In short
Podcast Episode Notes: Alex Cooper: What Nobody Knows About Call Her Daddy and my $100M+ Media Empire
Podcast Overview Podcast Title: The Burnouts with Phoebe & Sophia Hosts: Phoebe Gates and Sophia Kianni Guest: Alex Cooper Focus: Startup insights, business strategies, and the complexities of being young professionals.
Episode Description In this episode, Alex Cooper, creator of *Call Her Daddy* and co-founder of Unwell, discusses the unseen business intricacies of her success, including the journey from a scrappy startup to negotiating multi-million dollar deals, and insights into podcasting revenue.
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Key Discussions
Introduction
- Cooper expresses how she wants to share the less visible aspects of her career, especially her evolution from podcast host to CEO.
- The hosts reflect on their early interactions and experiences with Cooper, acknowledging her significant role in their entrepreneurial journey.
A Day in the Life
- Cooper describes the daily chaos of running Unwell, which includes producing several reality shows, overseeing acquisitions, and preparing for her *Call Her Daddy* interviews.
- Highlights the balance between creative production and business management.
Revenue Generation for Unwell
- Primary Revenue Streams:
- Podcast advertising (particularly through *Call Her Daddy*).
- Live events, merchandising, and consumer products.
- New creative agency launched to streamline brand partnerships.
- Importance of Adaptation:
- Shift from traditional media to a more nimble, bootstrapped approach.
- Focus on acquiring existing successful shows to expand reach.
Negotiation and Deal-making
- Discussion of significant deals with Spotify and Amazon, including:
- How deals are structured (cash flow, performance metrics).
- The importance of understanding contract terms and ensuring favorable conditions.
- Cooper emphasizes the need for clear communication and documentation in business dealings to avoid misunderstandings.
Mistakes Made
- Reflects on trust issues and the necessity of having agreements in writing.
- Shares experiences of walking away from lucrative deals to maintain integrity and brand reputation.
Company Culture and Hiring
- Description of Unwell's culture as “work hard, play hard,” emphasizing high standards and a dynamic work environment.
- Insights into the hiring process, focusing on attracting top talent from reputable companies and the evolution of roles within their growing team.
Decision-Making Dynamics
- Cooper and her partner Matt exhibit a collaborative decision-making approach, leveraging their individual strengths.
- There’s an emphasis on the importance of having a strong team and surrounding themselves with competent individuals.
Gender Dynamics in Business
- Cooper addresses perceptions of women in leadership roles, the balance of ambition, and the stereotypes that accompany success.
- She discusses the emotional aspects of business decisions and maintaining resilience against external judgments.
Future Directions
- Discussion about potential partnerships with private equity to expand Unwell’s capabilities.
- Interest in finding the right partners and investors to scale the company further while remaining true to their vision.
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Key Takeaways
- Evolving Roles: Transitioning from a public persona (podcaster) to a business leader requires adaptation and constant learning.
- Complex Revenue Models: Diverse income streams are essential for modern media companies, especially in the podcasting landscape.
- Documentation is Crucial: Proper documentation and clear communication can prevent costly misunderstandings.
- Empowering Culture: Building a supportive, ambitious culture fosters growth and satisfaction among employees.
- Resilience Against Misunderstanding: Maintaining self-awareness and confidence is key to overcoming stereotypes and external perceptions.
Conclusion The episode encapsulates Alex Cooper’s journey through the complexities of entrepreneurship in the media industry, shedding light on the often-unseen elements of building a successful media empire. The discussion emphasizes the importance of adaptability, clear communication, and fostering a strong, supportive workplace culture.
Follow the Burnouts:
- [Phoebe Gates](https://www.instagram.com/phoebegates)
- [Sophia Kianni](https://www.instagram.com/sophiakianni)
- [Alex Cooper](https://www.instagram.com/alexandracooper)
- [Call Her Daddy](https://www.instagram.com/callherdaddy)
- [Unwell](https://www.instagram.com/unwell)
Support Phia: Download the fashion-tech app [Phia](https://www.phia.com) to support the hosts.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOReflecting on Success and Relationships
0:46 to 1:32
Alex discusses her journey and connection with the hosts.
“I was just saying before we started recording, like, I'm so proud of you guys.”
The Multi-Dimensional Identity
1:33 to 2:28
Exploring Alex's transition from podcast personality to CEO.
“And you've done$60 million deals,$125 million deals.”
A Day in the Life of a CEO
2:29 to 3:56
Alex describes her daily responsibilities at Unwell.
“But that's what I feel like people want to know.”
Understanding Unwell's Revenue Model
3:57 to 5:30
Alex explains how Unwell generates income across various streams.
“So if I usually have an interview, I will stay, work from home and prep my interview all morning and then go to the Call Her Daddy studio, do the interview, and then I'll come to the office after.”
The Evolution of Advertising and Partnerships
5:31 to 8:12
Alex delves into how advertising has changed and their key partnerships.
“So when it really all started, when Matt and I were dating and he had a film and television company and he had output deals with Netflix and Lionsgate and he was making film and television.”
Navigating Big Deals in the Industry
8:13 to 10:32
Alex shares insights on her major deals and their structures.
