Find the Right Podcast Membership Benefits with Stephen Hackett

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Stephen Hackett is one of my favorite podcasters, and cofounded my favorite podcast network, Back in 2018, I spoke to his co-founder Myke Hurley about starting podcasts. Since then, Relay has really ramped up their membership program and I though Stephen would be the perfect guy to talk to about putting out tons of content and deciding what to make free, and what to make paid.

I think they’re doing a fantastic job over there, and Stephen’s inspired me to reconsider my own membership program for this show. Have a listen – I know you’ll get some great ideas too! 

Show Notes

Want to start your own podcast? Check out my course, Podcast Liftoff. Use the code BUILDIT for a listener-exclusive discount!


Intro: Stephen Hackett is one of my favorite podcasters and co-founder of my favorite podcast network, Relay FM. Back in 2018, I spoke to his co-founder, Myke Hurley, about starting podcasts and some tips and tricks he had to offer. Since then, Relay has really ramped up their membership program, and I thought Stephen would be the perfect guy to talk to about putting out tons of content and deciding what to make free, and what to make paid, and how to balance that across lots of different hosts and different shows.


I think they’re doing a fantastic job over there, and Stephens inspired me to reconsider my own membership program for this show. Have a listen. I know you’ll get some great ideas about memberships finding a group of diverse voices and much, much more.


But first, let’s hear from our first sponsor.


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And now back to the show.


Joe: Hey everybody, and welcome to another episode of How I built It, the podcast that asks, how did you build that today? My guest is Steven Hackett. He is the co-founder of Relay FM, a podcast network that I am a very big fan of, so I’m happy to have him on the show. Steven, how are you?


Stephen: I’m good. Thanks for having me, and thanks for the kind words about Relay. That means a lot.


Joe: My pleasure. I regularly mention your shows on this show because Relay probably accounts for like 70% of the podcasts I actively listen to. Sweet. So you guys are doing really great work over there. And that’s one of the reasons I wanted to have you on. Because this season of my show, I’m focusing a lot on how small business owners can increase their audience and their reach through good content. You all over at Relay FM have a penchant for putting out good content. So I figured we could dig deep into that.


But first, why don’t we start off with a little bit about who you are and what you do?


Stephen: Yeah, sure. I’m a native of Memphis, Tennessee. So if I sound like I’m talking slowly, that’s just how I speak. Just I came through it naturally. I’ve got a background both in journalism and tech. I went to journalism school, but then had an IT career for about 10 years or so before the podcasting thing became my full-time job. As we record this, I’m coming up on five years of doing podcasting and content creation as my full-time job, which is very exciting. It’s hard to believe it’s been that long. That’s me.


The content that I make mostly focused on Apple and technology history, but really covers a lot more than that, of course.


Joe: Yeah, yeah, absolutely. I don’t think I realized that you had a background in journalism. One of your shows is Mac Power Users. And I listened to that a lot and Connected, where you mentioned your background as Apple Store genius. Is that the official title?


Stephen: Yeah. That’s the ridiculous title.


Joe: I didn’t realize that you’re in journalism too. How did you get into podcasting initially?


Stephen: For me, it was a long and winding road. I got my journalism degree, but I graduated in the middle of the recession, and there weren’t any real journalism jobs. I had worked at Apple at the Genius Bar for my last couple of years in college and then pursued an IT career full-time. But after I left the Apple Store, I started blogging at, which I’ve run continuously now for almost 12 years.


I just wanted to write about technology and design and where those things met, and I thought, “Well, I know a lot about tech, but I have this education and how to write and how to tell stories.” So I combined those in blogging because it was 2008, 2009 that’s what you did.


A couple years ago later, I met Myke Hurley, my co-founder at Relay FM. He had a little tech show at the time. He interviewed me after reading some stuff that I’d written about I think the iPad launch or something is about that time. He and I really hit it off. Eventually, we started doing a couple projects together. Then it sort of spun up over time until six years ago when we started Relay FM as a company, you kind of slowly burning it from a hobby into a career.


Joe: Got you. Got you. I interviewed Myke on this podcast—I will link to that in the show notes, which will be available over at along with links to all of Stephen’s content here. Because there’s a lot. The 512 Pixels, I think is really interesting because you’re a bit of a Mac historian, or an Apple historian, I would say. I like that content a lot because I have a degree in software engineering, I’ve been into computers for my whole life basically. But I didn’t get into Apple until probably 2008, 2009. I was a bit of a hater up until then. And then I saw the light.


Actually, quick Fun fact, I switched from Android to Apple in 2015, and Phil Schiller tweeted a link to the blog post about me switching. He didn’t retweet it or anything. He just tweeted, “Joe switched,” and then a link to my blog. And that is, to date, the most popular blog post I’ve ever written.


Stephen: I bet. I have a couple of interactions with Phil Schiller. One of them was I was going through some Apple archive stuff that I had found online. I found a picture of very 90s Phil Schiller with kind of hair over his collar and I tweeted it at him. And then he responded with like some song lyrics from the 80s, which is pretty funny. Then we went back and forth once about a picture of a squirrel they use in a keynote. And years later, they’re like, “Oh, it’s another picture of the same squirrel.” And we talked about that briefly. So, yeah, it’s fun.


I think out of all the apple executives, he is the most sort of outgoing on social media. Tim Cook is there to announce things, but Phil Schiller, he gets in there and shares links. I know he shared a lot of links to MacStories, which is written by my co-host on Connected, Federico Viticci. A lot of things Federico has written; Phil Schiller will share. That’s always really cool to see someone being engaged with the audience.


