How To Monetize Your Media Business Effectively And Sustainably (with Brian Morrissey, former Editor-In-Chief at Digiday)

Ben Aston is joined by Brian Morrissey, former president, and editor-in-chief of Digiday media and founder of The Rebooting. He is focused on the audience side of the business that included editorial memberships, product development design, multimedia, and events programming. Listen to learn how to monetize your media business effectively and sustainably.

Interview Highlights:

  • For nearly a decade, Brian has been the president and editor in chief at Digiday media running Digiday, Glossy, and Modern Retail. Focused on the audience side of the business that included editorial memberships, product development design, multimedia, and events programming. [0:28]
  • Brian got into publishing early in his career. He was curious about how things worked and he liked writing and it turned out that he could still build a career doing that. [1:30]
  • Digiday’s mission is to create change in media and marketing, and at least on the editorial side. [3:16]
  • For Brian, sustainable media is taking in more revenue than your costs and being able to do it on a consistent basis. [4:19]
  • In general, Brian used to always counsel reporters a week. They talk about a monolith of media or publishing. [4:39]

“In general, you want to be able to create high-quality content that reaches a targeted audience and through various mechanisms, you can make more money than your costs.” — Brian Morrissey

  • At Digiday, they had a paywall. It was a meter system after seven years. It really helped because they built the top of the funnel and the middle of the funnel before they really focused on the bottom of the funnel. [12:03]
  • The part that Brian is sort of struggling with is figuring out the audience’s growth aspects in ways that make sense to him. [15:06]
  • Digiday started as an events business, primarily that was the monetization model. The company had been around for a couple of years as an offense business founded by Nick Friese. [18:25]

“You need to think about what makes the most sense for your community or audience. And you have to be honest about whether you have what you have.” — Brian Morrissey

  • It’s rare in the media that anything is bought. It’s almost always sold like Google ads or bought Facebook ads. [30:01]
  • One of the principles that Brian pushed was to centralize all that can be centralized and keep unique all that can’t be centralized. [36:40]

“You have to be honest about what works for you internally, not just financially.” — Brian Morrissey

  • One of the things Brian learned from building a membership was that everything didn’t translate. [39:53]
  • There are two things when you think about what model is right because there’s a lot of different flavors of subscription and membership only. [43:22]
  • When they first started the membership, they wanted to create a completely different experience for members. [44:01]
  • They started around like a magazine, meetups, community and stuff like that. And what they quickly realized was that it didn’t make sense to both their audience. [44:22]

“Have a degree of patience because for most people the cliche is, it takes twice as long and it’s twice as hard or twice as expensive.” — Brian Morrissey

  • Brian’s one piece of advice is being patient is important as long as you’re focused and driven. [57:26]
  • Currently, Brian has a pretty narrow focus. It’s on building sustainable media businesses in particular. [1:07:29]

Guest Bio:

Brian Morrissey is the editor-in-chief at Digiday, a vertical media company focused on the digital media and marketing industries. At Digiday, Brian leads all content development, both in digital publications and over a dozen events per year. He’s spent the past decade covering the development of the Internet advertising industry.

Prior to joining Digiday in February, Brian spent six years as a digital editor at Adweek, where he led all coverage of the digital industry, including developments in social media, advertising technology, and publisher monetization strategies. Brian is a frequent speaker at industry events, presenting both in the U.S. and abroad.

Brian Morrissey is a graduate of Providence College and has masters degrees from the University of Leuven (Belgium) and Columbia University. He also did graduate research at Jagiellonian University in Krakow, Poland.

“You have to take what seemed like your disadvantages and try to figure out a way to use them as an advantage.”

— Brian Morrissey

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Read the Transcript:

Ben Aston

Welcome to the IndieMediaClub podcast. I’m Ben Aston, founder of the indiemediaclub. We’re on a mission to help independent bootstrapped media entrepreneurs succeed to help people who create, promote, and monetize through content. Do it better. Check out to find out more.

So today I’m joined by Brian Morrissey and for nearly a decade, Brian has been the president and editor in chief at Digiday media running Digiday, Glossy, and Modern Retail focused on the audience side of the business that included editorial memberships, product development design. Multimedia and events programming.

And now he’s writing a weekly newsletter, all about sustainable modern media. What that looks like, how it works at The Rebooting. You can check them out on substack and we’ll put a link in the show notes. And that is exactly what we’re going to be talking about today. So keep listening to today’s podcast to learn how to monetize your media business effectively and sustainably.

Hey Brian, thanks so much for joining us today. 

Brian Morrissey

Thanks for having me, Ben. 

Ben Aston

And I want to start just by digging a bit into your backstory, your whole career. As I looked at your LinkedIn was all about writing reporting. Where did that passion come from? That decision to get into publishing? 

Brian Morrissey

That is a good question.

Although I hate to say it’s a good question. Cause they usually start with the top here. We can edit that out. No, I mean, I got into it, sort of obviously early in my career. I didn’t really think about it as a career, in journalism, in a really considered I wasn’t on the high school newspaper or the college paper, any of that.

I always liked writing, but I never, I thought of that as something you learned to do when you’re like four or so. And then you developed other skills. I had no idea you could like actually make a living, not developing any other skills. So, I was curious about how things worked and I liked writing and it turned out that you could still build a career doing that.

So, I went to journalism school, which I think, a lot of people have strong opinions. I don’t one way or the other. I think it can serve a role too. If you’re, looking to get into break into the field, it’s a lot more expensive now than when I went, but it was still expensive.

And then I just, decided that I really want, I was mostly interested in the intersection of news and business. I didn’t want to write for a local newspaper. I went to Columbia and they seem to be still training people in 2000 to go work for a local newspapers that were dying out. And then work your way up to eventually get a job at The Daily News.

And those jobs don’t exist anymore. So a lot of colleagues from that time who’ve dropped out of the profession. And he goes, I started, reporting more. It was very obvious that it was a broken profession, particularly focused on business. And I was focused on technology businesses.