“And then on top of that, the output deals that we have with the Netflix's, the Lions Gates of the world, we're also making money through film and television.”
Navigating Podcast Deals: From Spotify to SiriusXM
14:00 to 18:04
Learn about the intricacies of negotiating podcast deals and the evolution of podcasting revenue models.
“I was just trying to look at how will I be able to execute this type of deal in a capacity that I feel like I'm actually capable of because I want it to be a good partner.”
The Importance of Trust and Communication in Business
18:04 to 21:30
Discover the lessons learned from negotiating contracts and the importance of clear communication in business relationships.
“So you sign like one hundred and twenty five million dollar deal.”
Building a Successful Team: Hiring Practices and Company Culture
21:30 to 28:01
Understand the hiring process and the importance of a supportive company culture in a rapidly changing environment.
Building a Strong Team Culture
28:01 to 30:05
Learn how the interview process and team culture at Unwell promotes high performance.
“Now it's like we have multiple people in the brand division and our CMO versus our like all these people have very clear specialist guidelines of what they do and what we like that they do and what they need to execute.”
Show all 16 chapters
Expectations and Growth at Unwell
30:06 to 31:26
Discover the expectations and growth opportunities available to employees at Unwell.
“But at the same time, there is going to be moments where we are having to adjust last minute.”
Funding and Future Plans for Unwell
31:27 to 33:11
Understand the funding strategies and future plans for scaling Unwell's operations.
“And so right now, Matt and I are completely funding this entire company and it has been incredible and lucrative.”
Collaboration and Decision Making
33:12 to 34:48
Explore how Alex and Matt collaborate and make decisions within their business.
“It's interesting, I think, more in terms of who are the people with these funds.”
Matt's Influence on Business Strategy
34:49 to 36:46
Learn about Matt's strengths and how they contribute to the overall success of their business.
“Like if you both disagree on something, how do you come to a conclusion?”
Navigating Gendered Business Perceptions
36:47 to 39:08
Discuss how gender perceptions can affect business relationships and personal branding.
“And I think it's so funny because when I met him and him being a film and television producer, I to watch him grow into more of like this business lane.”
Closing Remarks and Gratitude
42:00 to 42:10
Alex expresses appreciation for the opportunity to be on the show.
Transcript
Automatic transcript. May contain errors.0:00The energy was so fucking good. 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. I think it's all Call Her Daddy and no business.
0:09Sophia:I want to go to the super famous 60 million, 125 million dollar deals. What was the most stressful moment? No one teaches you this shit. It is hard to go from the Call Her Daddy girl to also a CEO and a founder. So I've walked away from like millions of dollars. Oh my God. The worst mistake I made. Alex Cooper, welcome to the burnouts. Thank you for having me, guys. This is obviously extremely full circle for us because we've learned so much from you. So we wanted to use this as an opportunity to have you talk about business, unwell, call her daddy, all of it. And also, of course, your relationship with Matt.
0:45Oh, my God. And Matt. No, I love it. I was just saying before we started recording, like, I'm so proud of you guys. And it's so funny to think back to when we first met to then our episode of Call Her Daddy and you launching and you being sleep deprived and just launching Fia and also doing the episode of Call Her Daddy and all happening in like 24 hours of each other. It was such a rush to be a part of it with you guys. And I'm just so happy. And you guys have had such success. And I love knowing you guys.
1:13Sophia:We're honored because you took a bet on us. I mean, so early on before you had like fully founded Unwell and stuff is when we pitched you and you said we should do a podcast about starting the business. which has become so core to everything we've done. I mean, it's in every investor deck. It's become our entire community that we've created. But I also want to use this to get into, because I feel like there's a huge part of you that people don't see on Call Her Daddy, which is you're a business mastermind. And you've done$60 million deals,$125 million deals. You're running this entire business with Unwell.
1:42Sophia:You guys now have like, you know, you have the drink, you have an investing arm, like you're founding all of these and acquiring all of these new podcasts and stuff. So I'm excited to get into the business side of your stuff as well. Oh, my God. I know. I feel like it's something that I don't talk about as often because publicly, obviously, Call Her Daddy has always been the main thing that I've led with. So that's been kind of who I've been known as, which I love. And I've been a host and a producer. But I think once Unwell launched, it was almost like I needed to build it first to be able to really understand like how I would want to publicly speak about it.
2:15Because it is hard to be a woman who is multidimensional and to go from the call her daddy girl to also a CEO and a founder, which I recognize is kind of a weird thing to publicly say because I don't think people think that at all. They think it's all call her daddy and no probably business. But that's what I feel like people want to know. I know I want to know, like as a founder, as a CEO, what does a day in your life look like? Like, how do you balance all of this? It's every single day is very different. And I think about when Unwell started, it was so different than what it is today. But when it started really at its core, it was just this little media company where Matt and I were merging our companies, which I can get more into.
2:53But now on a day to day, it's like there are some days where I am in a full edit with our unscripted reality department division. We have multiple reality shows out right now. We have one with Hulu. We have one with Netflix. And so we are producing these shows. And so we are in the pre-production of casting and choosing who's going to be on these shows and location and scouting. Like I'm a part of all of that. Then to the shoot and then to the post-production. So my whole day could be a post-production process on our unscripted. And then going into an acquisition meeting where we're talking about in the beginning with Unwell, we were launching shows that we were believing in people and we still are doing that.
