Casey Adams: From Neck Brace to MediaKits Exit at 26

0:00All right. We are here on the Rebels podcast. Today, I'm not recording in Silicon Country. I'm here in beautiful Venice, California, at the Lighthouse Studios. Didn't even know this place exists. It's pretty dope. Um, while I was on vacation this year, I got reached out to by, uh, an entrepreneur named Casey Andrews. Admittedly, did not know that much about him but, uh, when I looked him up, I was like,"Whoa, this guy's had an awesome career." I sit down to find out today this guy's 26 years old, making me feel old as fuck but also very inspired. Uh, I had a lot of mentors in my career who used to tell me,"When you don't know what the answer is, ask the youngest person in the room. They usually have the correct answer." And after my conversation with Casey today, I found this is a guy who you're gonna know and want to know in the future. Um, a- an incredible story of perseverance. Uh, you know, started podcasting at 16 years old, so he's 10 years into the game. He's interviewed icons like Larry King along the way. He has

1:03built and sold a business already at 26. You don't wanna know what Jingle Jared was doing at 26, but certainly not founding companies. I was a hot mess playing in bands, but I love it. Um, you're never too young to start, you're never too old to keep learning is, uh, some of the lessons of today. But this is the Rebels podcast, brought to you by Rebel Audio. If you are curious about starting a podcast, you can definitely go to rebelaudio.ai and start your first podcast today. And I hope you enjoy this conversation with Casey on the Rebels podcast, brought to you by Rebel Audio, and, uh, away we go. Let's rock and roll. All right. So, uh, we're here with Casey Adams. Um, another incredible entrepreneur, rebel, uh, outlier in the media space. Someone who, uh, immediately when we started connecting, I was like,"This is somebody I need to know." Uh, this is someone who... You know, I g- I get hit up a lot just by, by

2:06random people, and in the LinkedIn world of things, some of it is just, uh, sometimes, like, sales calls or spam and something like that. Yeah, yeah. I was like,"Oh, this is, like, a real dude. Dude, like,""And we probably got lots to talk about." Yeah, tons of rabbit holes. And, yeah. And, and just, uh, the more I've learned about you, the more I'm like, um, very curious about your story. Um, and today in our, uh, Podcastpalooza event where I... He just interviewed me for his incredible show. I figured we'd turn the tables, and now, uh- That's great ... get some time learning about you. So, um, I know we d- you know, we've, uh, w- fairly new to each other's worlds, but just remind me, uh, where are you from originally, what brought you to- Yeah ... LA, and- Yeah, of course ... uh, yeah, what's the backstory? Yeah, I appreciate you having me on, uh, your show, you know? We're back to back. I always like that. Um, and yeah, you know, I- I've been in LA now for about six years, but I'm born and raised in Virginia, so East Coast. Actually, I have family in, in Tennessee as well. All right. So we love that. Um, but yeah, born and raised right, right outside of Richmond.

3:06Very small town. I always like to say the, the least entrepreneurial family- Hmm ... in that sense. And, um, you know, I'm one of three. I have two older brothers. I'm the youngest of the bunch. And yeah, I, I think my entrepreneurial journey, I always like to preface, you know, it kind of started when I was in high school by accident, where I... It was freshman year going into sophomore year. I was almost paralyzed playing football. I was ended up in a neck brace for six months. And I went from this kid who had dreams and aspirations to play lacrosse at UVA during freshman year of high school to in a neck brace, can't play football, can just barely is able to come back and play lacrosse in a couple years for my senior year. But it was during that six-month period where I just, like, lost all sense of identity and who I was as a 15, 16-year-old kid, and sort of first three months were just the most depressing period of my life. But was able to kind of build back my identity, which kind of fell into the world of business, entrepreneurship, um, kind

4:07of reading about founders- Hmm ... uh, on, on social media and these different rabbit holes, and that sort of planted the seed for what has now become my, my entrepreneurial journey over the last eight plus years now. So. You've done a lot in those eight plus years. First, before we get into the, even the, the founding of Business One, uh, you were telling me that at 19 years old, you interviewed Larry King. How did that come about? It, it's, it's a crazy story. So, you know, I was looking to say, and this is why I was, I was so excited to also have you on my show in the sense of, like, your appreciation for the medium of podcasting and what you're building in it. Uh,'cause for me, like, podcasting has been my, like, my whole entire foundation of my career, where I started the show when I was 17 years old, literally in my bedroom on a pair of wired Apple headphones. Wow. And, you know, kinda coming out of that neck injury, for context, I probably had a six month where I was just, like, learning as much as possible about, of, like, business owners, and I quickly realized if I wanna start a business, I know nothing about anything. How do I go sit down and interview and learn from people? And I

