Growing Darknet Diaries to $15,000 a Month in Memberships with Jack Rhysider - S1E11

Feb 23, 2021
Jason Sew Hoy

Jack Rhysider, host of the award-winning Darknet Diaries podcast, shares how he grew his show from zero to $15,000 a month in paid memberships.

Key takeaways

  • 📖The book that gave Jack the confidence to launch his podcast
  • 🎙️How Jack got his show to sound amazing right from episode 1
  • 💁How to find mentors who will support you & your podcast
  • 🔎How Jack generates a constant stream of interesting stories for new episodes
  • 😯 What surprised Jack about what people were willing to pay
  • 😍The perks Jack’s subscribers love best

Get the bonus content with Jack

Subscribe to Supercasters Premium to get bonus content with every episode. It’s free, takes two minutes, and there are no special apps to download.

For this week’s bonus, Jack reflects on his 2020 podcast marketing plan, what worked best, and what he wouldn’t do again.

Jason Sew Hoy: Hey everyone, welcome to Supercasters. I'm Jason Sew Hoy, co-founder and CEO of Supercast. And on this show, we interview world-class podcasters, deconstruct their growth strategies and find out how they built sustainable independent businesses that thrive on a strong relationship with their listeners. In this episode, I'm speaking with Jack Rhysider, the creator and driving force behind Darknet Diaries, a podcast that did over 15 million downloads last year, and someone who's running a very strong paid membership program. Jack, welcome to the show.

Jack Rhysider: So glad to be here. I've been following you and what you've been doing, so I'm really honored to be part of this podcast.

Jason Sew Hoy: Likewise. I’ve got to say I'm super excited for this conversation for a while because I followed your story for a long time. Frankly just because it's such a great show but also because you're so good at sharing that behind-the-scenes creator journey. And I purposely left the description of Darknet Diaries out of the setup because I wanted folks to get more than a typical elevator pitch introduction. So would you be so kind.

Jack Rhysider: Yeah. Darknet Diaries is like true crime meets cyber crime where I talk about the hacker stories but try to do it in a very storytelling kind of way. So true crime is  popular because you start to gather some suspects and think who did it. And then, you'll get all the information at some point. So I often have to wait a long time before I can do a story on cyber crime, before I can get the whole details. But yeah, when all the details come out, that's when I put together a show and then I add a lot of music and I try to get any interviews I can from victims or the criminal or the law enforcement and just bring it all together and makes quite an interesting show. And I made it because this is a show I wanted to hear, you know? And so, yeah, I couldn't find it and I just decided, okay, I'll make it myself. Cause I'm a big fan of podcasts myself.

Jason Sew Hoy: Yeah. And you also have a background in tech security, right?

Jack Rhysider: That's right. So like 10 years before starting this, I was in infosec, so IT security and securing firewalls and routers and those kinds of things. And I mean, if you're going to ask me what's my advantage I have over the common person is because I know a lot about this particular subject. And so that's what I kind of brought to the podcasting scene is all my skills and knowledge in this, but not just to teach it but to actually do like storytelling around it.

Jason Sew Hoy: Right. How did those two worlds kind of crossover? There's a clear intersection obviously in terms of you bringing that subject matter to podcasting, but how did that transition take hold?

Jack Rhysider: I [have] always been a fan of like This American Life and Radiolab and just super glued to it and just amazed at the storytelling. It's so good. Like it's just so good. This was the last thing I could ever think that I'd ever end up doing is making a podcast. And I came up with the idea and I was like, no way, there's no way I can storytell and do all the interviews and the music and everything. And so I kinda just put it to the side for like six more months and then finally picked up a book called Out on the Wire, which is a book by a lot of those people. It's Ira Glass from This American Life and Roman Mars from 99% Invisible and Radiolab and this kind of thing. These guys put together a book on how to do audio storytelling and that was just what I needed to feel confident enough to give it a shot. I just said, yeah, I want to hear this kind of podcast. Where is it? Couldn't find it and decided to make what I wanted to hear.