Joe: Yeah, absolutely. Absolutely. Awesome. So we have the stage set a little bit. Let’s talk about podcast networks. You run a podcast network. I’ve talked about just starting a podcast…sorry about this. Do you hear that at all?


Stephen: I don’t.


Joe: Okay. Alexa decided she was just going to start yelling about prizes. I’m going to go turn her off real quick.


Stephen: Alexa, order paper towels.


Joe: I muted it and it’s still talking. I have no idea why.


Stephen: I keep my home pod in my office set to “not listen” because it would just go off all the time.


Joe: It was like apropos of nothing. She was like, “welcome to Alexa prize.” And I’m like, “I don’t know.” Alexa stop. Oh, boy. So I’m going to clap my hands and restart that question.


Stephen: All right.


Joe: I’ve talked a lot about podcasting on the show. I’ve interviewed people about starting podcasts, but we haven’t really talked about podcast networks. So could you tell us a little bit about what a podcast network is and what the benefits are of running one?


Stephen: Sure. I mean, the way we view it is it’s just like a TV network. So let’s talk about ESPN, for example. I know there are people out there who might not be sports fans, but I think it’s a good analogy, where you have this sort of central company. It can do all the tech and all the business stuff, but then you have a bunch of different shows covering a bunch of different things. ESPN changes throughout the year, where you got people covering baseball, basketball, football, whatever. But they’re all kind of doing it under the umbrella of ESPN, but they all have their own voices and the other different shows look and sound different. That’s really the way that we view it.


Relay FM exists to be a backbone for a lot of creators to do their own thing. That wasn’t necessarily what we started out thinking. We really started the network because we had this handful of shows and we needed someplace to put them all. I think Myke, in your interview with him, y’all talk some about his history. Our history, obviously, is the same in a lot of ways. But he had a little network and then we were on 5by5 for a while, and then we left. It was like, “We got to have a network because we have these five shows and we want more.” But the goal wasn’t ever really to build a network. The goal was just to build a place to put all of our shows.


Over time, our vision of that shifted a little bit. Now we are just as interested in making content as we are making a place for other people to make their content. So there’s a lot of shows now that we’re not on, that other than support have very little to do with. But they’re on the network. They’re doing their own thing. So it’s kind of become an umbrella for a lot of people to work under. That’s something we’re really proud of.


Joe: That’s really fantastic. Because I think probably a barrier for a lot of people is actually starting the podcast. “How do I host it? What do I do? How do I get the artwork together? And things like that. You know, is this just going to be a money pit for me?” I think that’s probably something a lot of people think about.


Stephen: Sure.


Joe: It sounds like with the podcast network, individual podcasters might get a little bit more support by having some people who are experienced helping them out.


Stephen: Yeah. Our goal really is if someone shows up, we’re going to start a show—I think we’re going to talk about that in a second—we want to take care of everything we can so they can just show up and do what they do best. Talking to the microphone, share their ideas, and thoughts on things. So that means that we have a graphic designer on retainer. That means that we built our own content management system that makes it really easy to publish this stuff and put all the links together in the show notes. It means that we have a hosting solution already built for them.


So they really can. A lot of our hosts do just show up and hit record every couple of weeks or every week or whatever it is, and we take care of the rest. We even have a freelance editor who does a lot of our editing. We have some hosts that want to do more. Like I edit a bunch of shows that I’m on. Myke edits a bunch of shows that he’s on. But not everyone has those skills or that time. Because a lot of our hosts, podcasting is not their full-time job. It may be part of their job, but they may also have a day job and there’s podcasting on the side. So we can provide solutions to all that other stuff so they can focus on their content. We found that that works really well over the years.


Joe: Again, that sounds really fantastic. I do some editing sometimes, but I mostly hire an editor out to do this stuff, even though he’s just basically lining up the audio.


Stephen: Sure.


Joe: Sorry, Joe.


Stephen: Joe we love you.


Joe: I think you’re so great.


Stephen: Don’t leave Joe.


Joe: But it’s great to have that kind of support. I’ve heard some opinions, I think Myke might have mentioned this, that a podcast network today might not be something one needs. If you have multiple shows, or if you are having trouble getting up and running on your own, is a podcast network something that anybody can or should look into?


Stephen: I think it depends on where you are. If you are a creator and you have multiple shows, yeah, maybe it makes sense to have some sort of branding shared between them. That’s the other really important part about Relay is we have this idea that if you see a show with our branding, you should know what you’re going to get. Because if you think about it objectively, funding a podcast is a really weird thing, because Apple, Overcast, Pocket Casts, Castro, you know, wherever you’re listening, Spotify now, you’re looking at visual artwork to decide on what audio program to listen to. That’s Goofy.


Some people are trying to change stuff around that. But for us, it means that all of our branding is really tight. So if someone sees artwork with that Gotham typeface, and that are on the cut on the upper left hand corner, if they’re familiar with any of our work, we want it to speak well of our work. If you’re a creator out there and you have these multiple projects, that can be a really powerful thing. If someone likes one thing you do and they stumble across something else you do, you want to be able to link those two things together for them. You don’t have to have a network to do that, but it may help.


The problem a lot of people run into is there’s not a lot of great solutions out there to build a network on. So Myke’s little network that he had before, 5by5, we had built on Squarespace. You can totally do that. Disclaimer, Squarespace sponsors, a bunch of work that I do, but it’s a great podcasting platform. There’s some others that have sort of put the network idea out there. I think Fireside you can do some things like relate shows together.


