“A surprising gift”: How A.J. Daulerio Turned the Worst Time in His Life Into Something Beautiful

There was a moment when A.J. Daulerio was arguably the most notorious blogger in America. As a defendant in a 2016 trial mounted by Terry “Hulk Hogan” Bollea against the website Gawker for running a sex tape without the wrestler’s permission, Daulerio got the kind of press a certain type of thirsty blogger could only dream of. His name and photo were regularly in the news and he was the subject of profiles in G.Q. and Esquire, featuring photos of Daulerio in symbolic locations like a public bathroom stall or next to a trash pile.

The trial was an awful time in Daulerio’s life. Raw, broke, unemployed, sporadically in the spotlight and not in a good way, he had plenty of horrible things to google about himself in his spare time as he waited out the trial.  

To make matters more unpleasant, Daulerio had also recently completed rehab for drug and alcohol addiction. “I just decided to stop fucking around and lock in to the program,” he wrote in a 2022 essay. “I’d spent too much time preoccupied with all the legal drama in my life, very much convinced it was impossible to be 100% sober and potentially owe millions of dollars to a professional wrestler at the same time.”

It could be the type of nadir to make many people quit — writing, publishing, life in the public eye. But instead, Daulerio has since reinvented himself as a newsletter writer and producer. To me, he seems like a much more sincere, nurturing person online, no longer just a cynical, nihilistic prankster. 

His newsletter, The Small Bow, is an extension of those experiences and the insights Daulerio unpacked in his post-Gawker, post-trial, post-substances life. It launched in 2018, and now, about 7,000 subscribers receive Daulerio’s twice-weekly interviews and essays on addiction, recovery, sobriety, mental health, ego, and modern life, plus check-ins where readers anonymously share how they’ve been doing mentally or in their recovery. The newsletter is supported by both one-off donors and members. (Membership costs $5 a month or $45 per year, and members get a bonus email every Sunday.) 

Daulerio, separate from the notoriety of his time at Gawker, has been a working journalist and editor since the late ‘90’s. Newsletter readers may come for stories about Daulerio’s partying, the trial, or his emotional reckoning with his ailing father, but they stay for the writing, the vulnerable yet wry voice that can only come from decades of writing professionally and honing a good instinct for what people respond to online. 

The Small Bow has featured interviews with and guest posts by some high-profile people discussing addiction and humility, like Heather Havrilesky, Jayson Blair, Jia Tolentino and Kristen Johnston. But as a space for spare, elegant, witty essays and illustrations, The Small Bow can still feel like something honest from an earlier age of the internet, which Daulerio considers a point of pride. One of his favorite compliments he’s gotten on the project has been that “The Small Bow is quiet in a way the internet isn’t that quiet anymore.” 

The Small Bow goes beyond newsletters. Five times a week, members of The Small Bow community come together for recovery meetings hosted on Zoom, very loosely based on the Alcoholics Anonymous format. There aren’t formal leaders, and meetings aren’t restricted to paid subscribers or people with a specific addiction. It’s just something Daulerio created to try to help others.

I have known Daulerio since 2002 when we were both writers plying our trade as indie bloggers (this was a noteworthy trend once upon a time!). Pre-Gawker, he was a co-founder of  the irreverent yet insightful site The Black Table, which I contributed to. Later on, Daulerio occasionally tapped me to write an occasional piece for Deadspin. Post-Gawker, our careers intersected again when he and I both found ourselves writing newsletters about life while also raising young families in a pandemic world — a far cry from our freewheeling, experimental twenties. 

I reached to Daulerio to learn about all of it: How the transition to quiet newsletters has been after fast-paced high-profile blog life, what’s working with The Small Bow, his goals, how he walks the line between being creative online and having peace of mind, and how after surviving both the blog bubble and bankruptcy, he’s making money currently from writing — this time, via a newsletter.

How did The Small Bow start?

It was 2018. Civil had funded us and other sites. I was building a site and was going to have contributors that I paid for. We got a pretty healthy grant, but none of the crypto funding stuff worked out.