3:35But now we're also looking to start leaning into our acquisition model, which would be to acquire shows that already exist that have large platforms. And so all of these things are really what my day to day is like. And then I go and once a week I do my Call Her Daddy interview. So it's like, it's kind of crazy, but I love it so much. And if anything, it's made me actually love Call Her more because it's almost like that's like the candy of the week like that's my favorite thing to do I get to pop in I get to do my interviews but the behind the scenes is chaos at all times and also dealing with employees and hiring and all of that wait I was gonna say because are you in the office five days a week yeah what does that look so most of the time if I have an interview for call her daddy our main office for unwell um is where everybody works that's not where call her Daddy is.
4:24Call Her Daddy is like 15 minutes away. So if I usually have an interview, I will stay, work from home and prep my interview all morning and then go to the Call Her Daddy studio, do the interview, and then I'll come to the office after. But every other day I'm in the office at my desk taking meetings. That's crazy. I want to see an Alex Cooper day in the life of you at the office. It is kind of crazy because Matt and I have offices right next to each other and we are constantly in each other's offices or we don't see each other at all during that day. Like it's very case dependent on what those meetings are because I think Matt and I have really, we are very good at delegating between like what he's really good at and strong at when it comes to business and what I'm very good at.
5:09And so I think we've both kind of been able to run with different parts of the business, but they all do kind of coincide together at some point, but we each take leads on things, if that makes sense.
5:19Sophia:That makes a ton of sense. And can you walk us back into like, how does Unwell make money? Like what is the divide between, you know, ad sales, brand deals you're doing on the personal side? I'd love to understand that a little bit more. Yes. So let me go back to the beginning of Unwell. So when it really all started, when Matt and I were dating and he had a film and television company and he had output deals with Netflix and Lionsgate and he was making film and television. Great. My dream. I went to school for film and TV. I was like, I wanted to be a director one day. So I was always fascinated in his side of the business.
5:52And then I had the podcast. As we continued to date, Matt was looking to potentially sell his company. Someone had come to him and been interested in buying his company. Throughout that process, he realized that there was such a turn happening in media where it would be more advantageous to hold on to it and to grow it and grow different verticals because essentially media companies now are so different than what they used to be. These conglomerates that were more traditional media companies that you had to have a huge name like a Disney next to you. Now you are able to kind of bootstrap it and do it yourselves.
6:28And then you can sell it for even more. So Matt was like, wow, like they were talking about, you know, they want to acquire event companies and they want to acquire podcast companies. And he's like, I'm sitting there. I'm like, I could just do all that myself. And then we're looking at each other and like, we could do all of that ourselves? Like, why aren't we doing this? So we put Unwell together, which is basically our film and television department and Matt's entire finance and production backend. And then also my podcast knowledge of wanting to launch a podcast network. And that's kind of where it started.
6:57So the majority of where we were initially making money was on the podcast side. As we signed podcasters, we have a rev split with our podcasters and we make money off of AdSense. call her daddy is kind of like the mothership where we have my initial a huge deal that I get every three to four years and that is mostly on AdSense yes um but it's so crazy because even when I signed my deal with Sirius XM let's say VHRs didn't even exist which her video host read ads and I say that because it's like the funniest most random thing that came about where before I would read it on a microphone and you wouldn't see my face reading ads.
7:38And now the CPM has gone, has skyrocketed because when you see my face reading an ad compared to just my voice, it's worth like 10 times more. And so that wasn't even in my initial contract with SiriusXM. And so we had to like go back to the drawing board because now we have all these integrations that are literally 10 times more money. And so it's that already has changed the game in terms of what we have gotten back in terms of what the initial deal was and what they wanted us to make each year. And the first year we had exceeded everything. And it was like so shocking. And VHRs were a huge part of that business.
8:15So that was exciting. And then on top of that, the output deals that we have with the Netflix's, the Lions Gates of the world, we're also making money through film and television. As we have expanded, though, we have our live events business, which has been so lucrative for us because we are bringing thousands of women. Like for example, Las Vegas, we had almost five to 7 ,000 women come through Las Vegas on a weekend. We put live programming together. We put these live events and these shows and it was variety shows and we have all these different talents. And so that's a great moment to integrate brands.
8:54So all of these different brands paid to come and to be a part so they could be touch points for the women. So there's all these different avenues of money making. Also, we now just launched our agency, which has been wild to see how it started really where we would work with brands and they would always have a third party agency. And so all these agencies come in and not to shit on them, but like we kept finding that they didn't understand Unwell. And so they're pitching Unwell to a brand and we're like, wait, you don't get it. This is how we would do it. So all of the brands we started to work with would fire the outside agencies that they worked with.
9:30And we're like, can you guys just do it? And so that was when Matt and I looked at each other one night. We're like, why are we not just launching our own creative agency? And our first partner was Google. And it's a multi-year deal, which was so incredible for Unwell to be able to, you know, work with a company of that stature. And that's another great avenue for money making, right? we will basically have a client like Google. They are looking for us to produce commercials to get their products out there or to get whatever message they want that quarter out there. And we as the creative agency will create the creative and we have the production backend to facilitate an entire campaign for these companies.