But most software as a service for podcasting is really still built around the idea of a single show when it comes to hosting and having a website and stuff. So you can kind of hobble something together. But at the same time, I also agree with Myke that you should focus on your content first and only build the network if it’s something that you really need. It was something that we really needed at the time and we definitely need now. But most people starting out don’t need that.


I would say, if you’ve got one or two podcasts, you’re thinking about adding some more, make sure that your first ones are really solid before you do that. I think people want to branch out and do more maybe too quickly. I know myself I’m guilty of that at times. So all of that has to be taken into account. The branding, the tech, is it the right answer for your project and your business? It’s a complicated set of questions.


Joe: I mean, especially finding a good platform to manage everything is super important. I’m a web developer by trade, I’ve been embedded in WordPress since I think it was like less than a year old when I started using it. So I know a lot of people in my field will say, “Well, you could do that easily with WordPress.” And I’m like, “Easily is definitely a word I would not use for that.”


Stephen: Sure.


Joe: It’s possible, of course, but finding a good platform…You know, you I’ve heard that you’ve mentioned that you built your own CMS. Was that a custom build or was that based on some other software?


Stephen: Someone had built sort of a very small version of it, and we purchased it from them and have run with it now. It does a lot of stuff more than it ever did in the beginning. But yeah, it’s custom to us. For us, it’s really powerful because, for instance, we’re right on the edge of doing some cool membership stuff, and like “Okay, well, I need these features in the CMS.” I talked to our developer, we mapped them out and figured it out. For us at our scale it makes sense. But starting out, I don’t think it does. I think if you’re starting out with one or two shows, you can go a really long way having them on something like Transistor or Simplecast or something and just sort of branding them to look alike.


Joe: Yeah, yeah, absolutely. Or there’s a WordPress plugin that allows you to have multiple shows in WordPress instance, right?


Stephen: Yeah.


Joe: That makes a lot of sense. Then for Audio hosting, is that something that you rolled your own or are you using one of the one of the bigger names?


Stephen: Yeah, we use Libsyn. The file hosting itself is a business that we didn’t necessarily want to be in. It’s hard to do. It’s hard to keep those costs right. Honestly Libsyn has been doing it really for a long time and they were really good at it. All our mp3 are actually hosted on Libsyn, and then we feed them into our CMS where all the metadata and show notes and everything get added to it before it goes out the door.


Joe: Got you. Got you. That’s the same exact way I do it. I basically just treat Libsyn as a file repository, and then my website as everything else.


Stephen: And you get stats through Libsyn and stuff. They use the IAB stat system, so you know the stats are going to be consistent. For us, it’s really the back end to the back end.


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And now back to the show.


Joe: As you mentioned, starting a podcast network, you want to make sure that maybe your first couple of shows are really good before branching out and doing a whole bunch. How did you decide your first slate of shows for Relay? Because both you and Myke were doing I think probably more than one podcast by the time Relay FM started, right?


Stephen: I was just doing one, Myke was doing four, and then we added a fifth. To back into the history a little bit, we were on 5by5 another network, and we had several shows there. Some of them came from Myke’s original network that he had, some of them we started new on 5by5. But when it was time to branch out on our own, we looked at the shows we had and we selected four to carry on to whatever the new thing was going to be.


Those were Connected to Pen Addict, Inquisitive and Virtual. The Connected had pre-existed as a prompt, The Pen Addict is actually Myke’s oldest show. Then Inquisitive was Myke’s interview show. It’s kind of been put to rest now. Then Virtual is now remaster, where they talk about video games. So we had four shows that were pre-existing that we rebranded, but we knew, “Okay, this show is basically going to be the same here on this new thing.”


Then we added Analog(ue) where Myke and Casey speak about feelings and stuff. So we launched with five. Looking back at that now, it’s been almost six years, that was a lot to launch with. But what we were doing, because we were already doing it, it didn’t seem like a lot. We were already doing multiple shows. Starting at zero, if you weren’t aware of our work previously to Relay FM, five years would have looked like a lot. But it really wasn’t because we were already up and running at that speed.


One thing we did not do a good job at, though, was diversity. If you look at those original shows, it’s a bunch of dudes. That was something that we were wrong about. We’ve worked really hard in the year since to correct. We still obviously have a lot of work to do in that area. But that was something when I look back at, that earliest shows is something I wish we had done a better job of.


Joe: That could be really tough. Right? I was told early on, I think after my first like 50 episodes or so, that the show was not very diverse. Even today, as I’m actively thinking about it…You know, back then first of all, it was easy for me to say “Well, the tech space is mostly white dudes. So what am I supposed to do?” Even keeping that in mind today doing this, when I reach out to guests, it can be tough. Do you have any tips? This is not something that I told you I’d ask you and I just thought about it now. But is there anything that you found works in order to try to find a more diverse set of voices for your shows? Either for guests or for new shows?


Stephen: I would say that it requires work. The default, unfortunately, in the tech industry is me. It’s like middle aged, white dude with a beard. That is something that you have to be really aware of and really work on. For us, it means that we’re always looking at new voices in the space where people launch projects. We check out and listen to a lot of stuff that we don’t necessarily talk about, just kind of seeing who’s out there, seeing what people are doing.


We also look at the guests that we’ve had in the past and guests on other shows, like not on Relay, and try to find new voices that way. But really, I think it’s most important just to always be aware of it. When we launch a new show, or when we’re thinking about a new show, that’s always one of the questions: does this further are our efforts in this area? Is it something that we want to do just because we want to do it or is it something that we need to change, something we need to push harder on to find the right people and the right voices? That’s always part of the conversation when we are launching something new.


