Magazines are the new handbags!!!
Dirt Media CEO Daisy Alioto on human-made media, implicit censorship, and the Pisces of it all
ST. ALBERT — On summer nights, mom would drive me and my sister to the recycling depot to toss our old cans and newspapers. And then I would hunt for magazines.
The depot sat on a dusty plot of nothing near the edge of town. Its centerpiece was a series of large covered dumpsters, including one exclusively for magazines. For whatever reason, none of the magazines were ever bagged. If the pile was big enough, I could reach in from the safety of the platform and pull something to read. Otherwise, I would crawl through the opening and pray that no one saw.
Inside, with my mom and sister standing guard, I would maneuver across mountains of already-forgotten information. I would pan glossy pages for gold. My favourite was Entertainment Weekly. I would sit in the sunroom at the back of our house and read about George Clooney and Julia Roberts. About James Cameron and the domestic box office.
Twenty years later, this is the kind of feral media consumption Daisy Alioto (presumably) dreams about. As the CEO and co-founder of Dirt Media, she’s given herself the not-insignificant task of developing a better business model, of finding superfans and giving them a reason to believe. Drawing inspiration from crypto-bros and streetwear companies, Daisy and the Dirt team have shown a willingness to experiment, and found solid support, raising $1.2M in seed money to build what they describe as a community-oriented media ecosystem.
But while the tech-adjacent jargon sometimes makes my brain Factory Reset, the publication nevertheless manages to operate with a human sensibility, much of it coming from Alioto herself.
Our conversation, edited and condensed for clarity, touched on workaholic tendencies, star signs, lessons from her early days in audience development, magazines as the new handbags, and her low-key desire to build a more beautiful and truthful world.
As I got a little older, there were fewer magazines in the recycling. Everything had moved online and our neighbours were less interested in physical media. Eventually, my mom stopped asking my sister and I to tag along. Now and then we would drive by the lot and I would stare through the chain link fence at the steel monoliths of my youth.
I would recall The Dixie Chicks naked and exclusive, and Tobey Macguire talking about Spiderman. I would recall Mike Meyers and Beyoncé promoting Austin Powers in Goldmember.
I would recall a life more interesting than this.
ES: Do you normally say yes to weekend interviews? Or am I the exception?
DA: I actually prefer working on the weekends… It gives you the illusion that nobody’s going to bother you. Working regular hours, there’s a piece of your brain reserved for the possibility somebody might interrupt. It’s sort of similar to why some people like working late at night, or parents that wake up early before their kids. It’s not enough to have time to work, there’s something nice about minimal interruptions.
ES: When do you take a day off, though?
DA: Well, I don’t ever really take days off. Laughs. I would have to turn my phone off and throw it in the ocean to stop working entirely. But that’s okay. I chose this life, so I can’t really complain about it.
ES: Would you say the founder lifestyle agrees with you, then?
DA: It must work for me more than the average person, otherwise everyone would do it. Having a startup is supposed to be hard. I think people understand that having a media company is hard, even if they don’t understand the specifics… But with startups — I don’t think they’ve been easy — but there was this period of Zero-Interest Rate Policy (ZIRP) when capital was a lot more available to people building in tech… I think it gave people the illusion that having a startup was easier. I’ve heard that people who came up during that period are unprepared for this post-ZIRP-era, and the realities of raising money and dealing with investors… It requires a certain amount of grit. I forget her name, but there’s this woman on Shark Tank sometimes that I really like, and she prefers to fund people who had a hard childhood. Like, “This person has a chip on their shoulder, they’re going to make it work no matter what.” Which is a little bit sad.
ES: And how was your childhood?
DA: Thank you so much for asking. My childhood was great. I’m a very fortunate person. I had a roof over my head, I had food on my plate. I have experienced unconditional love.
I just read this great piece by Rachel Connolly in The Cut about “parentified children”. Children who had to be emotionally mature at a very young age because their parents were emotionally immature. It’s part of a bigger package on mental health and makes a lot of good points, including that this might not be a useful identity for us to attach to. Most of the people she talked to said, “Yeah the adults in my life did do this to me, but I have a somewhat functional relationship with them now because I want to or I have to.” At the end of the day, that’s still your parent. And I think that that’s true for a lot of things.
My childhood definitely wasn’t perfect. My parents are divorced. There were dynamics around that that were difficult, and still are difficult, but I’ve never felt like I need to make that a core part of my identity because it’s just not helpful. Trauma is real even in very wealthy households, and very wealthy environments. I don’t know. I think if you had a roof over your head, food on your plate, and a place to go if everything fell apart… You’re kind of the 1%. If you have experienced unconditional love or support from at least one of your parents, I see that as almost being greater than financial privilege, in terms of setting somebody up for success.
ES: Do you feel like you had to grow up at an early age? Because obviously, you’ve accomplished a lot. You’re what, 30?
