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[upbeat music] Welcome to the Rebooting show.

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I'm Brian Morrissey. Usually, I'm talking to people about how they're building sustainable media businesses.

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But this week it's a little different 'cause the last few weeks and years really have been really rough for the media industry. And so this week I wanna talk about actually my own business a little bit.

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And that's because the Rebooting is launching paid memberships today. [upbeat music] All the details are on therebooting.com, and you will hopefully sign up there. I, I will absolutely hold it against you if you don't.

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Of course, no pressure. There are two tiers to the membership. TRB Pro is designed for those working in media and related industries like tech and marketing.

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And the benefits which we'll add to as we go are access to all TRB analysis and articles and content, participation in virtual events with media experts. I want this to be as useful as possible.

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And participation in regular in-person events like live podcasts and happy hours because I know that connection is incredibly important in networking for growth and business.

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And then also access to insights and research. We're gonna be doing regular surveys of our audience. Uh, we've been doing it with partners. We're also gonna do it for our, uh, members.

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And then there's also TRB Insider, which is built for executives who wanna support the Rebooting's vision and also wanna connect with peers at exclusive private events.

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These benefits include private dinners that we'll have regularly, events at industry tentpoles, as they call them, like CES possible, CAN, Advertising Week, and more. As well as a quarterly business update.

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I like the build in public ethos. Uh, it can get a little cringey, so hopefully I can dial that into the, the right level. And also my undying gratitude. But anyway, I wanted to use this podcast to go a bit meta.

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It's, it's not meant to, to try to sell you on, uh, the membership, but maybe indirectly.

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Because this business is a little meta, it's a media business about the media business at a time when I keep reading and sometimes write about how the media business is doomed, but it's really not.

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There's a lot of pockets of growth going on out there.

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But I thought I would go a little bit behind the scenes and, and talk about this membership and how I thought about it and fitting with the overall business, because I think this is something that I'm seeing, like, across all kinds of different publications that are springing up.

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'Cause I think we are at the point where we're gonna see a ton of new media businesses that emerge from all of the unfortunate, uh, wreckage of the previous era that will likely continue.

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[upbeat music] So to have this conversation, I wanted to bring in Reid Geramis, who was a former guest on this podcast when he was at Substack, and his episode was really popular.

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And so Reid is someone who I got to know over the pandemic when he was building YEM, which was a growth engine for independent creators.

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And Substack acquired YEM, and Reid was a growth PM there until late last year when he left, and he's now launched Caddy Labs, which is dedicated to helping independent media operators and small teams build out their own businesses.

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Reid has a lot of experience in growth.

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He'd been at Crunchyroll and also at HBO Max and Hulu, and he's just very thoughtful about these subjects, and he's been incredibly helpful in building out this membership program and really just handling all the product details that come along with it.

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And, you know, that's critical when operating a very lean media company, needless to say. And so I wanna thank Reid for that and his, his partner, Sh-Shirag.

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They've been just really instrumental and awesome to work with. So in this conversation, we talk about several things. You know, one is getting the timing right and sequencing, right?

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Because I always just think, "I'm doing this now three-plus years after I launched. Maybe I should have done it three years ago."

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I think it's easy to figure that out, but I think the sequencing is different for everyone's business, and it's unique to that, and we talk about that.

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And also we talk about the importance of first-party data in a niche media business, and I go through, like, sort of how it's the fulcrum of this business.

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Coordinating subscriptions for specific audience segments rather than the entire audience, I think this is very important to do. You can't just go out and offer all things to all people.

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And then figuring out pricing and finally also just the challenge of getting to start. And I think that's critical. I hear this again and again with other people who are running these small-scale businesses.

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You know, there's always a reason not to do something at a, a particular time, but you just have to get to start. And so I hope you enjoy this conversation, and also, I hope you consider becoming a Rebooting member.

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Visit therebooting.com and sign up. The TRB Pro is two hundred dollars a year, and TRB Insider is a thousand dollars a year. They're both gonna be totally worth it, so hope to get you over and sign up.

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Here's my conversation with Reid. [upbeat music] Reid, thanks so much for joining me on this big day, for me at least. [chuckles] For you too, I hope. Yeah. Long time in the making.

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So I talked about in the intro the Rebooting membership program, and I went through all the ins and outs, and it's on therebooting.com.

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And I wanted to have you on to talk about the decisions that we made when it comes to memberships in this case.

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Because I think that it has resonance with what is going on in a lot of what is the most vibrant area of media, which is this kind of independent operator media. I don't know, we need a term for it. Do you have one?

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I don't, no. We definitely need some terminology. All right. I'm the words guy. I gotta come up with that.

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So, you know, when I was thinking about it, I was like, been three years plus since I started the Rebooting, and I have to give a shout-out to John Yedniack, who for three years has been asking me when I'm gonna be doing subscriptions so he could pay.

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And so, John, if you don't subscribe, I'm gonna be bugging you repeatedly.But I kept, like, kind of putting it off in some ways. I was bothering you as well during those years too. Yeah. No, you were.

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I mean, 'cause we started talking during the pandemic when you were doing YEM, and then when you were at Substack, and I didn't do subscriptions for a long time.

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And in some ways, I told myself that the reason was I didn't fully understand the, like, you know, the product market fit and stuff like this. And then here we are.

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[laughs] Honestly, it's not that different than how I would've done it three years ago. Yeah. So what are, like, some of the takeaways for you because of that? I don't live life with a lot of regret.

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I don't look backwards. I think you just make decisions with information at the time and in the context you're in, and that's fine. But, you know, I think in some ways it was probably a mistake to wait.

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Now, what I was thinking of was based on my previous experience at Digiday, where we had a brand...

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We had a coup- we had a few brands, but we had a, the sort of marquee brand was Digiday, and then we had these other brands that one was in fashion and beauty called Glossy. And a brand, and I just stop saying we.

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They had these brands in, uh, retail, modern retail, and then subsequently in the, the future of work with work life.

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But the experience of Digiday, what I took away i- in building that was the top of the funnel was really important, and, and developing that habit was very important in order to have a membership.

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I saw when we did a membership for Glossy that it, it was tougher because it didn't have the top of the funnel. So- Mm-hmm... in some ways, I think that's a tremendous benefit.

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And I think a lot of times in this space, people don't have some of the, quote unquote, "advantages" I had because I had a lot of confidence that I could stand up a sponsorship business 'cause I knew- Yeah...

