Becoming a Full-Time Podcaster Thanks to Subscription Revenue with Kyle Cray - S2E11

Dec 15, 2021
Jennifer Tribe

Kyle Cray shares how he was able to quit his job as a software engineer to go all-in on his podcast thanks to paying subscribers.

Jennifer Tribe, host: We’ve got a treat for you today, folks. My guest is Kyle Cray, co-host of a podcast called 90 Day Fiance Cray Cray, a reality TV commentary podcast. 

And big news, as you heard at the top Kyle was recently able to quit his job and go full-time on the podcast thanks to the revenue he and his co-host have built using subscription. 

Do not be deceived by the subject matter of his show, which might seem frivolous. Kyle takes podcasting very seriously and it shows. We’re going to dive into his story, and learn all about how he and his co-host built the podcast, the thinking behind it, how they launched the subscription piece and how they’ve grown it to a thriving full-time business.


Jennifer: Hey Kyle. Welcome to Supercasters.


Kyle Cray, guest: Thank you so much for having me.

Jennifer: You are the co-host of two shows, right? You have 90 Day Fiance Cray Cray. And there’s a second one as well.


Kyle: Yeah, we just launched a second podcast on our premium tiers only called D-Sides, which is a documentary companion pod.


Jennifer: So that's an entirely different podcast. It's not an extension of 90 Day Fiance Cray Cray.


Kyle: Right. And we are only offering it to a new tier of subscribers on our already existing content. So you can't subscribe just to that podcast. You have to be in like one of our higher tiers to get it.

Talking trash about a dumpster fire


Jennifer: Right, got it. OK, and we're going to dig more into that. But first, let's set the scene and give our audience some context. So tell us what 90 Day Fiancé Cray Cray is about and how it got started.


Kyle: Well, 90 Day Fiance Cray Cray is about principally the reality show 90 Day Fiancé on TLC. It's been a show that's been extremely popular for the last almost nine years now, and about three years ago, my best friend and longtime coworker Kim asked me to do a podcast about it because I had recently quit the job that we both worked at, and we were just best work buddies and missed hanging out. And so the format of the show originally started as, Hey, we're just going to watch this dumb show, and then we're going to sit around, have a couple of beers and just talk trash about this dumpster fire. And it's just a really wacky show. Sometimes it's interesting and informative, but most of the time it's it's typical reality show. Just junk, right?


Kyle: So the show started off— I mean, I'm sure that you've heard many times and my experience with other projects lends to this too, starting a podcast is really hard in terms of growing an initial audience. And I don't know exactly why or how, but we really hit the right time, right place lottery with it, because the show itself, 90 Day Fiancé, really started to take off on social media. There were even celebrities tweeting about it all the time. And it became the number one cable show on television, even beating Monday Night Football not soon after we had started our podcast. And we were really the first reality TV podcast to cover 90 Day Fiancé exclusively, meaning we didn't just give it a 15 minute treatment on a podcast that was covering other stuff. That was all we talked about.


Kyle: And the friendship dynamic that Kim and I have, and our kind of unbiased, amateurish opinions and takes on things really spoke to people and it took off like crazy. And the reason that we started premium content was really only because there was a lull in the show. The season had ended about four months after we started podcasting and we had had a couple of advertisers, but nothing big, and they weren't going to have a new season of the show for three months. And so we figured, Well, what the heck? Let's just start some premium content so that we can go back and cover old seasons and see if people will pay for it. We didn't really have a lot of expectations and it went completely berserk, and now it's our primary source of revenue by a huge margin. And I recently quit my job as a software engineer to be able to just focus on podcasting full time.


Jennifer:  Wow, that's amazing. So when did the podcast start? What year?


Kyle: We started in August 2018, and we just put out about our 430th total episode.

Producing four hours of content a week

Jennifer: Holy smokes, how often do you publish?


Kyle: The way that our show is structured and this has evolved and changed over time, but it's been pretty consistent for the last two years, we put out one free show on our main podcast RSS feed, like I'm sure everyone that listens to you does. And that show is one hour and includes ads. And on our premium feed, we put out absolutely everything that we do ad free. And so that one is the more important way to answer your question. And we put out typically, two episodes a week that are around two hours each. One of them is our main show plus with an extended version so that it's just an extra hour of us talking that we edit out of our main show. And then our second show is 100 percent premium only. And that covers other reality shows that we're talking about, gossip, news, events and things like that. The majority of it is covering completely different shows that our fans also watch that are interested.