Jason Sew Hoy: That's amazing. And did it start out kind of as a side hobby to a regular day job or your tech security gigs and then it bloomed into a full-time thing. How did that….? 

Jack Rhysider: For the last 20 years or so, I've just been throwing things at the wall, trying to make it stick as far as being my own entrepreneurial boss or something, doing something from the internet to have my own business. Right. And so I've just been throwing things at the wall for all this time. And this podcast, I just kind of threw at the wall, said is this something other people would like and stuff. So after a few episodes, it was really early on, people were just really into it. And I knew right away, there's something here that can have some potential and I've already got it all structured so I just need to keep it going. So, yeah, it was actually I went to a conference and I met people who I've never known in my life — they're not a friend of mine or a family member, it was just total strangers — told me that they listen to every episode and they can't wait for the next one.

And that was the early indicator, like, Oh my gosh, I've got people's attention for that long, every single episode you've consumed. And there only was like six episodes in at that point. So that's when I knew, okay, I gotta focus on this. So yeah, I still have my day job and probably like six months into that I quit my day job to give this podcast like a full effort and all my focus and yeah, about a year after starting it is when it was finally enough listeners to monetize and start making money on it.

Jason Sew Hoy: Last night I went back, I scrolled all the way back through the feed and listened to what I think is the first episode, PBX Hacking. Was that the very first episode?

Jack Rhysider: Yeah

Jason Sew Hoy: I listened to the whole episode because I was kind of like, Oh, I want to see what the first raw episode was like, and I was blown away. It's as high quality of production— I mean, I'm sure it's not but it just sounds super high quality straight off the bat. Was it kind of deliberate? How did get it to such a high level right from the first episode?

Jack Rhysider: I spent three months on that first day. So it wasn't like every two weeks I'm making episodes now. So it wasn't a short production period. So I scrapped the first few episodes, I worked almost to the end of them and said, no, this isn't gonna work. And so then I had to keep pivoting, which episode to start with and yeah I mean that one, it was all right. I think I interviewed two people in that one and it was really just going through the motions and I can hear how I was just beginning at it but still it, it got put together. So yeah, it was just a lot of following directions and putting it all together and seeing how it goes and since then I've found my voice and my stride and all that kinda stuff. 

Jason Sew Hoy: The generic advice of course that you always hear for podcasters is niche down, find your audience and then just be consistent. And honestly, I can't think of a better execution than what you've done with Darknet Diaries. Can you give us a sense of what that growth has been like from your perspective since then?

Jack Rhysider: I had kind of a head start at the beginning. I was a blogger and I had a couple thousand Twitter followers. So the blog was actually getting tens of thousands of viewers a month. So I plastered my podcast all over the blog saying, check this out, listen to this. And it's an IT security blog, right? So it's in the same vein. I got seven clicks a day to my podcast website. I could see people were coming from there, so it was nice just to get very passively seven new people a day to check out what I was working on and then a couple thousand people on Twitter. So that was where I started and that gave me a few hundred downloads per episode, just out the gate. You usually see people liking it and you're like, okay, I'll make more. And since then, I think my goal has just been kind of like a 5% growth every month, just maintain growth. 

I think that's my big thing is anywhere between zero, like one and 5% is good and anything above zero is actually growth, right. So as long as you're growing and you've got more audience coming, it's working. I’ve got to say I was frustrated that the growth wasn't faster because you see viral stuff hitting the internet constantly. And you're like, why isn't my show blowing up? But it just takes time and I'm glad it kind of took time because I had to iron out some improvements on how I can make things better and get some mentorship along the way and all kinds of stuff to really make a better show.

But maybe it would have been premature if I had blown up right away. So I'm glad it took a couple of years for things to just get there because it let me practice and get good at this because I had no radio experience before or anything. It just kept growing and I did a lot of marketing techniques to try to get it to grow.

Jason Sew Hoy: One point in there that I just picked up on. Who were your mentors?

