Very Fine Day #49: Brian Morrissey
"It's not a fraud, it’s a conspiracy, because everyone knows it and they pretend it doesn't exist."
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“You thought you were savvy, but you got seduced by he dumb free snacks and shit. Oh, we’re all family! But you’re making $40,000 a year.”
Bit of inside baseball today, folks. BRIAN MORRISSEY is our guest on VERY FINE DAY this week. Brian was the president and editor-in-chief of Digiday until fairly recently. Setting things up, watching it grow, working and living through the latest digital publishing boom.
After a decade of doing that, and building something rather substantial, he moved to Miami and is now writing the always-captivating newsletter, The Rebooting.
I found Brian through his newsletter, and think his perspective on the way the media industry is changing, growing, and – often – letting itself down, is always fresh and insightful. Which is all to say that I know this edition is very how-do-things-work / industry talk heavy, but trust me, it’s a good one. Have I ever let you down? (Do not answer that).
Into February now. God, I hate that. Tell a friend about VFD today!
I’ll see you down the road.
Brian Morrissey: Give me a break, there’s palm trees surrounding me right now and we’ve got iguanas running around. We’ve got iguanas at risk of falling out of trees because we’re gonna have this cold spell this weekend. And so when it gets cold enough – I don’t know what the celsius is but it’s in the 40s – they start to fall out of the trees. It starts raining iguanas.
VFD: I don’t know how I’ve never heard about iguanas in Miami.
Brian Morrissey: Yeah, I mean, it’s a tropical place.
VFD: I’m sure when you get into Florida and Miami it’s a different kind of vibe. Alright – let’s crack in.
Brian Morrissey: Get started.
VFD: I have to be honest with you, I found your writing through your newsletter – which is great, by the way – but I was thinking back and, well, look: I don’t think, even in the early parts of my career, that I was a huge Digiday reader. Maybe I should have been. But the concept of it all was a little foreign to me.
I wouldn’t say I’ve crammed it, but I’ve definitely seen things on it and been aware of it. But I think the construction of it as something that is sustainable – at least it seems sustainable – is really impressive. And you were part of that from the beginning, right?
Brian Morrissey: Yeah. Digiday existed for a couple years, mostly as an events company, so I joined, I guess, 10 years ago? A couple years after it started. And the idea was that a lot of trade media; they were events businesses with websites. The content and the publishing is really just an excuse to market the events. And I think that’s why a lot of the content sucks. Because it just needs to be good enough to have an excuse – to maintain an email database to market to people.
VFD: Right, yeah.
Brian Morrissey: But I think what it provided was a stable initial revenue platform in order to really figure out the publishing side. And to really make the publishing as a real publishing business, versus content marketing for an events business.
VFD: And where were you coming from to enter that role?
Brian Morrissey: Oh, I’d been a reporter and editor for various publications. Just about all of my career was focused on the digital media world. Prior to Digiday I was the digital editor at Adweek.
VFD: Oh, OK.
Brian Morrissey: For me it was a good opportunity to build a publication that I would want to exist, but at the same time to have the backing of the events was really critical. Because that was 85% of the revenue of the business up until about four or five years ago.
VFD: Right. Were you confident that you could do it? Because obviously: reporting, editing, and then building out a media brand… those are different.
Brian Morrissey: I guess I was just like: Well, if it doesn’t work out I’ll get a job somewhere else. Are they gonna hold it against me?
No, I was pretty confident that as long as we stayed focused and really figured out a way to differentiate – and we talked a lot about differentiation - that was really important.
Even for the first few years, I used to make a point – but also just because I was super busy because you have to do 1000 jobs – but I didn't even read the other publications strategically. Because it’s like that cliche: if you’re always focused on the horse in front of you, your view doesn’t change. You’ve got an ass in front of you. And I just think it can pull you in a different direction. I think you can become too insular and too esoteric to some degree.
But I do think differentiation is so critically important when there’s a lot of different alternatives. I know that when I first went to Digiday, people were like: Oh, there’s no need for it. And that’s what I hear a lot of times when people start a new publication. And it’s like: Well, there's a lot of different ways to do things in life. And if people in every other industry, if they said: Oh, we’re not going to try and build this phone, because people have already built phones before…
But I feel like in the publishing industry, for some reason, that is an impulse of: these people do this, and that person doesn't. And publishing is a different business. And you can differentiate in all sorts of different ways. You can differentiate in format and tone. But the most powerful way is to just differentiate in your point of view of the world and of a particular area.