5:10started my show, uh, this is kind of tied into the Larry King story. Started my show December 2017, and you know, back in those days, like, the ability to start a podcast was not as simple, and there just wasn't as enough platforms out there to make it very simple. So video wasn't even in the question. Mm-hmm. It was just me in my bedroom on a- Pair of Apple headphones. And fast-forward two years, I, I sort of caught the podcast bug, and I set a goal, and I wanted to do 60 interviews in 90 days. Wow. Because I ended up setting up a meeting with Gary Vaynerchuk in New York City, and I was like,"Okay, what am I gonna go talk to him about?" Um, and I got in touch with his, uh, right-hand guy at Instagram. He's like,"Yeah," like,"I'll set up 10 minutes with you and Gary." And I was just starting my show, so I blitz-scale it, I guess you could say, of, like, interviewing anyone and everyone in the world of business. Some of my young founder friends that I was meeting on social media who were 16, 17. That's crazy. Um, and long story short, Larry King, you know, this was someone that if you have your, like, dream list of guests, he was someone that was on that list from the

6:12moment I started because, you know, he had not only the, the best interviewing skills and my ability, but he was just blunt and real and authentic for his interview style. And long story short, um, I ended up interviewing, um, a guy named Tilman Fertitta, who's the owner of the Houston Rockets. Oh, yeah. And big restaurateur. One of my friends, uh, was working for him when he was coming out with his book called Shut Up and Listen. This was 20... Let me think. 2019. And after I interviewed Tilman, he invited myself and a lot of other creators that helped with the book promotion to the Mastro's in Beverly Hills. So I was living in Scottsdale at the time. Mm-hmm. 'Cause, uh, I didn't go to college. I moved to Scottsdale a month after I graduated high school. College is overrated. You know, and I could talk- Yeah ... about it for an hour just about that. But I, you know, I end up just going out to LA, walking into this dinner, not know who I was gonna meet or sit down with. It was probably about 30 people, and long story short, I end up sitting next to a guy named Chance King, who happened to be- Hmm ... Larry King's son. And I didn't realize until sort of the end of the dinner where

7:17Tilman Fertitta stands up, he's like,"Chance, it was such a pleasure being on your father's show today. You know, Larry is someone I've always respected, and make sure you send him my love." So by that time, like, me and Chance were just hit it off. We're both- Yeah ... 19. I'm 19, he's 20, and I was telling him all about my podcast before I knew his dad was Larry King. And by the end of the dinner, I know this, you know, it's like kinda just knowing when to ask, but not being- Yeah ... you know, like, not expecting anything. It's like- That's a skill. Yeah. And I, I think it was pretty much I left him with, like, you know,"If there was ever an opportunity to have your father on my show, like, he's someone I look up to, um, it would be such a privilege and an honor," and kinda left it at that. And this is where, and I'll kinda tie the bow on the story, this is where fate and sort of, uh, happenstance is like you can't make this up, where a week after I met Chance King, my girlfriend, now wife, at the time, we're walking around Century City Mall here in LA, and as we're about to leave, I see Larry King in his wheelchair- Unreal ... rolling around the corner. And I'm like,"What in the world?" So you have those

8:22moments in life where- Dude, that is, it, it, literally, that's the sa- That's the message. You meet someone once, and then you have the second accidental. Yeah. And it hooks in. Yeah. So you have those moments out, in life where I think it's like you have that gut of- Yeah ... being afraid. That's why I love that- Yeah ... Ari story of I'm like,"Oh, do I go say hello? He's in his wheelchair. I don't wanna bother him." Mm. But I get the courage. I go up, and I say,"You know, Larry, it's such a prev- privilege to meet you. I, I met your son Chance last week. I just wanted to say, like, I look up to you, and, you know, I've had my podcast for two years now, um, and just wanted to say hello and introduce myself." So took a selfie, sent it to Chance, and it was one of those moments where he's like,"Hey," like,"I'm gonna, uh, ask my dad if he'd like to be on your show." And about a week later, he was like, "Hey," this is around Thanksgiving time,"Hey, my dad said he'd be open to it. Like, when are you gonna be in LA next?" And I'm like,"Give me a date. I'll be there." Mm. And I remember, it was, like, December 10th, 2019. Oh, yeah. Um, I was 19 years old at the time, and I remember sitting in his studio waiting for him, and he rolls in on his wheelchair. And again, this is someone who's 87 years

