Caitlin Dewey: I’m happy to just shoot the s***
The "Links I Would GChat You If We Were Friends" author talks life in Buffalo, leaving CEOs on read, the future of newsletters, and how self-promotion sucks
VANCOUVER – A few weeks ago, I followed ’s lead, and made the unusual decision to excavate my Gmail archives.
I wasn’t looking for anything in particular. I was just copying what she had already done. Combing the depths of my inbox, hoping to dredge up some long-lost emails.
I experimented with different searches.
I clicked into the search bar and typed.
“before:2014 AND Leah”
Nothing.
“before:2017 AND Leah”
Better.
25 emails, most of them centering on the search for our first apartment.
I decided to try a new approach, a new character.
I cleared the search bar and typed:
“before:2017 AND Valerie"
Enter.
More than 100 emails to and from my mom emerged. Updated contact info, phone numbers, resumes. One chain focused on our family’s Christmas plans. Another included a never-actioned quote to ship my parent’s old car from Ontario to Alberta for $1150.
I also noticed three or four emails with unusual subject lines. “To read if you want a small break” and “mindless reading for Friday” and “Read this - Lena Dunham interviews Hillary Clinton.”
I clicked to learn more.
Despite their subject lines, I don’t think I had read a single one. If I did, I certainly didn’t reply. I don’t like what this says about me.
I do, however, like what it says about her.
I’ve met a lot of moms in my life (dare I say dozens of them), but I haven’t encountered one who sends their kids quite so many links, who tries to involve them in her own curiosity.
Occasionally, this inclination verges on overwhelming, as if my mom expects me to read, or watch, or think about everything she herself has experienced on a given day.
More often than not, though, it fosters something veering on communion.
Every link reveals something ourselves. Our interests, our tastes, our humours, our fears.
I’m often reminded of this reading Caitlin’s work, too. While it feels like everybody and their mother (literally) is sending weekly roundups these days, Caitlin has perfected the craft over the past decade. Her popular reading list, Links I Would GChat You If We Were Friends, circulates to more than 20,000 readers and contains a combination of personal essays and great stories.
Last month, she relaunched Links with a new look. To help commemorate the moment, we scheduled an interview. Our edited and condensed conversation touched on her life in Buffalo, the emo-to-journalism pipeline, leaving Substack CEO Hamish McKenzie on read, whether newsletters are the new YouTube (spoiler: no), and how she listens to a lot of Canadian radio.
If you like it, link it.
CD: Are you from Vancouver originally?
ES: No, I’m from Edmonton, Alberta. I moved here in 2015 or so, and before that, I lived in Ontario.
CD: Where were you in Ontario?
ES: I was in London and then I was in Hamilton for a very brief spell. You’re Buffalo-born and raised, right?
CD: For better or worse.
ES: I actually visited there once or twice when I was out east. I really liked it.
CD: That’s really kind. I’m always skeptical of visitors from Toronto who say they love Buffalo. I’m like, Why? You’re from Toronto. Laughs.
ES: In my case, I liked it because we went to the Frank Lloyd Wright house.
CD: That’s in my neighborhood. I live two blocks away from it.
ES: That’s a very beautiful part of the city.
CD: It is. I’m on the least nice street in this very nice neighborhood.
ES: That’s an important qualifier.
CD: Sometimes we tell people we live in Parkside and they Ooh and Aww and I’m like, to be clear, we live on the street that backs up on the train tracks.
ES: Are the train tracks what distinguishes it from the other streets?
CD: This neighborhood was laid out around Delaware Park, which is an Olmsted-designed park. Very cool for Buffalo. The houses near the park are all gigantic. They have big lots with garages. Some of them used to be carriage houses for servants. As you get further from the park, and toward the train tracks, it’s more industrial. Historically, the houses around where I live were smaller and closer together. But I absolutely love this neighborhood and my house.
Did you do anything else while you were here?
ES: I remember we went downtown, which was not that exciting because it was Sunday… American downtowns in general tend to have nice architecture… I remember it felt more historic and cool compared to Toronto.
CD: I did a story a couple of years ago on something around this. As late as the 1950s, Buffalo and Toronto were essentially peer cities. They were similar sizes. I think Buffalo was even considered more culturally significant. In 2024 that’s no longer the case, so I did a story on “How did Toronto end up being Toronto?” A city planner from the Toronto government took me on a tour. It’s an interesting problem for them because they have explosive population growth, but they’re also trying to do some historic preservation. They’re building these gigantic skyscrapers with the façade of historic buildings on the front.