Jack Rhysider: Okay. So I had been posting a lot of things, my thoughts and stuff, on Reddit and stuff, just talking in a podcast subreddit. Somebody who was really picking up what I was putting down and so we started talking and then we ended up talking on the phone and stuff like that. And she turned out to be executive producer over at Wondery after awhile. And it was just fun to have somebody who just really knows podcasts really well to just be friends with and to kind of bounce ideas with, and she helped me produce an episode or two and she taught me a lot. And so it was just one of those things. I met somebody at a conference that was a celebrity actually.

So one of the early things I did was I sent a ton of emails out to as many people who have a following as I could. So journalists, YouTubers, podcasters, anyone with a big Twitter following, I just sent an email saying, Hey, I think you'd like the show. That was pretty much it. Because you might want to share it with your audience. And so out of like a hundred or 200 I sent, I got like two people who actually took me up on it. And one of them was a person who has a million followers on Twitter and he's actually a celebrity, makes a TV show on National Geographic about hacking and stuff.

He was like, wow this is really good and he listened and then he started tweeting it. And then I ended up meeting him at a conference and we went and had coffee and all this stuff, and we really kicked it off. So he actually was able to help mentor me as well,  we call each other on the phone sometimes and talk about stuff. So it really is just a matter of when you're finding a mentor, it's just a matter of being in front of as many people as you can and interacting with as many people as you can. I was going to podcast conferences and tech conferences and being part of social media and joining in and all this kind of stuff and local meetups, anything I could to just be part of the podcast scene and constantly emailing other podcasters, like look, I'm a big fan of your thing.

Here's what I'm making. Do you have any pointers on this particular part of it? And I'd say, just listen to this, the first five minutes. What’s the intro like to you or something. So I was just meeting with as many people as I can. And I think eventually it's just inevitable that you're going to find somebody who you really click with, who likes what you're doing and you can find a mentor in that way.

Jason Sew Hoy: I love that. For people that I guess they're thinking about that growth strategy of trying to get in front of other podcasts and try to get their attention, that angle of, Hey I’d just appreciate if you could listen to five minutes and give me some feedback. Did that work or are there some nuggets in there that you could share in terms of what people are more likely to respond to?

Jack Rhysider:  I just keep it simple when I'm reaching out. Like I know you write about IT security and sometimes you even write about podcasts. I do a podcast about IT security. It's a little bit different than I think you might normally know about or something, but I think it's worth checking out. Your audience might like it. And just keep it simple. And if people listen and they listen oh well. If they don't, cause I know it's kind of a numbers game and it kind of feels sleazy to email like 200 people like, please listen, please check out my show. But yeah, even if one or two picks it up.

I mean the other one, so one picked it up was that Twitter celebrity, the other one was The Guardian newspaper. So they picked it up, they saw it and they ended up writing an article about it. It was really just a paragraph. It was like a podcast article. And then I was just mentioned in a paragraph or two. Just that one little mention is that social proofing where it's like, okay, this guy is getting written up in The Guardian. And then from there the next newspaper who looks into me can see that The Guardian has already written about this guy. We should write about him too.So they can, that social proofing really does go a long way. So you want to really showcase that stuff on your website.

If you can say look, this is all the places that's really talking about me and reviewing me and giving out awards or whatever it is. And it's good for the listener to say, Oh man, I've been missing out. It sounds great. And it's also good for other journalists to say, Oh yeah, I should be reviewing this too.

Jason Sew Hoy: That's a great tip. Now just going back to content itself because I am just really curious about how you pull a story together. There's just so much to your episodes. There's kind of ‘be careful what you do on the internet’ kind of advice, there's first-person narrative, and then this last Jetsetters episode, there's travel hacks and tips on saving money. How do you think about all the different kinds of things that a show can do?

Jack Rhysider: I've been around for a while, so I know what kind of the big hacks are that I want to talk about. So I have a big list, I have some Google alerts that look for like when a hacker is arrested or indicted or sentenced. A Google alert for ‘hacker sentenced’ is great because now once they get sentenced, I know all the bits of the story. I know, OK they were sentenced. That must mean they were found guilty. And if they were found guilty that means they must've been arrested. And if they were arrested that must've been they did a crime and if they did a crime, what is the crime and all that stuff can come out. 