10:12So now it's like all of these different verticals, film and television, podcast network, the live events, the merchandise, the consumer products and now the creative agency and it's a lot wait and then how did that relate no that's amazing i mean it's so cool yeah literally whoa raking it in but i mean it's so interesting because you're so right when unwell started it was very much like this initial bootstrappy startup and now you guys have expanded so much i would be curious if you feel comfortable explaining like actually revenue wise how does that split into the different divisions like is one that's the cash king one that's a startup like how does it look so i would say that in a beautiful way the podcast division is really the cash king um but now i would say the creative agency and we have had this thing running for about five to six months not even um that has been basically now going toe to toe because all of these agencies are looking to sign multi-year deals So when you're sitting with a Google and they're offering you and, you know, a huge paycheck to basically bring to life our idea, like it's like 120 million.
11:23I don't know if I'm allowed to say, but I think what's exciting about that is we have basically said the difference that we've been watching as a company that has been so in the weeds of all of these changes and being kind of at the forefront of media right now and being so nimble is all of these companies are looking for something bigger than a one off. and influencers to their credit in the beginning days were so incredible because they were able to put their camera and film an ad and it was amazing and it was lucrative. Now, because of the oversaturation, I think people are less interested in these one-off deals.
12:04And so yes, you could sign a year deal with an influencer and get 10 videos or you could sign a multi-year deal with Unwell who has an entire production office, an entire finance office, who has hundreds of employees. we have directors we have line producers we have all these people so you essentially have the built-in agency that you would also have to get and an influencer so it's all in one so we can think like a cmo we can activate like an agency and we can produce like a full production house which is something that's i think allowed for us to garner these type of deals pretty quickly and that has kind of changed the game and i think with film and tv we've been able to get more selective.
12:48Matt and I have been with the output deals that we have, we could be churning out more content. But I think with film and television now, because of social media, you want to be doing one big movie a year or you want to be doing one television show a year. So I think we're spacing it out more and we have that ability because of the other revenue streams at the company.
13:16Sophia:I'm curious. I want to go back to the super famous 60 million,$125 million deals. Can you explain like just to our audience, like how are those structured? Is it like just all cash up front? It's like, hey, this is over time and you have to hit certain KPIs. And what was the most exciting moment of those deals for you and the most like stressful moment? Oh my God. Okay. So let's go all the way back. So I will never forget when I was about to sign with Spotify and it was between Amazon and Spotify. I don't think I've ever said that because at the time it was like, these are two huge companies. And there was so much that I was looking at both companies and recognizing the value of both company um spotify to be honest it was the same amount of money basically and a little less work so i was like why would i not do that yeah and so because with the amazon deal it was like so many more episodes and there was um it was more behind like certain paywalls and like it was just like a lot as a creator at the time who didn't have a company behind me and it was just I was a one woman show.
14:23I was just trying to look at how will I be able to execute this type of deal in a capacity that I feel like I'm actually capable of because I want it to be a good partner. When someone is handing you that type of money, you want to make sure that you're exceeding their expectations. And so with everything that I looked at with the Spotify deal, I felt like I actually could wrap my head around the deliverables. So it would be 52 episodes a year. Every single month I was paid a check and it was all guaranteed money, which was so crazy. I didn't have to hit benchmarks. I didn't have to hit anything.
14:59which like now in hindsight I'm like oh my god Spotify I love you so much Daniel forever love you it was a really crazy deal and the other deals I had I did have to have like hit a certain amount of downloads and then you could x but I think understandably what Spotify was trying to do at the time was they were trying to gobble up all of the main large competitors in the space and they wanted every big name to be on that platform because I had an exclusive deal so I was also taking a hit by taking that Spotify deal because I was going essentially behind a paywall and I was exclusive to Spotify.
15:33You could no longer find me on Apple, which was my biggest platform at the time. And I converted and all of these millennial Gen Z women came to Spotify and it was fabulous. And I think what was fun for me was I was kind of their Trojan horse when it came to getting women for podcasting onto the platform and then obviously Joe for men. And it was successful. I think I yes, I made all that money, which was great. But I think in terms of the new deal I have. One, I think I've gotten so much more savvy in all of the different like caveats and carve outs that you can do in podcasting. Also, podcasting has just expanded when I first started.
16:13Like if you think about it, I had to beg Spotify to let me do video promos on Instagram. Like they're like it wasn't even a video podcast at the time. Think about that. It was just audio. so like the the industry has transformed so significantly like putting a product in a video now is you can get paid for that back then there was no way to monetize that it was just audio so when I got my deal then with Sirius XM I was recognizing that there were so many more levers that I could pull and I think as much as I loved my deal at Spotify it felt very limiting and singular by the time I had hit that three-year window I was like there's I want to do live events.
16:53I want to be able to like integrate merch into selling on the platform. I want to be able to have comment sections be actually go viral. And that's probably going to happen on YouTube. And so I think being able to be accessible everywhere became more important than the money. And then the money ended up just happening to still be there, obviously, because of the brand recognition. And also now there's more integration opportunities. So SiriusXM has been such an incredible partner. they've integrated into our live events. We have been able to monetize in the show in a capacity that I could have never imagined.