I figured out very early on that the site wasn’t going to work and that the newsletter needed more consistency. Once I read Luke O’Neil’s Welcome to Hell World, I was like, “Man, this guy’s doing shit that I didn’t think you were able to do with a newsletter.” I liked the writing that he was doing. I was like, “Oh, maybe I can do that.” But it doesn’t have to be fully about me. I can incorporate Edith [Zimmerman, my illustrator]. 

She and I had never really worked together before. We were coming up in the same graduating class of bloggers. [Zimmerman founded the website The Hairpin.] It’s a very unique working relationship. I think of an idea that I want her to draw, and I like whatever comes out from her. That sets the tone for how I’m gonna write. It’s just a very collaborative process that I’m so grateful for because I never had a working relationship like that, frankly.

She was there from day one. Her role has expanded a little bit. She’s been my consistently paid employee. I would say that 40% of the income that we have goes towards her. Once we started doing the merchandise stuff [which brings in an extra $150-$400 per month], we split that as well. 

I’m not able to support our family on The Small Bow by any stretch of the imagination. But it is income. It feels like something that’s bigger than me; there’s an audience that loves it in ways that I could have never planned for. 

In 2019 I was on Mailchimp initially — Civil was paying for that. I was gonna switch over to Substack, so there is a Small Bow Substack that exists. But I got hooked into Squarespace. I liked the way Claire and Erica’s site looked, and I liked how their newsletter and their podcasts were all in one place. That’s what I wanted. I wanted to combine both those things. Squarespace gave me that capability. The problem is that Squarespace is great for Etsy shops and little boutique ebusinesses. I’ve had a lot of problems losing subscribers. I need to address it. I don’t know when. But I don’t want to go through the process of losing paid subscribers to transfer over to a [new] thing.

I’d like to have a site where every day, I post something on the site, and people go to the site. I built the site as a way to promote the newsletter. I want to have a website that also has a newsletter, as opposed to a newsletter that has a website.

What is your process for putting an issue of The Small Bow out? 

I make an old school editorial calendar, just on an $8 one from Amazon. Once The Small Bow started to become a thing, which was about three years ago, I wanted to give myself a schedule. 

The first of the month is when we do reader things where they send in check-ins [where readers send in anonymous updates on their sobriety or mental health]. I try to do the Q&A. Then I try to look on the calendar to see if there’s any sort of anniversary that I can speak about and write an essay about it in some capacity. I have an idea book that I try to be pretty vigilant about, too, because you do run out of stuff when you’re talking about yourself. 

There used to be four essays I was willing to publish online, and I wanted to save the rest for when the personal history issue of the New Yorker or the big book comes along. I was just holding the good stuff. Then I was just like, “Okay, I’m gonna empty the chamber here and see what comes up next.” Stuff did come up. I just have to continue to believe that when I think I’m out of ideas, something will come.

When you began writing about sobriety and mental health after the Gawker trial, how did you evaluate the emotional dangers of putting yourself back out there?

I was so paranoid that people would think it’s a redemption arc that I was trying to force on people. A lot of that was in my head, just thinking that I was constantly going to be associated with Gawker and the Gawker trial. For a time period of time, that may have been true, but eventually, I had people that came to The Small Bow who had no clue about that stuff.

I had a really good conversation with [journalist] Gabriel Schneider. He texted me because there’s the Hogan special coming out. Then there’s the Ben Smith book [“Traffic”], right? He’s like, “How are you feeling about this stuff?” I haven’t read into it. I haven’t looked at it. I haven’t worried about it. Because I know if I do, I will find something that will bother me. I know enough now not to do that. I think it’s just I’m past the Hogan fella in my recovery. 

I wanted to get to a point where I wasn’t bitter about it. I created a platform that helped me do that. I was finding these little resentments that I had that I can try to just work through. I was just really working through that in a way that I probably couldn’t have been able to do at therapy. That’s been quite a surprising gift out of this whole entire thing.

As someone who’s known you for a long time, it’s nice to see the success that comes from your talent and hard work. It’s not about the flash of Gawker, or the controversy or anything like that.