So once I have that whole package together, that's really nice to then go back to the beginning and say, okay, we can tell this whole story. That's a really cool tip for finding good stories is just get a whole bunch of Google alerts. So some other Google alerts I have are ‘hacker died,’ ‘hacker  suicide,’ ‘hacker sentenced’. Like I have a ‘this hacker story reads like a movie script.’ If there's a news article that says that I want to read that right. Or ‘biggest hack ever,’ ‘biggest hack of the year,’ ‘biggest something.’ 

I’ve got a ton of Google alerts and this all just sends me like daily events of what's going on out there because I really want to wait until everything's done before I can start the story. So that's one way I get stories. Another way, people reach out to me and say, I've got a story for you. And that took a while for it to get there. It wasn't right away. But then I also go to, I tune into conferences and I hear people talk about their personal stories and stuff. Those help too. I pay attention to all the things going on and pick up what I find interesting. If I can get some interviews, that's great. And then I'll edit it up and narrate some stuff in between and add some music and produce it and then publish it.

Jason Sew Hoy: That's great. I love that tip. How would you describe a typical Darknet Diaries listener and why do they come to the show?

Jack Rhysider: I've always struggled with this because I watch like the Discovery Channel and I'm like this is so not for me. This is not even 101-level stuff. This is like elementary school stuff I'm seeing on here. You start dissecting Einstein's life and it's like, well, let's talk about E equals MC squared. Explain it to me and the way he understood and they just totally gloss over it, you know? And I'm like, no, I want to know this part. And so I wanted that to be this extra bit of, Well, let's really learn some stuff from this. Even if I've been in this field for 10 years, I still want to learn something from one of these episodes, me personally if I was listening to it.

So I don't want it to be dumbed down just for beginners and at the same time I don't want to exclude them because these stories are just so exciting. So I somehow thread the line between let's make it accessible for everyone but also make it enjoyable for those who are really in this as their career and they still will find value out of it. And that's kind of a struggle I have. So I think my average listener is going to be someone who uses tech on a daily basis and is interested in hacking stories because I think a lot of us are like, you hear about it in the news but you see the headline and then it just kind of goes away.

But what really happened, who were these people that did this and why and all this kind of stuff. And so you might have this curiosity of what could have been done to prevent it or something like that. So, yeah, somewhere in between just the everyday tech user, because so many of us are using tech so much in our lives. We have a phone and a tablet and a smart TV and computers, they'll use computers at work. And we're so invested in this, but we don't know that much about the security of it. So I really like targeting them and amazingly enough, I've targeted so many of them that they'll actually say that they've quit their job and started, they went down IT security as a new career path because they just think this is so exciting to defend against hackers or something. So it's been really fun seeing  all the responses people have had.

Jason Sew Hoy: It's funny. Listening to that PBX Hacking episode, I would have been that guy that hired the cheapest contractor to get any old PBX installed to get things done. But now that I've listened to the show and heard the story of the company that racks up a $300,000 phone bill from getting hacked and calling pay-per-call lines. I mean, that's just crazy town.

Jack Rhysider: Well, I know for a fact that you use good people to make Supercast with so I wouldn't undersell yourself for it for that. Because I've talked with that team that made that and I'm like, wow, these guys are really, really sharp and they really know their stuff and I almost used them for a project of mine. So you do really use a good team there.

Jason Sew Hoy: We also don't have a PBX. All right monetization, would love to switch gears a bit. Can you tell us how you monetize the show?

Jack Rhysider: Yep. So there's ads in there. I just throw two ads in. I don't want to overdo it. I don't like to give people a sour taste and overdo it in that way. So there's two ads, 60 seconds each. I started Patreon before I knew Supercast existed, so I got a Patreon ongoing as well. And then I've also got a Shopify store that has all kinds of different shirts. It's not just the podcast shirts, but I've also made all kinds of it hacking culture shirts as well. 

Jason Sew Hoy: Awesome. How did you decide on direct listener support?