17:28So I think that has been wild. And with Sirius, the money is, yes, there is guaranteed. And then in a positive, which I didn't have at Spotify, there's also ability to make fresh cash on top of that initial deal that you read about. So that has blown my mind because like I said, when we had our first year and we exceeded and we hit our numbers and then we were making fresh cash in the first year. I was like, holy shit, this is this is so incredible because they've been such good partners that they want to do that and they want to try to make as much obviously money with us as we can. So it's been kind of crazy.
18:06And then how does it work with? So you sign like one hundred and twenty five million dollar deal. How much of that goes to an agent? How much of it goes to you? How much of it goes to the company? How does that work? I love my agent. I love my agent, but but love you. So we had to have a really honest conversation when I was going into negotiating this new deal with Sirius XM. And I think just like anyone even listening to this, I want to preface like I have made so many mistakes in business and so much of it, especially as a young woman, is no one's going to give you the answers. No one wants to give you the answers because no one really wants you to succeed.
18:50And so, so much of what I've learned has been through just experiencing it and really observing. And if anything, trying to get my nose into rooms and like trying to listen and trying to ask questions and then they don't answer. And whenever someone doesn't want to answer the question, I'm like, okay, now I need to go know that answer because clearly that's important information that they're gatekeeping and they don't want me to have. So in the beginning days, I was so green. I didn't know what I was, what I didn't know. Right. Um, like I remember when I signed my Spotify deal and thank God, I forget, I think it was like Matt and my parents.
19:25And I was like, Oh, it's so weird. Like they're going to deposit the check to UTA and then they're going to send it to me. And I, and then, and then as I said that, I was like, wait a second. And I realized like, So Spotify was like, where do we send the X amount of million dollars per month? And I was like, I owe. And then UTA is like, they'll send it to us. Then we'll take our percentage out and then we'll send it to you. And I was like, wait, no, I want that in my bank account. And then I'll send you your 10 percent. Because that doesn't make sense. But understandably, as an agency, you want that X amount of millions of dollars coming into whatever agency, UTA, WME, CAA, and then giving it because then they can put that as basically that is in their revenue for the year.
20:13And so I'm like, oh, I see how all this is going. And so not even that they were being shady. It was one of those just things that clearly many talent just didn't know that. And they're like, oh, great. They'll just send me my check through my agency. agency and immediately I sniffed that out and was like wait no no no you're gonna send that to my bank account and then I'll send you your 10 so these are little things that you just don't no one teaches you this shit right and so I started to learn that the way things go in business it can go the way you want it to go especially if you are the one that is creating the revenue but when so many systems are put in place and so many people have relationships to each other like I know that my agency is friends with the Spotify people.
20:57It all is very interconnected. And so I learned very quickly that I never wanted my agents to be friends with my lawyers. If anything, I wanted them to hate each other. And I didn't want the company that I was working with to have done deals, hopefully prior with any of the people that I was working with. And if they had, like it was not a friendship because all of these people then talk and that's how people lose all their fucking money because everyone's working behind your back. So I made sure in the beginning days that my lawyer my agent fucking hate each other and I don't have a manager wow okay well you're a genius for doing that that makes no but I think that's like people skills like that's what's weird is like again and thank god for my parents and my husband like talking about this shit when you are in business you kind of just you can so easily get bulldozed in rooms where especially as a young woman where you're like okay and you're looking around and you don't know really what's going on and you feel like an idiot if you're like can you explain that to me but I think from a very young age my mom always instilled in me like you need to nope you go in and talk to your teacher and no you go in and you talk to the doctor and I always was like mom I want to I literally want to kill you like I don't want to do that but it was such a good skill that she taught me from such a young age because it's not even advocating for yourself it's actually using your voice to understand what you are agreeing to is sounds so straightforward and it's not because you can be like yes sounds good and then if you ask someone back what did you disagree to you're like I don't know because in these rooms with all these men it's really intimidating so each deal each opportunity I think I've just gotten more savvy um what was the worst mistake you made oh my god i think i've made mistakes in terms of trusting people where i wish i would have put more things in writing so that i could back up what really happened because i think when business it's so crazy how much emotion can get tied into business as much as everyone's like it's business it's not personal everyone takes it fucking personal especially if it is your own company or your brand and so many people that I'm sure you guys are dealing with it's their money they're wanting to know what's going on like there's so much emotion and I think sometimes the biggest mistakes I made was being forthright and honest up front and and having a conversation with someone and then it turning around and someone being like oh Alex Cooper did this and I'm like wait that never happened but I guess I technically should have put that in writing so that I so I think now I put everything in writing I put everything in writing after I have a meeting I send the follow-up of like and this is what we discussed and this is what you said and I take notes of everything every single phone call if I know it's a little sus or something take full notes chronologically put the time the date and exactly the transcript how much did those mistakes cost you I think more it's more like reputationally than money um I would say I've gotten pretty good about not.
24:03Yeah, but then, you know, there are some times where it's been like, oh, I'm going to lose. I'm going to lose a deal because we all agreed to something in the room and you looked at me in the eyes and you told me this is what we were going to do. And we were all about to sign the paperwork. And then I was about to go do it. You changed your tune and you slid something in there that my team found. And now we're already starting on a bad faith negotiation. And so then I ended up just pulling out and it would be like a couple million dollars that I would walk away from instead of sacrificing my brand and my name.