Or honestly, when a project winds down. If a project ends, which happens sometimes, what does that do from the diversity angle? Are we losing a voice that we really want on the network? Do we want to create a different project with that person? Do we want to keep them as part of the Relay family? We’ve had people come and go over the years, but that’s…Really what I was saying is it always has to be part of the conversation. If it’s something that you just think about the last minute, you’re already doing it wrong. It’s got to be just part of the conversation, part of the fabric of your decision making at all times.


Joe: I like that. I like that a lot. Like you said, it does take work. I’m pretty active in my communities and I really need to sit down and think and say, “Who is not just going to be another, like you said version of me? I’m in my mid-30s, I’m a white guy with a beard. And there’s a lot of us. So how do I bring new voices onto the show?


Stephen: And the thing is those voices are out there. It is a matter of not only doing the work to identify them, and approach those people. And present yourself as approachable to the world. I never want someone to think that they can’t contact me about something or ask me a question. But also, the more we do that, the more that young people look to podcasts in whatever field they’re interested in, and the more likely they are to see someone who looks like them, to hear someone that sounds like them, the more likely they are to want to get involved in the future. So I view this as not only are we working to make the present better, we’re also working to make the future better.


Joe: I like that a lot. That goes a lot of what I think about in the programming space too. Because programming space is mostly guys, and whatever. I think my graduating class was all guys. So it’s, again, things to think about. If we include more people now, that’s better for the future especially. I think about that a lot more now that I have a daughter, which I don’t know if that’s wrong or right, but it’s something that’s true of me.


Stephen: Sure.


Joe: Anyway. So you had your first slate of shows—we just touched on this a little bit—but you have added more shows since then. When you add a new show to your network? Is it people pitching you? Do you do outreach? Is it some combination of both?


Stephen: Yeah, it’s a combination of both. We get a lot of pitches. We get pitches almost every day. The reality is we just can’t respond to all of them. I try to, but it’s difficult to do. But sometimes someone pitches an idea and it’s like, “Oh, this is a really interesting idea.” Or you do seem like you’ve got something to say that’s unique, maybe we should have a conversation. Over time, that would have shifted more towards us instigating projects or finding somebody to work with through people we already know or other outlets, or somebody finding a project to bring on to the network. So it is a little bit of both.


We’re not an open platform. I always get an email like, “Okay, how do I get my show on your network?” Well, that’s not how that works at all. It’s a partnership. It’s something that we enter to. We are not a hosting service. But it is something that we do spend a lot of time on. Really the first couple of years really grew pretty quickly in terms of the number of shows, and that slowed way down over the years. That’s also on purpose. We want to really focus on what we have in the roster now, making sure that everything we’re doing now is sustainable and healthy. When we add things now, they are much more…not much more considered. That’s not the right way to say it. But it’s much more rare to do it now.


Something else we’ve changed thinking about new shows is we openly now discuss like, is the show open ended, or is it going to be half seasons, or is it going to be a short run show? Flashback, which is a show I do with Quinn Nelson, Snazzy Labs over on YouTube—check out Flashback—He and I are just doing one season so far. So we did 10 episodes. Episode 10 will be out a few weeks after we record this. And then we’ll be back in the fall sometime with Season 2. So we’re taking a break over the summer.


That’s never something we would have done in the early days. But now we feel like we have the freedom to sort of mix and match formats and schedules if needed. So that’s something we’ve experimented with as well as we’ve gotten a little bit older.


Joe: Yeah, that’s really interesting. I mean, I don’t want to jump too far ahead, but I think it’s really important to experiment here. I’ve been enjoying Flashback a lot.


Stephen: Thank you.


Joe: When you all talked about the Zune, I lament the Zune’s demise regularly. I thought it was such a great thing. I’m trying to think of the best way to put this because I don’t want to make it seem like you are actively accepting pitches or is something that you regularly do. Obviously, you just said you don’t. But what makes a good pitch? Let’s say that there are networks out there actively looking for pitches. I suspect that just going to a network and saying, “I have an idea for a podcast” is probably not the best.


Stephen: What we want to see is a project that already has been proven. One thing that comes with our scale now is we can’t really do a project that we don’t feel confident would be successful to some degree. So if you’ve never had a podcast before, you just have an idea, my answer always is, “Go do it. Get some episodes under your belt, and let me know how it goes.” That’s not a promise that we would have you on the network at some point. It’s just to say you need to go do it. Like you need to go and launch something and record something and see if it’s for you.


We don’t want to be in a situation where we invest in a new show, and it doesn’t go anywhere and it’s kind of a bad deal for everybody. It’s tricky because podcasting at the end of the day is really just a trade for content for people’s time. Sometimes content for money, but mostly just time. And we wouldn’t be really respectful of that. That means that we aren’t super willing to jump into a project that is from somebody who hasn’t done one successfully yet, or one that hasn’t been proven yet.


That’s not to say that we don’t have people who are new to podcasting. Most of our hosts were new to podcasting when they started on Relay. But we want to know that someone has the follow through and that the idea is right, and that sort of thing. So if you’ve got nothing but an idea, that’s not really a pitch. That’s just an idea. I think a pitch includes actual work. We’re kind of bleeding into the question of what makes a good show, but I think that’s the right question.


Joe: Yeah, that’s perfectly fine. Right. This talks about what goes into evaluating a show, which is also I think is really important.


Stephen: What I think about is what is the show’s or the host’s unfair advantage…That’s like a goofy business term that I hate, but it works. You know, what can you speak into where your point of view is unique that you have something to bring to the table, especially in tech, where we already have so much overlap? There’s only so many things to cover in tech. It’s really got to stand out and in a couple of ways. It would be different if we were a network of fiction podcasts or true crime or something like that where it’s broader. Like if you’re doing fiction, there’s no limit. Literally the limit is your imagination.