DA: I just turned 33 in March. I’ve always been a bit of an old soul. Maybe everyone thinks that about themselves, but even my teachers would sort of identify it in me. I think it’s a combination of nature and nurture. I’m very interested in people. I think I value emotional intelligence above raw intelligence. I think intuiting what other people need and helping them feel safe or helping bring potential out in them is one of the best skills that you can cultivate.
ES: That’s sort of the perfect segue to discuss the Pisces of it all. I’m a Pisces. You’re a Pisces. Let’s talk about it.
DA: I should have realized you were setting me up for this. Yeah, it’s really uncanny. I think there’s a natural proclivity to try to make your horoscope apply to you. But I just moved and I found these little cards somebody had given me as a gift. It was a little Pisces pack. And there was one card that listed all of the activities that Pisces are supposed to like. I genuinely love all of them.
There’s this other thing about Pisces being a little bit psychic and I do sometimes feel that I am. But I think it goes back to the emotional intelligence thing. The brain is just a very elegant computer and we are taking in a lot of inputs. Sometimes I think that sense of intuition is your brain subconsciously pattern-matching information to things that have happened in your life and saying, “This is going to go a certain way.” Like, you could attribute that to being a Pisces, or maybe you’re just a little more in touch with human behavior.
Do you feel like being a Pisces really represents you?
ES: I love being a Pisces. It’s a cornerstone of my identity. But what I find interesting is that, in my experience, it’s kind of uncommon for someone with the Pisces skill set to be in a position like yours. We’re as known for being serial killers as we are for being creative. That combination doesn’t always scream leadership.
DA: I don’t know as much about the other signs in my chart… It’s a little bit imprecise because I don’t know the exact time I was born. But I think my other big sign is Sagittarius or something with more bite. I’m basically a power Pisces, you know? I am sensitive and in touch with my emotions, but for whatever reason, I’m able to channel that into more of a driven, career-oriented, Girlboss path. Although I prefer the term Girlmoss.
ES: What do you do to relax?
DA: Relaxation is a problem for me because my hobby is writing, but writing is also kind of the currency of my company. I’m not so good at relaxing. I do love to take a nap. I’ll take a nap in the middle of the day. That is a Pisces thing. I also love to go to an art museum and take in a bunch of beauty. I will do creative writing that is not related to Dirt. Poetry, short stories. I read. I go through periods where I either watch television to unwind or read to unwind. Right now I’m reading a book by my friend Sasha Fletcher called Be Here to Love Me at the End of the World, which I strongly recommend.
But yeah, I’m definitely a workaholic. I put so much creative energy into Dirt. My husband and I just moved and I have paintings sitting on the floor because I don’t have the energy to curate my aesthetics. Everything is going into cultivating Dirt. I do try and listen to my body… Sometimes I only sleep five hours a night. Do I know why? No. But until it’s creating problems for me or the people around me, I’m not really going to question it.
ES: What are your keys to a good nap? Have you tried a coffee nap?
DA: Coffee naps are incredible but they often only happen to me by accident. I sort of subscribe to the idea that a nap has to be 30 minutes or three hours. There’s nothing worse than taking a weird hour-long nap and then waking up with a feeling in your stomach, not really knowing where you are. That said, I can nap anywhere and under any circumstances. Lights on, still in my clothes. I have terrible sleep hygiene. In college, my friends would make fun of me because I would sleep on a quarter of my bed, and the other part would be covered in textbooks, my hair dryer, my laptop. I would still do that if it weren’t for my husband.
A nap has to be 30 minutes or three hours
ES: Can we talk about rage for a second? I listened to an interview where you discussed rage being a motivating factor for you, and I wonder if you can expand on that. How do you find it a useful emotion?
DA: Rage is really useful when you’re low-key a rat in a cage…
ES: …?
DA: But no, I think that everyone experiences anger and rage and it’s not always productive. Sometimes it’s directed internally, sometimes it’s directed externally. I have never been interested in self-punishment… It’s not that I don’t ever have self-doubt or feel bad about myself. Everyone feels bad about themselves sometimes, but at my core, I really love myself and believe that I deserve good things. And I love other people and believe they deserve good things. My rage is not a hatred of myself or others. I think it’s a sense of wanting a more just and fair world, wanting a more beautiful world, wanting a more truthful world. The question becomes how can I use the platform that I have cultivated to make the world look more like how I wish it did. It sounds silly because Dirt isn’t overtly political, though I think any interpretation of the way I talk about culture, reflects how I think and feel. But over the past six to eight months, I have felt good about the fact that I have a publication where a freelancer doesn’t have to worry whether they’re going to be blacklisted because they expressed solidarity with Gaza. If my only impact is that writers feel free from censoring themselves then I would be good with that. That’s the lowest bar to hit right now.
ES: How serious do you think censorship is for companies right now?