24:34And because I'm very particular about what I put my name in my face next to, because at some point you're like, how much are you going to oversaturate yourself? So I've walked away from like millions of dollars because I'm like, that's just too much. And you threw things in there at the last minute because you were getting greedy as a brand or a company wanting me to do something that I don't feel comfortable in. And in the initial conversation, that's not what you presented it as. And I also, even if they rectified it, I think that you have to listen to who you're sitting across from in business.
25:02Like when someone is, if something's already going a little sour in the very beginning, instead of trying to fix it and be like, but it's there will be another moment like that because a lot of it is people. You need to like who you're in business with. And I think sometimes people don't talk about that enough. It's like, oh my gosh, but if they're so smart and if they're qualified and it's like, yeah, to a point. And I'm sure you guys have dealt with that where you're like, this person's genius.
25:26Sophia:yes you're like don't get me started one bag of eggs spoils the whole batch ego is the death especially in tech and i hate to rag on men particularly with men in tech it is so crazy that's also it's so funny i'm dealing with like almost the opposite where matt and i laugh about it he's like i am one of four men basically at this company we have almost a hundred employees at this point and it's about six men and we're like there's no men at this company by design but we're like I think we could like throw a couple more in there like they now it's like so much like like female energy I'm like okay maybe we could use like a little sprinkle of a couple more men but then we have our who does Matt work with Matt works with all women it's so funny when he's in every single day I'll walk in and it's Matt and then it's all women and then his main our main head of production is a man but he lives in vancouver so he's never in person so it's matt mainly with our head of podcasting is a woman our head of um social media is a woman our head of marketing is a woman our head of partnerships is a woman our head of the creative agency is a woman our president of the company is a woman um our head of merchandise is a woman our hr is a woman so all the heads of the company and how did you hire all these people okay it has been such a journey.
26:46And I will say, starting as a startup, which I am sure you guys can relate to, again, you have a vision when you're hiring of exactly the role you need. And then as you grow, what you hired that person for, as your company grows, the role changes. And so I give a lot of credit to a lot of our executives have been able to be really nimble and mold themselves throughout the years in adjusting and be like, OK, I'm I'm going to be malleable because in the beginning you hired me to do this. And now, oh, my God, our podcast division started as this. And now we're doing acquisition deals. And now I need to transform and do this.
27:24So there's so much that they've had to transform. And so a lot of the places we look to hire are places that we respect. Disney, Netflix. We have someone that's worked at HBO. We have people who have worked at Microsoft. We have people who have worked at SoFi. How do you interview these people? Well, we thank God our head of HR is fabulous. And she has been so incredible in really getting into the nitty gritty of we're looking for specialists at this point at Unwell. We have very, very specific roles that we are looking to fill. And I think back in the beginning days, it was more like just a head of brand.
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27:59And you're like, what the fuck does that mean? What do you do? What does that do? Now it's like we have multiple people in the brand division and our CMO versus our like all these people have very clear specialist guidelines of what they do and what we like that they do and what they need to execute. So when we are going into our interviewing process, our HR starts it with a we give her the clearest indicator of exactly what this person needs to do and what their background would probably look like. She does the preliminary first round and then it goes through a tiered system. We have like, I would say, four different executives who we trust, who will meet with these people individually.
28:36And then it gets to Matt and my desk. So they kind of have to go through like a round of like four interviews.
28:48Have you gotten anyone where everyone else is like them and you say no? You know what? Interestingly, no. there's been a couple where I'm like, I am interested to see what you guys see here, but I respect all of you. So I'm going to, I'm going to pull back on this. And some have worked and some haven't. And I was like, I was right. Oh, really? Yeah. Yeah. There's been a couple where I was like, cause again, it's more for me, like a personality thing. I think that like anyone that is coming to work here is going to, and if they have the right credentials are going to be capable of working hard it's actually now about can you adjust unwell is a really really fabulous and incredible and i think inspiring place to work but it is fucking hard yeah describe the culture okay matt i always laugh about this because matt's like you can't say it online but i can like if you don't want to work your fucking ass off then don't come to unwell and i'm like yeah i guess i can't say that because people would be like she's so difficult to work with She's such a monster, like blah, blah, blah.
29:49But Matt is right. We have such a culture of work hard, play hard. And I know that's like overused, but it's true where it's like you are going to get to experience some of the coolest things in the world. Like some of our company right now is working on the Hannah Montana special. And we're like, oh, my God, like this is the coolest thing in the world. Right. But at the same time, there is going to be moments where we are having to adjust last minute. You're going to have to work hard hours. There's going to be moments where creative is it is subjective and taste is subjective. Not really, but not really to Matt and I, but to some people.
30:26And so we really have a standard that we hold people to. And so it is it's a grind. It is a grind because we expect the best and we want to be the best. And I think everyone at this company can feel we are at such an exciting time where Unwell is driving culture right now. We are at the forefront in terms of a media company. I really believe no one else is doing what we are doing in the Gen Z female space. And we are getting affirmed by many companies that that is the case. And so we are we're on an uphill battle right now to keep that momentum. And so every single person at this company is bought in and needs to be like, you are growing personally, whether you want to run this company one day or you want us to write you the biggest, best letter of recommendation when you want to go work at Disney one day.