That’s wonderful to hear. Because I think that I’m just getting to the point where I’m starting to believe that a little bit. There was this article in the New York Times talking about Elizabeth Holmes. She had this quote where she was talking about all the movies being made about her. She said, “It’s not about me, it’s this character I created, and they’re doing a character of the character that I created.” I can see that similarity and judgment, what that feels like. I just have to remember that I don’t need to go back. I don’t need to revisit history, I don’t need to rewrite it. There’s probably stuff I can go back to if I wanted to investigate and see, “Oh, I got fucked over.” That probably is there.

[The trial] was a very hard 18 months of my life. All I remember is that I would wake up, I would smoke a lot of cigarettes, and I would wait for a call from a lawyer. I would just read some awful post about myself, and then bitch about it for the rest of the day, and then wait for whatever would come tomorrow to see if I can move on from my life. It felt like I wasn’t able to have a life unless this thing was officially over.

But that wasn’t true. I just didn’t know that at the time.

As someone who is making your living online and expressing yourself online, how do you still feel good about your day, your life, the world and be online at the same time?

Yeah, I’d say it’s weird, because I think one of the best compliments I ever got about The Small Bow was from someone who was working at Kickstarter. The person there said, “The Small Bow is quiet in a way the internet isn’t that quiet anymore.”

Admittedly, when I’m feeling bad about myself, I put my last name in Twitter and see if there’s anything in there. Nine times out of 10, nobody gives a shit. But there is stuff that I’m sure I can dig into where I can see the bad parts of the internet. I did a really good job ignoring the Trump presidency. That’s how I see the bad internet. I can ignore it. I just have to work at it. 

We had a really great Small Bow meeting today. That was built independently of me. I don’t go as much as I used to, but the people who do are on different ends of the spectrum in terms of just substance misuse or anything along those lines. People just go there and cry in front of strangers. 

I was like, “Man, good for the people in The Small Bow readership.” It’s pretty spectacular. I’m like, “Well, this is a good part of the internet that I had a little something to do with.” It’s putting something positive back into the world. I stumbled upon it; I didn’t plan it.

Tell me how the meetings got started.

When the pandemic was going on, there were a lot of Zoom meetings happening. I knew of a couple other places that were having site-specific meetings. So I figured I’d try it out. I was the host for a little bit of time. There were like 12 to 20 people that would attend all types of people. A weird dynamic, but I was like, “This a beautiful space.” 

It’s grown along with people’s schedules because when people really went back to work, Wednesday afternoons were not as convenient as in 2020 for people. I’ve tried to provide some oversight, but I’ve let it grow just independently. That’s just how it was taught in 12-Step. There is no formal leadership — it’s basically letting the room dictate to us what direction [we go].

Meetings and the newsletter are pretty independent of each other at this point. That’s why I stopped going for a little while because it felt like marketing. I didn’t want it to feel like that for me or for anyone else. I don’t like it when people reference the newsletter because it doesn’t help my recovery. I’m there to basically just say some things I can’t say anyplace else. So I stopped going for most of last year, and I started slowly coming back into it. 

What’s your marketing strategy when it comes to a newsletter so personal, vulnerable and as you say, quiet?

You probably know this — there’s stuff that we’ve done in our careers, where it’s basically just “Oh, this is just like a project for me.” But this turned into something bigger. This is a community. There’s an opportunity to step on the gas pedal here. But at what cost? I don’t want this to be my full-time job. Or maybe I do; I don’t know yet. 

I would love to market it more. I don’t know how to do that. Every time I try to get consistent with Instagram, my one social media channel, it always makes me feel bad. That feels like more work than I am willing to do for it. It just feels very hollow. 

You bought a billboard to promote The Small Bow. How many readers did that get you?

One. That one reader cost $10,000. I happened to ask her, “So where did you hear about us?” and she said,” I saw the billboard; I was driving through Venice.” I was like, “Yes, it’s working.” Then I remember three months later, when she unsubscribed, it was just, “Oh.”

Tell me about a newsletter where your readers responded in a way you didn’t expect. 

The one I was really proud of, and I thought, “This is just like the best thing I’ve ever written on The Small Bow” that just petered out was where I was writing about my father’s celebration of life. I wrote a little longer than I usually did. I wrote every single thing that I thought I needed to do. It was, “Alright, I emptied the gas tank there,” and it all felt really good. 