Jennifer: That is a tremendous amount of content in a week. And especially, I mean, you said you've recently quit your job to do podcasting full time, but presumably before that, both you and Kim were employed full time elsewhere. How do you find the time to do that and what does your production process look like?


Kyle: I would say that most other shows that are putting out four hours of content are probably pretty similar to ours in that the production values aren't crazy, right? Essentially what our show is is we watch the source material. I go over to her house and we just record in a spare bedroom, and that process is 100 percent improvised conversation between friends. There's no sound drops. There's nothing other than introductory and outro music. So in terms of the production side, it probably only takes an hour total each week on the production side. When we record a two hour show, the total amount of time it takes to actually create that content is probably if you double that, that's about the total investment because we have to watch the show, our editing process is very fast and then we really just upload stuff to Supercast and we're good to go.


Kyle: So I guess to answer your question, we probably spend on a typical week if you include lsocial media marketing and interacting with our fans in our Facebook group and stuff like that, I think probably the minimum that I could spend in a week is about 15 hours. To put out that much content. And lately, since I quit my job, obviously a lot more focus on the marketing end and putting out sample episodes and just trying to get more people to sign up. So that's obviously increased and our new podcast is much different. That one is much more long form and it's about 50 percent improvised and 50 percent produced. And that one is, you know, an order of magnitude higher. We just put out our first episode, so it's hard to know exactly how long it's going to take to produce that in the long term. But our first episode took probably about 25 hours to create so that one is going to be on a monthly cadence. It's definitely not going to be every week.


Jennifer: Well, yeah. Twenty five hours an episode that is intense.


Kyle: Yeah.


Jennifer: I want to talk a little bit before we get into some of the details of your plans and your subscription program. Kyle Cray and Kim Cray. Obviously not your real names.


Kyle: Right.

Anonymous… yet intimate

Jennifer: And you don't show your face anywhere. We're not recording video for this. You know, your social media accounts have other people's pictures up. Why anonymous?


Kyle: It's a good question. It still kind of blows me away whenever I think about it, that we've been able to grow this podcasting little mini empire over the last three years, with no one even knowing who we are. People don't even know where we live. For a long time most people were completely convinced that Kyle wasn't even my real name. I assure you it is. I didn't think that far ahead. But the reason that we try to keep it to a minimum what people know…. You know, it's funny. You obviously get to know someone pretty well after listening to them for almost a thousand hours, and that's how long our total catalog at this point is. People that listen to the podcast know me better than most of my friends in real life because we're always telling anecdotes and comparing what happens on the show to our personal lives.


Kyle: People know us really well and I'm sure other podcasters know that your audience develops this familiarity with you. But funnily enough, they don't know our names or where we live, what we look like. And so the reason that we originally went with that, was a decision that my podcast partner made from the very beginning. And it was based on, I think honestly at the time, it was based on paranoia, because it's kind of a big leap to think, well, what if this podcast gets big? Do we really want to be in the social media spotlight? And so we just decided to play it safe and just go that route. And I'm so glad that we did, to be honest, because we quickly became the biggest 90 Day Fiancé podcast out there.


Kyle: There was a time where we were number one on the iTunes podcast charts for television and movies category in the United States. And so we blew up really fast and very quickly the people that were on the reality shows that we were covering started to reach out to us. Either directly through social media or through a publicist or something like that. And for a while we did interact with them, we did do interviews, but it became clear very quickly that that was a bad idea. And since then there have been so many problematic cast members on this show. All the shows that we cover, I mean we cover another show that's about prisons. So you can imagine we don't want to be doing a podcast about people that just got out of prison, and talking crap about these people.


Kyle: It turns out a lot of them are just completely nuts. There's been cast members on these shows that stalk other podcasters, that harass bloggers and people on Instagram. It's just kind of a mess, and we just decided for our own privacy, we wanted to stay away from that and we made a decision pretty quickly to never talk to anyone on these shows ever again. And I think it's worked out pretty well for us. I think it's hard. You know, it's impossible to know if us being anonymous limits the growth potential of the show. But so far, we're happy with the downsides and the upsides of it.


Jennifer: Yeah. I mean, I was going to say one of the sort of tenets of podcasting is that you want to build that relationship with your audience and let them get to know you. And I was going to ask whether you thought being anonymous has hindered that in any way. But from what I'm hearing, they are getting to know you. They just don't know your name. From what I understand, your conversion rate from free listeners to paid listeners is phenomenal. It's something like 16 percent. Am I right about that?


