertainment and sports investment firm led by veteran Hollywood dealmaker Patrick Whitesell and Jason Lublin. WTSL is backed by private equity heavyweight Silver Lake.
The size of WTSL’s investment has not been made public, and the ownership breakdown among Cooper, Kaplan and any other existing stakeholders remains undisclosed. Still, the deal offers a firmer benchmark than a celebrity wealth estimate: an outside investor has put real money into Unwell at a $500 million pre-money valuation.
The message appears clear: Cooper and Kaplan are preparing to scale Unwell far beyond its current footprint.
Antony Jones/Getty Images
First, What Does A “$500 Million Pre-Money Valuation” Actually Mean?
To be clear, the valuation does not mean Alex Cooper personally received a $500 million check.
It also does not mean Unwell has been sold.
A “pre-money” valuation is what investors and the company agreed Unwell was worth immediately before WTSL’s new capital was added. So, hypothetically, if WTSL invested $50 million, the resulting post-money valuation would be $550 million, and WTSL would own roughly 9% of the company. That’s just an illustration. The actual investment amount has not been revealed.
What’s important is that Cooper and Kaplan had previously built and funded the operation without outside investors. This financing establishes a real-world benchmark for the business while leaving the founders with an undisclosed ownership position in a company now valued in the hundreds of millions.
How Much of Unwell Does Alex Own?
That’s the $500 million question.
Neither Alex Cooper nor Unwell has disclosed exactly how much of the company Cooper personally owns. We do know that Cooper and her husband, Matt Kaplan, co-founded the business and financed it themselves before the WTSL deal, which was described as Unwell’s first outside investment.
That makes it reasonable to assume Cooper still owns a very substantial percentage of the company, but any specific figure is necessarily an estimate.
If Cooper and Kaplan began with something close to an equal ownership split, Cooper might have owned roughly 50% before accounting for employee equity or other shareholders. The new WTSL investment would dilute that stake somewhat. For example, if WTSL invested $50 million at the reported $500 million pre-money valuation, the investor would own roughly 9% of the company after the deal. A hypothetical 50% Cooper stake would consequently fall to around 45%.
So, until more information becomes public, a reasonable working estimate would put Cooper’s ownership somewhere in the neighborhood of 40% to 50%.
At a $500 million valuation, a 40% stake would have a headline value of $200 million. A 45% stake would be worth $225 million. A 50% stake would be worth $250 million.
Who Is Patrick Whitesell?
If you’re trying to understand why this deal matters, the investor is almost as interesting as the valuation.
Patrick Whitesell spent decades building one of the most powerful careers in Hollywood representation. He previously served as co-CEO of WME and later held senior leadership roles at Endeavor alongside Ari Emanuel. Another fun fact about Patrick – his ex-wife is Lauren Sanchez, who is now married to Jeff Bezos.
After leaving Endeavor, Whitesell launched WTSL with backing from Silver Lake. The firm is specifically targeting businesses in media, sports, and entertainment – particularly companies that can become larger platforms rather than simply producing one successful piece of content.
One of WTSL’s other investments should sound familiar to CelebrityNetWorth readers.
In 2025, a Whitesell-led investment platform invested in Peyton Manning’s Omaha Productions at a valuation north of $750 million. The deal involved a stake of roughly 10%, meaning more than $75 million flowed into Manning’s media company. WTSL’s portfolio now includes Omaha alongside businesses such as Diamond Baseball Holdings, TMWR Sports, and League One Volleyball.
In other words, Whitesell isn’t simply buying into a popular podcast. He’s betting that Cooper can build Unwell into a diversified media company.
Unwell Is No Longer Just A Podcast Network
Cooper and Kaplan launched Unwell in 2023 under their holding company, Trending.
At first glance, the obvious centerpiece was “Call Her Daddy,” along with a network of podcasts built around younger creators. But Kaplan brought something important to the equation: Hollywood production infrastructure.
His ACE Entertainment produced Netflix’s hugely successful “To All the Boys” movies and the spinoff series “XO, Kitty.” Combining Kaplan’s film and television operation with Cooper’s enormous direct relationship with young female audiences created the foundation for something much broader than an audio network.
Today, Unwell has more than a dozen podcasts, film and television production, live events, consumer products, and a creative agency. Cooper says the company reaches around 70 million women per month.
Its biggest distribution relationship remains SiriusXM. In 2024, Cooper signed a three-year SiriusXM agreement worth as much as $125 million. Importantly, that contract was not merely a salary for Cooper to record “Call Her Daddy.” SiriusXM received advertising and distribution rights involving “Call Her Daddy” and Unwell’s wider roster of current and future shows, along with additional programming and events.
Unwell Has Been Expanding Fast
The company has been announcing deals well beyond podcasting.
Unwell is developing a series adaptation of Hannah Grace’s bestselling romance novel “Icebreaker” for Netflix and a film adaptation of Ali Hazelwood’s “Deep End.” It also has a Hulu adaptation of Aggie Blum Thompson’s mystery novel “You Deserve to Know” in development and has partnered with Google on the micro-drama project “Moving On.” The podcast network has continued adding shows as well.
The stated plan for WTSL’s capital is more expansion, including potential investments and acquisitions.
And there’s already another sign that Cooper is reorganizing around Unwell’s next phase.
This week, it emerged that Cooper is leaving UTA, the agency that helped negotiate her massive SiriusXM agreement, and moving to CAA. Sources close to Unwell told Page Six that the company has spent recent months mapping out its next stage of growth following the WTSL transaction, including reconsidering its traditional talent representation.
Unwell now employs more than 100 people, according to that report, and is attempting to operate simultaneously across podcasts, television, film, events, consumer products, and advertising.
That’s a very different business from the one Cooper launched with Sofia Franklyn eight years ago.
The Timing Isn’t Entirely Rosy
Interestingly, the $500 million financing comes during one of Cooper’s more complicated stretches in the public eye.
Her Unwell beverage operation, launched with Nestlé and sold prominently through Target, is reportedly being discontinued after less than two years. The line expanded from hydration drinks into energy, protein, and focus products, but remaining inventory is expected to be sold through this fall.
Unwell has also faced scrutiny over its workplace culture. A Vanity Fair investigation earlier this year included allegations from current and former employees about Kaplan’s management style. Cooper has disputed the broader portrayal of the company.
And Unwell’s relationship with Alix Earle, once one of the network’s marquee signings, ended when Earle’s “Hot Mess” podcast left the company.
From Barstool Contract Dispute To A $500 Million Company
There’s a pretty remarkable full-circle element to all of this.
Back in 2020, Cooper and Franklyn were locked in a very public fight with Dave Portnoy and Barstool Sports over their contracts and ownership of “Call Her Daddy.” Cooper ultimately made the crucial decision to return to Barstool, continue the show without Franklyn, and secure a path toward ownership of the intellectual property.
That decision laid the groundwork for the $60 million Spotify deal.
The Spotify deal helped lay the groundwork for Unwell.
Unwell helped produce the $125 million SiriusXM agreement.
And now an outside investment firm led by one of Hollywood’s most powerful dealmakers has agreed that the company Cooper and Kaplan built is worth $500 million before WTSL’s investment is even added.
Cooper started “Call Her Daddy” as a podcast. Eight years later, investors are valuing the company built around it like a serious Hollywood media business.