But when you cover content areas, we got to make sure that something is unique. Something like Flashback, Quinn and I had no interest in doing a tech news show. Relay has got a bunch of them. They’re a bunch of really good ones, not on relay. It’s like, what can we do that’s different? Quinn and I talked about that show for a year.


Joe: Wow.


Stephen: We talked about what our interests were, and we got to know each other. We both kind of realized that we had this shared interest in technology history. It was like, “You know what, maybe there’s something there.” And we talked and thought and talked and thought and we came up with this idea of “let’s talk about things that failed and what happened.” It’s been successful, and it’s been a lot of fun. That’s really kind of what I mean by an unfair advantage. It’s something that other people aren’t necessarily doing or you can do it in a way that is unique or better than other people.


So for Quinn and I, we have a really deep shared history of tech, me with Apple, him mostly outside of Apple as far as history stuff, and we made a good team in that. So thinking about those things are really important. Because honestly, the world probably doesn’t need another show running down the tech headlines of the week. But there’s always room for something that’s creative and engaging and interesting and funny based on any topic, including tech.


Joe: Yeah, absolutely. I mean, talking about Flashback for a minute, you released that, I don’t know if it was purposefully in conjunction with but at the same time as Test Drivers.


Stephen: Nothing’s back to that, my friend. It was designed to come out at the same time.


Joe: Yeah, it feels that way, because it’s almost like two sides of the same coin. You’re talking about history and then Myke and Austin are kind of testing out new technology and trying out new things. So I thought that was really interesting, and again, a unique concept I think in podcasting. You don’t really hear too much of that. Whereas interviews like this almost are a dime a dozen too. I constantly think of what my unfair advantage could be.


When it first launched, it was almost like I was not just telling the success story or I was digging into the tech side of business. It’s evolved a bit since then. But that’s really important to make your show stand out and I think that’s really good advice.


Stephen: Yeah. Yeah, it’s important. It can be just as different as we’re going to test new stuff and do it through this lens. With The Test Drivers, Austin as a successful tech YouTuber. He has access to a lot of companies. He reviews a lot of products. So for him to say, “What’s up with Android tablets?” It’s different than to me. I have to go buy one. I don’t have a flow of review that’s coming through my office. So he could tap into what he was already doing. The show, in a way, is an extension of his work elsewhere. That makes it a more natural fit. It means that it’s got overlap with what his audience expects elsewhere. And it means that those people were really receptive to it.


Joe: Yeah, yeah, absolutely. Aside from what sets it apart, there’s a few other things that go into evaluating a podcast. We have written down here format, schedule, host chemistry. As far as format goes… we can kind of loop in the last question here, too, right?


Stephen: Sure.


Joe: As far as format goes, I think picking the right format is important because you don’t want to lock yourself in too much, but you don’t want to give yourself this wide open space where you’re like, “Where do I start?” What advice do you have about evaluating on format and schedule and things like?


Stephen: I think one piece of advice is just because you start with something doesn’t mean it has to be that forever. You can introduce additional things. So upgrade I think is a good example of that on Relay where start is Myke and Jason talking about Apple stuff. But over the years, they’ve added things like Upstream where they talk about the streaming media landscape, which is super fascinating. Amazon, Hulu, apple, everybody. But that wasn’t a thing when they started the show six years ago. They’ve added it to the show. And now it’s a big part of what they do. So you can adapt things, you can plug things in, you can change things over time.


Another thing I think can be really helpful is you could have a couple of different formats and interchange between them. So on Mac Power Users, David and I have really three types of shows. We have deep dives where we talk about an app or some sort of workflow for an hour and a half. So we talked about keyboard Maestro, or BetterTouchTool or the Photos app or iCloud. And that’s it. We go deep. We talk about features, tips, gotchas. Like if you want to learn about photos, this is 90 minutes for you.


Then we have interview shows. We recently had James Thompson where we talked about his history, his development of PCalc, which he’s developed for decades. This great calculator app for the Mac and iOS devices. It’s not a show about PCalc. It’s a show about James, our friend doing this really cool project for a really long time and talking about the tech but through the angle of his story.


Then we do feedback shows which are basically just follow-up shows or topics got cut, or things that we want to circle back on. We just rotate between them. It’s content show, interview shows, feedback shows every six weeks, eight weeks or so. It’s really freeing to bounce between. And it’s not jarring because the audience has learned to expect those changes. So if you’re starting a show and the first 10 are about content of some sort, is “Hey, you know, next week, we’ve got an interview with somebody who’s an expert in this field.” And you interview them.


It can be as easy as saying, “Hey, this is something we want to do more of. So keep an eye out for future interviews.” That’s all it takes. And then the audience kind of expects that, “Okay, this show does interview sometimes.” No big deal.” So you can do that. The audience will follow you in those things as long as you tell them what you’re doing. You don’t need to drop an interview in if you’ve done 35 episodes of no interviews. You got to steer the ship a little bit. But that freedom to mix it up, to change it up, can keep things really fresh.


Joe: Yeah, awesome. Thank you for that. As a quick aside, the photos episode of Mac Power Users, I will link directly to that one because I gained a lot from the episode. I just moved my library off to a one terabyte SSD drive super recently. I got a lot from that episode. Then the interview you did with the space photography guy, that’s not doing justice really to what he does. But that episode I thought was really fascinating as well.


Stephen: It’s fun to get different people on that show and to have a wide range of topics and things. And it’s another place where we can have a diverse set of voices.