Kyle: It's in that neighborhood.


Jennifer: Which is crazy.


Kyle: Yeah. And we had explosive growth during the pandemic, too.

Converting 16% percent of listeners to paid subscriptions


Jennifer: Why do you think it's so high? I mean, we say typical conversion rates in the range of two to seven percent for most shows. So 16 is more than double the highest end of that scale. What do you attribute that to for your show?


Kyle: If I knew that I would be writing a book already or something, but I think that well, first of all, we tend to have a much more hardcore loyal type of listener. We engage a lot with our audience on our private Facebook group. And I think that that is really important for retention. So I'm not sure that we do anything outrageously innovative on the “converting new people over” side. You know, 75 percent of our content is paywalled. And because we started our premium content so early in our podcast life cycle, there wasn't really any resistance to that. I could see, you know, you have three hours of free content and then you move all of that over to your premium content that people would freak out about that. But we were only doing one hour up until that point anyway. I mean, I think we had had a couple of extended episodes that went out before we started premium.


Kyle: So when we have all that stuff and we cover so many different other shows, it gave us a lot more exposure because now, oh, you want to listen to a podcast that's talking about this show or that show or this show well, here you go. But you do have to pay. And I think maybe the thing that we do better — and I only say that because we put in so much effort into it — is retention. Over the last three years our retention for, like the number of people that have stuck around for the entire three years is, I think, around two thirds or 70 percent. And we do that by being extremely, extremely consistent on our releases, our length. I like to think that the quality is the same, but that's obviously subjective to the listeners.


Kyle: But we engage a lot in our private Facebook group, and I think that's been huge. Every time that someone signs up, they can apply to be in our private Facebook group for subscribers only. And once we approve them after we check their email address and stuff. After that, that's where we do daily interactions. I'm constantly in that group. It has over 3000 members now. And importantly, I do not kick people out if they cancel their subscription. Because I want people to be reminded that we're around if they want to resubscribe and still be engaged with the community. And I think that that's made a huge difference because we're always visible to people and they always know what's coming, what's released. There's review threads on the shows that we watch, there's reaction threads to our podcast, there's live watch threads, we have moderators. It's a well-oiled machine in there that I think keeps people really engaged with the show.


Jennifer: It's an interesting idea to keep people in the group after they've canceled their subscription, like a little tentacle that's still holding on to them and keeping your name in front of them. I love that idea.


Kyle: Exactly. And honestly, it would be a nightmare to go through and find people that have canceled and kicked them out.


Packaging and pricing the plans

Jennifer: So also just easy. All right, so let's take a look at your plans and what you've packaged into each plan.


Kyle: Sure. So we have our main tier of premium content, we have a name that's referential to the show. So it's like an inside joke that everyone would know. But that includes all of our reality TV-based content. It gets you access to our Facebook group, a discount on our merch. And actually, if you're a subscriber, we just give you everything at cost. So there's no profit markup whatsoever and anything that we accidentally make on our merch, we donate to charity and other than... I think that's it. And then we do have a $25 tier, but that extra $20 honestly, it's just a donation because we don't really give much beyond the base content and we only have a few people that are subscribed to that. And then our new tier, as I mentioned at the beginning, is $8.


Kyle: And that's everything that you get with our $5 tier, obviously, plus our new documentary-only podcast that comes out once a month. It's much more long form. Our first episode just came out today, so this is good timing. And it was an almost four-hour show that really deconstructs the documentary…. Our first episode is covering the documentary on HBO Max, What Happened to Brittany Murphy? And so that one just takes a lot more work to produce. And if it didn't, if it was just one of our kind of discussions and having a couple of beers shows it probably would have just been included in our normal $5 tier. But because it's about the same work as all of our other podcasts combined, we decided to put it into a new tier and charge a couple extra bucks for it.


Jennifer: How did you decide on what you were going to put in that initial $5 tier and price it at $5? Because that seems like a huge amount of value and access and content for people for $5?


Kyle: Yeah, thank you. When we first started, I think our first episode on our premium feed was in January 2019, our idea was just to put anything and everything into our feed, and it did evolve over time, for sure. So our first set of episodes was covering old seasons of the reality shows that we talked about. And also we had extended episodes. And an extended episode for us at the time was maybe an extra 20 minutes. And what we decided to put in those extended editions was more, I guess, even more unfiltered content. We would talk a little bit more about our personal lives and relate things that we saw in the show to anecdotes about us. That's something that we really try to keep to a minimum on our main show because again, we are anonymous. And so we wanted to make it a more intimate experience because people have been listening to us for months.