Jack Rhysider: This is interesting. I've gone to the conference where I met my fans and they're literally handing me money at the conference. Like, I don't know how to donate to your show so here just take this $20. And somebody even gave me a hundred dollars at the conference.

Jason Sew Hoy: Was that weird?

Jack Rhysider: That was weird. I was like, I'm just doing it for you. You don't have to do anything for me. It was very strange. And at the same time, I was not feeling comfortable holding my hand out saying if you want to give me something, here you go. I got email after email and it was actually five emails before I finally had to make a change, but it was like, I just didn't have any sort of way to just get direct money. If you write a book or if you make a movie, you pay for that movie before you know if it's good or not. So what I was doing was I was providing value to my listeners and they were like this is worth something to me. This is entertaining for hours and hours and hours. I should give something to this, help this out in some way. I want to hear more of it.

And so that's why I decided to go and set up a Patreon and get things set up there. And so then I could just direct people, if you want to help out the show, here's where you can go. I'm such a fan of it now because it is the most direct way to support the work you love. It's people want to help out, and I want to help out creators that I love. Having that kind of thing is just wonderful to just go directly to the person and say, here, I got some money for you. Take it and thank you for all your work you've done.

Jason Sew Hoy: Absolutely. Actually, it's so simple the way you just expressed it. With regards to a movie or a book, you paid before you know it's good and yet for some reason it's strange on other forms of creation to pay in advance. I hope we can close that gap. I just think the world is going to be a better place when we can pay creators what they deserve.

Jack Rhysider: It’s getting there. 

Jason Sew Hoy: It is getting there. So what does a paid member get and did that evolve over time? How did you kind of come up with that value that you're offering to your listeners?

Jack Rhysider: I'm really big on research and stats driven decision-making so I went to this website called Graphtreon, which shows you the top Patreon podcasts out there. I literally looked at all top 20 of them, the most profitable Patreon ones. I looked to see what are they giving. And what I concluded was they're all giving bonus content. There wasn't any other similarity of they've all gave the same perk but the bonus content, they were all giving it. So I knew for sure I needed to give bonus content. What I give is bonus content is bonus episodes.

I don't make them as fast as I should because it takes a lot of work to make an episode and throwing an extra one in there is a lot of time, but I have six so far, so at least there's something going there. It's also easy enough for me to send stickers out to Patreon members. I also give them a discount at the store for the shirts. Oh, and an ad-free feed. So when I have two ads in the episode, people don't need to listen to that if they're paying members. So I'll give them an ad-free feed as well. So those are the things I give and I think the ad-free feed and the bonus episodes are the most used, the stuff that people like the most.

Jason Sew Hoy: And you have a Discord as well, right?

Jack Rhysider: Yeah, there's different communities. You get Discord tag in the Discord group so they do get that but I'm not sure how much people really join because of that. What people want to join is because they want to support the show because I've even asked Patreon, they don't give you numbers on how many people listen to a bonus episode so I had to ask them specifically how many are listening? And they said something like 50% of my patrons are listening to the bonus content. So they don't even consume the stuff that I'm like saying here you get this extra stuff. So it's very strange that they don't but that's just seems to be what happens. So yeah, I think the majority of them are just there to help support me and again, they want to hear more episodes of the main feed.

Jason Sew Hoy: Totally. I would be remiss not to take the opportunity to plug Supercast being a podcast-first membership solution. Of course, we provide that visibility of what people are listening to right down to the individual subscriber. That's one of the things that we're really leaning into this year. We already provide that kind of who's listening to what level analytics, but we're also making use of the fact that we have individual private feeds as well, even starting to like tailor the content of what appears on the feeds and doing custom new member welcomes, just because we already have the setup to be able to do it.

Jack Rhysider: And I want to add that if I knew about it before starting, I would have joined Supercast for sure and I've thought about switching over to it many times. So I highly recommend Supercast as well.

Jason Sew Hoy: All right. Once your paid membership was available, how did that affect the connection with your listeners?