And you know, I think one of the things that has always been in the background of my own career is this conundrum of our times, which is finding a sustainable model for news in particular. And so I think it was a little bit meta at Digiday because, our mission was really to create change in media and marketing and at least on the editorial side, we really interpreted that in, in many ways as like figuring out how this profession continues to exist.

So that was met in that we were covering this quest, but also living at ourselves as a small, independent media company

Ben Aston

Cool. And so let’s talk a bit about your current project first the rebooting. And I think you’ve touched upon it there, but tell me a bit about sustainable media.

What, firstly, what is sustainable media for you? 

Brian Morrissey

For me, it’s it’s taking in more revenue than your costs and being able to do it on a consistent basis. That’s pretty much it. And so I’m very agnostic about the ways in which you can do that. I think there are many different models that work within media.

I think in general, I used to always counselor reporters a week. We talk about a monolith of media or publishing, but these are really very different businesses that the kinds of people who, create a gear review in order to get SEO traffic and then monetize through programmatic ads, that business is.

Almost unrelated to the kind of business that like a B2B publisher like digital would have. And so, a lot of times we lump all these things together, but there’s obvious, major differences and how they have to make money. But in general you want to be able to create high quality content that reaches a targeted audience and through various mechanisms, you can make more money than your costs.

Ben Aston

So let’s talk about that. Let’s talk about monetization models. And I know this is something that you recently wrote about on the rebooting, what monetization models excites you most or. Do you think are the most sustainable in terms of having longevity? I You’ve talked about, okay, you make more money than you spend that’s for me, that’s like the, that’s the foundation of sustainability but in terms of, yeah, monetization, what do you think is interesting and exciting?

And I know you’re on sub stack, which obviously in and of itself is a paid newsletter subscription platform, but what it, yeah. What excites you and what do you, where do you think the future lies. 

Brian Morrissey

I don’t know where the future lies, honestly, like in covering this stuff for so many years, I’m always reminded of it.

It’s like at least maybe in the US it’s like a children’s soccer game. Cause the ball goes to one part of the field and everyone pitch, I can translate here and everyone follows it and then it goes to another place. And then all the kids like clump together. So right now everyone’s clumped around subscriptions and newsletters and sub stack and stuff like this.

If you rewind 15 years, nobody was coming up with a business out of Silicon Valley and web 2.0, that was not going to monetize through advertising. Now nobody is pitching a business that monetizes through advertising Then this is just a pendulum. It will normalize to be honest with you.

So I don’t think that there is one model. If you look at, the success of morning brew that was purely on the back of advertising and advertising Dunwell can work for both the reader and the, I guess they’re calling them creators now or publisher. It can be difficult. It can just because the recipe sites are terrible does that mean that a newsletter can’t monetize through advertising, I’m writing for tomorrow’s newsletter about not boring and one of the more interesting newsletter success cases out there, it’s to me like the new Stratec Curry, except it’s making money through, through ads and the guy who does it, it’s guy Packy, McCormick.

He’s been doing it for, I don’t know, less than two years and 40,000 subscribers and. He’s gonna make a million dollars this year off this thing. He hasn’t gotten there yet, but they put it out there. And I think I did my own back of the envelope, math with with just the inventory and what he’s getting right now for sponsorships.

And it’s completely doable with very minimal costs outside of his time and focus. Because he doesn’t have to give a cut of that. He doesn’t have to pay even salespeople. So I think there are a lot of different models. I think subscriptions has the biggest upsides, like a dollar worth of subscription revenue is worth far more than a dollar of advertising or events, sponsorship revenue, because it’s recurring revenue.

Your costs on that revenue are far lower. There’s no salesperson to pay a big fat commission to there’s no like expense account. You have to pay for them to take people out for drinks in order to get that deal done. There’s no travel and so on and so forth. So yeah, subscriptions are to me for a lot of publishers now.

The ideal is if they are the base of their business model, but I don’t think it’s all or nothing and think everyone’s going to have a different portfolio. 

Ben Aston

Yeah. And so, obviously we’ve gone through well and some publishers still are paywall in content. And in order to encourage people to subscribe, as you’re thinking about the rebooting and your own evolution or monetization of that, do you have a point of view on.

How that will be monetized in the future, or is it more of just a passion project? 

Brian Morrissey

Somewhere in between. I did I sold one sponsorship that was a lucky deal. I really appreciate Mediaocean for taking a chance on a very new and honestly, quite small newsletter the modernization stuff right now, I’m interested in learning more.

I think, luckily right now I don’t have the pressures of immediate monetizations. So I’m really, and just to go back to that, maybe it’s because of top of mind, cause I was just writing like the not boring newsletter is you gotta decide if you put any friction in front ofof people you’re going to.

If not stop your growth, you’re going to really hurt your growth. And a paywall is a lot of friction. It’s a wall. There doesn’t get much more friction than running into a wall, I think. And so you’re going to like, there’s trade-offs to every model and the trade off of paywalls is often is audience growth, right?

And possibly impact. I think everyone who is putting something out in the world wants to have some kind of impact not to be all like Pollyannish about it. But you know, you’re doing this podcast for a reason and one of those reasons, I’m pretty sure it’s because you want to have them, am I right here? 

Ben Aston

Yeah. Yeah.

You’re like, no,

Okay, I’m sorry. Where was I going? I still have COVID fog. 

Ben Aston

No, that’s cool. You’re talking about, we’ll want to have impact Oh, the payroll because I, 

Brian Morrissey

Uh Okay, full Circle. . No, and so I don’t know. I haven’t figured it out yet. For me right now I would rather not be forced into closing the top of a funnel as far as, because you still figure it out the product.

I know, like at Digiday, we didn’t, we had a paywall that came in, it was a meter system after seven years. Okay. And like that really helped because we built the top of the funnel and the middle of the funnel before we really focused on the bottom of the funnel. And, we had an indirect business model that with events because digital was originally an events company that That paid for the newsroom, in addition to sponsor content and advertising and stuff like that and awards and stuff, but, waiting that period of time in order to have a really solid funnel because everyone ends up having to have a funnel was a great advantage.