DA: If it’s not a practice of censorship, then at the very least there is an illusion of censorship that has not been debunked. You have publications like The New York Times that will make examples of a couple of people, and that is enough to create a chilling effect. We saw the same thing happening in the tech community. There are a couple of people who spoke out early, like Paul Graham — who is essentially untouchable because of his stature as one of the founders of Y Combinator. He recognized that he is maybe one of the only people who could speak out early without repercussions… People still tried to punish him. Everyone seeing that was left feeling as if they have to self-censor.
A lot of times the very idea that there’s a blacklist, whether there is or not, is enough to change people’s behaviour. I think that’s really wrong. That’s not what democracy is about. That’s not what humanity is about. I personally think it’s worth losing any professional opportunity to maintain your integrity. But I say that from a position of financial stability. There are people who don’t have that same luxury.
ES: For sure, and if you don’t want to talk about this let me know.
DA: I think we should talk about this stuff. I’m ethnically Jewish but I grew up Christian. I was not raised with a strong connection to the state of Israel, or to believe that the state of Israel had to do with me and my safety in the world. I feel like I may as well be outspoken. My chances of getting venture capital as a solo female are about 7%, give or take, and I would say the odds of getting a media staff job right now are also about 7% for anyone with a decent resume. In other words, you have a 7% chance at getting the thing that you want, that you’d censor yourself to achieve, but a 100% chance of living with yourself for the rest of your life. Are you really going to take those odds? Are you really going to stay quiet about this horrible thing that’s happening for the slim chance that you might get something?
People will not be willing to pay for anything that could be done by ChatGPT. You have to be creating something that cannot be duplicated by a bot.
ES: That calculus really speaks to the disarray we’re seeing across media right now.
DA: We’re in a very interesting time because the media industry is struggling, but the idea of media has never been stronger. People spend their whole day consuming media across various platforms. And so… I think the real work is to look 20 years down the line and ask ”What would I do now to shape the direction that media takes?” Because it’s not going away. It’s just reinventing itself, as it does in every era of technology. That’s sort of how I view Dirt.
I’ve been lucky enough to have the resources to play around with some of these theories and ideas, but I think it will require a lot of people to put these things into practice… Everyone wants to say they’re starting a media company, but you really should say you’re starting a small business because that’s what you’re doing. And there’s not a lot of glory in that, in being the person who figures out how everyone’s going to get paid. Yet everyone wants to get paid, so somebody has to do it… There are so many different ways to go about it… It could be some sort of new business model. It could be a collective, like Defector, or it could be like The Drift and take money from one wealthy individual. But I don’t want to see an entire generation of people who aspired to be in the media industry not be able to live out that dream because nobody wanted to touch money.
ES: How much pressure do you feel at the moment to become a multi-media company, whether it’s integrating audio or video?
DA: I would love to do multimedia, but I think every channel you start should be done with intention and when you have the resources to support it. I come from the world of audience development, and I’ve seen larger media companies say “Do the pivot to Snapchat” or “Do the pivot to Instagram” without a lot of thought or strategy behind it. But yes, I think every media company, for the most part, will need to have multiple revenue streams and multiple platforms.
I see it almost like a streetwear brand where you foster a strong impulse to collect around the media model. Dirt’s big idea early on was to embrace an e-commerce component. I could buy hundreds of things from Supreme, but for most magazines, you can usually only get a subscription or tote bag. Why are we under-serving like our super fans? Whether people value those digital goods in the same way that they value other aspects of the brand is still sort of being worked out, but I think it holds up in an environment where AI can create cheap, easy content.
People will not be willing to pay for anything that could be done by ChatGPT. You have to be creating something that cannot be duplicated by a bot. Human-made, bespoke, thoughtful, multidimensional media with a strong culture of collecting around it is now in the same box as LVMH. We might see that magazines are the new handbags. We might see that books are the new handbags. But it also might be a smaller number of people making more money off of those things. That’s a real shift, and it’s scary. The money that’s been made up until now is not because people valued media or monetized it smartly, but because it was being falsely subsidized by VCs who benefitted from people putting money into their firms instead of the stock market because of low interest rates. When you see that, you start to see the whole picture.
ES: You mentioned grit earlier. I get the vibe that you’re a pretty persistent person.
DA: I remember having this conversation with one of my favorite English professors in college, and she teed me up for a compliment. She said, “You know, Daisy, you’re going to go far in life.” And I thought she was going to compliment my writing. But instead, she said, “Because you don’t give up.” And I was like, “Okay…” I was initially disappointed she didn’t say something about my talent. But now I realize she actually gave me a bigger compliment because there are so many talented people, and some of them do not succeed… They give up too early. I think everything is usually a combination of talent, perseverance, and luck. But if I had to pick one, it’s got to be perseverance. Because when you’re perseverant you can make your own luck, too.