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how the dynamics of those work. When you started the Rebooting, did you start at zero email list, or did you have some people that, like, some following that you'd built up before- Oh, yeah... launching the Rebooting?

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Well, yeah. I mean, that was, like, you know, another of the, the, quote unquote, "advantages." Like, I, I used to call them, like, unfair advantages, and I'm like, wait- Yeah... no, they're not unfair- You earned...

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like, I earned them- Yeah [laughs]... by doing, by doing the work for, like, 20 years. Yeah, like, you know, the, these are not advantages that people who are, are, like, you know, 27 have.

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But then again, when they get up, like, random things don't hurt them, so they've got other advantages. Uh, there's trade-offs of every- everything in life.

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But no, I mean, I obviously had something of a, of reputation in the marketplace, and I think Twitter followers, X followers are, are really overrated. But I actually saw something from...

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I remember it was Austin Rief who... I think he tweeted sometime. It was like, "Anytime you're, like, leaving a job or anything," he goes, "Always collect email addresses." [laughs] And I was just like...

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I had been focused on leaving Digiday for a few months before it, just, like, the details and whatnot.

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And I saw what was going on with Substack, and so I didn't know what I was gonna do afterwards, but I was like, "Oh, I'll just... I'm gonna get a lot of attention for, like, leaving," [laughs] you know? Mm-hmm.

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'Cause people like to have that, you know? I don't know. And so I collected, like, a few thousand, I don't know, 2,000 or 3,000 before I hit send. Yeah, 2,000- Yeah... I think, before I hit send.

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So that was, like, a real big benefit. And- And your first post was about some of the stuff you learned from Digiday. Yeah. Right? Yeah. And so I... Yeah, that was something I wanted to do more of...

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You know, I call it, like, the mechanics of building a media business, and I wanted to have a different type of publication in which I could use some of my own experiences having lived in this, having, you know, built membership program before.

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It's not like I was, like, operating Hearst Magazines like Troy, [laughs] you know? But, like, I ha- have dealt with some of these challenges, you know, personally. Mm-hmm.

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And so I looked at the meta aspect of what I, I was doing as, like, how do you use this as a, a benefit? 'Cause the way I... The meta aspect is, like, it's a media business about media businesses. [laughs] You know?

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Yeah. It's just like, it's crazy. And, and so...

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And that's, uh, actually feeds into, you know, the thinking a little bit of doing this podcast is just giving a behind-the-scenes look about the thinking of it, rather than just trying to, like, promote it like Crazy Eddie or something.

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And although I will, that's important. We will have to get to that- [laughs]... 'cause I am terrible at promotion, but I gotta get over that.

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Related to that line of thinking, we were talking about taking time launching memberships, launching a subscription product. Yeah.

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If you could go back to day zero, this is something I think about a lot when I talk to people in this space, like, whether or not to encourage them to turn on paid right away or whether, you know, wait a little bit, build a top of funnel, build some momentum, build a, a little bit of an audience, and then launch

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a- Mm... a paid product. And you and I have talked about memberships for a couple years now. Yeah. And yeah, I'd be curious. You kinda alluded to it, like, maybe your thinking hasn't really changed much.

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Well, my thinking on the product has not changed that much. Like, I mean, I remember sitting down and sketching out, like, the company I wanted to build.

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Like, really, when I was at the end of Digiday, when I was like, "Oh, I'm definitely leaving here." And it's not all that different, to be honest [laughs] with you.

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There's like lots of twists- From, from the starting point? No. There's a lot of, like- Yeah... twists and turns. Like, I didn't expect the...

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There was a lot of advantages, like, I would say, in doing it the way I did it. So I think it... I don't know whether it was a mistake or not.

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Like, for instance, like, I think when you're building a business, the end goal is one thing and, like, what you want that business to look like, but how you get there is gonna be incremental at the end of the day.

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And- Yeah... there's different thought processes to this 'cause, for instance, Sean Griffey, you know, who's an amazing entrepreneur a- and he built Industry Dive and, and had an amazing exit from Industry Dive.

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And I remember him telling me that-They started with three publications because most people wanna perfect a first publication before they expand into different publications. Yeah.

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And the problem is they never, they never feel like they've perfected it, so the other publications never happen. Right.

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I think in some ways the same thing can apply to the business lines, because when you're building- Yes, revenue streams... a media business, you should be looking to have multiple revenue streams, right? Like- Yeah...

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I think you have to. But- There's no, no big media business has a single revenue stream anymore. Yeah, that's true. Yeah.

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And like- Netflix was the last holdout on subscription only, and now their ads business is, is off to a pretty solid start. Yeah.

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So that's actually a good example because, like, if Greg Peters had given an interview to Ben Thompson, Stratechery, where he talked- Mm-hmm... about how, you know, ads came out of a crisis, right?

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And it was a crisis of, you know, Netflix has had a mostly charmed existence, you know, Qwikster, and then they hit, like, a wall, you know, about a year ago. And they, you know, they were sort of forced into ads.

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I'm not being, like, sort of forced- In their US business. Yeah. I think international's still, like, you know, rocket ship mode, but domestic has been a, a bit of, like, a slow growth business for a few years now. Yeah.

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But, I mean, [laughs] slow growth. W- wh- in that market if you look at [laughs] what their competitors are dealing with, it's like- Oh, yeah... you know, so they're gonna...

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You know, I think it's, it seems like they've won that in some ways.

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But I guess my point is there's balancing sequencing, which is something I've talked about with Justin Smith at Semafor and, uh, John Kelly at Puck, which is you have to sequence what you're gonna be doing in some ways.

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And just because you wanna get to somewhere doesn't mean you start with, like, everything. Like Uber- Yes... did not start with Uber Eats. And so getting that sequencing right is really important, and that's the balance.

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So I'm glad that I started with sponsorships, because I think that it laid a really good foundation.

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And now I'm ready to sort of move, 'cause you start with sponsorships, like, the way I look at it is, like, you, you stack bricks, right? And you start with newsletter sponsorships. And then I added podcasts.

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I didn't do a podcast for the first year. Mostly I think 'cause I didn't, like, get the equipment.

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And then added, I think after podcasts, added, like, reports and things like that, and then added the private dinners, right? And then you just keep adding things as you see.

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Did the people you were working with, the people who were buying sponsorships, did they kind of pull those products out of you, or did you have that directionally in mind when you started?

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I mean, I had that in mind, to be honest with you. I think a lot of people kinda make too much out of, like, inventing new things almost in media, and particularly in B2B, 'cause the playbooks are, like, established.