We instituted a paywalls for newer brands a lot earlier in their life. And the dynamics were as expected. They’re different, you hit a wall quicker. I don’t know if there’s a law of funnels, but it exists. If you don’t build up a loyal audience and you can only hope to most people say between six and 10% conversion, well, it’s better to do six or 10% of a hundred thousand than 10,000.

I think. 

Ben Aston

Yeah, and sudden

Brian Morrissey

But a lot of people can’t wait. You need to make money, every, everyone needs to like, I would need to pay rent or mortgages or anything like that. So, I think that’s why I think it’s not all or nothing. Like you could use advertising to get by in order to get to the point where your product is mature enough, that you feel confident in, in, in having a paid version of that.

And you gotta be honest with yourself sometimes. I’m honest. Like I don’t think the newsletter I’m doing right now is to the point where I would I would charge for it, but if I do it tomorrow, everyone should buy it.

No, it takes some time. I don’t understand. I don’t know, I maybe it’s being middle-aged or something like this and it just it’s a problem. But I think everyone is like infected with this like overnight success story thing. And media is really hard. And so for everyone who’s reading tweets about the creator economy is Oh my God, this person went from like zero to 40,000.

I was just talking about the guy I did a and like 18 months, that those are outliers. It takes a long time. I think I got like 55, like new subscribers, like in the last like week and it’s free, but it’s it’s slow. I’ve been doing this for 20 years and someone who like looked at like the numbers and be like, wow, you’ve got whatever, 40 something thousand Twitter followers and all this.

It’s not like I can’t stand. I live. I’m just like, I am not like the self promotion stuff. This is just it’s it might be the gen X in me that I’m just like I, it pains me I’m like the idea of doing a tweet thread about a newsletter. It’s I’m going queasy right now. 

It’s it’s really hard. And I know for me personally, the part that I am struggling with is figuring out the audience growth aspects in ways that make sense to me in some ways, you know what I mean? Cause the way you grow a newsletter, as far as I can tell, other than it’s like guest posting and other newsletters, it’s like tweet storms.

Brian Morrissey

Ben Aston

Well, wanna, I wanna go from

Brian Morrissey

Pay someone to write the tweet thread for me, so I don’t have to like, feel terrible.

Ben Aston

Yeah. Why not? 

Then you don’t have that awkward feeling. But no, I think you’re so right though, in terms of, I think when we, you read about the hustle and what they’ve done and. You read about these success stories, but you don’t see the, and yeah, I totally agree that they are the outliers.

And I think sometimes people expect, Hey, I can start this new thing. And within six months or 18 months go from zero to 40 dollars, subscribers, 

Brian Morrissey

We always have this. Right. I remember I remember reading in Forbes, fortune or whatever. It’s little things it’s like this company went from zero to 50 million users at 18 months.

And it’s true. They did like you, I got the comScore numbers, like little things that this was a pet food company that pivoted into being feel good. Mo like content that gets shared on Facebook nonstop back when that was going off, like a rocket ship problem was, it was all sort of artificial.

It was like based off of growth hacks. And so some of the stuff going on now, there’s a lot of growth hacks going on. And then that can work. That always works for time. Yeah, whether it works. Long-term when we talk about sustainable is another story. It didn’t did it become very sustainable for little things.

But I think, and everyone gravitates towards the The overnight success kind of things I’m reminded of like the tour de France during the height of doping and like the Peloton was like going up like Malvin to like the steepest mountain that like 23 miles an hour, the French were like bother normal.

It’s not normal. It wasn’t normal. It’s because they were there, like blood was bare. Their hearts were barely working because their blood was so filled with like red blood cells. It was like sludge. 

Ben Aston

So talking about things that work in things that don’t work, I want to shift the conversation to what you were doing for a decade.

And that was at Digiday. You talk about, you’ve touched on. Things take a lot of time, things work for a time and then stop working, particularly with growth hacks. There’s a limited amount of hacking you can do before the hack effectiveness starts dropping off. But I’m curious, you mentioned Digiday started as an events business, primarily that was the monetization model.

And then you introduced membership you and other ways of monetizing. So can you tell me a bit about that evolution from being an events company really to the way that monetization model kind of shifted over the years and what went well and what didn’t go so well? 

Brian Morrissey

Yeah, like I joined, I guess it was 10 years ago, this last month and Digiday had been around for a couple of years as an offense business founded by Nick Friese

And like a lot of events, businesses, they also had a newsletter. But I’ve never really been into events. I I do events, but it’s not really my passion. But they’re a means to an ends. And I think in my previous employer at the time ad week was really, they were treating events as like an afterthought and we’re really focused on protecting their core business, which was mostly a magazine full-page self full-page magazine ads and particular like congratulatory ads.

Trade publications, love congratulatory ads like nonstop. That’s why there’s all those lists, it’s like the up and coming CMOs to know. Cause then they go and they shake down the CMOs clients to, to run a congratulatory at works. Promise if you keep going back to that. Well, it’s like very thin economic value.

So I, I prefer to that. I was like, anything’s gotta be better than that because 90% of our audience was getting our content through outside of the print magazine yet, if not 90% of our revenue and just internal focus was on this print product. So I like the idea if it’s going to be an indirect model of having, events.

I just think that if you put community at the core of it and it gave us time critically to figure out the editorial part, cause like I said, it takes time and the, and that time was invaluable. Because he, you don’t just start with an audience. I remember going back I don’t know we were getting I joined I don’t know, maybe 10,000, like page views a month.

You know what I mean? It was like, it was minuscule. But it’s a cliche for a reason, the scarcest things you have are your focus and your time. And if you can devote both of those to, to building the publishing part while still operating, the vents business, like I, I used to call events like my full-time part-time job because they said they weren’t, I was never passionate about events, even though I like organized and conduct like hundreds of them.

But they enabled us to build a newsroom that was like, 30 people at the time I left with no venture capital or any of that. And so if that meant, having to go to new Orleans and talk about programmatic advertising for three days, I’ll do it. I’ll make me do it, but don’t miss it.