9:24old, like, the absolute great in the broadcasting world, taking the time to be on some 19-year-old kid's podcast. Beautiful. And that really kind of instilled so many great life lessons during that time in my life. But I think that just speaks to the power of podcasting, the, the, the courage to know when to ask, um, and the butterfly effect of, like, those 60 or 100 interviews that I did beforehand is what gave me that opportunity to be prepared- And- ... for that opportunity ... the idea of, like, the curiosity of, like, at that age, you know, him saying yes to things. I think that's awesome. Like, that, you know, it's easier in life just to be like,"No, uh, not a good time for me," or,"I don't do that anymore." But the, the fact that he was doing that all the way until, like, those are the things as an entrepreneur you carry with you. Yeah. That's- And I- That's unbelievable ... I think too is that we all have those meetings or calls or things that maybe we don't wanna do, or we don't think it's a good use of our time sometimes. And I always go back, I'm like, Larry King took, you know, an hour and a half out of his day to come do this thing with me. Like-

10:25Yeah ... that was not something he was- No, that's right ... amped up about to go do It's like we're never too busy for, like- Yeah. I'm, look, I'm reflexing the muscle as well. Like, when I was running Jingle Punks, it was the nonstop Jingle Jared tour. Yeah. You know, refiring up the, the brain, the muscles, the engine of just being, like, const- in this creator economy, you know, also illogically saying yes to things. Like, I didn't even wanna go to Cannes Lions this year, but I was certainly glad that I did. Yeah. Um, so- Absolutely ... at what point did what you were doing with podcasting turn into your first entrepreneurial venture? Like, where did this thing, the rubber meet the road with- Yeah ... with your business life? Absolutely. That's a great question. And I think so much even, like, leading up to, like, 2019, even 2020, before I launched my first tech startup, MediaKits, which I'll, I'll dive into, like, I look at that era from, like, 16 to 19 of just, like, pure hustle. I got my first company that allowed me to have some money to travel and, like, pay for my own plane tickets was pretty much a local Facebook advertising agency where I was doing the Facebook ads and social media management for my local

11:28dentist- So cool ... my chiropractor. And I remember being 16, 17 years old, like, having these monthly retainers of companies that are paying me, where junior and senior year of high school, I, like, I think I missed 80 days of high school, like, convincing my parents, um, to he- like, let me travel to LA to interview Jay Shetty and Jake Paul- Wow ... and all these people. And I remember it was, like, one of those days where, like, I interviewed Jake Paul and Jay Shetty on the same day in 2018 when I'm 17 years old in high school. Yeah. And long story short, like, the three big things that I even tell up-and-coming podcasters today was like, know why you're doing it. It's a hard medium. There's a lot of in- you know, long format. It's hard to get attention. It's hard to build that, like, true listener base. But if you're clear with why you're doing it, it should never feel like that heavy lift. And for me, that was I wanna meet great entrepreneurs and individuals, I wanna learn from them, and I wanna create business opportunity, and I was extremely clear on that. And then I think that's what's led me to d- be doing this for nine years as a staple of content and, like, an

12:28educational pillar in my life, which then has opened up to now kinda get into the business context, like, so many doors for me, where, you know, it was- 2020, my past co-founder and I, we, we had this idea, um, which inevitably became MediaKits, because one of our good friends, uh, he was a big automotive YouTuber, his name's JR Garage, and, and I remember him, he came to us one day, and he knew we were in, you know, we were in marketing agencies. He's like,"Hey guys, I have a million followers on, on, uh, subscribers on YouTube. This big automotive brand wants to do a sponsorship with me. They asked for me for my media kit. Uh, can you help me make one on Canva or Photoshop?'Cause I need to send them this, like, one-pager." We're like,"Sure." You know, we kind of built this one-pager. It took us a couple hours. We sent it to him. He got the brand deal, and then probably two, three months later, he came back to us and was like,"Hey guys, this other company reached out, but since then I've grown 100,000 subscribers." Hmm. "My engagement rate's way different. I'm a much bigger creator on Instagram and Facebook. Can you go update all my numbers so I can resend it?" So that's when we

13:29kind of thought to ourselves, you know, why isn't there an easy way for social creators, uh- Smart ... just any type of social creator to aggregate all of their cross-platform data to easily pitch it and represent it to brands, given that EPKs and, like, the, a media kit was always a known thing. Hmm. So long story short, we are very naive, 20, 19, 20-year-olds. I moved to LA to kind of start this business and, um, you know, we initially set out to raise some money 'cause at the time, AI coding tools weren't a thing. We weren't technical, my co-founder and I. Hmm. And we needed to go hire some, a software engineer or two. Um, long story short, we ended up raising just about $1.5 million. It took us probably eight months to go do. I remember, um, one of my still board members, investors in my current company, Aristotle Loomis, I gotta give a big shout-out to him. I met him through Stephen Galanis, the CEO of Cameo. Yeah. And he was the guy in my life that, still is, like, held our hand through the process of like- Yeah ..."Hey, this is a safe note." Yeah. "This is how you take money. This is how you fundraise. Like, let's get into it."

