WTSL Backs Unwell at $500M // What Cooper Plans to Buy

–COMPANY: Unwell–

Overview

• Digital media co built for Gen Z women
• Spans podcasts, social, film/TV, live events, and a creative agency
• Co-founded 2023 by Alex Cooper and Matt Kaplan, who serve as co-CEOs
• Self-funded from founding until Aug 2026
• Operates under holdco Trending
• Roughly 100 employees
• HQ in New York

Company Highlights

• Call Her Daddy is the #4 largest podcast in the US (Edison Podcast Metrics)
• 13.3M monthly Call Her Daddy downloads (Podscribe est)
• 12 shows in the Unwell Network
• 70M women reached monthly
• 100M followers across the ecosystem
• Unwell Creative Agency clients include Google, Babylist
• There are press reports of team and leadership challenges. You can Google those – I don’t know what’s true VS speculation. Overall, there are some growing pains that need to be sorted.

Founding Story

• Going back to the early days…
• Cooper and Sofia Franklyn launched Call Her Daddy in 2018. Barstool signed them about a month later, on a 3-year deal that gave Barstool the IP
• In 2020, contract talks blew up. The show went dark, Barstool founder Dave Portnoy said publicly he was losing about $100K per missed episode, and Franklyn walked. Cooper then re-signed solo. The deal that brought her back had the IP reverting to her in the future. Her line to Fortune: “The moment Dave Portnoy was like, ‘I will give you your IP,’ I was like, ‘Great, I will do anything'”
• Cooper served out her Barstool term and then signed with Spotify in June 2021, a deal reported at $60M+ over three years. I believe Barstool kept no economics in the show, just a merch collaboration
• Cooper and Kaplan (married 2024) launched Trending in 2023 as the holdco for their ventures, and the Unwell Network followed in Aug with Alix Earle and Madeline Argy as founding talent
• Kaplan brought ACE Entertainment, his prod co behind To All the Boys I’ve Loved Before and XO Kitty. Per the co’s release, ACE’s “production, financing, and distribution infrastructure” folded into Unwell from the start
• Disclosure: I worked with Kaplan and various members of the Unwell team during my time at AwesomenessTV

Business Model & Services

• Podcast network…
• 12 shows. SiriusXM holds exclusive global ad sales rights to the audio and video eps, so Unwell does not sell its own network inventory. Fees come from the SiriusXM agreement (est $100M+ over 3 years, signed 2024) less rev share to hosts.
• Unwell Creative Agency…
• Launched Oct 2025. Creative and media work for brands, with Google and Babylist named. Project and retainer fees.
• Film and TV…
• Netflix (Icebreaker, Let’s Marry Harry), Hulu (Love Overboard, plus the Call Her Alex doc), Disney+ (Hannah Montana 20th anniversary special). Production fees and backend.
• Live events…
• Theater-scale tours plus branded activations at SXSW and Vegas. Fees via ticketing and sponsorships.
• Consumer products…
• Unwell Beverages, launched with Nestlé at Target in Jan 2025. Wound down Aug 13, 2026.

Ownership

• Cooper and Kaplan retain majority ownership post-investment
• WTSL’s stake was not disclosed

Financials

• Unwell is private and has never disclosed financials. Cooper told CNBC the co has been “profitable since day one” and that the round “wasn’t about needing cash infusion.” The only revenue benchmark we have is from the SiriusXM deal mentioned above.

Select Capital Markets History

• 2023: Cooper and Kaplan founded Trending, self-funded. Unwell Network launches in Aug
• Jan 2025: Unwell acquires the Going West and Cheers! podcasts, terms undisclosed
• Oct 2025: Unwell Creative Agency launched as its own entity
• Aug 12, 2026: WTSL makes a strategic investment at a $500M valuation

–INVESTOR: WTSL–

Overview

• Investment firm founded by Patrick Whitesell, co-founder of WME and former Executive Chairman of Endeavor
• Focused on media, entertainment, and sports
• Backed by Silver Lake with a reported $250M commitment
• Jason Lublin, Endeavor’s longtime CFO, joined as President and Partner in June 2025
• Josh Pyatt joined as Partner in 2026 to run WIN Artists

Founding Story

• Here’s an executive summary, because the Endeavor unwind is quite complicated → Silver Lake took Endeavor private in a ~$25B deal that closed in Mar 2025. Whitesell cashed out and departed, reportedly taking $100M at closing, and as part of the same transaction Silver Lake committed $250M to seed WTSL. 
• Separately, because Silver Lake co-CEO Egon Durban had bought about 7.5% of the Raiders, NFL conflict rules forced WME to divest its football representation biz. Whitesell took it and relaunched it as WIN Sports Group.