31:15Whatever you see for your path, like we want to help provide insight and feedback to everyone because I recognize that Matt and I have our dream. We're getting to run this company. This may be a stepping stone for some people or this may be where people end up retiring one day. they can decide that um and you're gonna work your ass off is that how it works this is something that's like hasn't happened yet but we have been looking at investors um i think there's been pe opportunities um because with private equity i think when we're talking about acquisition deals for the podcast right like to go buy and gobble up some of the biggest podcasts that you can think of, that's going to take a lot of money and a lot of cash.
32:01And so right now, Matt and I are completely funding this entire company and it has been incredible and lucrative. And we've been in the green every single year and that's been great. But to get to the next level, I think that's going to take a certain person to come in as a partner to invest money to the capacity where we can take it to the true next level. And if that happens, then yes, there would be an equity play for people.
32:28Sophia:It beckons the question of why not, you know, you could do with a private equity firm. Why not just spin up your own fund that you and Matt are the managers of and then just get a bunch of LPs? Like, I mean, how much you you it's like you're in my conversations at dinner with Matt and I. We have been talking about this for so long. And we've also waited so long because we were like, how long can we basically like squeeze the lemon of like, have it be our own cash, have it be all self-funded and see how genuinely far we could take it and how big we could make it and how many new IPs we could build and how big the brands could get to then be like, OK, now we need another another lever to hit.
33:09And I think that's kind of where we're sitting right now. It's like those conversations have been had. I think private equity is. It's interesting, I think, more in terms of who are the people with these funds. I think Matt and I are looking for partners, to be quite honest. I think Matt and I only have so many hours in a day and we are interested in working with people who can walk into a room and it doesn't just have to be Matt or I who is sitting at the head of the boardroom and saying, this is what we want to do. We want to do a multi-year deal. We want to do an output deal. We want to have the television, podcasting, all of it gobbled up here.
33:44Like there's only so many times Matt and I can do that conversation. So I think it's also about the right people back to it's not just money. It's also people. So this is all in the works. No, that makes sense. I mean, what I was also going to say is, at least for us, a huge learning has been some of the best people that we've attracted to our startup have been heavily incentivized by equity. Because if they have a portion of the outcome and you're raising venture funding and the valuation continues to increase, then they actually have really tangible upside. Which is why I was interested for your executives, if they're incentivized by a profit split or by equity, how do you keep really top players in the game for as long as possible?
34:21So there's a lot of people at the top who have benchmarks that they can hit that they are incentivized to grow their division, to get it over to the finish line and then some, which is, I think, extremely, I agree, important for people to have that incentivization. So they actually are showing up to work every single day to know that if what I put into this, I actually will get out of it. Yeah, it's like sales, like milestone based incentives, I definitely think works well. And I wanted to shift gears a little bit to also understand for you and Matt, how do you guys split decision making? Like if you both disagree on something, how do you come to a conclusion?
34:58Okay. This is like a boring answer, but we don't really ever disagree on things. And we have yet to have a moment where... Or is there something you think you're really good at and then Matt's really good at? Like there will be moments where Matt and I will definitely be like, oh, I think we should do it this way. And he's like, but the minute it comes to creative, he's like, I agree with you. Like, you know what? I trust you. You know that better than me. I think with Matt, he's so good with systems and business where he will recognize, no, this is like this is the pattern. We need to do it this way or this is this is an opportunity.
35:37We need to take this. I just feel like we've done such a good job, though, in we're so in lockstep right now, especially with every single decision of this company has been built on Matt and I's both of our brains. And so we haven't been really faced with a moment where we disagree because we just want the best for this company. And has he ever looked at one of your contracts and said, that's all wrong, we need to redo it? Like when you guys first started dating, did he give you any business advice? Oh, my God. Matt is brilliant. Like, I love being in a room with Matt because and I think everyone does because he is so fucking brilliant.
36:19Like, I will give him his flowers. He is so aware of this industry. He has had decade long relationships. He knows so many people. He's watched so many deals go down. And I think he has had kind of this front back seat to watch all of these things happen in the industry from a very young age as a kid. And now he has been able to kind of put into place, yes, what he watched, but what he wants to do differently. And I think it's so funny because when I met him and him being a film and television producer, I to watch him grow into more of like this business lane. It has been really incredible because I remember we were at the Google shoot.
37:08We were filming the campaign and he had hired his friends to direct it who created Catfish. Henry and Rel, shout out. We love you. And they were amazing and they're doing their thing. and Matt's in the trailer pacing back and forth on calls. And I'm like, oh, I feel so bad. Like he's missing out on the creative because like he's taking a call about whatever. And he, at the end of the day, we get into the car and he looks at me and he goes, I just had the craziest realization today. This is the first time in my life where I wasn't sad that I wasn't getting to be a part of the creative because I'm so fulfilled by the business side of things right now.