14:30Um, but we ended up raising, you know, $1.5 million from 37 angel investors, and you'll love this and then I'll, I'll pause for a moment. Pretty much all of those 37 angel investors were past guests on my podcast. Hell yeah. From Wiz Khalifa's manager to- Business development on- Yeah ... steroids. Yeah. The get to know you, like, kind of thing. Exactly. It's genius. So that was a great, like, full circle moment for me to be like,"Okay, we wanna raise money. Let me start, go asking and pitching and sharing what we wanna go build with these very successful entrepreneurs," and it started a domino effect. And as of yesterday, it was five years as of yesterday from, we did this big launch party at, in 2021 with Wiz Khalifa performed. We had 700 creators, and then to make a long story short, 18 months later is when we got acquired by a, a big, um, um, talent agency in Canada called Viral Nation. So- Oh, yeah ... that's the, the, the long story short. How did they find out about you, and were you on an earn-out after they acquired it? So we, we... It's so funny. You brought this up in my podcast around, like, social

15:32media. The CEO, Joe, DM'd me on LinkedIn- Hmm ... uh, to kind of like,"Hey, saw what you guys are doing, and we're interested." They wanted us there for a little bit longer than we ended up staying, um, but I was always, I was only there for just under a year. That's a good earn-out. They were there for, like, up to four. Um- I had a seven-year, I had a five and a two. Wow. Which was wild. Yeah. Yeah. I think, too, like, the biggest thing, and I was also, like, learning from you in our past conversation earlier is for us, like, we were at this place in the business where as young founders, raised this money. We were going out to do a proper seed round after a harsh fundraising process. We finally got a term sheet, and we were floored about it, but then this acquisition conversation came up, and we looked at that as an opportunity to just get a win on the board, right? Hmm. It was very uncertain. You know, we were by no means in this, like, we have it all figured out just yet. Mm-hmm. Cap table, all the things you figure out as a young founder, where for us it was,

16:33like, getting a great win on the board and being able to utilize that into future ventures, and I think that's what my co-founder and I, Kieran, were so aligned on. Um, so I mean, that was just- I mean- ... one of those full circle stories that I think from the podcast to the fundraising to then executing People wanna know- Ourselves ... always, like, when is the right time to exit, and I remember the first company that I worked at in New York was called Heavy.com, and they had an offer for $250 million from Warner Brothers-... and all, like I stay in touch with these people to this day. It was my first job, and they turned it down. It was like that meme. He turned it down. I turned it down. Turned it down. 5, 10, 15. Exactly. Something like that. 250 something. They were much younger. Um, but they, I learned that, like, when you were young, you can always invent more ideas. I think when someone is serious about acquiring your business, you just know, you never know how the wave is gonna turn. Yeah. And you know, I joke that, you know, they said they bought me with my own money at WME-... because ultimately the revenue in the next several years made up for the

17:33entire purchase they bought us with. Yeah. But I- I mean, what advice would you give to first-time founders if they're just starting out and you, you know, you're struggling, trying to pay rent, and someone just goes,"We'll take this off your hands for a million bucks." Like, w- how do you balance that, you know, in your brain? I, I think there's three big things that I think about a lot still to this day with my current company, Listner.com, but re- I'm 26 now. Reflecting on the 20- You're an old man now. I know. Reflecting on the 20, 21-year-old version of myself when we were kind of even thinking about this acquisition that was on the table, I think the biggest thing that I've learned, and I've underst- I've come to understand this a lot from all of the great founders I've ha- I've had on the show, where it's like, hey, look, a, a huge part of business is not only proving it to others, to the doubters, the people that didn't believe in you, that passed on you, but most importantly it's, like, proving to yourself that you're capable. To take something from idea to

18:34execute and bring it to life, whether that's software or a real physical, you know, CPG-type product, and not only just launching it, but growing it, scaling it, sustaining it, or exiting it. And I think for us, like, the ability to go through, for me before I get to the, like, three core points, like, that full life cycle of a business, um, even though it was, like, an early win- Mm-hmm ... I learned so much, and I think my advice would be, not only to myself, but people out there, is- You know, I think when you're in, in this VC world, they're like,"Oh, don't ever tell a venture capitalist that you wanna get acquired." And I think, yeah- Mm-hmm ... there are exceptions to every rule, where it's like you get the Facebooks and all these founders that turned down on the billion-dollar offers. Yeah. Like, there's always an exception to a rule. But when you have something that you've built that you maybe feel like you've gotten it to the, the biggest and best place that you can based on the resources today, and the future's uncertain, and you also are kind of having partners that may wanna do other things, and you're early in the