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Yeah. And so it's true across all media, but I think it's most acute in B2B in that it's really just an execution game. Yeah. Like, you really just have to execute. Doesn't mean it's easy.

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Everything is hard, and everything's doubly hard in any sector of media business it seems. Yeah. But you're not inventing something completely new to some degree.

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I mean, that was always why I didn't understand when people were saying, "Oh, it's just subs," blah.

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Like, 'cause I'm like, "Okay, I don't think so in the overall media world, but I know in my bones it isn't true in B2B." Like, it took a pandemic for people not to want to go to, like, you know, industry events. Mm-hmm.

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Yeah. And even then, I think during the pandemic, like, if you had, like, an underground ad tech party, I think you could fill it. I think you could've filled it in, like, [laughs] middle of 2020. Yeah.

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So I think about it as just when you're gonna get to things, and I don't know whether the sequencing was right. I'm glad that the sponsorship business is doing well.

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And I think one of the things that I did learn was that really that matchmaking element was s- is such, like, a big driver of it, that the newsletter ad inventory is not...

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It's important, but it's not, like, everything of the business. It's one ingredient. Like, right.

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Most of my conversations, and I think this is something for anyone who is selling sponsorships or wants to sell sponsorships, is you have to understand the motivations of your clients. Yep.

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And business is always about trying to solve a problem for your clients, but in a way that also you, it benefits you because you extract some value of the value that's created.

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But to do that, you have to understand what your client values. And I think s- too many times when people get into sponsorships, because they just think about themselves and, like, what's good for their business.

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But that's short term to me.

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You have to, if you want long-term relationships in any field of life, you better sort of check your own ego [laughs] and start to, like, you know, get in touch with what motivates, you know, the other party and what they value.

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Yeah. And I know in this space people value, understandably, connectivity and commercial connections. That is the way business still gets done. I do not think...

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You know, Jeff Bezos says, you know, "Focus on the things that will not change." It is not going to change that humans are gonna be connecting with other humans. Yeah. I don't care about the Vision Pro.

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It's not gonna change. And just to, I wanna underscore this, 'cause I think I've learned a lot from how you do sponsorships.

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And when you mention connecting, like, these high-value connections, specifically it's, like, publishers, people with media businesses- Yeah... and largely SaaS providers, people who sell into those. Right. Yeah.

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And I think if you're listening to this and you're thinking about how to do sponsorships, you can, I don't think everybody has the same audience dynamics that you do, where you're able to make these high-value connections, but I think that's a much better sponsorship product than selling cost per click or cost per impression.

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Yeah. Because the people who are buying- Right...

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those ads are comparing performance against Facebook, Google, TikTok, and those are just really hard ad products to compete againstYou're gonna lose And it's really hard to turn- [laughs] I'll cut to it.

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You're gonna lose... it's, it's really hard to turn it into, like, a meaningful revenue stream. You gotta sell a lot of clicks. Yeah.

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You, you get into a treadmill, and you start to have misaligned incentives, and that's when you see... You know, I'm a little...

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I don't wanna say I'm down on the newsletter space 'cause I don't consider this a newsletter business because, you know, to me, the newsletter f- was kind of like a...

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It was both a minimally viable product, but it was also just a way I wanted to build a more personal media brand, uh, uh, as like a strategic imperative- Yeah...

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'cause I, I, you know, as I said, I think it gives you a tremendous amount of leverage in, in a lot of different areas. And I wanna talk about the leverage I think, and we'll see if it provides for the rebooting.

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But I wanted to have that personal connection, and email was important for that. That's why podcasts are important for that, the human voice.

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You know, I run into [laughs] people, like industry events, and they're like, "Oh my God, I listen to your podcast all the time," and stuff like this. And they seem, like, genuinely into it. Yeah. So must be something.

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And I think that just provides, like, a lot of leverage. But I think that it's completely different from a newsletter business that is about... You know, I see a lot of these, this growth hacking happening- Yeah...

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and I don't know if we can peel off and talk about all these, like, paid recommendations things, but it just, it feels a little Ponzi scheme to me.

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Like, I mean, I don't know the value that you're creating necessarily trading- Right... those audiences around. Whereas my, you know, I, I know the value that's being created from that segment of my audience.

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That said, I think what's really important, talking about sponsorships or membership or however you're gonna... courses, however you're gonna make money, is you gotta understand your audience- Yes... right?

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And even within a focused audience, you're gonna have segments- Yep... right? And to do that, you have to understand who... 'Cause they have different needs. Yeah.

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And I saw this before when we did a membership program at my last job, in that we had a thriving events business, and we were trying to tie the membership program to it.

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But what we quickly found [laughs] out was that they were totally different audiences. Mm-hmm.

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The people who went to the events and consumed the events product were not the people who wanted our membership product that was built around content and insights and original research and original reporting and stuff.

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Yeah. They didn't want... 'Cause the people at the events wanted commercial connections on the sell side. And on the buy side, you know, they were going for a whole variety of different reasons. Yeah.

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But a lot of it was that marketplace dynamic.

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Um- So you, like, over time, you're kinda gradually building your audience, you're developing a better understanding of who the different segments are, and you're shaping products- Yeah... around those segments.

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And those are not always, like, totally overlapped- Yeah... which is good. That's like, this is why you want multiple revenue streams, so that you're kinda monetizing your entire audience. Yep.

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Which that's the part I wanna, wanna th- focus on here, is what I realized was there's a segment of the audience that as long as I engage and provide value with, that are highly monetized, right?

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And those are the people who make technology buying decisions, mostly at publishers, but also at brands and, and agencies increasingly. But those are the people who most of my partners want to reach- Mm-hmm... right?

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I love my people on editorial, but they're not making technology buying decisions. Yeah, they don't own, they don't own the budgets- [laughs]... for some of that stuff. You know, that's, like, the reality.

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I mean, why do you think these other publications write constantly about ad tech? Yeah. Like, it, like, [laughs] it's like, come on. It's like we're... And like, you, you have to choose about how much you're gonna...

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You can't just, like, chase money. You gotta, like, have an... I think you have to have a vision.

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I think you see a lo- you're getting a lot of publishers, they're just chasing money, and that's why you can't tell what they're about. Yeah. But I have other segments of the audience.

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That's why when we were talking about memberships and what we were gonna do, I thought, the way I was, like, thinking about it or w- or in our discussions was, what are areas where the rebooting can provide a ton of va- a lot of value, a lot of unique value that others cannot easily provide, but that also I can't really monetize very easily through my existing products.