Three-part operating structure

WTSL is not just a check writer. There are three pieces of its business.

• The investment arm buys minority stakes.
• WIN Sports Group is a full NFL representation business, repping Joe Burrow, Justin Jefferson, and Nick Bosa. 
• WIN Artists, launched Mar 2026 under Josh Pyatt, manages athletes and entertainers building companies outside their primary field.

What’s noteworthy: WTSL bought ~10% of Peyton Manning’s Omaha Productions in Mar 2025, and twelve months later WIN Artists launched with Omaha named as a client. So they first bought an ownership stake, and then layered on their agency service offering.

One structural note. I couldn’t find a Form D for WTSL in SEC full-text search. A Form D is the short filing a private fund or company makes when it raises money under an exemption from full SEC registration, and it’s usually the first public datapoint from a fund. No Form D + a single named backer + the word “initial” attached to that $250M suggests the structure is a balance-sheet holdco VS a committed fund with a defined life. Aka long term, flexible capital that’s attractive to portfolio companies who don’t want to operate under a ticking clock. 

Investment Portfolio

WTSL doesn’t publish a portfolio list. A few write-ups attached a list to this deal, but I couldn’t confirm most of it. Here’s what I could verify via quick research:

• Mar 2025: ~10% of Omaha Productions at a valuation north of $750M, per CNBC sources
• Jun 2025: joint venture with Universal Music Group on artist and estate IP outside recorded music, terms undisclosed
• Mar 2026: led the Series A in Working Capital Partners, which lends against athlete and entertainer future revenue, terms undisclosed
• Aug 2026: strategic investment in Unwell

–DEAL DETAILS–

Overview

• Announced Aug 12, 2026
• WTSL makes a strategic investment in Unwell at a $500M valuation (unsure if pre or post money)
• Forbes framed the investment as into “The Unwell Network” specifically, where other outlets said “Unwell” broadly
• Unwell’s first outside capital since its 2023 founding
• Cooper and Kaplan retain majority ownership
• Key deal terms are undisclosed

Strategic Rationale

Investor (WTSL):

• Buys a minority position in a founder-controlled, profitable media co. Similar to the Omaha deal seventeen months earlier
• Gets exposure to a top-5 US podcast without buying the whole business
• Can attach WIN Artists to the roster like it did with Omaha Prod
• Whitesell spent twenty years doing talent deals at WME, expert in the asset class
• Whitesell: “Alex, Matt, and the team have demonstrated an exceptional ability to anticipate where audiences are headed”

Company (Unwell):

• Cooper says the co didn’t need the money, which means the funding is for growth and acquisitions
  
• I’d guess this wasn’t a quick process. A profitable co with no funding need doesn’t run a capital raise process… it takes meetings until an investor has an aligned vision and cultural fit is strong
• Brings Endeavor-grade dealmaking to a corp dev function that was just stood up in 2026 under Samir Sama, ex-Raine Group
• Cooper: “the company is now also poised to accelerate our media platform’s growth through acquisitions and investments”

Post-Deal Operations

• Cooper and Kaplan stay on as co-CEOs
• Joanne Bradford, hired as President in Apr 2026 out of Honey, SoFi and Pinterest, runs the operating business
• No announced leadership or structural changes tied to the investment
• Unwell Beverages wound down the following day

–WHAT ELSE I FIND INTERESTING–

Nobody in creator-led media has grown primarily this way…yet

Personality-led media co’s typically build their audience and capabilities organically, VS growing inorganically through M&A.

For example, Dude Perfect took $100M+ from Highmount in 2024 and spent it on a Texas HQ and executive hires, not acquisition targets. Dhar Mann built a YouTube studio to 200 people and a 125,000 sq ft Burbank lot without doing any acquisitions (though he hired a head of corp dev out of Jellysmack last year, so that may be changing). Mythical is an interesting datapoint… they bought Smosh out of the Defy bankruptcy in 2019, sold a majority stake back to the founders in 2023 while keeping a minority piece, and have since been divesting non core assets like the Sporked sale to Savage Ventures (our analysis). 

Going back even further, The Ringer (led by Bill Simmons) and Team Coco (led by Conan O’Brien) both exited for nine figures without ever buying a company. Barstool (led by Dave Portnoy) did two small bolt-ons early on, but the talent and show roster was built, not bought. 