Ben Aston

So I’m interested. You said starting out like humble beginnings, everyone starts out small. That’s just how growth happens. But tell me how you tell me how that community, you talked about page views, but page views, aren’t the same as community, but there’s an interesting dynamic you have with events and real life that is more community orientated.

So what works for you to cultivate that community and that, that kind of symbiotic relationship between events and community and the website. Can you talk to me about how that worked and what didn’t work about leveraging that community? 

Brian Morrissey

Yeah, I think what worked was Well, I always think you have to take none of this is like earth shattering, so I apologize in advance, but like you have to take, what are your sort of, what seemed like your disadvantages and try to figure out a way to use them as an advantage.

Now, early on at Digiday where the editorial teams like you, me and Mike Shields, Jack Marshall, and Sile Weissman. And that was it like having a three-day event in Fort Myers, Florida was, it was so disruptive because nobody who was getting out or email newsletter and the pressure we put on ourselves.

Oh, it’s fine. You have an event. You just do focus on the event. That’s enough work or something. No, you had to like, just fake it and do them both at once. But the way you use it as an advantage, it’s like you’ve got you’re in Fort Myers, Florida with 150 top publishers, and then the equal number of like tech providers that, that are the business model.

You can figure out things that your competitors couldn’t, it’s a very efficient way of taking a pulse of the market and finding out what you’re doing, which is working and not working. And if you repeat that, dozens of times a year that’s an advantage, right? Same thing, honestly, with putting on good events, like the biggest disadvantaged I felt like we had was how many free and events we did.

But the advantage we had is that we had more opportunities to screw up. And if you have more opportunities to screw up and I used to joke, we committed every atrocity possible on the events side. You had more chances to improve. Then, if you only do an event once a year, you only get one chance a year to screw up and then you had to wait another year to fix it.

That sucks. So I think the biggest advantage was you come face to face with your audience and you find out what it’s really on their minds. Like we had a lot of on background sessions that enabled real real conversations and real challenges. We really focused on that. And that really helped because it, as I’m sure, like a lot of the stuff that’s discussed in media and marketing is just complete bullshit.

It’s generated by it’s PR I don’t know how else to put it. So that was an advantage. The disadvantage was that are the people who consumed and came to our events were a small subset of our overall audience. And they had a particular view because of the business model and the reason. So they over-indexed and ad tech and stuff like this.

If you just judge the media industry by Digiday events, it was nothing other than, collecting a bunch of audience data in order to target and auto target ads through automated system. But that’s it, that’s the only thing that not the only thing, but that’s and that’s part of media, but it’s not the full story.

Ben Aston


I’m interested. You mentioned atrocities and you’ve got me I’d 

love to know 

Brian Morrissey

How long can we go? 

Ben Aston

What, tell me about some of the biggest 

Brian Morrissey

Which category. You need to categorize things. There’s after hours atrocities on stage atrocities there’s attendee, atrocities, organization, atrocities, 

Ben Aston

Strategic atrocities, where you didn’t event and no one turned up or something.

Brian Morrissey

No, we never, I don’t think we ever did that. I think if I were say any sort of strategic atrocities and I think a lot of people, I think the overall events industry ends up in that is you do too much. And I think this is a problem that infects a lot of media is once you have an infrastructure.

In place and by infrastructure, I don’t just mean technology. People, right. Once you have that in place and processes and infrastructure and processes in place you want to utilize it. You don’t want it to be running at 70% capacity. You want it to be 110% capacity, right? So what that inevitably pushes you into doing is the answer is always do another event, right?

Because you want to get that infrastructure humming at 110%, but you’re left to the situation where you can both exhaust your audience because you need to market those events to your audience. And you also will end up inevitably diluting the product because it will become like a bit of a conveyor belt.

And that is those things are really challenging because if you’re doing. Like 60 events a year. They can’t be, they can’t be unique. I’m sorry. Like I use just that’s not possible. You have to sacrifice at some point, as I said before, everything is trade off. And so if you’re going to do, if you’re going to here to optimize, to having your infrastructure at 110%, that’s the hit that you’re going to take is on the sort of uniqueness of the events, because you’re going to have to stamp out certain aspects.

Think you can look for different things to do in order to make each event unique in its own way, but they’re going to be fairly superficial.  

Ben Aston

Yeah, Interesting. And I’d love to know what in terms of your time 

Brian Morrissey

I would rather, I would much rather have 

 A model where you do five gigantic events a year, then two 15, but it’s always better to make a bunch of money.

Five different times than a smaller amount of money 15 times. . 

Ben Aston

Yeah, So in terms of translating them, that event to diversify the monetization from events, through monetizing, the Digiday platform, let’s call it what really drove that growth and what was most successful in seeing that evolve and diversify.

Brian Morrissey

So look, as I said, like events were an amazing gift, but then the opposite side is there’s always a cost to it. Right? And one of the costs is that events are difficult to run. And depending on the event they can be difficult to to monetize me. There’s certain trade shows where.

I’ve heard at least sounds like an amazing business leads back in the day, like sponsors at the end of the trade show would literally get in line to sign their contracts for the next year. Like you’ve that’s, it’s rare in media that that anything is bought, it’s almost always sold like Google ads or bought Facebook ads or bought this trade show thing apparently.

And maybe this is just apocryphal that’s bought, which is about every other thing you gotta be out there and you got to sell and that’s it’s a pain in the ass and it’s super expensive, because you’re, used to have Neil Strauss. I gotta give Neil a shout out is he’s still ended today’s sales team, but great sales guy.

And he used to always like post to Slack and he closed the deal. He’s 154 emails later, close the deal. And that’s the reality. I would show that to like our our reporters and be like, don’t think any of this is easy. Even if you tell, when you reached out to someone, unlike Neil’s set in 154 emails to sign, cool.

I want to see that same effort. They’ll tell me you can’t get a third-party source. So anyway, I think as things evolved revenue is usually a lagging indicator, a brand, right. And the brand was in my biased view had gotten to the point where it could support itself with, we started with sponsored content earlier and advertising and stuff like this.