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Right. You know? Like, if you're... And that's why we're doing this- Yeah... in some ways [laughs] because- Mm-hmm...

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just to be totally transparent, because, you know, I think, like, a great segment for this membership and where I wanna, like, create a lot of content around, and, and in-person events and virtual events, is helping people who are building independent media businesses.

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Yes. Because I hear from those people all the time, and they're always asking questions. [laughs] Yes.

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They may not be the best buyer for lar- like, huge, complex software, SaaS products, but they still want to know how...

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They want, like, insights into how to build a media business, which is very much what the rebooting- Yeah... covers. And, like, back to your, the world- Yeah...

142
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view North Star point, that is very much aligned with what you want to write about and cover. And it's definitely, like, a- Yeah... firm segment of your audience. Yeah.

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I think th- the only challenge that would probably get, like, pushback is, like, wait, aren't you going to the people who are, like, most likely to be like, "Oh, I don't have the $200"? I don't know.

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I feel like people will find $200. Yeah. I mean, it's- I'm hopeful. It, yeah. It, it kinda depends on how much value we're able to provide, you know? And, uh, whether it's a value- Yeah, exactly... it's a value decision.

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So let's talk about that, 'cause we talked about, like, what the benefits... I talked to the, at, at the start, like, what the benefits are gonna be.

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And, and I look at it as, it's so funny because it's, like, three years in, I should have this, like, all toted up. And in my view, it's gonna be fluid. Yeah.

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Because any room I have been in to discuss, it always ends up in what I call, like, the football phone, where, like, people are throwing out...

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And that's like, you're too young for this, but there was an old Sports Illustrated commercial-Where they were like, "You get the swimsuit issue. You get 52. You get this."

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And then finally they're like, "And if you order now, you get, um, this football phone." [laughs] It was a phone shaped like a phone. Mm-hmm. And I was like, "We cannot get to the football phone."

150
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And sure enough, you always ended up with the football phone. [laughs] Like, some kinda... 'Cause it's just, like, a list of stuff. Yeah. And it's, um- Only a few things really matter...

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I don't know, what go- what are common mistakes that you see people making when- Oh my gosh...

152
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'cause I, I don't think we, we got to that with this, but, like, what are sort of common mistakes you find that people make when thinking through what the product is gonna be? Yeah.

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So let's just, let's talk about how we went about it. So, you know, we started talking about- Yeah... what would a good membership program be for the rebooting.

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Whenever you are exploring that, there's a few really big decisions. One being, like, how many membership tiers do you wanna have? Another is, what price do you want those tiers to be, to be marked at? And then- Yeah...

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the value prop. What i- what does, like, each member of those tiers get? And man, I mean, like, there's a lot of...

156
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These are really hard decisions to make, by the way, especially when you're in a silo, and you're, like, kind of only looking at your data. And the other really hard aspect is there's no universal right answers.

157
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And so there's nothing that, you know...

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Like, at Substack, it was really hard to tell people best practices around these decisions, 'cause there's, like, a lot of different ways to go about building subscription businesses.

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Some people on Substack don't paywall anything. A couple, like, I think, like, two out of the top five are probab- they don't paywall anything. And then others paywall everything.

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But that's, like, Heather Cox Richardson and who? Judd Legum is another example, where he does- Okay... you know, investigative journalism, and yeah. Yeah. Yeah. Judd's a reader. I hope he'll be a subscriber.

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Judd, if you're listening- [laughs]... I want your $200. Is that good? Is that okay? Yeah, that's a great example. [laughs] Will this scale? Let's just go down the list.

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Let's do- So yeah, there's just, like, a lot of different ways to go about it. I think some common mistakes are probably overthinking it at, at the start too much, you know? [laughs] Are you talking about me or?

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You know, one of the, one of the things that I think you mentioned was, like, you just gotta get going, and you gotta try things out.

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Very similar to how your sponsorship products have evolved over time, I think that's how you gotta approach- Yeah... memberships and subscriptions. Like, your...

165
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Just because you launch at a certain price doesn't mean you gotta be there the whole time.

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And when we've talked about, like, the value prop up front, telling people what they get at certain tiers, it's okay to be kind of vague and say, "Hey, we're gonna go on this journey together, and I'm gonna listen to you and, like, bend these programs around what you want."

167
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Like, I think that makes a ton of sense. Yeah. I love that. I mean, I love it 'cause it's how I think, and it's also why I shouldn't have been overthinking this for three years.

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Because I just find, like, over the years, and this is something I wanna talk about before you get into, like, pricing and stuff, is any time, like, I've felt stuck, like, people have helped.

169
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Yeah You know, with the show. Like, I mean, the audience really does... I don't know, like, audience, community.

170
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I, I hope it's a community, but you really don't know until, you know, un- until you see if people wanna connect. I think that that, that, that, this community- Until you see the audience members connecting.

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That's the key piece. Yeah. Audience members wanting to connect to each other under your auspices- Yeah... is... And a l- look, a lot of people fake it, and the community sort of fades.

172
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Just because you have an events business does not mean you have a community. Yeah. Okay? Like, Jason Yanowitz, like, Jason, I hope you'll subscribe.

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[laughs] He, he, he runs Blockworks, and I was doing a podcast, and he called me out on being like, I'm like, "It's great for community" or something like this, and he's like, "Stop that."

174
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He goes- You, you said the C word?... "Events, the job that events do are revenue." [laughs] "That's margin." Yeah. And I was like, "Oh, thank you for calling me out, Jason." Mm-hmm.

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But yeah, no, I, I think, like, I think there's a community, but I wanna find out. Like, I wanna see if people want to, like, connect with each other. Yeah. Like, I...

176
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You know, one of the benefits is going to be regular, you know, live podcasts and things that are really meant to be... use content as, like, a convenience- Yeah... to get people to connect to one another. Yeah.

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You know, happy hours and things like that. You wanna keep the hard costs under control for that tier. Yeah. But then even with the premium tier, because I think... Look, I was a little reticent about the premium tier.

178
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It's $1,000, but John Yedinak told me that he was gonna subscribe, and I was like, "But I didn't say how much it was gonna be," so [laughs] it's the test. Yeah, that's a test.

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He's gonna be like, "I don't know who you are." [laughs] But no, but I think, like, that kinda tier for... And to me, the, that's for, you know, top executives who want this to exist in some ways.