And then there’s people who don’t have a point of view. So, then I get it - Because if you’re like: I’m gonna summarise the news. Well then, I would say a lot of people summarise the news.
VFD: Yeah, why not do it with bullet points,...
Brian Morrissey: Yeah, that’s when you go to format, or you go to personality. I've always found in my hierarchy of differentiation, personality is - it's like puns are the lowest form of humour - personality is the lowest form of publishing differentiation.
VFD: What about that with the comparison of, and I hate saying it, but the creator economy and individual publishers. That’s a personality, isn’t it?
Brian Morrissey: I guess my point on that is that it's really difficult to pull off. The unique personalities are fewer than most people think. And the people that think it, usually are not as unique as they think. None of us are that unique. There are people that are transcendent talent.. If people are that exception to the norm, I think that's great. I think it's an important part of the mix.
I think we're moving from a focus on institutions to individuals. And adding more personality to the product is good as long as it doesn't overwhelm it and as long as it's sort of organic, right? I think of someone like Trung Phan who's just amazing at memes and the intersection of business and humour and digital culture. I wouldn't even necessarily say what Trung is doing is personality, and he has a good personality, I talked to him a couple times. But I think he has a very repeatable way of being able to express that in a way that's unique. I guess I always differentiate between side dishes and main dishes.
VFD: Yeah, I think in media, too, there's a there's a fair amount of ego and self-belief involved
Brian Morrissey: There’s a reason all this shit has bylines.
VFD: Yeah, that's a good point.
Brian Morrissey: I bet most reporters, if you’re like: Okay, we'll give you a 20% raise, but we take your byline away. They wouldn't take it.
VFD: No. That's why they do it, man. Because they’re like: One day I’ll write a book.
Brian Morrissey: That’s why Twitter is the worst for reporters, because everyone's like: Oh, I want to make a difference. They wanted their byline on there too, though. They want to be out there a little bit.
VFD: How did you make that transition to thinking like, I run a business now, effectively.
Brian Morrissey: I was sort of building the group from scratch. I inherited a couple of people. A lot of it was trial by error. I always read these things about mentors - I never had a mentor. And I don't know if that's a generational thing. I was like: Was I supposed to ask, was there like a form that I didn't get? I don’t even remember. Maybe nobody ever saw something special in me. I never sort of had that. So it was learn as you go.
I think the hard part of management, at least when I look back on it and I remember I was talking to people about it, it's a lot of trial by error. And the problem is you're making your errors on people. And that sucks. I don’t have a lot of regrets, but you do learn from mistakes, right? And the sucky part about management is those mistakes, unfortunately, oftentimes involve other people. Y’know: you make wrong hires, and you've disrupted someone's life. Life goes on. But that sucks to think about, really. But it's also inevitably a part of the process.
There’s this great book, “Complications” by Atul Gawande, about becoming a doctor, a surgeon. Being able to intubate is a very critical thing, but nobody wants their loved one, much less themselves, to be the first person intubated by some trainee. But someone has to be the first person that this trainee intubates, trying to get the tube in.
VFD: And everything else. First surgery, first tooth removal…
Brian Morrissey: Yeah, just someone else.
VFD: Yeah. And you left last year, right?
Brian Morrissey: Yeah. October 2020.
VFD: Oh shit it’s 2022, oh god.
Brian Morrissey: Yeah I know. The whole company had gotten to 75, shrank a little bit with the pandemic and furloughs and stuff because the events were still 65% of the business – in-person events. And that was a real challenge.
VFD: It was not happening.
Brian Morrissey: I reread the Shackleton book, “Endurance”, during the early pandemic. That's how I felt. He went across Antarctica, but then everything went shitty and he was like: Oh God now we got to move, success is like survival. It's not being the first to get to this place, it’s now surviving. That's kind of how the feeling was in the early pandemic. Gotta survive.
VFD: Did you feel like you did that, though?
Brian Morrissey: Yeah, you gotta eat the penguins first.
VFD: You felt like you got to that point with it? I mean, obviously Digiday still exists,
Brian Morrissey: Look, there were a few things that happened during the pandemic. One is that, obviously, it forced people to adapt. Digiday’s sales team was really expert at selling in-person events, and probably came at the cost of selling other products like advertising, and even in various digitally delivered sponsorships and content marketing, although they were pretty good at that.