Kyle: And I think a lot of people felt that they didn't know anything about us. And so how could we kind of make that connection to the audience a little bit stronger? And that again, as we started doing it through our Facebook group, but also the content of the show is materially different. I wouldn't say that our public show is censored in any way. It's really not. But we would just move more intimate details over to our premium subscription. And over time, that extended episode started to get longer and longer, and eventually the length of our main show that we do every week ended up being double, and we decided, you know, on these reality shows, I'm sure you know, they follow like a chunk of couples. On 90 Day Fiance, it's typically six or seven different storylines happening with different couples and they're not like interacting with each other. They're all completely separate. And so what we would end up doing is we would take the best couples, the most entertaining, and we would put those on our premium feed.

Subscriptions created life-changing revenue


Kyle: And sometimes we would experiment with putting the best ones on our public and putting maybe more boring ones on our premium feed. And we've kind of come to a middle ground there. But the goal was always from the beginning to convert every single person we possibly could from our free show. Because as I'm sure you know, podcast advertising on a small to midsize show, that doesn't pay the bills. It's a hobbyist’s income and it's nice, it's great. But moving to premium content for us was life changing. It wasn't just a change for the show, it was literally a change in both of our lives. And what it did for me was it gave me the flexibility to walk away from my day jobs if I just didn't like them or there was some dispute or I was bored, or it really gave me the privilege to look at my day job in a different light.


Kyle: I ended up leaving like three different companies since being a podcaster, just because I thought I was bored or I thought that there would be a better opportunity. And when I left my last company to do this full time, it was because I wanted to do it full time. I walked away from the best day job I had ever had by far —best salary, best benefits, best people, working conditions. I wasn't bored. I was working on interesting stuff. But at the end of the day, this is my venture, right? And this is something that I wanted to grow and give my full attention to. And there's no way I could have done that without our subscribers. Not even close.

Kyle: For a long time, we were on a different premium feed service, and we still have that as an option. But Supercast has really helped us in a lot of ways. There's so many more features that it provides. We're so happy with it and I think that Supercast has helped us expand the podcast and just make it more... The barrier to entry is so low that when we got on board with Supercast, I completely redid our website so that the call to action entry path is just as simple as it could possibly be, and it's worked out really well for us.


Jennifer: What do you think will change now that you can devote yourself to this full time? I mean, you've already mentioned you're launching a second show. Anything else that you think will change?


Kyle: Since I quit my job, I effort on marketing to more people and being even more engaged with our subscribers. I started a Twitter account as an example that I just felt like I didn't have time to do before. More Instagram staff, more horsing around, more memes, more joking with fans. And yeah, this podcast, this new podcast had been in development for a couple of months trying to figure out how we were going to structure it, how we were going to do it. And up until then, up until we decided to do that, I was thinking maybe even just going directly into true crime itself. And instead kind of met in the middle because we kind of did a documentary about a true crime case. So in terms of what I do all day since I quit, it's really marketing.


Kyle: I've even been able to do some surveys and learning more about our subscribers. And we've actually changed some things because of that feedback. And it's just stuff I wouldn't have time to do before. I wouldn't say that the podcast was a secondary thing, but it definitely was kind of relegated to a little bit of a side hustle for the first two and a half years because I had to work eight hours a day and so I would watch the shows at night after work. We still record after Kimberly is done with her job, but ultimately it was an extra 15 hours a week of work that I just had to tack on to my day job as a software engineer. And my wife was very understanding about that, especially after the premium feed started because she could see the money coming in.


Kyle: But until then, it was definitely just something I did for fun, and it's still fun. I don't think that the show would be good if it wasn't. But now it's definitely evolved into a How do I grow this thing, and maybe just as importantly, how do we not burn out. And I think that we have done a really good job….As you said, four hours of content does sound like a lot, but we've done a really good job of managing our own workload and our psyche so that we don't just lose it one day because the shows that we cover are pretty ridiculous, and sometimes they're really funny and enjoyable to watch. And other times, the quality fluctuates a lot. And so I think that we do a really good job of just staying consistent without getting bored with it, and I think that has a lot to do with our friendship.