37:48he's like I've never felt more stimulated he's reading everything Matt is up at 5 a.m reading every single possible thing that you can possibly see in the news in business everything he's just a sponge right now and he's so good and I think he's such a great leader so I've learned so much from him and I think we've also had to balance him and I as a duo and we're looking for more people to surround us so it's not just Matt and I walking into rooms being like this is what we want because it's hard to like negotiate your own deals. So, but then also it's like, you then have to trust your agency.
38:23I don't have a manager. You have to trust your lawyers. We have incredible people around us, but it's taken a while and it's taking some shifting to actually get people that we think, I believe in you to advocate for us. Cause Matt and I are the type of people that are like, no one can do it better than us. I'm like, there's no one that can walk into that room and actually get the deal done in the way that Matt and I want it. And so we're both like, all right, practice it again. Tell us what you're going to say. And we're walking it through with these people because I'm like, we know exactly what we want.
38:50So sometimes it's frustrating. And sometimes we do walk into the room and we'll just be like, fuck it. Let's just ask for it. But sometimes that's the name of the game, right? You have to have the agents and the lawyers go in and kind of like schmooze everyone up and lube them up and tell them what they want. So sometimes Matt and I are like, oh, fuck, we wish we could be in there.
39:06Sophia:But it's fine. It's fine. That's so funny. Do you feel like when you stop working with certain people like Alex, do you feel like these things become gendered where people are kind of like, oh, it's a catfighter. things like that when you know it's really a business transaction it sounds like yeah I think I've definitely gotten better at
39:27actually taking the emotion out of that aspect I think that I've like I just understand my position and I I think I am not someone who is very apologetic about my success and I've talked with my therapist and my mom about this a lot. I think that there are people who do a really good job that I'm sure you guys also know, where like they come online and they're so grateful and they're so grateful. And then you meet them and they're like a fucking asshole in person. You're like, wait, that's a whole shtick. Like, I'm not gonna do a shtick. I deserve to be where I am. I've worked my fucking ass off.
40:01And so I think there is sort of this narrative around me that people think I'm cold or, you know, I'm gonna fuck people over to get what I want. When you experience the culture, when you meet me, when you know me, like you don't say those things. So I think I just have to let that roll off my back because at the end of the day, like the deals are coming in, the money is being made, the audience is still there. Call Her Daddy has never been bigger. The numbers have never been bigger. The brand IP has never been worth more. So it's like, I will go away when everyone wants me to go away. But it's like, you're thriving.
40:36It's never been more successful. So I think I also have to take it with a grain of salt when people spin this narrative. And so I'm like, I kind of have had to just let it go because it doesn't, it really used to upset me. Being misunderstood is really hard and it's upsetting. And especially when you're like, wait, I want to correct this. But I've just found the more you try to correct it, the more that you're actually putting yourself in a position that's inauthentic. And so now I kind of just sit back and I just chill. Alex, thank you so much for coming on the burnout. Oh my God. I am so honored that I finally got to do this and I'm so proud of you guys.
41:15And I'm so happy as a woman in this industry to know both of you. You're such an inspiration. I obviously follow everything you guys are doing. I have Fia on my phone. I'm always using it. My little toggle beep, beep, beep. I'm like, boom. Yes. I want to find the other option. Thank you very much. Save me some money. You guys are brilliant and everything you're doing is such and inspiration and the fact that you have your business plus you've done such an incredible job with the podcast you guys work so fucking hard and everyone at the company talks about it like you guys are a force to be reckoned with you're constantly uploading your cutdowns like I think a lot of times my biggest fear with podcasters it's like it kind of has to be your full-time job and this somehow always looks like it's your full-time job meanwhile like they literally just started their whole fucking company and they're coding in the back rooms but then they're somehow managing to do all this like you guys are one of one so thank you so much for obviously giving me the time and letting me come on the show
From the publisher
Alex Cooper breaks down the business side nobody sees: how she and her husband Matt built Unwell up from a scrappy startup, how podcasting revenue really works, and what rules she learned the hard way negotiating $60M and $125M deals.
Alex Cooper is the creator and host of Call Her Daddy and the co-founder of Unwell, a modern media company spanning podcasts, TV/film, live events, consumer products, and a fast-growing creative agency.
Chapters
00:00 - Alex on going “full circle” and revealing the CEO side
02:00 - Building Unwell from Host to Founder
02:45 - A day in the life
05:20 - How Unwell makes money
07:15 - The video ad revolution
08:10 - Live events, merch, and consumer products as revenue engines
09:05 - Launching the Unwell creative agency
10:50 - Which division is the “cash king” (and what’s catching up fast)
13:30 - Inside mega-deals: Spotify vs Amazon
16:15 - Why distribution mattered
18:30 - Agents, fees, and who should get paid first (her “wait—no” moment)
21:10 - The hard rule: keep incentives clean (and avoid cozy backchannels)
23:00 - The biggest mistakes: trust, documentation, and walking away from millions
26:20 - Hiring top operators and building a high-standard culture
31:40 - PE, acquisitions, and what it takes to go to the next level
34:25 - Incentives for execs
35:05 - How Alex and Matt split decision-making
39:25 - Handling narratives about ambition, success, and being misunderstood
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About The Burnouts
The Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, athletes, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to reveal the real stories behind ambitious careers.
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