The strategy is the same across all of them, which I wrote about back in 2020 (our analysis). Lead talent-as-founders with real taste, curate and empower the next tier of talent behind them. As I put it then, “many of the most popular fan favorites on the Barstool roster of 70 personalities were incubated from within,” and Simmons “uses his taste and instincts to curate a talented pool of personalities that align with, and expand the scope of, his voice.” Then as part of that strategy, companies often strike a few tentpole deals that lift everything underneath it. Team Coco did that, with a premium talent partnership like the Literally! with Rob Lowe show. Of note, the flagship show Conan O’Brien Needs a Friend was the anchor that incubated the whole network, and up-and-comer creators including his long time assistant, around it (our analysis).

As we assess the current creator-led media landscape, the closest precedent is Steven Bartlett. His prior agency business made a few small tuck-ins back in 2022 and 2023. But the creator company he’s building now was built organically (our analysis of their recent fundraise). And he came up in the business through agencies, so he was buying in a market he already knew. If Unwell acquires agencies, they’d be running that trajectory in reverse, going from media and audience into services.

Of course, the organic growth path for creator-led brands isn’t a sure thing either. 

Bloomberg’s Ashley Carman just published a deep dive on Audiochuck, which is an organic build…Crime Junkie is still the #2 podcast in the US, and last year Ashley Flowers took $40M from TCG (our deal analysis), hired executives, and set out to diversify the business beyond herself. Since then roughly 30 of 100 employees have left including the new CEO, the subscription product plateaued around 75,000 members, the second-biggest show got canceled, and former programming partners are suing. Carman’s read is that it speaks to “the difficulties creators have when trying to diversify their businesses beyond themselves, having to cede control and partner with new people.”

Same problem Unwell has. Flowers hired to solve it, where Cooper plans to buy. 

Of note, I don’t think this is only about agencies. Cooper’s line in the release was about accelerating “our media platform’s growth through acquisitions and investments,” which is broader than services. My takeway is that the target list runs across talent relationships, new show formats, and agency capability all at once… and they already bought two podcasts in Jan 2025, so the template exists on the media side too.

Which raises a question; do they have leadership who can acquire AND run social agencies, or is that outside the current in-house expertise? WTSL brings real deal chops, but integrating agencies post-close and continuing to grow them thereafter is a different beast entirely.

Marketing agency consolidation is something we’ve covered extensively on our deal blog, where the simplest industrial logic is cross-selling more services into more brand relationships. It just hasn’t been the growth engine of a personality-led media co before. New precedent, and we’ll be tracking it closely.

What we found when we sized the Unwell network

We did a review of the assets that could be part of this deal, starting with the network talent and shows.

The cleanest third-party data comes from Edison. Call Her Daddy is the #4 podcast in the US. No other Unwell show appears anywhere in Edison’s Top 50.

On magnitude, we use Apple US ratings counts as a rough proxy: Call Her Daddy has 163,458 against 17,365 for the other eleven shows combined. Cooper’s show is roughly 9x the rest of her network put together.

A caveat on that proxy…ratings accumulate over a show’s life, so an older show looks bigger than it actually plays today. But the gap here is quite wide and noteworthy.

There also seems to be two content networks, not just one.

Going West does 10,562 Apple US ratings on 2,667 YouTube subs. Audio-first, true crime, a 700+ episode back catalog that Unwell acquired in Jan 2025. In Your Dreams does 136 Apple US ratings against 27.9M YouTube views. Video-first, built in house.

There’s no single metric that values both halves; the audio AND the video businesses. Which is exactly the convergence we walked through in the Backyard Ventures analysis last week (our analysis)… podcast businesses are video businesses now, and the operators who win are the ones who can sell across both. Worth noting SiriusXM took audio AND video rights back in 2024 when they did the deal with Unwell. They saw it coming.

Which raises the question: what’s actually in this deal?

Forbes framed the investment as into “The Unwell Network.” Every other outlet said “Unwell” broadly. The beverage biz wound down the day after the announcement. ACE Entertainment still runs its own website with no Unwell branding on it. And we don’t know whether the SiriusXM contract sits inside the perimeter of this deal or alongside it.

For a diversified talent business, that distinction is key to the total $500M valuation. I want to know what’s in and what’s held back from the new WTSL partnership. At that valuation range, my bet is that it includes the SiriusXM partnership.

Here’s what I do find telling. Shows two and four by audience, Going West and Cheers!, were both acquired in Jan 2025. Terms undisclosed, and Going West still credits Dark West Productions as producer, which might signal more of a distribution or licensing deal than a clean buyout. Either way, a chunk of the network was bought or licensed rather than built.

Therefore, Unwell isn’t proposing something they’ve never done. They ran the experiment eighteen months ago at a smaller scale, and it seems to have been a good bet. With funding behind them I’d expect that to accelerate, through licensing as much as acquisition. More shows means more inventory, and inventory is what the agency business needs to sell against.

The Unwell ad sales rights are the prize

SiriusXM holds exclusive global ad sales rights to Call Her Daddy and the entire Unwell slate: audio and video, and current and future shows.