ES: I went to the University of Western Ontario and they essentially did the same thing. Every new building was made to look really old. It was like Disneyland or something. It was silly but it allowed me to live this very Tumblr-coded, dark academia collegiate fantasy.
CD: That’s really funny. Did you study journalism?
ES: No. I’m sure some readers are sick of this story by now, but my journalism career was fairly accidental. I wanted to do it when I was young but my dad was a copy editor and warned against it. So I wrote for fun and, somehow, that cascaded into an actual career. I joke it’s because I gave Drake four-and-a-half stars in the Western Gazette.
CD: I also kind of came to journalism accidentally, albeit a little bit earlier than you. Originally, I had the very specific career goal of wanting to work for The UN. But in high school, I wrote music reviews for the Buffalo News. It used to have a teen section called “NeXt” (sic). I was writing music reviews for them, mostly so that I could go to emo shows for free, but I included those reviews as a supplement in my college application, and they decided they were going to put me in journalism school. I wound up completing a dual major in journalism and international relations.
ES: Oh my god. Did you do Model UN in high school?
Substack exists in the same undifferentiated swamp as everything else now. Consumers have to decide “Do I want to spend my $7 on Paramount+ this month, or do I want to spend it on Caitlin’s Substack?”
CD: No. I went to a small all-girls Catholic school and we didn’t have Model UN, but I did do a mock trial. We were the state champions one year, which is something I never get to brag about, so thank you for bringing it up.
ES: What did you want to do for The UN, though?
CD: I didn’t have a super sophisticated understanding of global non-governmental organizations at that point. I visited The UN headquarters in high school and I remember tearing up. I had this really naïve, beautiful notion about global unity and prosperity. I still like The UN if I’m being honest. Laughs. I probably thought I would do some sort of communications role… But Syracuse University derailed my plans.
ES: You know, I wondered whether you had emo roots, given that Buffalo is home to one of the greatest hardcore bands of all time, Every Time I Die. Were they in your orbit at all?
CD: That wasn’t part of my particular strand of adolescent angst, but I am of course aware of Every Time I Die.
ES: Would you say they’re hometown heroes? I don’t understand how they function within the city’s wider framework.
CD: That’s a really interesting question. Are they local heroes...? I think that band is… How do I want to phrase this… The strain of Buffalo culture that you encounter on a daily basis is very mainstream and suburban. This isn’t Portland, OR, or someplace where a fringe band would be local heroes. Laughs. I would say The Goo Goo Dolls fill that role for some people. Football players. That sort of thing speaks more to Buffalo’s culture.
ES: What were you listening to at that point in your life? I know you’re a fan of Death Cab for Cutie because I read your newsletter about it.
CD: Yes, I got into Death Cab through The O.C., like everyone at that point. I interviewed The Spill Canvas once. Did you listen to them?
ES: Oh, you definitely went to Christian high school.
CD: I love The Spill Canvas. I loved Brand New. I reviewed their albums and their shows, but I never interviewed them. I loved Something Corporate.
ES: I was just listening to Something Corporate yesterday.
CD: If I’m not mistaken, they’re going on a 20th anniversary tour.
ES: You were kinda leaning into that piano-y emo pop thing, hey?
CD: Yeah, there’s definitely a little bit of that. I added Los Campesinos! album release date to my calendar after I read your interview. I didn’t know they were still producing music.
ES: In your defense, they have been gone seven years. But I’m flattered you read that! I’ve been listening to them since, like, 2008.
CD: That’s almost a 20-year anniversary. Ugh.
ES: I did have some actual questions for you, if you wanna get serious.
CD: Of course, though, I’m happy to just shoot the shit. I was delighted when you said we were going to talk informally.
ES: I’ve been thinking a lot lately, about the future of *this* platform. Your newsletter has existed in previous iterations, you’ve been with legacy media, and now Substack. Are we on the ground floor of the next YouTube or podcasts? Or am I completely delusional???
CD: I would hesitate to say Substack is the new YouTube or podcasts because, by all indicators, online content is trending towards the audio-visual. Which is terrifying for me. If I was interested in being filmed, I would have gotten into broadcast journalism. I have absolutely no desire to do video.