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There's an aspect of a lot of these things, and that's where I think it's really interesting with the sort of personal aspect of it, because, you know, right now, although I work with you and Chirag, and I work with Elaine and Jesse on events and sales, and Tyler Kamen, my man, on, [laughs] on account management, and Jay with podcasting, so all the solo stuff is, you know, fake, because there's a lot of people.

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But the brand itself, you know, is still tied to me, and there's upsides and downsides to that. But I think one of the upsides is there's an aspect... And you're not gonna...

182
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Again, it's, like, kind of like with the sponsorships with the network thing. It's not gonna get you all the way there. Yeah.

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But I think the first step is there is an aspect of people wanting something to exist and feeling like, "I get value out of this, and I want to..." I don't wanna say pay it forward, but yeah, I wanna recognize that.

184
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Yeah. And it's less of, like, a pure transaction.

185
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And my theory is, and I wanna get your take on this, is that these brands that are built on, like, a smaller, more personal level have a higher proportion of their audience who is likely to convert on that basis.

186
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I think that's exactly right.

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I think you correctly assume that some people are going to join the membership program just because they wanna support the rebooting and what you do, and I think that dynamic exists kinda throughout this corner of the internetAnd yeah.

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Well, I saw that with pledges, right? Yeah. Like, I mean, pledges to me are, is, was an interesting, is when I was like talking about it like it's past tense. It is for me. But it, it, like, that...

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I don't wanna say it like quote unquote encouraged me. I think that was supposed to. Like, I had a fair bit of confidence that I would be able to convert. I still don't know how to come up with a forecast.

190
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Maybe we can talk about that- Yeah... 'cause you came up with a forecast and I was like, "Oh."

191
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But yeah, the pledges show that some people will actually pay for the rebooting as it is today, without any like quote, you know, membership benefits. Yeah. I mean, I guess it was, like, encouraging.

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I mean, but to me, I'm like a signals person. Like, I love data and stuff, but I think it's coming from a reporting background. Like, I look for signals, you know? Mm-hmm.

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And just because of my background, the signals to me, and again, it's just, it's all biases from what your experience is. They tend not to be buried in spreadsheets or, you know, in surveys.

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Those are fine and stuff like this. But for instance, I look at, particularly with these small... Like, who are the people I hear from? Mm-hmm. You know? Who, how often do I hear from them, and who are they? Yeah. Right?

195
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And that's why when I'm thinking through the membership, I was like, well, I think I can provide a, a lot of unique value to people who are building, who are building their own media businesses, and also people who are operating within, you know, larger media businesses in specific areas.

196
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Yeah. Right?

197
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So to help them do their jobs better, and also to connect with other people in their role, um- But not ju- And you know, we've talked about individuals and small teams building their own media business, like kind of the Substack profile.

198
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Yeah. But there's also the operators at bigger media companies, like the head of subscriptions or the, the VP of... Yeah. That's what I mean, yeah. Those- That's the other segment. Yep.

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Those are very important segments, I think, for the rebooting, and were a big part- Yeah... of how we thought about the primary subscription tier. Yeah. And also, like, those signals, like, they show up in other things.

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So everything you're doing is producing signals. You just have to be, like- Yeah... alert to it in some ways, in that, for instance, like doing a subscriptions report with Blueconic, on the one hand it was for...

201
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'Cause I think a lot of times these things are in opposition, like sponsorship and like... And I look at it as it's all one product.

202
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And but that gave me a signal that there are a lot of subscriptions, you know, leaders in, you know, the rebooting's audience who are finding value in it and are hungry for more information- Yeah...

203
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because they're, you know, a thousand of them, you know, gave their credentials in order to access the report. Right. And I was like, "Okay, that's interesting."

204
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Well, it's really powerful to know how your business is doing relative to, you know, quote benchmarks or just your peer group, 'cause then you can, you know- Yeah... whether you're focusing on the right thing or not.

205
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Like, should we be shifting our focus toward retention, or raising prices, or making more money per customer, or should we be back in the acquisition game? Should we be pressing the gas to the floor? Yeah. So- Yeah.

206
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So let's talk about pricing- Yeah... 'cause that's what, uh, people love money and stuff, right? To me, there's no formula. I've never seen a formula.

207
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Look around what other people are charging and, like, try to be plausible- Yeah... but be somewhat aggressive. Let's talk about, let's talk about what we did for the rebooting. Like- Okay... you did surveys. Yeah.

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That was good information. Like, you got some good stuff there. Yeah. I did it, like, I did it a couple years ago, like, a couple years ago, so it wasn't, like, super fresh.

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But, like, I did one, that's why it's, I've been dragging my feet. And, like, I don't know, like, 64% of people who responded said they were gonna unsubscribe. Yeah. So we gotta get 64%- [laughs] Right...

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of the audience to subscribe. It's gonna be the most successful subscription program in history.

211
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Maybe there was a little bit of selection bias in that survey, but- Well, if you're taking a, you're taking a subscription...

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I can't imagine someone actually, God bless all of you, who took a, an entire subscription survey to tell me they hate it. They're not gonna [laughs] Never, maybe. [laughs] It's, yeah.

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But, like, a, a lot of people said they could expense it in that survey. A lot of people- Yeah. Well, that's important... gave good feed- I th- And I think that's, yeah, I think that's important for anybody listening.

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If you're thinking about whether you ha- If you have a professional newsletter, there's some stuff you can do around the edges to make it easy to expense the newsletter.

215
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One thing that Lenny's done that I liked was, like, he had a Google Do- It's Lenny Rachitsky. Yeah. Uh, of Lenny's newsletter- Yes...

216
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is he has a Google Doc template that you can just, like, send to your manager to expense his newsletter. So there's little stuff like- That works. Hey, every little bit helps, you know? You don't know.

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I mean, this is, like, kind of the important thing. We're in the l- little bit of the Wild West here, and it's good to try stuff out. Are we doing that? Are we doing that? [laughs] Do I gotta write...

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[laughs] I was gonna go to the meet you after this. I gotta write an expense, please let me expense, like, rebooting. Yeah. We can get to that later. Okay. I'll do it. That doesn't have to be pre-launch. I'll do it.

219
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On the pricing, okay, so did the surveys a couple years ago. That was informative. You look around at your peer group. Once you look around at your peer group too, you'll notice there's kind of a narrow band.

220
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You're not thinking about, you know, 1,000 versus- Yeah... 10,000 a year.