But when there's no events to sell, we sell a lot of the other stuff. So I think that ended up helping diversify the business. And business continued. After that rocky first month or so - and I’d always say this to our team - the needs of our clients did not change. They still needed the services we used to provide them, but they just needed to accomplish them in a different way, that was the trick. I mean, I left in October 2020, and it seems to be doing okay.
VFD: Were you part of this great resignation, was that you? Were you just completely like: I fucking hate this.
Brian Morrissey: It had been almost 10 years and 10 years of doing anything is a long time. I mean, the company changed so much, it was like a handful of us when I started and it got to 75 people and maybe shrank down to 60. So the company changed and my job changed along the way. I never really subscribed to the burnout thing. I know it’s real, it's probably generational and I'm Gen X and nobody ever asked us if we were burnt out, we just don’t think about it, I guess. It was time for me to do something new, and it was a good time.
VFD: And that was the newsletter, right?
Brian Morrissey: Yeah, that was mostly a bit of a placeholder. I left without really having much of a plan. Maybe in retrospect I’ll make up one.
VFD: The plan was Miami.
Brian Morrissey: Yeah, this is the plan. I started the SubStack because if you say you're gonna leave somewhere, you get a lot of attention so you might as well convert it into first-party data.
I had a non-compete and stuff, so it wasn't as if I could take a job somewhere else, so I knew that I wanted to do stuff to remain active. I moved to Florida so it sounds like I retired. I think I knew in the back of my head that I wanted to build something new. So to me “The Rebooting” is like the kernel of a new publication. I'm just trying to do it a little bit differently, and a little bit more the way I want to do things.
VFD: Which is how?
Brian Morrissey: Again, I think this shift from institutions to individuals is really interesting. I saw what was going on with the newsletter world and to me newsletters themselves are kind of uninteresting. It's just a delivery mechanism. So what's underneath that? And I think what's underneath that is that you have a different relationship with the audience than you do if you're just publishing a website.
I don't know why this is. I don't know if it's just because it comes on the phone to an email inbox or something. But I know that publishing things as an email is very different than publishing things as a web page, in my experience. Podcasts are more powerful because of the human voice. And I think there is an emerging newsletter writing style that is a little bit more personal. The best of it is that it has personal touches, but it's not like Dear Diary. Some people are too Dear Diary for my taste.
VFD: it's kind of like an evolution of the blogging era, with a little bit more of a format and a bit more of a structure to it. The ones that are good.
Brian Morrissey: I think the big difference with the blogging era, because I do think it’s a throwback to that time, is there’s a cadence to it. The thing I’ve said about newsletters is be consistent. Consistency matters. And I think what newsletters give is that you can have a cadence that makes sense for what you're trying to accomplish, whether it's weekly, or some people do daily, but it’s not random. Blogging is random, just like: I’m gonna make a blog. So I feel like newsletters are slightly different.
First of all that direct connection, I think blogs had that, sort of, with RSS, but I think it's a little bit different - but I do think there's a lot of aspects of that two-way thing. I think the best newsletters, and I haven't solved this, but are more two-way than just one-way.
VFD: You mean hearing from your audience and going back and forth?
Brian Morrissey: Yeah, you hear from people.
VFD: Like, directly.
Brian Morrissey: Although if anyone has ever sent me an email and I haven’t replied to it, it’s not because I was so overwhelmed by thousands of emails and it’s not because I’m a dick. It’s more just because of Gmail’s threading and my own disorginisation.
VFD: Yeah, for sure. I think the inbox, even if it's not really the truth, people have this fake idea of it being a private space still, like a private social spot. And so the newsletter is a warmer thing, that even though all this data has been scraped by Google, or whoever, they enjoy.
Brian Morrissey: A lot of newsletter formats are really just an essay that could be on a web page…I don’t know, it’s like a web page sent by email.
VFD: Yeah, yeah.
Brian Morrissey: I do think there's something interesting underneath it. Because I do think that, for a whole variety of factors, people have more connection to individuals than some brand that you're giving human-like characteristics.