19:35journey, I think you have to kind of balance like the time and effort ratio to outcome ratio to then understand that how do you take that as a lesson to learn and build from, and, um, to kind of have a, I guess you could say like a win on the board. I think entrepreneurship, you know, take it or leave it, people are measuring like the scoreboard from companies that go public to- Nothing makes me more marketable than the fact that I had an exit. Nothing makes you- Yeah ... more marketable than the fact that you... And I think that's a pure entrepreneur mindset, because I th- I describe it as like flipping houses or building apartment units. Like, I wanna get it to the point where it like is fully livable, scalable without me- Yeah ... and then move on to like the next thing. Like, I think for some people, staying in it for years and years is more of like a death sentence more than a, a treat. You know, like- Yeah ... the... And then again, not to discount, some people build incredible ongoing mom-and-pop businesses, whether it's like restaurants or, and, and plumbers or, uh,

20:39you know, people who just have like a s- a single idea. But I think that the, the game of entrepreneurialism, uh, the way that you've described it resonates the most with me. I love that. And, and I think too, it's learning from your story of, of how you've built and, you know, sold businesses of you couldn't... And this is what I always was like so fascinated with, and I still ask the question of like,"Oh, how did the WME conversation happen for you?" Still to this day, even though I've went through an acquisition, like I think so many young founders are just, they're unclear of how the end game comes together because it's all so different. It's all an accident. The whole thing- Yeah ... is an accident. Like fundraising, you can have a structured approach, but like the right buyer, you could think it's X, but it's really Y. And or maybe all those ideal buyers would never, you know, you talk to them and they're just like,"Oh, we would never buy this business." Well- And I think there's a lot of- VCs always want the certainty who's gonna acquire you. Not in a million years if you asked me to write down on a piece of paper in 2008 who I thought would buy my business, I would've said,"Oh, Sony, Warner, Universal, History Channel, NBC." Never

21:40in my wildest dreams would I would have said a talent agency. And like the- Yeah ... the world changes. Like the, the model of, of what you're building and why it's useful to somebody else is continually shifting on the chessboard while you're playing the game. Yeah. Absolutely. And I, I think too, I, f- so many, um, like my former co-founder, after we sold, he started, which I was a, you know, smaller partner in, um, an automotive- Hmm ... uh, a company called ShopGenie, which is an auto remba- auto repair shop CRM product where it helped auto repair shops sell more effectively and manage their entire operation. And- Cool ... two years into that journey, they got acquired by a huge, uh- Holy ... like private equity-backed company down in, in Texas. And I think not only seeing him do that again, but I think once you do it once, you prove to yourself and you understand the process of like what are the things that need to be in place, having your books clean, clean cap table- Mm-hmm ... capital efficient, knowing maybe a strategic acquirer that you could, you know,

22:44plant the seeds with early on. Like there's- Mm-hmm ... the strategy to the game that I think once you see it and you're in it, again, every business is different. Um, but I think from a tech perspective, like there's always gaps that need to be filled, and if you can service customers better- Mm-hmm ... have a single focus. We always like to say like we were an inch- Own a category too. Yeah. We were an inch wide and a mile deep. Like our name was mediakits.com. Yeah. Yeah. The easiest way to build- Yeah ... a media kit. And there's so many creator tools that I think did a lot of things good, but not one thing great, and I think that's what we tried to avoid early on, which then proved to be true. And I think that's something that as a, now building Listnr.com, it's like we're trying to take that a similar philosophy of like how do we do one thing great and then build off of that. So tell us, you know, what is Listnr.com?'Cause that's how you and I connected. Yeah. I was like,"This is cool.""This guy..." And, and first of all, like again, like I think it's a mutual admiration fan club here because you, I, I, I also didn't realize, uh, how young you were when you started. Like this is incredible. Like-

23:47I appreciate it ... you, it's like these are all just like the, the whole thing you present as someone who's been around the block for a while too. So that's, kudos to that. But- Appreciate it ... you know, when you hit me up, it was like certainly magnetized. So I was like, ooh, there, there's a lot going on in the podcast space. And trust me, I've met a lot of the people, and some of it's slightly, some of the personalities in the space are slightly underwhelming, but that's all, that's all good. Yeah. But you, you got, you have a, some like magnetic energy around how you build- Appreciate it ... what you're building. So what are you building? Yeah. And, and, and I would say same to you. I think, you know, and for the context, right, like the podcast industry, I, I've learned so much the last two or three years as I was launching Listnr.com where I ki- I came from the like creator lens of having a show, building creator tools. And the podcast business, like the nuance of the ad sales companies and how operate, networks operate, I wasn't too in that world. And I think as I was getting ready to launch Listnr, I learned so much of what you're talking about- Mm ... of like so much of the old school podcast industry is like these audio natives