Joe: Yeah, for sure. It probably makes it a little bit easier for you and David as well because you’re not…I don’t know how much you script or how much you outline, but I’m sure the feedback episodes probably lighten the load a little bit from the deep dives, right?


Stephen: Oh, yes. We outline every episode of MPU. But the deep dives can be five, six, seven pages of outlines, especially if there’s something like keyboard Maestro or any automation type thing where you’re talking about “Okay, this app has 15 ways to trigger something.” Well, we got to talk about all 15. That is a lot of space. A lot of those outlines for MPU, those deep dives, we’re working on several of them at a time usually. It’s not always the case, but usually it is, where Dave and I sit down about once a month and plan the next four to six weeks out.


We often say, “Okay, I’ll take this one, you take that one. You kind of lead this interview, I’ll lead this interview.” So we split the work up between us. But even then it is a lot of time. I mean, MPU is, you know, for every hour on the air, I probably have at least another hour in research and prep, if not more. Probably a couple hours depending on the topic if I’m not real familiar with it myself. Hopefully it shows, but it is a time consuming project. But one that really happy that people can years later listen to Photos or drafts or whatever it is I’m going to focus and learn something, that’s really cool that that back catalogue can be so useful.


Joe: Yeah, for sure. Well, it definitely does show. You mentioned that you were from Memphis, and that’s why you talk slow. I’m from New York, which is probably why I talk fast. I tend to do things a little fast sometimes. But with the show content like this, I try to slow down, think of the questions I want to ask because I want to have good content for people to listen to. Like you said, we’re trading time for content. That’s important, right? Because if you’re not putting the right effort into it, there’s lots of other podcasts that people can fill their time with.


Stephen: Yeah. When I listen to a show, I can tell when they haven’t prepared. The worst thing is don’t say you didn’t prepare. Even if you didn’t, just don’t say it. Edit it out. Because listeners feel disrespected. I only have a set amount of time a week to listen to something. I’ve chosen to invest that time in your show. And if you couldn’t be bothered to prepare, then why should I bother listening? If you don’t care about it, that’s how I read that. “I shouldn’t care about it.”


So we spent a lot of time in preparation of all of our shows. It’s different per show because it’s different hosts and different chemistry, different things. But that prep work is vital to how we work. I think it pays off because the shows will be much more organized and you don’t leave out obvious things. Or if you think about something for two weeks, you’re going to go down every rabbit hole mentally, and that means that you can pull out the important ones in your conversation.


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Now back to the show.


Joe: I’m going to kind of combine this next question with another thought that I had. I recently wrote a blog post about whether you should or should not script a show. But I’ve heard you talk about demo episodes to make sure the idea is good, that you have good chemistry. I suspect that since I think all of your shows you have at least one co-host, is that accurate?


Stephen: Yeah, I don’t do anything alone. So you probably don’t script those shows. Well, actually, that’s not even true. I know of one that you scrapped, right?


Stephen: Yeah. We script Ungeniused, which is a show Myke and I talk about weird stuff on Wikipedia. But that show is totally different. It’s completely edited. There’s no uhms or ahhs or restatements. It’s very tight. It’s only 10 minutes long. So it’s different than an hour and forty five minutes of Connected where me, Myke and Federico are talking about whatever. So it’s a different beast. But everything we do is at the very least outlined.


Outlines, the way I’ve explained it in the past, is they’re sort of like the flags that you need to the gates you need to hit going down the ski slope. You can deviate and you can have freedom to do something else, but they’re just milestones we want to make sure we pass. It’s not about reading something exactly but just making sure that everything we’ve thought about gets covered in one way or the other.


Joe: So you script Ungeniused specifically because it’s a short show, right? It’s a very short form shows that…


Stephen: Yeah, very short form. That was just something that we wanted to be part of the personality of the show, where the show just is very tight. That works really well for that show. I couldn’t do that at least with an hour long show because then the script is going to be a billion pages long and the edit would take forever. But on a short show like that where we want it to be a little podcast snack is what Myke calls it, then it was important to us to make it just really as smooth and as well packaged as possible.


Joe: That’s really well done I think. Because I did not realize it was scripted until you explicitly mentioned it at some point.


Stephen: We definitely live from the scripted times, but overall, we tend to stay on it.


Joe: Got you. So the second part of this question, which is I’ve heard you talk about demo episodes, what are the odds that a show will get scrapped at this phase?


Stephen: You know, I was thinking about that. I think that we’ve probably had a project or two that died in the demo stage, or lots of plans that have died in the planning stage. Again, you think about an idea, and it’s like two weeks and like, “That’s not a good idea at all.” So a lot of projects never even make it to demo, right? Or where someone has an idea, we talk about it, and it doesn’t work out for whatever reason.


But for us, though, because we have the experience we have, if we’ve made it to a demo, most of the time, we know the show’s moving forward. And the demo is much more about ironing out the details. So do we want music? Do we want an introduction as the same every time? How is that? The chemistry between the hosts. What’s the edit going to look like? It’s much more about those bells and whistles not so much about is this show going to work at all. This is something we’ve gained with experience. But if you’re out there and you want to start a show, I do really like the idea of demos because it can teach you a lot about the idea itself. And maybe it doesn’t work or maybe that it works with a tweak or change.


Recently, we were talking about Flashback a couple minutes ago. Quinn and I did a demo of Flashback and we ended up releasing it to our members because I had it. I was like, “This would be fun for people to hear.” But in some ways, it’s very much like the show but otherwise, it’s pretty different. The edit is a little bit different. The way we approach the topic is different. It wasn’t as structured as the show ended up becoming. It kind of taught us like, “These are some things, we need to change. These are things we need to tweak.” I hated the microphone Quinn was using so when I was editing, like, “You got to buy something else.” So it just let us iron out those details.