My main theory on this comes from Ezra Klein’s. He was chatting about the downfall of media on Search Engine, and he said something that I thought was really smart. It’s this idea that newspapers and other conventional media have succeeded financially and journalistically because they created a package of fluff that people would pay for, which helped fund the stuff that is more serious and expensive and time-consuming. Substack is just a disaggregation of that, right? For the most part, newsletters are fluff. Some people make a go of different things and start more rigorous media ventures. But could my Substack subscribers pony-up enough money for me to do long-form investigations? Not at this rate, certainly.
For me, Substack exists in the same undifferentiated swamp as everything else now. Consumers have to decide “Do I want to spend my $7 on Paramount+ this month, or do I want to spend it on Caitlin’s Substack?”
ES: I think you’re right. Even in terms of uncovering new voices or new stories. Some people break through, but for the most part, it feels like the people succeeding here — and I mean that in a purely economic way — are the ones who already had an audience, maybe through working for a traditional media brand. Substack is sick if you’re Stephen King because it’s another revenue source… But you can’t afford a lawyer to cover your libel case charging $7 a month.
CD: It’s telling to me that Substack is courting audio and video creators. It’s such a transparent play to get more people into their subscriber ecosystem. To me, that says you’ve already maxed out the people you think will pay for words. They’re hoping to attract video people and try to persuade them to pay for words. That doesn’t feel super promising to me. That said, I’ve built my house on Substack’s foundation, and I’m wishing them all the best.
ES: Every now and then I hear whispers that people with larger subscriber bases have Substack’s ear. Have you had any conversations with them about any of these things? Have they reached out to you?
CD: I wish I had Substack’s ear. No. It’s funny, though, when the platform first launched, I think Hamish McKenzie sent me an email asking if I would move over. And I was like, “Who are you? What is this?” I ignored that email. I should have taken him up on it because he will never answer an email from me now.
ES: Not you leaving Hamish on read!
CD: Substack does have a writer’s team. I was working with a woman on that team before my relaunch. She was lovely. She gave me a lot of advice.
ES: The more I do this, the more I realize that there is a cottage industry around certain Substacks. It can be a surprisingly complex operation with editors and other hired hands. Are you running Links all by yourself or is there a secret team I don’t know about?
CD: Funny you ask, Ethan. I am in the process of creating my team of one and a half people. The other person running Links is my husband, Jason, who has been given a small set of newsletter tasks to do this week. And let me tell you — he will not appreciate me saying this publicly — but he is not good at his job. He's maybe going to get fired.
ES: Oh no! C’mon Jason.
CD: Substack is not his strong suit. But there’s so much that goes into running a newsletter beyond the actual writing and reporting. There’s administrative work. Now that I have payments turned on, I have to deal with Stripe, I have all kinds of international tax paperwork I have to fill out. It’s a lot.
The hope was — and is — that Jason could start handling my social media, which I am absolutely incapable of keeping up with. I like to send emails to the people I feature, letting them know they’ve been included in the email. Jason’s tasked with drafting those emails. It’s early days, but so far he keeps forgetting to do it.
ES: My fiancée is essentially the silent partner in Human Pursuits too… I always tell people that nothing gets published without her stamp of approval. And I often feel guilty about that; about the fact that she’s being so supportive and providing me all this unpaid labour.
CD: Before I relaunched, I did a lot of research into how people structure their businesses. And I had a friend who offered to introduce me to a very big Substacker, who will go nameless. When I emailed this person, I got an automated response that went “Thank you so much for your email. I receive so many messages, I don’t answer them. If this is about ads, email this person. If this is about my book, contact so-and-so…” It was a very telling moment for me. I was like, Okay, so as far as I can tell from your public persona you’re one person who’s killing it. But you’re really a little media empire… It made me feel better about whatever it is I have going on over here.
ES: The ecosystem that exists in traditional media extends to new media as well. Once you hit a certain point, there is still a level of gatekeeping, which is only fair. But I think Substack likes to present it as 1-to-1. Regular guys and gals drinking coffee and sending Notes off into space.
If I wanted to promote a brand, I would have gone into public relations.
CD: Yeah. I'm curious. What are your goals with your newsletter? Is it like creative fulfillment…?