24:50that turned podcasts that were resistant of video. And then you have this creator ecosystem that's like building the biggest shows that the podcast industry doesn't even like recognize as podcasts. And it's like, oh, there's this big disconnect of like- Mm-hmm ... where this is moving, but it's all moving to the same similar point. So Listnr.com, for context, we launched in April 2025 with the simple idea of how do we build the AI-powered analytics and intelligence system for modern podcast publishers? And what does that mean in, in simplistic terms is we aggregate audio, video, and social data to help the top 1% of publishers represent their data and their campaigns more effectively- Hmm ... to their advertisers. And we like to say like we help- The top publishers put their best foot forward when it comes to representing their actual show. And kind of to kind of peel the layers back a little bit, like we've gone after the biggest shows in the world as a initial go-to-market because they typically have the most analytics that they- Yeah ... have for their show in terms of video views and downloads. They're the ones that

25:52are monetizing the most effectively. And third, like they have a lot of problems in terms of how they're representing their YouTube, their social clips, their audio data. They all live on different platforms. So what we build, and this is a long-winded answer, but I just wanna like speak to it a little differently- Mm-hmm ... is, you know, teams that are running 20 to 50 show networks, they can finally pull in their audio data from their podcast hosting platforms, their YouTube long form data, and then all of the social clips that in my opinion, in our thesis, like is a part of the show. Absolutely. Like it is not just a promotional vehicle, it is the host itself. For a while, clipping has been like the dark arts of promotion-... but it's also part of the actual content strategy. Yeah. Like I would argue, like you know, people talk about this a lot of like, oh, the clips, if you get, you know, 100,000 views on a clip, it's, but you get X downloads on the show, like the downloads matter. It's like I can point to 10 shows where I, I haven't listened to the in-depth podcast- Right ... but I'm familiar with their content. Yeah. I know how they talk. I, I appreciate their content and I learn from it on the clips

26:52and I am a sort of like a, I'm a version of a listener that still consumes their show and there's value to that. Advertisers wanna be a part of that. So- Like look at Channel 5, what they're doing right now. Yeah. Look at Theo Von. Like- Yep ... that, Shane Gillis went on like the world tour of like couch like podcasts. Yeah. And he's now, like how they've converted his clip culture into a tangible, huge, live product- Yeah ... is nuts. Like- Absolutely ... and needs to be understood better- Yeah ... at the consumer and customer level because if people are discounting that as an avenue of discovery, they're missing the whole point. Yeah. I think another like great example of that, one of our investors is a podcaster comedian, um, Caleb Pressley- Oh, yeah ... who, um, is, you know, with his show, he's represented by Shadow Line, Tom Brady's agency, and he doesn't even have an audio, like Apple, Spotify feed, but it's, it's like one of the top comedy podcasts. And the way that he sells, you know, he'll be talking to DJ Khaled, he's like,"Oh, do you mind if White Claw does a

27:54little presentation real quick?" Mm-hmm, mm-hmm. And you know, it's comedic, it's funny, but like the way they integrate ads into it and, you know, 10 of those, you know, clips and they're all getting a million views, like the way that modern podcasts are sold and then measured in terms of campaign success has always been tricky and I think that's where, like he's a great example that we're excited to have on board because like they're, they've built- That's awesome. So he's in the cap table as an advisor or investor? He's an investor. Wow. So, and, and I gotta give a shout-out to my, um, Ben Kaplan. He's, he brought in some great strategics. Um, Ben was an investor in my last company. That's awesome. Founder of Fuck Jerry Media. Yeah. Big media brand. So I think those are the types of like north star- And by the way, those are, there's a lot of parallels between those digital networks that are around the Fuck Jerry era and like where podcasting is going now. It's almost mirroring, you know, it was like magazines, then website ag- Yep. How many d- brands did they own under the Fuck Jerry brand? I don't, I don't know exactly. I don't wanna misrepresent. But it was dozens, right? But I mean, they still, so Ben, for context, like they, they launched a huge game