It was just really difficult to get a sales team that could execute on both. This is a knock on digitally sales team. It’s great sales team. But it’s hard to have people who are awesome at both things just the same way as like on the editorial side, just to be totally fair, do some self-criticism.

It was really difficult to, start a magazine to have people and processes from me down that were good at making a magazine, but also good at doing great newsletters and website and podcasts and God forbid video or any of that stuff. So it’s just really difficult to balance.

And that’s what I think the pandemic has actually helped. 

Ben Aston

Yeah. And so 

Brian Morrissey

It’s forced, with events gone you got to, you’re not going to eat if you don’t some miraculously I notice more ads. 

Ben Aston

So part of the diversification was through the website and obviously membership through that.

But also part of it was diversification in the publication as well. Right. We’re starting glossy and modern retail.  

Brian Morrissey

Sure. Well, because like

The media and marketing industry is not, it’s not gigantic, it’s not the energy sector or something like this, look it’s, overcovered clearly, and for the amount of money at stake that, there’s a lot of money that goes into advertising.

It just goes to Google and Facebook do you really need, that’s it’s not much of a story. So, I think, there’s the ways that you can expand. You’re like Tam, if you will, is we did a few things. One is geographical was typically with the events model the live events model, there was a capacity to expand into Europe and we did that several years ago, starting in the UK.

But then we did events all through Europe and stuff. So that, that helped because, while the US is a gigantic market and draws and Canada and stuff like that, it’s not the only market clearly in the world. So we started with Europe, we did a partnership deal to, to do events and a publication in Japan that helped a little bit and then new markets, so, with glossy, it was beauty and fashion.

It was originally just fashion and luxury, but then moved into beauty, which is great. Jill now off of that idea, great idea, Joe, great execution as well, Joe and Priya And then modern retail, which was, the larger retail landscape is checking panic. And a lot of the same dynamics that were at play in publishing were at play in these markets.

So again, but it’s also, it’s a way to utilize your infrastructure, right? Because if you can create a larger addressable market, you’ll have less than that exhaustion problem and stuff, and you can still have your infrastructure running at 110% capacity. Because that was, to me the biggest, like gating factor, I’m like talking to cliche now, but is, we had an issue with how much can you market to your audience?

Like I had a few metaphors like that I’ll use word alone was like the the Holland tunnel is we, their office used to be on Mercer street and in Soho, In New York and at around four o’clock every Friday back when people moved around the honking would start on canal street for all the cars lined up, trying to get through to the Holland tunnel.

And problem is it’s just one tunnel. There’s two lanes. I feel like it’s the same way with marketing. There’s just one tunnel. You can only send so many emails through the funnel.

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Ben Aston

And so, I mean 

Brian Morrissey

Everyone from Digiday is sick of Eddie Otis, listening to this, hearing that again, they’re like, Oh my God, I’ve never thought I’d hear the whole thing again. 

Ben Aston

So you talked about your infrastructure and running and having the infrastructure in place. And that was your. Well, a limiting factor for you.

Can you talk to me about how your team was structured and how it grew and evolved as the publications grew and evolved as well, to support that diversification of revenue and you needed to adapt your product as well, which primarily was the content. So how did that, how did you change and how did that evolve?

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Brian Morrissey

Do you mean like the team structure or 

Ben Aston

Yeah, the team structure. 

Brian Morrissey

Well, I think one thing, I wasn’t great at the organization fully admit that, but I think one of the sort of principles that. I certainly, pushed was like centralize all that can be centralized and keep unique, all that should, that, that can’t be centralized.

And you really got to start to think about what is, I don’t want to say commoditized, but to a degree is you don’t want to recreate things like I’ve been in multibrand publishing organizations and they’re horribly inefficient. I used to love to go back to some story about like Conde Nast having 153 CMS is because each brand needs to be super unique.

I You don’t need a brick in your own CMS. That’s insane waste, and they’re still, I think stamping some of the South is probably like some like Vogue Polska that’s using their own ad server. So you don’t, you can’t duplicate technology. You’re not going to like, so you got to centralize that, but you can centralize a lot more that’s programming.

We centralized, there was no need to have two different events, programming teams for uni you’re a need to have somewhat generalists. They might not be as expert and stuff like this, but we wanted the editors and reporters driving a lot of the content anyway. So you want to centralize that you want to centralize multimedia, but you don’t want to centralize, like editorial.

So to a degree glossy amount of retail had their own editors who led it, but we treated it at the time. This is when I was there. I don’t know if that’s the case now, but we treated it as one editorial team and one audience side group, which included technology and memberships and multimedia and events programming.

So. To me that was key. And there’s things like, for instance, like copy editing, even on the editorial load level, you can, whether a copy editor can work across different types of content and she just really have to be thoughtful to me, like about the areas you can be more efficient in any areas you absolutely should not try to be more efficient.

And because you’ll end up in a DePaul looking the same. 

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Ben Aston


Brian Morrissey

No, and we didn’t always get and get it right. There was all sorts of like quirks with the technology infrastructure, just because we were trying to go too fast, my view, but that’s always a trade off. 

Ben Aston

Yeah. And in terms of that infrastructure that you built for membership, because you said that.

You introduced the membership on the new platforms on glossy and modern retail earlier. What were some of the lessons that you learned from building a membership that you were able to translate effectively over to the other side? 

Brian Morrissey

Well, I think one of the things we learned was that everything didn’t translate.

So as it turns out when you talk about audience and more specifically communities have different, like mores, if you will. I had lived in, in, in Brooklyn or New York city for 20 years, and then I got an early on the Exodus to Miami. And so I’m in Miami and it’s a different, it’s a different community on here.

The things work differently. Same thing really when it comes to the different communities in media and marketing, for the most part, the community aspect is it’s there. But it’s constrained a little bit by a few factors. And there’s also more like self-loathing in the media and marketing industry, I feel like, but when you move into cloud into class and beauty and fashion like for instance, we did these confessions all the time, which people loved because it gave them an unvarnished view of all that screwed up in the media marketing worlds.