Jack Rhysider: I don't think it affected that much. I mean, I hear from the paid members sometimes but they're mostly quiet. One of the things I like to do is find my listeners and go as close to them as I can and be involved somehow. And one of the things I do is just go to them. So if you asked me where would you make a community for your podcast? Would you do it on this random obscure website that just has podcast communities? I'd be like, no, you go to the podcast listener. If your listeners are on Twitter, go to Twitter.

If they're on Facebook, go to Facebook. If they're on Instagram, go to Instagram. And so I was going to all these places, LinkedIn and everything. I made a subreddit for my podcast listeners and that's growing, but my fans themselves created a Discord, which I wasn't too familiar with Discord so I'm glad they did and not me. So my Discord channel is actually made by fans and I really want to take a step back from it and let them control it and run it and do everything and I'm just there sometimes. So yeah, it's by them, for them that's going great. I made it the official one cause I'm like, this is great. That's kind of the thing and there's all these different communities of where my listeners are and I don't put them in one place because they're not all on one place and I don't want to make them go through this extra step of go to this website you've never heard of and sign up and then you can be part of the community. No, I don't think it works like that. I would get like 1% as many people if I made them do that.

Jason Sew Hoy: So you've got, let's see, 4,457 members paying nearly $15,000 a month, which is awesome. How important is that when it comes to your paid membership? I guess that flowing through to the goals that you have and telling people what you'll do with the money and all that sort of stuff.

Jack Rhysider: It's really weird to publicly show your numbers like that but one person who really inspired me was Pat Flynn on the podcast Smart Passive income, as well as John Lee Dumas on the podcast Entrepreneur On Fire. They talk about how to make money online and stuff and they actually post all their numbers. I love the transparency. It was just so inspiring to me to see somebody say this is what I've tried, and this is what has… how much I've made out of that. How much are you making from podcast ads? How much are you making from YouTube ads? How much are you making from this and that? And it's just so exciting to see and so wonderful so I leave it up as a thank-you to them.

 Maybe that'll inspire someone else to start something. I don't know. Because you can hide it. You can hide how much you're doing, but I also love seeing other people's Patreon statistics. So I'm like, if I like watching everyone else, I might as well show mine as well. It's kind of like that. So one of the things I do is because I don't want to be super transparent about how much income I have, I have no problem being super transparent about the stats on my show. And so that's kind of the thing I do is I decide, okay, ask me anything about stats. I'll be happy to share it. And I'll even make a yearly post on all the stats that my show has. I think what we'll do in this episode is we'll talk about that in the bonus content.

Jason Sew Hoy: Yeah. And we're going to talk about the marketing, kind of the marketing experiments that you did last year as well, but that is your annual roundup. And just the stats that you put on your site are just incredible for anybody that wants to check them out and go to And then I think it's in the About section, right? And that's where you post, Jack literally gives it all away. You get to see all of the download stats, whereas traffic is coming from, what's worked, what hasn't. It's just an incredible resource. You are definitely paying it back or paying it forward when it comes to kind of taking the lead from Pat Flynn.

Jack Rhysider: Well, it's one of those things where I kind of appreciate an annual report on how did I do, right? And so if I'm making it for myself, then I might as well publish it. I have no problem. I mean, we see stats on YouTube. On every YouTube channel we can see the stats. So to me, it's the same. I don't know why people hide from stats so much.

Jason Sew Hoy: Totally. what do you think podcasts has get wrong when constructing when they're asking for money from their listeners.

Jack Rhysider: I don't like when I hear a podcast super full of ads, and then also asking for Patreon support or something like that. So some things… like, I really try to keep my ads to a minimum because I get that extra support from listeners and then my goal is to just to eventually get rid of ads altogether and just be 100% listener-supported. Sam Harris is like that and some other shows.  It's really wonderful to see people like that just say, yeah, I don't have to worry about ad sponsors at all and I can talk about any company in the world without having any sort of  fear that they're going to pull ad money away or something like that. And so, yeah, one day I would like to get to that point. I'm not sure what else people do wrong.