That’s the single biggest margin opportunity in the business, and Unwell currently doesn’t control it.

Last week we walked through what these sales rights and capabilities are worth. Acast paid $20M for Backyard Ventures, a podcast and creator ad sales business doing $16.1M gross bookings at 12% adjusted EBITDA, which equates to a 10x valuation multiple (our analysis). Backyard charges “industry standard” commission on brand revenue, which is likely in the 20-30% range based on our own client experience. Audioboom, which is public, runs a 21.5% gross margin on the same model.

So call it 20-30 points of margin that currently sits with SiriusXM rather than Unwell – though the counterpoint is that SiriusXM might be taking a smaller % spread when you net the upfront minimum guarantee paid each year to Unwell. Which siriusXM is prob glad to do in order to have a tentpole asset in its offerings for media buyers, which improves its client pitches and overall network sell-thru).

This makes me think about Omaha Productions as an informative benchmark. 

Omaha counts Silver Tribe as a key sales partner, and Silver Tribe was itself bought by TPG-backed Initial Group last December (our analysis). So even with WIN Artists servicing Omaha, the company still needed a third party for D2C and brand partnerships. Unwell bringing network ad sales in-house would be a different answer to the same problem.

Buy or build that function and Unwell recaptures the spread, and more importantly owns the brand relationships directly. Those same relationships are what you cross-sell agency services into (and those new services are what Unwell now plans to go and acquire). That is very likely the math Unwell is running ahead of its renewal with SiriusXM, and in turn, it gives them significant deal leverage they don’t have today.

This is timely. The deal was signed Aug 2024 on a reported three-year term, but content didn’t start rolling out until 2025. If the clock runs from signing, they’re prob in negotiation talks right now. If it runs from launch, they have another year.

What I do know is that SiriusXM is in a strange spot to be renewing into. Their merger talks with iHeart collapsed in June over which stations would need divesting. Podcasting is their bright spot, up 30% in Q2. And they just became the exclusive US audio ad sales rep for YouTube, which their CFO said won’t contribute meaningfully until the back half of 2027.

So the Unwell renewal probably will be sorted before the YouTube deal pays off. Either SiriusXM needs this asset more than ever to hold their podcast momentum, or they’re stretched heading into it. Their equity market cap is roughly $9.5B against $9.45B of long-term debt, and content dollars are visibly migrating toward sports. To be clear, $42M a year is only about 3% of their guided free cash flow, so affordability isn’t the question…appetite might be.

(btw we represent some agencies that could bring these sales capabilities to Unwell. We look forward to talking with their corp dev team).

How Cooper got her IP back, and why it matters

I had Claude run the USPTO records.

Barstool filed the Call Her Daddy trademarks in Nov 2018 and owned them outright. The 2020 renegotiation is when the ownership changed. Portnoy had said publicly, “We’re not gonna do this deal if you don’t give us ownership of Call Her Daddy because it makes no sense.” Within weeks he’d conceded it to keep Cooper from walking. The IP assignment to Cooper was recorded in Nov 2021, and the marks now sit with Cooper’s holdco IP entity (TRNDG IP, LLC) alongside the Unwell portfolio.

Another interesting factoid: Barstool filed a Call Her Daddy mark for alcoholic beverages in 2019, took five extensions, and then let it go abandoned in Mar 2023. Cooper’s team filed Popular Vodka in Nov 2024.

There’s more research one could do here and I don’t know whether Barstool kept any future rev share in that 2020 deal. Portnoy has said the ongoing relationship was merch plus an unnamed project, with no revenue guarantees.

Of note, none of this changes the WTSL deal. But it matters for anyone building a talent holdco, because big talent will come and go, and how entry and exit deals get struck is something that any holdco operator needs to know how to navigate. Alix Earle walked out of Unwell with the Hot Mess IP in Feb 2025. Cooper walked out of Barstool with hers. Talent holdcos will be a foundation of the modern creator economy, and the ones that last will get these structures, in both the coming and going of talent, right.

On the $500M valuation, I just don’t know

A valuation attached to an undisclosed check is not a significant valuation benchmark IMO. 

If the check is 1% of the cap table, that number cost the buyer very little to agree to. If it’s 20%, it’s a real price with real conviction, and likely material capital, behind it. Nobody has reported any of these details, and the press outlets can’t even agree whether it’s pre or post money.

We see much of this in early fast-growing industries, which includes the creator economy. People react to a headline instead of doing the work to understand what sits underneath it, and there’s almost always more nuance in these deals than gets reported. If you’re buying or selling in this space, knowing that difference is how you make good strategic decisions.