28:57division, um, like What Do You Meme? Yeah. Their card game is- Yeah ... a massive hit. Whoa, that's theirs. They, yeah. Yeah, that's theirs. Ben was the creator of What Do You Meme? What? Uh, but they have a, I don't wanna again speak for them, but they have dozens and dozens and dozens of game IP that they've built up- Sweet ... off the back of meme culture and like the internet native, um, you know, like fandom in a sense. That's awesome. So, uh, I know we don't got a ton of time left, but two things I wanted to cover is y- in your fundraising odyssey, which is my favorite topic to talk about all day, all night, like where are you in that right now and what advice would you give to people that are building these businesses, you know, in the world of AI? It's, you know, I think about this every day, what are the most valuable things that you need when you're taking money?'Cause if everything product-wise can be built somewhat inexpensively- Yeah ... even for non-technical, where are you in the journey and what advice would you give to people as they're stepping out into that journey? Yeah, I mean, I, I think I, I also feel like take my advice with a grain of salt,

29:58right? Like I, I feel sometimes the advice people give is just based on purely their own experiences. Mm-hmm. Which is true to a certain extent, but I think for me, like with MediaKit, we raised a million and a half dollars first time founders before we had a product and that made sense for us during that time. This go around with Listener, like we haven't done a proper round. Like I've brought on strategic capital, my former co-founder, my former board member, people that wanted to back me again, um, people like Ben, et cetera, and you know, people like Caleb who make sense given their strategic interest as like he has a big podcast. So I think for like how we think about Listener, is like we're a small team of three people. Mm-hmm. And we've kept things extremely lean. You know, we launched last April and we've just been extremely focused on building something that is a true, I guess you could say, um, like a need in the market that we're looking to serve because I think in this AI era, you know, when you go to market with something and you have customers that are like,"Wait, like could we just build this?" They, if people are asking those questions, I think the first six months, like we wanted to give ourselves the,

31:02the relief to say,"Okay, like we, we're probably gonna have to like shift the gears a little bit in terms of our product direction" and I'm so glad we didn't have like, uh, I guess you could say like a conviction that we weren't willing to move on. Mm-hmm. Where, you know, if you asked me last year the question of fundraising or the, who is Li- what is Listener, it's shifted so much and I think that's the approach that I've really tried to bring into Listener as, you know, as a second time founder is keep it lean for now. Mm-hmm. But have, and I think this is my biggest lesson as a founder which is- Give yourself the ability to have optionality. Like, we have great investors and the option to, if we wanted to go raise a, like, a proper round, I could commit to that path. We have the option to continue to grow sustainably and build with our customer base, and we've- we're- we're killing it right now compared to, you know, where we were last year of, like, not having a core product direction. Uh, or, like, we were just getting kind of off the ground. And then thirdly, I think is when you think about the long tail of, like, strategic acquirers or partners or whomever, it's like we

32:04never wanna be in the place where we over-raised and we haven't figured it out- Yeah ... and we're just like,"Okay, we have to. We have to sell or we have to return capital," whatever it may be. Yeah. So I think we've... I've really, um, have had some of the battle scars, but also the foresight through 500 conversations with founders to think that right now this makes the most sense for Listnr. Um, but I think every month, every quarter, like, the conviction and the excitement around what we're doing, like you said, of like- Hmm ... in, in our podcast conversation of, like, feeling the momentum, like, I feel that in such a strong way right now where I think that's, like- And I can see that at a distance. Like, I can tell when people are, like, have stuff going on and don't have stuff going on. I like- I like the sort of urgency of being in it. Uh, you left me with a good question that I answered on your show, but I'm gonna leave you with a big philosophical question here. Please. Five years from now, you know, you've built and you've sold a few companies, where do you see yourself? Uh, holy shit, you're only 20 26. 26 right now, man. When I was 26, I was a hot mess. You know, I had... I was broke

33:05at 30. Like, no... But where do you see yourself, uh, I mean, five, 10 years from now? That would still be pre-40. Yeah, pre-40. But where, where are you gonna be? Oh, man. You know, I, I gotta say, I, as someone who's a family man, you have five kids, right? Yeah, yeah. I, I got married last year. Um, you know, when I think about founder journey and, you know, one thing that I'll kind of say to go to my question is I, I interviewed one of the co-founders of Netflix, Marc Randolph. Wow. And he said,"I never wanted to be," again, hi- in his words, like,"On my seventh company and my seventh wife." Yeah. And he just talked about this idea of, like, every Friday he had a hard stop, whether Netflix was going public or- Wow ... it was a chill day of like,"I'm going on a date with my wife," and I have, like, that consistency where, you know, I, I wanna build a family. I think that's a huge priority in my life. But then secondly, on the business front, I've... I haven't done that much angel investing, but I, I have such an affinity where I, I've done an SPV, I've done some angel investments, and I just love backing founders at the