221
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It's, like, kinda within the primary subscription tier, which we want, like, you know, 80 to 90% of paid subscribers to buy, and then have the ultra-premium tier, you know, somewhere betw- between 10 and 20%.

222
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I'd be okay if 80%- It'd be great. Yeah... like, take the, the premium tier. It would be awesome. I don't know. I don't mean to, like, push back on your strategy, but- Uh, yeah. [laughs] It would be great.

223
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I mean, it'd be a, a nice pleasant surprise. Yeah. So or we, or I guess we would be underselling a lot of the, you know, primary subscription. I guess. Anyway, so yeah.

224
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We were in a narrow band using survey as information, and then I think we talked a lot about stretching towards the higher end. You wanna be a little uncomfortable with where you land your final price. Yeah.

225
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And part of that is because a niche media business is usually gonna be held back more by potential pool of subscribers or target audience than ARPU or revenue per customer. For sure. And so- Yeah...

226
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it's good to kinda stretch toward the upper bound of your comfort zone for that reason.

227
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And then the other big thing is it's much easier to lower your price through discounting infrequent promotions, discounting bundled offers, versus increasing price, which, you know, we were talking about Quickster earlier with Netflix.

228
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Increasing price is a really hard thing to execute well.And you don't wanna be doing it very frequently.

229
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And so by starting at a little bit higher price point, you h- it's easier to kinda nudge that down in select cases, versus like kinda having to pull it up over time, which is hard. Yeah.

230
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You gotta be plausible too, right? I mean, because Ben Thompson has sort of set... I, it's just like, I think he's sort of set the- Bellwether... bar. Yeah. For a lot. You know?

231
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Even if you're not in, you know- Category... fuel, category, whatever you wanna call it, like, I mean, it's, that has sort of, you know, been a pace setter.

232
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And ultimately you have pace setters out there, and you gotta be realistic. There are always exceptions in finance- Yeah...

233
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and crypto and, and things that people can take that information and it gives them a competitive edge, particularly if it's, like, trading stocks- Yeah... and anything like that. But that is a really particular category.

234
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Um- One of my favorite examples of that is Edwin Dorsey, who has, like, a pretty high- Yeah, the Bare Cakes... yeah, he has a pretty high price point.

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And I saw one time he tweeted out, he was like, "How would you feel if I increased my price?"

236
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And some of his existing subscribers were like, "Go for it," 'cause I want, like, less people paying, having paid access to your newsletter. [laughs] I like it.

237
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That's a really interesting dynamic to have within your membership program. Well, one of... Someone on that, someone at, at our... This is why it all works together. I did an online forum about subscriptions. Go watch.

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With, with my friends at Plutonic. And [laughs] which you can watch. And I, one of the, one of the questions was just super smart, was about creating, like, an apply to be, like, a member. Yeah.

239
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And, like, I love that, like, as like an idea. Yeah. Maybe it's Miami and running into these, like, rope lines. Right. [laughs] Like out of, like, random places all the time, like a taco place. Yeah.

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But, like, there is something there with that. I don't know. I wouldn't have the... I, it doesn't fit my, the brand that I, I, I am. Yeah. It's, it's hard to turn away paid subscribers, but you do see it on Patreon.

241
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Sometimes they have, like, a call-out super high tier, and there's only, like, five- Yeah... subscriptions available. So it happens. I think, you know, there's some good examples of it, but usually it's- Yeah...

242
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I wouldn't necessarily advise the average business to do that. Yeah. And the other thing is subscription versus membership. Like, I was very...

243
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I was, I try to be as, like, plain spoken about the stuff as possible, 'cause I... You know, a lot of the media industry is powered by bullshit, [laughs] let's be real.

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And I think that's a differentiator [laughs] in some ways. That's why I was not gonna do the 199. Yeah. I don't know. We'll see. I just always look at it and I'm like, "Really?" Like... Got me again.

245
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I mean, I guess it works. Yeah. That's- Do you have data? Does it work? No, we- I mean, let's just do it. I don't know.

246
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I'll, I'll change my mind if it has some, [laughs] some major- We did some, we did some pricing experiments at Substack and saw... We did, like, kinda the 99 cent version of it and saw that it led- Yeah...

247
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to less revenue, less conversions. Interesting. Yeah. And I think part of that is because people aren't buying these subscriptions out of, like, a functional motivation, you know?

248
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Like, they're kind of, they want to support. And so tricky, having, like, some trickery around price actually can backfire. Yeah. And I think the other big question that people end up having is how much...

249
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And they always go to content. It's like, how much content should go behind the wall? Yeah. Yeah. That's, like, the hard... That's equally as hard as the pricing question.

250
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I think you just gotta use your intuition and make a good first call, and be very open-minded to changing that over time.

251
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Because there's some people on Substack who pay wall nothing, some people pay wall everything, and a lot in between, as we were talking about earlier. So I think you just gotta, like, go with your gut.

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You, the one thing that you and I have talked about is not creating extra work for yourself. Oftentimes I see people who are, you know, are going from free to paid. They say, "I'm gonna introduce a new email send."

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And that's not necessarily what people wanna pay for, you know, more emails. Yeah, no. So- People do not want more content. Yeah. They, I'm, I, I don't have no data on this.

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I, it's purely vibes face, but I'm fairly certain on it. I mean, just think about yourself. Like, that- Like, do you wanna... Like, would you necessarily wanna pay for more- It's like a threat... just more volume? Yeah.

255
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I look at the membership as a way to focus more on content. Operating a, even when I went through all the people who I partner with to, to make this little business a reality, you know, it involves a lot, right?

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I mean, we talked about sales and outbound and, like, I'm lucky I have, like, some amazing partners. I have, I think I have 12 partners, uh, so far I'm working with just this year.

257
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I think last year I had, like, 20, 23 or so. But you reach a limit, right? Yeah. And there's only so much time and focus and energy that you have.

258
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And I talk about alignment a lot, and I wanna be really aligned with the audience. And I'm a capitalist, I believe in incentives. I think incentives make the world go around. Yeah.

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And, you know, whatever the saying is, show me a messed up outcome, I'll show you messed up incentives.

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I think it's critical, if you can, and it's not in every category, but to have that, that direct audience revenue, it just focuses, it focuses the organization different.

261
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I mean, Julia Baser, the chief product officer at Bloomberg Media on that, uh, online forum, you know, she talked about it being a more honest model, right? And again, it is not like an either/or.

262
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I'm, like, an and person, not an or person. And you can, should, and frankly must do both. Yeah. But I think it introduces a different dynamic in it, in that you can get sucked into being...