It doesn’t work as well for whatever reason and beauty and fashion. I feel like they don’t have just don’t like that sort of thing. They’re a little bit more optimistic and it’s great different dynamics, but also when we would have Events in that area. And also in retail, like people would be taking notes.

People would be there’d be a lot of engagement, a lot of, any sort of community based stuff we did was always over subscribed. They just, it just had different dynamics. Whereas like in media and marketing and you had a lot of people felt like they needed to act like the smartest person in the room and stuff like that.

Ben Aston

Yeah. That’s interesting. Yeah. 

Brian Morrissey

I think it’s agency people. That’s my guess. Yeah. They’re always out the agency. People are always out there. It’s I got to call, I got a rush back for a minute. I got to be in Houston for meeting. I was like, I don’t know if any of these agency people have used this time in the past year to think that they didn’t really need to be in Houston for that meeting.

Like where are the stories about the agency? People would be like, what have I been doing? Like the last 20 years of my life flying to Houston for the meeting.  

Ben Aston

Man, that’s my

Brian Morrissey

So busy back to back. 

Ben Aston

Yeah, no worries. It’s the culture. It’s the expectation that you’ll, let me just hop on a plane. I’ll be there. 

Brian Morrissey

So we used to have, we used to have metrics for the amount of drop off we’d have at events. And it would be, you would have to like, plus it up by 30% for agency people, because the entire business model of agencies is the reality, but also the perception of being too busy and go figure agencies are incredibly inefficient.

You wonder what? And they wonder why like clients are taking this stuff in out. 

Ben Aston

Yeah. So in terms of the one of the things you talked about was introducing to Digiday like the metered paywall I’m curious about that component and how that. Translated or didn’t translate well as you launched these new sites and how the community dynamic impacted that, maybe.

Brian Morrissey

So I think there’s two things. When you think about what model is right for, cause there’s a lot of different flavors of subscription and membership only, and you need to think about what makes the most sense for your community or audience. And you have to be honest about whether you have which you have.

But also you have to be honest about what works for you internally, not just financially. And I think that’s really critical because sometimes you get it, it’s more than just accounting. Like people are involved in it and people are not don’t neatly fit into spreadsheets.

So what I mean by that is when we first started the membership. We wanted to create a completely different experience for members. And the idea was like, it was going to be, I know it’s like cliche now that everyone uses plus. But at the time it wasn’t and got pushback from people internally so that you can name it.

Digiday plus because Google plus was such a disaster, I’m like, nobody’s going to hold Google plus against us and then give me a break. Anyway, I’m glad we went with plus, but the idea was you like digitally navigate Digiday plus, and I see this like tech crunch, extra crunch. Okay, great. So we started around like a magazine and like meet ups and community and stuff like this.

And what we quickly realized was that we were, this didn’t make sense to both our audience and internally it didn’t make sense to our audience because it wasn’t, we were, they really liked like our core product. And we were saying, no, here’s another product you should pay for. Even if it’s a related product, it was weird.

And internally it didn’t work was because, like we had a machine built and optimized and people trained in order to execute on a particular product, well newsletters and websites and events and stuff like that. And then we were trying to introduce this other thing that required different dynamics and frankly, a different skill sets than you necessarily had when it came to a magazine, for instance.

So we just rethought it and went back to what we were best at. And T to me, a meter made the most sense because it allowed us to externally be like, look, you really, you like this product. And so, We’re going to give you some of it for free, but if you’re really into the product you’re going to need to pay.

It’s very, I think it’s fairly clear. And then internally more importantly, it could be just focused on making good shit that people want to pay in order to read. That’s it and the stuff you’re good at this stuff. You’re good at already doing, keep doing it, do more of it. Not necessarily do more of it, but do it better, go deeper.

And the other stuff, whether it’s a magazine or meetups and stuff like this, that’s extra that’s. Cause to me, that’s not like enough of a core value proposition. So I know there’s downsides to, to metering, but to me it struck me that the best balance between what the needs were of the community and what the needs were.

Both financially for the company, but also like internally for keeping people saying and putting them in positions to succeed. 

Ben Aston

Yeah. So in terms of the, so the primary component of the membership was the unlimited access to content. 

Brian Morrissey

Yeah. I found that like before we had the meter, I used to go on like our events and I’d be like, listen, I need a slide, every blah, blah, blah, every four sessions in order to like, be selling this membership thing.

I was like the sales person and chief and what I found was like, the slide just had these walls of like bullet points and stuff like that. And you get this and you get this and. Yeah. When we started sketching out this membership program I was joking. I said, the one thing we can’t do is the football phone.

And there was this like sports illustrated ad back in the 1980s, that was like, you get 52 issues and you get the swimsuit issue. And also if you act now you get the football phone. And even as a kid, I was like, my God, they’re just like, try it. Anything. I want that what does a football phone have to do with I just wanted the football phone.

I don’t know. I just felt we were trying to throw a lot of stuff against the wall and see if it stuck. Whereas like personally, I think, less is more, I don’t trust those Greek diners with the, like the 47 pages, the menu. Like they can’t make half that stuff in a way. Are they going to make a shrimp scampi at 3:00 AM second?

Why even have it on there, stick to the meatloaf and the eggs and stuff. And then 

Ben Aston

I think the interesting thing about there’s an interesting dynamic here, because I think what you’re talking about in terms of a metered paywall that to me sounds like more of a you have more of an audience more than you have a community who would be willing to pay for that.

But then I think the interesting dynamic at play here is that you do have a community, but the compute, the community is more competitive among themselves. So that’s maybe why that type of Event with the VAT type of membership works better because the collapse there, people are less collaborative.

Brian Morrissey

Yeah. I definitely saw that. For instance, we had like member events for years. And I remember like the first one, like seven people freaking showed up to our office. Oh my God, that was, this is what you got to like grit and just go through any poor eighth and Stephanopoulos from now this poor guy, I had him come over.