And when you think about it, the key is differentiation. And it's a lot easier when it's an individual because we're all different in some ways. So that, and a personality, is a good way to differentiate. But I do think that the strongest differentiation when you're talking about an individual or an institutional brand is on point of view and your lens on the world. And some people don't have it.
I think it's easier to execute consistently when it's an individual, too, because it's just you. If you're trying to get a bunch of people , who are not me and who are probably very different from me, it’s harder to congeal around this idea and this point of view, and execute on it. And it might not be their point of view.
In some ways, I feel like I was sort of forcing my point of view onto other people, because otherwise you've got some random mishmash. I don't know what it adds up to. I always thought that the test of a good publication was if you could take all the branding off and be like: Yep. And you can do that with, with like, The Economist.
VFD: Yeah, yeah.
Brian Morrissey: For better or for worse, you know. Or Business Week.
VFD: Yeah, I think the thing you were saying about consistency as well is so strong, and it's also the reason I see - failure is a strong word - but you see people start, and they're like: I'm gonna write four things a week. And that's what you can expect for me. And after three months, it's like: I can't do that. That sucks.
Brian Morrissey: One of the things that I love about this sort of mini newsletter boom is that it has given both permission and outlet and impetus for people who are experts in their fields to contribute to understanding. I feel like a lot of journalists get all: Grrrrrrr about that, like: This person isn’t accredited! But I’m like: I didn't know that there was some journalism seminary you needed to go to??
VFD: Oh yeah, there’s a lot of them.
Brian Morrissey: And you know what, people are doing different things. But I find the people who have deep experience in these fields are producing some of the best freaking content, as far as I'm concerned.
I just noticed my consumption patterns were totally different. I really think there’s a flight to focus but I also think there’s a flight to expertise. My original idea with Digiday was really more along having experts in different areas, people who were really deep in those areas.
I think my first hire was my former colleague, Mike Shields. He knew so much about video and the publishing world that he's a true expert in it. And that was the idea: have these different experts. What I quickly realised is that does not work. Because it's too expensive.
I don't know what it's like in Australia, but I got on that elevator at 1 Liberty, and Business Insider was in the same building, and it made me feel really old because every single freaking person getting on that elevator was between the ages of 23 and 25. That's not because they know TikTok. That's because they have four roommates in Bushwick. It's a model.
And, to me - and this is not necessarily about Business Insider - it's not a model that leads to the most valuable content. I really do think that you're going to see a lot of publications that are smaller, more focused, and more expert. I think that there's a place for that sort of churn and burn model. But to me, that's the opening that I'm really interested in. I just knew that the model we had to do was predicated on having a few people who were super experienced but an army of people who were just simply not. And that's fine, everyone's got to learn, but I mean, where did these people go? Most are in PR, or they're working for companies, because guess what: the economic models are based on paying such low salaries that people literally cannot have middle-class normal adult lifestyles when you have adult things like mortgages and stuff like this.
Nobody ever talks about ageism, I always find that very strange. All the stories that constantly got pitched, I got pitched every single -ism story possible in newsrooms. Never did I get pitched ageism stories. Yet if you go to these newsrooms, sure as hell they got a lot of fucking people in their 20s. And I don't think that's a problem. But find people in their 50s. Try to find people in their frickin 60s. Never gonna find them. And it's not because they don't know TikTok.
VFD: Yeah.
Brian Morrissey: I just think it’s funny - lots of things like old people don't know how to use email. We know how to use email.
VFD: I mean, I'll be interested to see if people who are in college now who have experienced this - I feel like there's more awareness of that model and how predatory it can be - and whether or not they will participate as willingly as, say, my generation that was like: Fuck yeah.
Brian Morrissey: Yeah, don't sleep on Gen Z, because the Millenials got done.
VFD: We blew it, man.
Brian Morrissey: You thought you were savvy, but you got seduced by he dumb free snacks and shit. Oh, we’re all family! But you’re making $40,000 a year.
VFD: Yeah, I never knew you could be made redundant from a family.
Brian Morrissey: But Gen Z is like: Hell no. CTC. Cut the check. We know what we’re doing.
VFD: Which is good. I think, overwhelmingly.
Brian Morrissey: I just think that there's gonna be lots of different models. I think one of the good things about publishing right now is there’s a lot of different ways to make money. Just the act of being able to aggregate an audience in a specific area has been recognised to be incredibly powerful. And that’s good, because you can make money through lots of different ways, not just through advertising.