34:07ground floor and having- Yeah ... these conversations and not only from, like, being in it myself, but from the, the kind of, like, dipping my toes in here and there, where, you know, I, I have a lot of admiration for, for Harry Stebbings' podcast or that kind of off the back of his podcast raised a $50 million fund, then a $100 million fund, now has a- It's incredible ... $400 million fund, where I definitely have an appetite to not just raise a fund to raise a co- fund, but to back founders, um, based on my experience and through the network of people, the media investor sort of parallels I think are very interesting to me outside of being a founder myself. But I'll end it with this as well of, I think what worked in the past isn't gonna work in the future, right? Like, we're in this era where, you know, I'm reading a book from the founder of Zynga right now, and I think it's Life at the Speed of Play. Hmm. And he talks about, like, these fundamental shifts, and, like, we're in one right now with AI, with robotics, with AI, with space, with so many companies are

35:08launching, like, hardware startups. My friend has a drone company where I just think that I also want to, as someone who's 26, that I think, you know, your, your brain's developed, you're kind of stuck in your ways a little bit. I think it's an important to, like, shed experience to, like, have that curiosity about the world and to kind of look at the world as it is today, not just have the experiences that let you hold strong beliefs that don't let you see the, you know, what's ahead, uh, or, like, kind of what's coming in a sense. So my long-winded answer, I think family, I think I'm a- I'm an entrepreneur at my core, where I think I'll always be starting things- Yeah ... or wanting to be involved in things from the ground floor. Um, I think this, the media, you know, having my podcast and kind of taking it to the next level, level in the next five years is- Yeah ... definitely a priority as someone who's just committed to the long game of it. Yeah. Um, so yeah, I think that's, uh, a little bit. I think that's incredible, man. Your, your intentions and your values are, like, awesome. Like, as someone who's the old cowboy here-... like, I've learned the long

36:08way and the hard way that literally the whole thing is family. Like, that's the, you know, I've had- Yeah ... the best past few months of my life just where I've, instead of just, like, chasing, like,"Oh, I'll take my vacation tomorrow," I had just a awesome time up in Canada with my kids and my parents. You sent me pictures everywhere. And I, like, for the first time, I could feel my brain resetting to a non-panic fight or flight mode for, in a while. And like, you know, if you let it run you, you know, being an entrepreneur, it'll, it'll run you. But if you're... I love that. Like, the, you gotta have a cutoff switch. You gotta have your own life within your life, and those two things can coexist, so- Yeah ... amen to that, man. I appreciate it, man. You are, you're a fascinating dude. And, and I think last thing that I'll end with as well, which is relevant, where, like, the last four years of my life, I've, I've run a marathon every year. And I'm going to Australia in two weeks to run the Sydney Marathon on, uh, August 30th. And I, I mention this because I think it's, it's, it's sort of this aspect of my life that I think is like, it allows me to see things from a bird's-eye view when I'm

37:09doing these two-hour, three-hour runs- Yeah ... where I'm just, like, thinking about things. It's just, I wanna be someone that's always pushing myself. Mm-hmm. Pushing myself, bettering myself, but being rooted in, you know, trying to have a, a life that I'm excited about I think is, like, a great North Star for every founder. Every entrepreneur that I know has one of these interesting hobbies-... whether it's rock climbing, skiing. Yeah. Mine is cycling- Yep ... and tennis these days. But yes, you do literally, like, my... It sets your brainwave back to, um, you're seeing the world. Yeah. Like, you're literally, you're not on your phone, and w- it, it, the world we live in, I think we're maybe over the hump of it now, but, like, the amount of people that are just, like, addicted to, like-... the doom scroll. Yeah. I think that the next generation's gonna be a little bit smarter than the one that, that came before. Yeah. We will know, right? I think it'll be a good guiding light for, for that. Absolutely. But I really appreciate you taking the time. I'm really excited to see where everything's going in your world, and we gotta figure out how to partner across our businesses too. Absolutely. Thank you. We'll, we'll do that indeed. And thank you so much for having me on the show today. Rock and roll. Thank you. Wow. Great stories from, uh, Casey. What a winner. Um, a-

38:13as mentioned, I'm recording today from the beautiful Lighthouse, uh, Studio here in, uh, Venice. We're seeing more and more people creating businesses to support, uh, the creator community, much like our business, Rebel Audio, for everyday creators looking to start and take their first podcast. Whether you're a podcaster, whether you're an expert, or you're podcast curious, go to rebelaudio.ai and start your podcast today. I hope you enjoyed, uh, our conversation, and this is a show every week where we bring you disruptors, rebels, uh, entrepreneurs, creators of all types. And, uh, to learn more about Casey and his business, go to listnr.com. And, uh, we hope to be doing lots more with him in the future. Thanks, y'all. Yee-haw. Amen. See you next time. Ooh la la. Audio up.