It was only a short walk really, but he’s like talking in front of seven people. Sorry. I don’t think he has. He hasn’t been, we haven’t been in touch in a while. I wonder why. But what I noticed was the D dynamics on glossy were totally different. We had member meetups I remember going to a member meetup right before the pandemic hit.

It’s like packed and great energy and stuff like this. And different groups have different dynamics. I, and I think, the truth of the matter is you’ve got most people have a mix of an audience and a community people just like to say it’s community right now. Look, the wall street journal talks about like membership, like really?

How do you have a membership of like hundreds and hundreds of thousands of people?

Ben Aston


Brian Morrissey

I just, it just seems like you’re just calling it that I appreciate that the New York times was like, yes, subscribe, you get access to like journalism. 

Ben Aston


Brian Morrissey

Go figure. But to me like the thing with a membership in a community is do those people want to interact with each other?

And can you convene them? So we, to me like Digiday has, I guess, did use past tense with me a community, but it’s a subset of an audience. 

Ben Aston


Brian Morrissey

Is that makes sense?. 

Ben Aston

Yeah, no, it does. It totally makes sense

Brian Morrissey

And I don’t know, like in some ways it was frustrating that we never, to my mind, like nailed the community aspect on the paid side and we tried like a Slack channel and I don’t know whether it was the tools or whether it was the fact that we didn’t for the most part, have a community where you add an audience.

But I don’t know. None of them really stuck, I guess. 

Ben Aston

Yeah. Yeah. Yeah. I think it’s incredibly challenging that my, my experience of Tran trying to transition from a, an audience to a community has been. That it is a lot of work similarly, to creating a publication. Like these things don’t just happen.

You don’t get, there’s not, yeah, you don’t just 

Brian Morrissey

Who needs it then? 

Ben Aston

But for me that’s more community and actually helping people as individuals, rather than as individual page views. For me, that’s way more rewarding. Ultimately, 

Brian Morrissey

It’s definitely more, I don’t know, to me, it’s yeah there’s room for both.

I don’t mean to be like kind of mealy mouth about it, but there is room for both and it’s really difficult to me. It was very. Important particularly early on was that we did do things that don’t scale. And don’t worry about when we have 30,000 members, we don’t, so who cares? I don’t want to like talk to me when we have 30,000 I’ll take all the problems we have the workflow problems we have because we put in place when we have 3000 members that didn’t think that we’d have 30,000, I’ll take that problem.

So I think it was important always to do things that don’t scale and being like, open to, cause there’s so many disadvantages to not having scale that. You. So for instance I’m doing some like advisories stuff now. And a lot of people talk to me about like membership. Then they go to the tech platform and stuff like this.

And to me, like with all the different tech platforms, almost all of them are too much tool than small publishers need. And that’s because a lot of the fancy optimization  stuff that they can theoretically do requires more data than most publishers have. So, you can just skip it. You know what I mean?

I don’t know, the Bloomberg is running I don’t know, like 363 concurrent multi-variate tests and stuff like this. You cannot do that on a small scale. You can run like two experiments that have an error rate of 48%. Yeah. 

Ben Aston

Yeah. And then it wasn’t really worth it.

Brian Morrissey

It’s like ad tech at determining whether a, the gender of a person they’re usually right about 48, 49% of the time. 

Ben Aston

So, I, I curious

Going back to you and the Rebooting, tell me what are your goals for this year? You started on this new side project.

Brian Morrissey

My wife comes down every morning.

What are the goals for the year, a cup of coffee. I’m using this period as like my own sort of reboot. And I think that’s why I like named it that although there’s like reboot out there and now say, so I have this like brand problem, but I’m using it as a way, because you’re so focused over 10 years, at least I was that I really, I would have so many times people, particularly who knew me from Pre Digiday, always cause people pigeonhole you as like where you were at certain points of their life, they knew you best.

So if you were like a reporter at ad week writing, like funny ad freak blog posts about ha look at this ad Crispin, did they think that still what you’re doing, which I get it, I do the same thing. But people would always ask me like, Oh, what’s the most interesting thing going on? What do you, and I’m like, I have no idea.

Like I’m dealing with 19 fires at one time internally that that’s the only thing I can focus on. So I’m just using this as I don’t have those fires anymore. Nobody reports to me which is great. Although I loved working with my former colleagues but using it as a time to explore the different.

Trends going on right now and to figure out what lane I want to go in next for my career, whether that’s starting something on my own, like that’s more of a solo endeavor, whether that’s maybe at some point starting a small media brand itself. Cause I do working with people or that’s joining like an existing organization in ways that ideally I would find rewarding and they can, hopefully I would have something all for them.

So that’s my exploration 

Ben Aston

Now for someone, I guess, in some ways, similar to you right now at the start at the restart, the reboot of their digital media journey. What what was one piece of advice that you’d give them? And what are you telling yourself as you start the rebooting? What are you?

What’s one piece of advice that you’re giving yourself. 

Brian Morrissey

I don’t know if this is good advice, but I’ll go with it anyway. I always counsel patients and I think in many ways, like the reason I say, I don’t know if it’s good advice, it is because I think in some ways I’ve been too patient in my career too.

I’ve been complacent, but I’ve, I’ve rebranded it as patient which is bad. But I do think that being patient is important as long as you’re focused and driven being patient is incredibly important because Everyone. Everyone loves an overnight success through it. I’ve never trusted prodigies.

I don’t know if I’m the only person, but I’ve always looked at prodigies with somewhere in us. I don’t know people who meet immediate success early in life, usually things go wrong. So, that’s my goal. I guess my goal, I guess my advice would be to have a degree of patience because for most people the cliche is, it takes twice as long and it’s twice as hard or twice as expensive.

And it’s that way for a reason because it does, it takes a long time. And if you’re going to try to like, build something new or get good at say like writing a newsletter or something, I know a lot of times it’s I am very rusty, but if you were like, say how long does it take you to do the newsletter?

And it doesn’t take that long really, but. The reason is I’ve been doing, I’ve been writing like for 20 years. So, you start to, I would always find that like really difficult internally, because like your people will have different like capacities at different parts of their career.