Quinn and I are both professional content creators, but we haven’t ever worked together. And even though we’ve built a friendship over the last year, when you hit “record”, it’s a different thing. We just had to work out some things between us in the way that we hosted together. That demo was a very useful tool to work those things out. We were committed to the idea, but we knew that we wanted to practice run. So that demo served as that.


Normally those demos don’t get shared, but we felt it was good enough to send to our members. We liked the topic, and we didn’t want to redo the topic, so we let members have it. I think they enjoyed that. That of like 90% of what the show became.


Joe: Great. Great. As somebody who has recently done this out in the open, I can’t stress enough that having a couple of demo episodes. A friend and I released a show for small businesses, a local pot, like local to our county around COVID-19. We wanted to get it out fast, so we didn’t iron any of that out for the first couple of episodes. You can tell that we’re kind of figuring it out as we go along. I’ve been podcasting for six years. So I mean, it’s not like a lack of experience. It’s just a new thing with a different co-host, with a different topic and stuff like that.


Stephen: Definitely. Actually, Quinn and I are both pros, and have done it a long time, but we still needed it. It’s just something that no matter how many times you’ve done something, when you do it with somebody new or new project, it is new. It’s new thing. Like my shows, I’ll have their distinct identities from each other, even though I’m a common denominator on them. It really helps to work that stuff out.


Joe: Yeah, yeah. This has been great. I want to be respectful of your time, but I do have one question before I get to my favorite question of the show that I asked in every episode.


Stephen: Okay.


Joe: It’s a little bit unrelated to what we’ve been talking about, but on Relay FM, you have sponsors, you also have a membership. This is something that I’ve put a lot of thought into. I’m sure a lot of the listeners have put a lot of thought into. But when you’re putting out content, how do you decide what is members only content and what isn’t?


Stephen: That’s a really good question, man. It’s kind of the question, honestly. The way we think about it—and then I’ll give some general advice, hopefully that would be helpful—is that Relay FM is primarily an ad supported business. That’s reflected in our books. That’s reflected in our content. So for us, the public facing free content is always going to be the first priority.


Over the years we have, though, increased the amount of stuff we do just for members and we’re getting ready to do some more stuff along those lines. We introduced Backstage, not too long ago, a monthly show with me and Myke talking about the stuff we’re talking about today, like how to do this stuff. That’s one thing but there’s more coming up here this summer. So for us, it’s a we’re never going to take something away that’s free and make it paid. We’re never going to switcheroo somebody behind a paywall. We feel like that’s unfair to people. We don’t want that done to us. So why would we do that to anybody else?


So the way we think about it is that bonus stuff is extras. So it is stuff like Backstage where it’s like people who are members of a podcast network are probably into podcasting. So let’s make something for those people who are already predisposed to be interested in this either, in doing it themselves or just inside baseball kind of thing.


Joe: Right.


Stephen: We also view the membership stuff as a way for people to see and hear behind the scenes and hear combinations of people who don’t normally work together. So we have Fusion, which is a members’ only show where I interview to host a month about something. Whatever is topical that month. It’s people who don’t have shows together. So people who may have never recorded together only record together very rarely. So that’s always fun to intermix voices and people and get people together in weird combinations. Then we’ve got things like our annual specials and other content that is just made for members that is fun and loosey-goosey and a reward for backing us and for supporting our work.


So for us, the membership content is extra stuff. I don’t think we would ever launch a show like Connected or upgrade like a tech news show and make it members only. That it doesn’t make sense at this point in our business. It may be five years from now, but it doesn’t today. So the membership content is stuff that is extra that is made just for those members.


Joe: I was going to say that I think that makes a lot of sense. Like Backstage is really good. You’re taking a topic in episode and showing people a little bit how the sausage gets made but also how they can make their own sausage, which sounds weird. Then the membership shows, man, I love the membership shows. That’s worth the price of admission for me.


Stephen: Thank you.


Joe: I wanted to ask this because I think you guys are really doing it right.


Stephen: Yeah, no, I appreciate that. I think you’ll like what we’re doing this summer then.


Joe: Awesome.


Stephen: But I think if you’re out there and you’re thinking about this, the word of advice I have is really just to make sure that the timing is correct. I see so many creators rush into monetization through support on Patreon or members for whatever mechanism you use. And you promised a bunch of perks and your show is not big enough, your product is not big enough to really support that. What I mean by that is people may sign up, but then are you on the hook for an extra episode every month for eight people? That’s a lot of work for the money you’re getting in return.


So, my advice is always make sure the timing is right, make sure you have some momentum behind your project. And start small. People who really want to support you will support you even if all they get is a sticker. You can add additional content to membership stuff over time. You can never take it away. That’s the thing. If you commit to something and people back you to get it, or they get it because they back you, which it’s the same sentence backwards and forwards to say different things, that’s really difficult is to back something out of that. So you got to be really careful in adding things to make sure that you’re not actually spending more time and more effort than is justified.


That’s how we’ve done it. We start very small and we’ve added stuff over time. And now membership is a lot of how I spend some weeks out of a month, depending what week it is. Some weeks, it’s basically all I do is membership stuff. As it’s grown in size and importance, we’ve added content to it. And it’s kind of become this virtuous cycle. We add more stuff to it, more people show up, so we had more stuff to it, so more people show up. That’s really where you want to get, but it can take a long time.


