“I Walked Away from Millions”: Alex Cooper on Bad-Faith Deals and Brand Integrity
In a candid conversation on The Burnouts, Alex Cooper opened up about building Unwell from a bootstrap startup into a multi-vertical media company — and why she’s no longer afraid to claim the CEO title.
“There’s a huge part of you that people don’t see”
Call Her Daddy has always been the main thing that I’ve led with. They think it’s all Call Her Daddy and no business.
For years, Alex was known primarily as the host behind one of podcasting’s biggest shows. But behind the scenes, she was negotiating $60M and $125M deals, launching a podcast network, and building out film, TV, live events, merch, and a creative agency — all under Unwell.
It is hard to go from the Call Her Daddy girl to also a CEO and a founder.
She admits that publicly embracing the founder identity felt strange at first — but necessary as Unwell grew beyond a one-woman operation.
A day in the life: chaos, candy, and boardrooms
Alex’s weeks swing between high-level acquisition meetings, post-production edits on Netflix and Hulu reality shows, and her weekly Call Her Daddy interview — which she now treats as “the candy of the week.”
That’s my favorite thing to do. I get to pop in, do my interviews, but the behind the scenes is chaos at all times.
Most days, she’s at Unwell’s office, delegating across divisions with Matt — her business partner and husband — while leading a largely female executive team.
How Unwell makes money — and what’s the “cash king”
Unwell’s revenue engine is diversified:
- Podcasts (AdSense, host-read video ads, rev splits with creators)
- Film & TV (output deals with Netflix, Lionsgate)
- Live events (thousands of attendees, brand integrations)
- Merch & consumer products
- Creative agency (multi-year brand campaigns, starting with Google)“In a beautiful way, the podcast division is really the cash king… now the creative agency has been basically going toe-to-toe.”
Video host-read ads (VHRs) alone have transformed CPMs — worth “10 times more” than audio-only reads — and helped Unwell exceed first-year targets.
Inside the mega-deals: Spotify vs. Amazon
Alex revealed her landmark Spotify deal was chosen over Amazon because it offered guaranteed money with no download benchmarks — a rare structure at the time.
I didn’t have to hit benchmarks. I didn’t have to hit anything… It was a really crazy deal.
But by the time she renegotiated with SiriusXM, distribution flexibility mattered more than exclusivity. YouTube, live events, and merch integration made being everywhere more valuable than being locked behind a paywall.
Being able to be accessible everywhere became more important than the money. And then the money ended up just happening to still be there.
“Wait — no”: taking control of commissions and backchannels
Early on, Alex caught a subtle but costly industry norm: agencies expecting deal proceeds to flow through them first, letting them book the full amount as revenue before forwarding the talent’s share.
Wait, no. I want that in my bank account and then I’ll send you your 10%.
She also instituted a hard rule: keep incentives clean. Her agent and lawyer shouldn’t be friends; cozy backchannels lead to talent losing money.
I made sure in the beginning days that my lawyer and my agent hate each other.
The biggest mistakes: trust, documentation, and walking away
Alex’s costliest errors weren’t financial but reputational — trusting verbal agreements that later shifted. Now, she documents everything.
I’ve walked away from like millions of dollars because I’m like, that’s just too much… you threw things in there at the last minute because you were getting greedy.
She’s learned to read the room early: if a negotiation starts in bad faith, it’s better to exit than oversaturate her brand.
Hiring, culture, and the “work hard, play hard” standard
Unwell hires specialists from Disney, Netflix, HBO, Microsoft, and SoFi, using a four-round interview gauntlet before reaching Alex and Matt.
If you don’t want to work your ass off, then don’t come to Unwell.
The culture is intense but rewarding — from working on the Hannah Montana special to last-minute creative pivots. Equity and milestone-based incentives keep top operators aligned.
PE, acquisitions, and the next level
While Unwell has been self-funded and profitable every year, Alex says scaling to acquire major podcasts will require outside capital — ideally from partners, not just funds.
It’s not just money, it’s also people… We want to do a multi-year deal. We want to have the television, podcasting, all of it gobbled up here.
Decision-making with Matt: “We don’t really ever disagree”
Alex and Matt split domains by strength: he leads systems, finance, and pattern recognition; she leads creative and brand.
The minute it comes to creative, he’s like, ‘I agree with you. You know that better than me.’
Matt’s evolution from film/TV producer to business-focused CEO has been a major force multiplier for Unwell.
On being misunderstood: “I deserve to be where I am”
Alex acknowledges the narrative that she’s “cold” or overly ambitious — but refuses to perform false gratitude.
I’m not going to do a shtick. I deserve to be where I am. I’ve worked my ass off.
With Call Her Daddy at its biggest ever and Unwell driving culture in the Gen Z female media space, she’s learned to let the noise fade.
I will go away when everyone wants me to go away, but it’s like you’re thriving. It’s never been more successful.
This recap is based on Alex Cooper’s appearance on The Burnouts podcast. For the full episode, click on the YouTube link at the top or listen wherever you get your podcasts.