I think the trick for sustainable publishing businesses, no matter what the monetization method is, is the infrastructure costs have to get lower. The truth of the matter is that inside the publishing function serves a lot of different roles. And as publishers have tried to do more and more and more things, it's just led to almost mission creep.
Publishers become massive bureaucracies. I used to always think you either create the stuff, or you sell the stuff, or you’re overhead. And the reality is, when you have scarce resources, you've got to put them against people creating the content or selling ads. When you go towards the direct revenue model, well, then you get a lot of leverage.
The story that I have not seen written that I would like, is how different the mix of people who are focused on the content creation - which is the product, okay, that is the product - versus all the other stuff. A model like The Information, their biggest leverage is the fact that I would guess 60 to 70% of the entire company is focused on the editorial.
VFD: That's not quite normal, right?
Brian Morrissey: When you get publications, you have more people in marketing than they assign to an entire editorial team for a brand. And that's because their real business is not actually the editorial. So if they think that people are going to pay them when they're not putting the resources against it - not gonna happen.
VFD: I wanted to ask you about how, over the scope of your time at Digiday, I feel like you got the very start and then the crash and burn of an entire media cycle. In my opinion it's cyclical, we just do it again and again, nothing's new, and we fire and hire and whatever. Do you agree with that? And what was that like? And did you at any point see the end coming earlier?
Brian Morrissey: I think my first crash, I sort of started right at the tail end of the dot-com boom, so that was more of a specific crash to me because I lost my job. A lot of the media industry really, really suffered after September 11 and the dot-com crash, because traditional media was already weakened. Publishing has always been a hard business. I don't know, if someone's looking to make a lot of money…
VFD: Sell something else.
Brain Morrissey: It’s a very rewarding career, but if you want to optimise to that I would say that there's probably other areas to go into - laundromats, pretty much anything.
I think it just shifts slightly, right? It’s always been a difficult business, but at the same time I think there's a lot to be optimistic about as far as the state of the business now goes. Because, again, I think there's so many different models, and I feel like the way publishing is evolving, there's a lot more opportunities outside of massive scale. And so they're much more tangible.
Building a billion-dollar business, I have no idea how you do that. I'm fairly certain I never will be part of building a billion-dollar business, but I would go into FinTech. I think that there are a lot of opportunities in publishing. I see them, I've consulted with these guys. You can have very nice and profitable media businesses. Many of them are not as big but there's a lot of nice and profitable media businesses. And I think that there's that opportunity when it becomes less about the obsession with big numbers. The reality of media is that it has to get used to smaller numbers.
VFD: Yeah. Certainly over the last 10 years.
Brian Morrissey: It’s like Zimbabwe with inflation, right? At some point you just want to chop five zeros off the denomination. And that is a lot of publishing, because a lot of the numbers, big numbers that people traffic in, are flimsy. Completely flimsy. And just the fact that most publications that claim however many views - it's just random people who search.
Like, 75% of it is randoms who search for some super-optimised page that probably has nothing to do with what you say that your publication is about. And that is the reality. And it's not a fraud, it’s a conspiracy, because everyone knows it and they pretend it doesn't exist. But if you want to reach real audiences, I think that smaller tends to be better. You can audit it better. The shift to first party data is making it more provable, people having direct relationships, up to and including them having direct financial support from the audience. I think these are all positives because it can normalise the media business to a degree. Ideally, you'd have a lot less bullshit.
VFD: I remember being at BuzzFeed and being 25 or something and seeing one of my posts get 400,000 views or something. And then for whatever reason it ticked in my brain on that day: That is not real. There's no way that this is happening. But you’re right, everyone buys in. We’ll all just agree that’s real.
Brian Morrissey: The biggest thing is we just have got to get comfortable with smaller numbers. If you want real, the number’s are gonna be smaller. Do you want it good or do you want to cheat? Which do you want? You gotta choose. And everyone’s like: I want both.
VFD: Which I think, again, is the thing with newsletters. People have that realisation where they’re like, Oh, this is actually how many people care about what I'm doing. In a little bit more of an explicit way, rather than, like you said, SEO or like three seconds on a video on Facebook.
Brian Morrissey: Yeah, there's nothing wrong with it. But it’s not substantive.
VFD: It’s pulp. Well, thanks man.