I don’t say that to be discouraging. I know that it’s easy to hear somebody who has found a little bit of success in this, say, “Oh, well, you can’t jump into it and be successful off the bat.” I don’t say that to put anybody’s project down. I say that because I’ve made those mistakes. I say that because I’ve been frustrated with that in my own work outside of Relay of, “Hey, why is no one interested?”


Like I wrote my blog for like six years for anyone cared. The first time I was on daring fireball, a friend of mine read a post and they got fireball. I was like, “Come on.” I’ve been there. I’ve toiled. I’ve done that work where no one’s paying attention. And the truth of the matter is the internet is a big place, it takes time to be discovered. And when you add the monetization to it, it complicates all those decisions. So start small, make sure the timing is right, make sure you got some momentum.


Any creative project you should do because you want to do it, not because you think it’s going to pay the bills because most creative projects don’t pay the bills. I’ve got shows that I do that, on paper don’t make sense because they’re not big enough, or they don’t sell enough, or whatever it may be. My website and YouTube channel are still in that most months of like, “It’s a lot of time here. It’s kind of breakeven on the spreadsheet.” But I choose to do it because I want to. All that has got to go into that decision making. It’s not just about flipping on the button on Patreon. It’s all those decisions that go into it beforehand.


Joe: That’s great advice. I definitely feel that because when I hit I think like 50,000 lifetimes downloads, which was like pretty early on in the show, I thought this was enough of an audience to launch a Patreon. So I launched a Patreon and I promised way too much. And then like, “ad free shows,” because I was just taking what other people were doing on Patreon and I thought, “This will work for me.” And I got one patron at the lowest level, and I was like, “Now I have to do all this stuff for $2.” So what you said should not be taken as discouraging by anybody. It is advice that should be heated. You should take that advice to heart.


We’ve been talking for nearly an hour at this point. So I do want to get to my favorite question, which is, do you have any trade secrets for us? Now trade secrets in this context. That’s like just good advice that you like to impart on people that you think people need to hear.


Stephen: I’d love to tell you about the secret underground pockets bunker which some of us have tickets to. Not that. That doesn’t exist.


Joe: That’s what I meant. That’s what I meant.


Stephen: Yeah, that’s sort of the desert in Nevada.


Joe: CGP Gray just did a video on that, I think.


Stephen: Yeah, seriously. I was so worried. When I saw that video was like, “Don’t go with a tunnel, you’re going to die.”


Joe: I know.


Stephen: I was like, “How are you going to get out?” So he released it. So he did but I’m still nervous about it.


Joe: Yeah,


Stephen: Someone release it. It could have been him.


Joe: That’s true. That’s a good question. I think for me it comes back to what we just talked about is that these things take time. So sort of my thing is just be patient with yourself and be patient with your project. Very few things in this world are successful overnight. Podcasting is not just like anything. Very few things hit overnight. You need to be aware of that so you don’t get frustrated. You need to be aware of that so you can make sound decisions around content creativity, business, all those factors.


I think you should be aware of it because you can be in a situation where you can throw the towel in too early. A story I’ve told before, so forgive me, but in like 2010, 2011 probably I really took a swing at, can I make 512 Pixels a job? Can I really turn it into a blog that people show up and read every day and sell enough ads or do a membership or do something and it pay my bills? I spent about two years really, really pushing it, and it didn’t really work. I think it made the blog worse in those years. So I backed off of it.


Every year since I backed off of it, the site has been bigger than the year before, which is why something 12 years in, and also like people just don’t read blogs anymore. I attribute that to I was patient, I tried something, I tried it for a couple of years, it didn’t work, and then I changed my mind about some things. It’s really lame when you work really hard and no one shows up. But you may have to do that to get to the thing that’s going to be successful. You may have to do that to learn something about yourself or about your work to unlock it at the next level.


That just takes time and patience and perseverance. Those are things that at least I’m not very good at sometimes—I don’t think I’m alone in that. But if you can really think about things in that way, you can really find victory at the end of it.


Joe: I love that. I think that’s so true. You are certainly not alone in that. Like I’ve been in panic mode before where I’m like, “I need to make money right now so I’m going to do this.” That has worked out exactly zero times. So these things take time. Be patient. Very few things hit overnight. I think that’s really great advice to end on. Stephen, thank you so much for your time. Where can people find you?


Stephen: You can find me at I host a bunch of shows there. And you can find my writing at And I’m on Twitter as @ismh.


Joe: Awesome. I will link to all of those and everything we talked about in the show notes. I will probably just link to Relay FM since we mentioned like all of the shows. But I will definitely link to some specific episodes that we mentioned here. So thank you again, so much for your time. I really appreciate it.


Stephen: Yeah, thanks for having me.


Outro: Thanks again so much to Steven for joining us today. I think he offered a lot of great advice. Some of the tips that are big takeaways for me are, make sure the timing is correct, because I fell into the trap of rushing into paid support and parks. Start small. I thought that I needed to offer everything under the sun to people who were going to throw even just a couple of bucks at me. So, again, after this conversation, after we recorded this I started to really think about the How I Built It membership. I have some fun things in store hopefully for this fall, but we’ll see about that. If you were to become a member, let me know of what would you want to see from this.


You can get notes and links and everything that we talked about over at Thanks so much to Yes Plz, iThemes and TextExpander for sponsoring this week. I’m really excited about this lineup of sponsors. I’ve been drinking Yes Plz coffee for several weeks now. I use TextExpander every single day and iThemes constantly puts out great products and the team over there is fantastic. So definitely do check them out and thank them for their support of this show. If you like this episode, be sure to give it a rating and review on Apple Podcasts. And until next time, get out there and build something.


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