ES: World domination, obviously. No. I dunno. I’m always searching for a clearer purpose but maybe there isn’t one. I like doing this, and thankfully things are growing at a decent enough rate that I feel like I’m not wasting my time. I view it as a free education in publishing.
CD: That's a really good approach. You just do the work that’s interesting to you in the moment.
ES: Yeah. I’ve learned so much about myself, but also how to run what essentially amounts to a small business.
But let me turn the table and ask you the same question: What’s next for Links?
CD: I’m asking myself that question every day.
ES: We’re just two confused people trying to navigate this digital life.
CD: I really can’t emphasize my confusion enough. I left my local news job in October. I got off to a slow start in this new phase because I had a lot of personal complications that meant I wasn’t working for a couple of months. Now, I feel like I’m working all the time. It doesn’t feel good. Jason and I are constantly checking in with each other. Like, Why did I quit my 9 to 5 job just to be working from 6:30 a.m. to 9 p.m. every day for less money and less security?
I feel like the next stage involves rightsizing the effort and the time and figuring out what this type of career looks like to me. The Links relaunch went very, very well and I was very happy with that. But it didn’t go so well that I can afford not to do other work. I replaced a little less than half of my local news salary with the newsletter, and I had a good salary… I’m freelancing, I’ve done some teaching, and some consulting. It just feels like a lot. I need to work out a career that provides some financial stability, but also offers work-life balance and feels creatively fulfilling to me. If this feels like work all the time if it’s just as laborious, then I might as well be back in a local newsroom, you know?
ES: I appreciate you saying that because many people might see Links has over 20,000 subscribers and think “Wow, she made it.” But there are trade-offs!
CD: Totally. 20,000 subscribers is fairly small fries in the grand scheme of things, and the path to that has not been smooth or constant. I’ve been doing this for over ten years. There was a long period, where, for every newsletter I sent, I would see a drop in subscribers afterward. It was the absolute worst feeling in the world; people were seeing my work in their inbox and thinking “I hate this so much I’m going to unsubscribe right now.” There would be months when I would only have like a dozen or two dozen new subscribers. But in the past couple of months, there’s been steep growth. It’s so random that it seems almost accidental. You’re at the whims of the internet and the Substack algorithm. None of it is merit-based. I really want to emphasize that: Substack is not a meritocracy.
ES: Have you been on Substack Notes lately? It’s so crazy.
CD: Substack Notes strikes me as so pathetic and deeply boring because it’s just people on Substack, talking about Substack. Give me a break.
ES: Every time I log in, it feels I’m inundated with posts talking about carrier pigeons and typewriters that get hundreds of likes. Like, What the fuck.
CD: When was the last time I was even on Substack notes? I feel like I need to check-in.
ES: You’ll probably see me re-sharing quotes from my own newsletters. Laughs.
CD: That’s what you have to do, though.
ES: You’re playing the algorithmic lottery.
CD: It’s also a little embarrassing. Hyping your own thing just to get two likes? Kill me. That’s why I tried to outsource social media to Jason. He’s always giving me a hard time and saying I don’t do enough self-promotion. If I wanted to promote a brand, I would have gone into public relations. I’m not like that. I’m just going to do the thing and people will either find it or they won’t.
ES: Okay, that was a lot of shop talk. What did you have for breakfast today? I’ve been very interested in this lately.
CD: I had yogurt and granola. Not exciting. Do ya’ll have ALDI grocery stores in Canada?
ES: No, what is that?
CD: You’re missing out! It's this German grocery store. Almost everything there is a generic brand. They sell these discount, no-name, cold brew coffee infusers. They are life-changing. I had one of those as well.
ES: Canada’s grocery options are much less differentiated than the U.S.
CD: I’m trying to think what grocery stores Canada even has. We listen exclusively to that radio station The Edge, which broadcasts from Toronto. I hear their grocery store ads all the time, but now I can’t think of any.
ES: You listen exclusively to The Edge?!
CD: There are no good independent or alternative music stations in Buffalo. I will say, however, The Edge used to have really good hosts, and in the last year or so, there seems to have been almost 100% turnover. The new hosts don’t do it for me.
ES: My last question then: favourite Canadian alternative rock act of all time?
CD: Metric is one of my favorite bands of all time. We saw them in Toronto in October, and it was great. Though I’d also shout out Broken Social Scene.
Caitlin Dewey is a writer and journalist. She lives in Buffalo.