263
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There've absolutely been weeks where the last thing on my list, honestly, is, is- Write the newsletter... the, what theoretically is, yeah. [laughs] Like, and that- That really stood out to me...

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I believe in force functions. I believe in them. That really stood out to me when we... You had a few things that, like, really resonated.

265
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One was, I got 12 things t- on my to-do list today, and not one of them is write the newsletter. And it's like, well- So... maybe [laughs] that should sneak its way on there. Yeah, maybe it should get in there, top 10.

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Yeah, I mean, that's just the reality of, of business.

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And all business is hard, and, you know, part of it is-Particularly early on, y- you gotta do so many more jobs, and I feel like this is now at a point where, you know, being able to partner with other people...

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'Cause, I mean, frankly, with you and Chirag, like, it wouldn't have happened without y- you both because even just getting, you know, the platform right and stuff that i- is so critical, and being able to think it through with you guys has been, like, so invaluable.

269
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And you also have, like, broader experience than I do in this, so that's been great, so thank you for that. Thank you for being patient zero.

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You know, it takes some courage to be the first customer of a new business, so appreciate you. Yeah.

271
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I mean, it was like, it's not like, I don't know if you've read Complications, but it's like, uh, Atul Gawande has, like, you know, someone has to be the first person who's been intubated by, like, a trainee doctor.

272
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[laughs] Mm-hmm. So it's not that. Yeah, yeah. It's not life or death. 'Cause I don't wanna be that person. Hopefully. If you come at me with, like, some kind of, like, the first intubation, like- No. Go down the hall.

273
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[laughs] You- you're in the wrong room. But yeah, so I mean, it's good to, like, kinda unpack that a little bit. I think for the Rebooting, you always, like, talk about how important the CRM- Yeah...

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understanding your audience, knowing more information about them. That was a big thing that you- Yeah... and I discussed over the past few years. And what are we talking... So CRM, you, you used air quotes.

275
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Uh, but, you know, it's thrown around a lot. I mean, what are we talking about here?

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Yeah, it doesn't have to be, like, a Salesforce CRM or, like, HubSpot, but it's like reading the Rebooting, how are they interacting with your products- Yeah... and where do they work, where do they live?

277
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'Cause that's actually important for some of your products, like the in-person events, and yeah. Yeah. It's not an email address. It is not an email address.

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Right, and you're actually unique- I think for me- You're unique in how much you don't like- Yeah, like-... Gmail accounts. Like, everybody else is like, "Great, it's not a- I know... ProtonMail or a Stoop Inbox.

279
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You know, it's like, it's not encrypted, it's not an aggregator. Great. So I, no, I get the, like I... I'm gonna, like, sort of- Backtrack from that a little bit? Okay. [laughs] Revise my remarks.

280
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I'm gonna revise my remarks. No, I, it's not like I have anything against Gmail. Someone's work email gives me a lot of information about them. It's just a- Yeah... shortcut, right?

281
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If someone has.dashmeredith email address, I know they're a publisher. Yeah. Mm-hmm. Okay? Like, I could bucket them out, and if someone's like, you know, fuzzyslippers1623- [laughs]... @gmail.com. Nice. Not so much.

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I can't believe you just outed my Gmail- Well-... my, my personal email account. [laughs] But, you know, that's, you know, but people switch jobs all the time. Yes. And, and then you get hard bounces- Yeah...

283
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and all the rest of that, and that sucks, right? Like, I, I know credit card failures is the biggest problem in B2B subscriptions because, um- People leave... people switch jobs. Yeah. Brex account goes down.

284
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Yeah, and then, yeah. Yeah. So I think it's actually great to have Gmail for that reason so that this paid subscription persists beyond a job change.

285
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'Cause usually a lot of people in your ecosystem are changing within the media industry, you know, so, like, the... You kinda want the paid subscription to keep rolling.

286
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But yeah, just, you can probably have your cake and eat it too. You can have the Gmail address, and you can get more information on who your audience is.

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So that's been a big part of, like, us building out new backend stuff to better understand. Yeah. And, like, help with some of these workflows.

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Like, you've mentioned it's kinda death by a thousand paper cuts with putting these events together or selling sponsorship packages.

289
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Like, there's just a lot of overhead that comes with sales, outbound sales, and making sure you get paid on time, and making sure the ad copy is, yeah. Invoicing. That's kind of the important part.

290
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I mean, chasing people down. I mean... So yeah. When it gets over 60 days late, that's when I start to get a little cranky. Yeah. You maintain your good cop status and send somebody else to knock on the door- Oh, yeah...

291
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shake 'em down. Yeah. I've been ta- Justin, another member of the team, uh, Justin Spiegel, my accountant, uh, he's gonna play bad cop. So any of my valued partners out there- [laughs] Who are delinquent...

292
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who are more than 60 days late, get ready for Justin. But we're talking about the CRM- Yeah... and you know, how critical it is. 'Cause, like, the way I look at it is just an email address doesn't tell you much.

293
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I need to know, like, the name of people, their title, their company, and what areas- Yeah... they're focused on. Mm-hmm. Because then you can start to really form, you know, products around it.

294
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You can be much smarter with, with marketing, with putting different types of content in front of people. Yeah. Certain things. It's just so valuable. Yeah. Yeah, you gotta have that.

295
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I mean, like, everyone goes on and on about, like, first party data, this and that, and it's a little bit of jargon really to say. It's like you gotta know who's in your audience at the end of the day. Yeah.

296
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And particularly for these niche models. Like, I would always run into this where people would be like, "Well, that won't scale." And I'm like, "Well, who cares?" Yeah.

297
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Like, c- can we deal with that, like- When you get there... when we have, like, a million? Yeah. But up until- I, I did a lot of tagging- Yeah... manually. I just went through the email list.

298
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And this is the thing, it's like you gotta get your uniform dirty at the end of the day. I was gonna say, I was gonna say that the CRM historically has mostly been in your head.

299
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Like, you'll forward me, like, new free subscriber email that's like, "This person does this and that." And you just, you know a lot of this stuff because you've been in the space for a while. But- Yeah...

300
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yeah, obviously. But I also, I spent a weekend, like, just going through- Mainly in Google Sheets, the VIP database...

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email list after email list, refra- like, you know, going, like, add more on, like, Substack in order to, like... And then Googling people, getting their titles, entering them into, like, a spreadsheet.