Learning the craft of podcasting


Jennifer: Listening to your story, I'm hearing there's a little bit of luck involved. So just the timing of when you launched it and some of the growth. But I'm also hearing about a lot of very careful crafting and thinking about what you were going to offer and how you were going to structure it. You said that you had not been in podcasting before you started this. It was sort of a whim that Kim got you into. How have you been learning the craft? Are there podcasts that you have modeled yourself on? Are there sources of learning that you've been tapping into?


Kyle: So in terms of learning the craft of podcasting, we were both in software and we both have worked for audio video companies. I wouldn't say that I have any real experience with editing or production, but in terms of the tools and the software, that was all pretty intuitive to us to jump into. And then our decision-making process, we both have been in various roles in software engineering. I've been as high as director level. Kim is like a product manager in her daily life, and so we're used to making decisions on how to structure things to target customers and things like that. But I certainly didn't know anything about podcasting beforehand in terms of how we just jumped in and got started on the show. We're certainly not professional public speakers or anything, but I was a debate team nerd in college and have a lot of public speaking experience. 


Kyle: And maybe it is just a lot of being in management in the corporate world. I'm just not shy at all, right? But in terms of the back end technical stuff, a lot of Googling, a lot of figuring some stuff out as we went along and in terms of shows that we look to to model ourselves after, I'm not really sure that there is one other than we definitely wanted the format to feel like a conversation between friends. And there's a lot of podcasts out there like that, right? And then some of our marketing decisions and some of our structure, around our tiers and our benefits and the way that we communicate, one of the podcasters that I admire the most that I've stolen a couple ideas from is Preet Bharara and his show Stay Tuned with Preet and his premium content. So he puts out sample episodes all the time and the way that he markets his premium content, I thought, is not too in-your-face. It's not too obtrusive, but it's still effective and it's very consistent. And so we try to do that as well.

Jennifer: Did you ever think when you started the podcast that this was where you’d end up?


Kyle: Yeah, I mean, this is a dream come true. Well, I don't know if it's a dream come true because I wouldn't say I ever thought that I would be a podcaster. But certainly when it started, you always wonder, Hey, what could this be? What could this turn into? And I couldn't have asked for anything more than what it's become, and we have an extremely loyal fan base. Our fan base is like 95 percent women. Typical ages between 35 and 55. They're so loyal to us. I mean, we have people that say we could listen to you guys just read the news or read a horoscope or something and we would listen. And just super grateful to all the people that have stuck with us over the years, and it's pretty remarkable.


Kyle: I don't really know what the magic is to create such a loyal fan base as we have. I guess it's just being available and engaged and listening. I think our fan base tends to skew toward people that watch reality TV a lot. Most of our listeners are professionals. They are people that are business owners. Obviously all walks of life, but somehow, we've been able to cultivate a retention and conversion that, yeah, like most people haven't heard of.


Jennifer: All right. Last question. Your $25 tier says that should you ever launch a live tour, they have tickets. How are you going to live tour when no one knows who you are?


Kyle: Excellent question. That tour has been obviously on hiatus since COVID has been around and because my podcast partner just had a baby, I may need to re convince her of doing that. But it's something that we've kind of wanted to do for a while. And at that point yeah, before we really commit to that, we would have to definitely accept within ourselves that people are going to figure out who we are and we need to be okay with that. So I'm not sure that that's ever going to happen. But if it does, yeah, our $25 people get first dibs.


Jennifer: Awesome. Well, thank you so much for joining us today, Kyle.


Kyle: Thank you so much for having me. Love Supercast and happy to be here.

Jennifer: That was Kyle Cray, co-host of the 90 Day Fiance Cray Cray podcast. Kyle and I are now going to jump over to the private interview room to talk about how Kyle and Kim promote their podcast subscription, including what they do on social, where they get about 20% of their paid audience. And how they use teaser episodes to regularly create what Kyle calls “subscription bumps.” 

You know how this works—you have to be a Supercasters Premium subscriber to access that extra content but hey, it’s free to join. If you’re not already a Premium subscriber, go to, click that free signup button and in just a couple of taps you’ll have the extra content in your favorite podcast player. 

And if you liked this episode, tweet us @supercast and let us know your biggest takeaway. 

‘Til next time, stay super out there.


Reality Cray Cray (website)

Reality Cray Cray (subscription page)

Reality Cray Cray (Twitter)

Reality Cray Cray (Instagram) NSFW

Stay Tuned With Preet (podcast)