Jason Sew Hoy: Cool. Well, not sure if you know, but the team that built Supercast built Sam Harris's selection as well. So we would love to be able to do something with you. Zooming out a little bit, there's very much a noticeable wider kind of community lean-in to your work as well as sharing all of your data and your successes. You’re blogging over at Lime Link and you're helping podcasts be better. Tell us a little bit about that and what that means to you.

Jack Rhysider:  To me I've got to sort things out in my head and try to figure out like if I'm doing research on anything in the podcast space, I'll get a bunch of information and I'm like, well, why should I just keep onto that? I might as well blog about it somewhere and share this with everyone else. So that's what Lime dot link, that's the whole URL, lime dot link is about. I just blog about podcasting. So some of the things I'll talk about, like one of the things I was really fascinated with is how big does my audience look if I were to put them all in a stadium. So I got all these pictures together of, this is what 50 people look like in a room. This is what 150 people look like in a room. This is what a thousand people look like in a room. And so there's all these images of what it looks like. 

And if you only have 150 listeners, I am pretty sure I would be nervous to stand in front of a room with 150 people and tell them about what I'm feeling about whatever it is. So yeah, I think it's just kind of encouraging to see certain things. That's one of the articles. I write about monetizing and marketing and challenges that podcasters have and how to sell merch and all kinds of stuff. Just because I’m out there doing all the research and I might as well publish what I find. So it's just kind of easy to put all my notes together. And I don't like having to remember it so once I put it down, it's easy just to go back to it and say, what was that I said about that.

Jason Sew Hoy: For sure. I love that you're doing this. You're obviously drilling down into some changes in the industry that, if they're not impacting us now, no doubt are going to have some impact on the future. I notice that you recently did a writeup on Megaphone’s target marketplace and how the tech they're starting to introduce now is not only causing some concern from privacy points of view, but also causing Megaphone to show up on block lists. Can you kind of fill us in on what's going on there?

Jack Rhysider: Megaphone is what, maybe the 15th most popular podcast host or something. They have a few thousand, maybe 3,000 podcasts that they run. And it's kind of a high-end podcast host where you have to have a certain amount of downloads before they'll really consider you. And what they have is a way to have automatic ads inserted into your show. So you might hear like, I don't make the ad. It just might show up from like Pepsi or Starbucks or somewhere else like a regular radio ad that you might hear or TV ad. That company made the ad and they gave it to Megaphone and Megaphone puts it in your show for you. And then you get some money for that. 

So that's what their targeted marketplace is. And that would be all right if it was just that  but what they do is they take listener info and say, okay, what is this listener? They compare it with Nielsen segments so they can then say, okay, so this listener is from Seattle and I've seen them go to a bicycle website recently and so maybe they like coffee or something. So they'll specifically target listeners, the show to specific ads. There is some collection of listener data from this, which is really strange because you just don't imagine, you feel like podcasts is kind of anonymous. 

When I listen I don't really feel like I'm being tracked or anything. There's no way, you don't sign up or anything. You just kind of download the MP3 and listen. Yeah, they're doing that. And it seems to have caught some attention of some anti-tracking apps, like I think uBlock Origin and Brave, the browser is a pro-privacy browser, have said, well, we don't want trackers. We don't like trackers. And if Megaphone is tracking your listeners, then let's block them. So these kind of plugins for browsers and stuff have been blocking just all of Megaphone, not just my show. And of course I don't like that feature so I turned that feature off for my show so you don't just get these ads and my listeners aren't being tracked, but it is one of those things where now I'm being added to block lists because they're just blocking all of Megaphone and I'm suffering kind of that collateral damage from it.

Jason Sew Hoy: Oh, wow. So turning it off doesn't unblock you?