302
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And, you know, you start to do that, and pretty soon, you know, you have, you know- Yeah... 1,500, 2,000, like, you know, records that are key segments of the audience.

303
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And the best part about, to me, the business, getting it all to work together, is, like, when you do reports and when you put things, y- you're getting data off that. People are telling you what they're interested in.

304
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Yeah. If they're downloading a subscription report, like, I don't know. I'm not, like... You don't need, like, an, a crazy algorithm- Right... to tell you that they're likely in the subscriptions business.

305
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And so for you, there's a way to stay true to your worldview, your North Star, with what you want the Rebooting to be, but have good input coming in from the audience about what to cover and how toPosition this for certain paid member, like this should be part of the paid membership.

306
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This should be sponsorship driven. This should kind of- Yeah. -fit both. Right. So the final thing I just wanna address, and I'm gonna go into more detail i-in a, a, a future post actually about this that will- Yeah.

307
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-that'll be members post about like figuring out, about building a platform, right? And to me, like just on a high level, anyone who's asked me about like which platform to use, I, I don't have a good answer.

308
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And that's because each platform, each tool, in my view, has different use cases, and sometimes those use cases are a perfect fit, sometimes those are not a fit, and you just have to ultimately evaluate every single platform and tool you're gonna use to see which, which are the best fit for your particular business.

309
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I will say the one philosophical thing that I, that in this, is that you need to decide whether you're building a business on a platform or a platform for your business. Yeah.

310
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And that's a distinction that I think is important that I'll go into more detail.

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But ultimately, you know, for a long time, I had a lot of benefits with the way the business was to be building, you know, basically a business on a platform.

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There comes a point where you run up against a ceiling of that, and you need to do something different.

313
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And I just think that is, yeah, it's just almost like a philosophical point, but it's also, it's just where, what kind of business you have. I think any... Yeah.

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I mean, any media business that starts to really hit exit velocity, I think starts to bump up against the seams of like a one-size-fits-all platform solution. Right.

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Whatever platform that is, like YouTube or any other, like the newsletter space. I'm severely biased, you know, 'cause I spent time at Substack. I love the team there. Yeah. Love the product.

316
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And I think it's the best platform for anybody running a paid newsletter. But it does start to make it a little harder once you get to a point where like you have other products or other media.

317
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And so I think with, with the rebooting, we've thought about like the podcast, the research reports, the events, the newsletter. Right.

318
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That's why I always said like, I don't have-- I don't believe that the rebooting is a newsletter business. And by that, I mean that the newsletter is one part of a, a, a broader business.

319
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I'm making it seem like it's like massive. Uh, John Kelly calls it my... John, you need to subscribe. I'm a subscriber to Puck. John Kelly calls it my cinematic universe. That's a great name for it.

320
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I think that's a little bit grand. I think that's a little grand. But it's one node. It's an important critical node, right? But it's one.

321
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There's a podcast, there's reports, there's dinners, there's events, there's this membership. They'll-- Maybe at some point there'll be like a community.

322
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I'm still skeptical of the Slack community, but if people truly want a Slack community, I'm totally all in on it. I think there's... Yeah.

323
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And there's a lot of like backend stuff that we're gonna try to build to make your life easier. Yeah.

324
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Because whenever you introduce a new revenue stream or a new growth channel, usually that comes with some new work to do.

325
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And so I think there's a lot we can do on the, the like software side to automate away some of that work. Yeah.

326
00:52:20.072 --> 00:52:32.372
And then, yeah, like, there's potential community features that could be built that kinda help bring your audience together in like high value ways. All right. So in, uh, I... We could go on for all weekend, right?

327
00:52:32.532 --> 00:52:35.402
But we should leave it there. But like before we go, like I wanna...

328
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I, honestly, like you and Chirag have been like amazing, like to work with and to integrate a little bit of like promotion here beyond like everyone, please, you know, subscribe to the membership, the rebooting.

329
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If people wanna like talk about like working together, if they-- Like, what is your... Are you like taking on like other clients other than the rebooting LLC?

330
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[chuckles] We have a little bit of bandwidth to work with more clients, and we're excited to, to do that.

331
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And I think it's really anybody who feels like they have momentum at their back, but they're starting to hit- Yeah.

332
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-some limitations or like they're spending a little too much time with like non-creative aspects of running the business. And, you know, we're still very early on trying to figure out like if there's...

333
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If we can like solve problems in this space. So thanks again for being patient zero on that. Yeah.

334
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But yeah, if you're interested in chatting, you know, we'd love to, we'd love to connect and explore ways to work together. What's your email? People wanna email you. It's Reid, R-E-I-D, @cadelabs.com.

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C-A-D-I-E-L-A-B-S.com. I love the name. I love the Caddie Labs name. Yeah. I'm a big golf nerd, so like... And caddies are kind of the important part of the team that kinda sit in the background. I don't know.

336
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It's really hard to get a URL these days, so that was part of it too. All right. Great. Well, I hope my shot doesn't go in the rough. If it is, I'm gonna blame you. That's what we're here for. No, I'm just kidding.

337
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[laughs] That's what we're here for. Awesome. Thank you so much. Really appreciate it.

338
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I hope you'll like come back 'cause I really think that, you know, as I said, like I w- I want this membership to like appeal to a bunch of different segments, but I have a particular affinity for those who are on this, this solo path, because I get it.

339
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Yeah. I really do.

340
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And, you know, whether you're on a solo path or you're building a independent media company and you're facing similar challenges, I mean, my hope is that we build like a community around that that can help build the sort of next generation of, you know, sustainable media companies, because there's a lot of like negativity, and some of it's in the rebooting, about the current state of the media business 'cause that's the reality, but it's only a part of the media business.

341
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I'm always... I'm regularly talking to people who have-- who are making it work on the, on- Independent. Yeah. -the niche level, and also like on the independent and smaller scale level. Yeah.

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So I'm incredibly optimistic about that. I am too, and I love talking about it, and it would be really fun to talk to your readers about some of the stuff that they're thinking about. So I'd love to do that. All right.

343
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Cool. Thanks, Brian. All right. Thank you. See ya. Everyone subscribe, the rebooting. [chuckles] Thousand dollar VIP tier. Yeah, start with that. If not, we'll take the two hundred. It's fine.

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[upbeat music] Thanks for listening. Thank you to Jay Sparks for producing the Rebooting show. If you have a podcast that you're considering making, you should check out Podhelp us and what Jay can do for you.

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Go to podhelp.us.

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[outro jingle]