And they can’t like, you need to get your reps, like the reason, quarterbacks need the reps and if you’re going to start a newsletter, start it and keep at it because you need to get, you need to get reps, you need to screw up. 

Ben Aston

Yeah. I think there’s that tenacity there’s patients and there’s also tenacity and, 

Brian Morrissey

Oh, yeah. 

Maybe I’ll rebrand that as tenacity. 

Ben Aston

Yeah, tenacity 

There you go. It’s when you, when it doesn’t succeed, keep going. And I think that’s that’s an important point and lesson for anyone who’s starting out to listen to keep going, because it’ll turn into something. 

Brian Morrissey

No matter what it’s going to get harder than you think.

I just think, I don’t know. You sometimes hear from people who’s just Oh, success is success. And it’s not really the case. I’m not like much of a failure fetishist, but the truth is everyone hits a wall like with any sort of longterm endeavor, you hit a wall and that wall can be like, the number of subscribers or newsletters has the number of members your membership program has.

And you need to figure out ways around it. And it’s really difficult. And sometimes you w some, sometimes people just won’t, but it doesn’t mean you don’t try. And I think it’s the same for people it’s even like writing, like I know, like over the years as a reporter I would get through periods where I didn’t think I wrote anything very good month or so I would see it like internally and I would have to go to reporters and be like, it’s okay.

Like I know you’re struggling right now and it gets normal. I’ve gone through these funks myself. I hope I’m not in one right now. 

Ben Aston

Well, let’s finish off with a lightning round. 

Brian Morrissey

I know I used to do this. I used to do word association.

Ben Aston

So I want to know we’ve talked about your best advice, but what is the best advice that you’ve ever received?

Brian Morrissey

I was just talking to them earlier today. As I mentioned, my wife many years ago, a a friend from the industry executive at some big technology company, I’ll go on named he told me that I should that I should get married if only for the reason that you need someone who who will tell you, when you start to look weird,

It turned out there was so much more to marriage, but like I thought that was really, it stuck with me. For some reason. He told me this like 12, 15 years ago. 

Ben Aston

Are you still waiting to be told?

Brian Morrissey

That’s the second thing I hear every morning.

Ben Aston

So talking about every morning, which of your personal habits do you think has contributed most to your success? , 

Brian Morrissey

Oh. God, I don’t know if I’ve had success to any degree. I’m, it’s funny, cause I’m actually about to start a second newsletter about running as a passion project, a second passion project because I’m really under running and it’s given me a lot like of tools to use in life.

It’s, again, a lot of people, a lot of people try to attach too much meaning to their running cause it’s an essentially mindless and ultimately selfish activity. But I think that there are principles cause you have to stick with it and it’s not a straight line and improvement is incremental and it takes a long time to to get good at it for most people.

There are people who just like suddenly are world-class runners with the, again, prodigies. 

Ben Aston

Can you share an internet resource or tool or website that you guys use regularly? 

Brian Morrissey

I don’t know. I use Twitter. I, look, I know everyone is is I too am torn every single time I get my screen time report from my phone and I’m like, Oh my God, what am I doing with my life? But anyone who’s like a sort of news junkie and wants to find out about it’s amazing how Twitter can be a horrible.

Hellscape all the rest of it and stuff like this. And I don’t have to deal with a lot of that. Obviously as a man and stuff like, for women and in many minority groups, it’s like awful place, so I don’t have to deal with any of that. And I’m very thankful and I think it’s, Twitter’s going to do a far better job at having healthy conversations on there, but the access that people have on Twitter to any number of successful important peoples, it’s amazing.

It’s amazing. I just, I hate it because it’s like, it’s so self promotion, self promotional. 

Ben Aston

Yeah, totally. 

Brian Morrissey

Like I never even liked tweeting, our stories that Digiday, not because I wasn’t proud of them, but I was like, Hey, you should just follow Digiday for that. Like, why do you need me?

Unless I have something to add to it, but if it is pure promotion, I’m just yeah, I don’t know. 

Ben Aston

So I’ll finish with promotion. What book would you what book would you recommend and why, 

Brian Morrissey

What book would I recommend Reading right now? Oh, I’m reading a book right now about about fairness, because I think a lot of, we’re having a lot of important conversations about equity in our society, but within companies and stuff like this and within management, and I know this is like a a really difficult time to be certainly to be like, In any organization, but to be leading groups within organizations and and figuring out like how to to treat everyone and to have an environment that is productive and healthy, the word toxic gets thrown around a lot.

And I can’t, I can’t stand it because it’s so vague and can encompass anything as far as I can tell all manner of ills. Whereas I, as an editor, I like specifics. Good. Thanks. Fairness is an interesting thing. So it doesn’t mean equal, like people needed to be treated fairly in my view as a lot of people who talk kindness and all this other stuff, but in my experience what people most want and again, it’s hard because it’s different for every single person it’s, to be given a fair shake and to many people within companies and within our.

Our overall society. Aren’t getting a fair shake and I think, the last year has hammered that home. Deanna quality and so that’s what I’m reading. 

Ben Aston


So, Brian, thank you so much for joining us today. Where can people find you on Twitter obviously? 

Brian Morrissey

Yeah, unfortunately I want to let her know check out the newsletter.

It’s the I have a, I have a unique URL. I gotta hook that up. And I only send it out once a week. So you won’t get every day too many people publish too much, there’s too much out there. So just once a week and for now I have a pretty narrow focus.

It’s really on building sustainable media businesses in particular. I’m really interested in this new crop of, whether it’s solo operators or whether it’s small groups like going on at a defector. I think there’s something interesting going on. I just haven’t totally figured it out. And so, as I explore what’s, the, this is very good. 

Ben Aston

Cool. If you like what you heard today, check out. Brian the rebooting, which has been talking about today, we’ll put the link in the show notes as well, but also please subscribe and stay in touch on But until next time, thank you so much for listening.

Brian Morrissey

Cool. Thanks., Ben!

Check this podcast out if you’re running out of content ideas: How To Effectively Repurpose Content To Increase Value (with Sean McCabe from Seanwes)

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