Jack Rhysider: No no, it's all of  The blog post explains exactly what the domains are that are being blocked and that kind of thing. But it's just strange that Adblock Plus and UBlock Origin and some DNS providers are blocking this podcast host. And as far as I know, this is the first podcast host ever to be blocked. So all two or 3,000 shows, whatever they have hosting, are being blocked by seven different block lists. And I think that this is something that Megaphone really needs to think about internally of like do we want to keep going with tracking listeners and being added to more and more block lists because obviously it's making them money dealing with these ads and stuff. Or do they want to say actually we don't like that. Megaphone just got bought out by Spotify and Spotify does use technology like that so I don't see them turning around anytime soon.

Jason Sew Hoy: Right. you also mentioned that ART19 has introduced something similar as well.

Jack Rhysider: Yep, ART19 has the same technology but they don't advertise it as much and so I don't think these block lists just know about ART19 or have been reported… nobody's reported them about that, I guess. I wouldn't be surprised if they're second to start getting blocked as well.

Jason Sew Hoy: Yeah. Interesting. So where do you see that headed? I mean, obviously if you've got block lists and more and more of these advertising platforms kind of coming face-to-face with each other. Do you take any kind of parallels from the way advertising has kind of evolved elsewhere on the internet to guide you in where this might go.

Jack Rhysider: I'm pro-privacy and anti-tracking kind of person. So you have websites like, which will look at all kinds of information on you and give you targeted ads. But then you have a search engine called that doesn't track you, but still gives you ads. And you're like, well, how did I get an ad? Well, if you search for vacation destination ideas, then there's tons of websites out there that want to advertise their vacation options or whatever. So it's easy for you to not be tracked and still get contextual ads because you just search for that term.

So just that term alone, you can get all kinds of things. And so I'm hoping that in the future, if my show's about IT security, then you can use IT security as part of… throw those kinds of ads in my show. I'm fine with that. All right. So it doesn't really have to be well, what's that listener, where's that listener live and what are their likes and dislikes and all these things. I don't want things to go in that direction. I prefer it to just be contextual and not really database-driven for the ads, but that's my hope. I don't think it's going to go that way. I think sponsors drive this kind of thing and if they want more information, they're probably gonna find a way to get more information.

Jason Sew Hoy: Right. Final question, if you could do something over again, what would you do differently with your journey? 

Jack Rhysider: Start sooner, I guess. It's hard to say for sure because everything has just been a learning experience on…. I knew when I was getting started, I knew I had to get 10 or 20 episodes in the can before I really felt like this was a thing and before I could really feel like I could compete with some of the other bigger shows out there. So it was always just a rush for me to get through, just get a whole bunch of stuff in the catalog. And at the same time, I knew I had to go through that kind of churning process of learning and everything to actually know what I was doing. So I was trying real fast to just rush through it all and get somewhere. But yeah, if I had started sooner, I wish that was the case. And that's, I think, that's my biggest thing I would have done differently. I also would've joined Supercast if I was starting it all over.

Jason Sew Hoy: What's the evolution of the team been like? 

Jack Rhysider: I started out just as solo and did that for probably 40 episodes, but then once I started monetizing, I was able to afford some help. And I think that was kind of the thing is I just couldn't afford to pay people at the beginning. So now I have editors and producers and sound designers and writers all pitching in working on different episodes. It doesn't quite feel like a team. It feels more like a hub and spoke kind of thing where I give somebody something to do, they get it done and they send it back to me and then I give it to the next person to get something done and then they send it back to me and then I give it to the next person to get something done. It's kind of weird, but I'm learning how to build a team right now. That's kinda my biggest struggle I'm working with.

Jason Sew Hoy: Awesome. Okay. Well, we are gonna park it there for our main episode and for our Supercasters Premium listeners, we're going to have a bonus section where we deep dive now into what Jack learned during 2020. I heard him say earlier he did a lot of experimenting with marketing, from promo swaps to writeups to paid marketing and we're going to get him to share what he learned, and also get some idea as to where he's going to be placing his bets in 2021.

So if you'd like to listen to that, you can sign up for Supercasters Premium feed. It's 100% free and you'll get the premium Supercasters feed in your podcast player in just a couple of taps. Jack, pleasure speaking with you today, and thank you so much for coming on the show  

Jack Rhysider: Yeah this was wonderful. Thanks for having me.