Then I published it. I always get this excitement on Tuesday nights [before publishing]. I was ready for the dopamine hit, to just feel all the love. It didn’t happen. I was like, “Man, I was on a pretty good run there, talking about my dad.” I thought that I’d done a nice coda to that thing. 

It didn’t work out that way. There were a lot of unsubscribes. Not a lot of donations. 

I think it had more to do with the length than anything else. What I try to do is not go over 2,000 words. I know that we’re competing with ten other things in people’s inboxes. That’s why I try to have it on the same day. Tuesday is my main issue. 

Look, I’m not going to win every single week. I’m not going to be the best thing that people read all the time. I have to be used to the fact it’s very deflating when that happens. That feels like back at Gawker and Deadspin, and we’d publish this beautiful feature by our writer that I adored. I’d watch it get just over 4,000 page views, and watch some dumb guy get hit in the nuts with a football for like a million. That’s the gig.

Do you know how many free readers you have versus how many paid?

No, I don’t. I can estimate, but our income is not just membership. I also have the equivalent of a tip jar. I feel like the memberships are finally starting to outpace that donation box a little bit. 

I had this hunch early on that when I’m writing about stuff that’s very personal to me, people will pay for that. I read Clancy Martin’s piece in Harper’s, when he did a thing about AA. I’d never seen anything like it before. I wanted to buy everyone a Harper’s subscription based solely off of that one essay because I was just saying, “Oh, man, this is the guy that I need to hear all the time.” I want to reward Harper’s for publishing it. So I was like, “I’ll have a donation box where people who feel that way can just throw it [money] there. When they get hit with something, that’ll work out for me.” It does. When I write something that new people walk into, it gives me 1,000 bucks a month. Like consistently, anyone who’s had a parent that went through dementia, 100 bucks. Anyone who’s had a death of a parent, 100 bucks.

What’s your process for copy editing before it goes out?

I did have a copy editor at one point, but she turned out to be more of a burden than anything else. So I went to Grammarly, and I just run it through there, although it doesn’t catch everything. It helps get rid of the bigger typos, for sure.

What are your goals for the short term when it comes to increasing revenue or readership?

I feel the subscriber thing isn’t as important. The ones that I don’t have aren’t as important as the ones I do have. I feel like I can do better at conversion. So that’s what I’m trying to figure out. I can make 80 bucks a person between merch and the membership or donations from half my readership. That’s a pretty good thing. I just have to figure out exactly what the formula is to get people to contribute because I think a lot of people do; they just don’t read that far. So I try to put a lot of the other stuff up higher. Sometimes it works. There are so many different factors as to why people either pay or unsubscribe or subscribe. I don’t feel like going through exactly what the algorithm is that makes that work. That’s a waste of time. I’m just trying different things. 

What is your favorite response to a newsletter that makes you feel like you’re doing what you set out to do?

One reader told me: “I’m not an addict. I don’t have any sort of other mental health things. I’m just here because I think this is beautiful.” I can’t ask for anything more than that.

Do you have guest contributors?

I do. I try to pay them what I can. I try to go to writers who are professional and don’t need heavy editing, because I do not want to do that at all. Most of the time, I tee up exactly what I want from the writer that I want. I’m just basically like, “We’re gonna publish an email, and we’re gonna tighten it up a few spots.” Initially, I would overpay people as much as possible. I would pay them before the thing came out just because I’ve been on the other side of chasing money from freelance places. That’s no fun. I would totally pay like three dollars a word. I can’t do that now, but I can pay people on time. I think the last person I paid, I was like, “I’ll pay you $300 this month. I can get on like another $150 down the road.”

You have three small kids. When do you work on The Small Bow?

Usually, I have a Friday, Saturday, Sunday, Monday schedule, with Monday being my biggest writing day. Monday is my big day where I will spend 12 to 15 hours on the newsletter for Tuesday. I usually do either a draft in my head or a physical one on Sunday, depending on the length of it. A good barometer of when things hit, because you usually open it early, is that if you like something, you’ll be one of the first people that emails me. 

Shit, I feel bad. That means now that if I don’t respond, it’s implied that I thought it was a bad issue.

No, please don’t. It’s just the things that I look for. It’s like, god, that was so exciting — I can remember back to Black Table stuff when we used to put something out that we’re really excited about. It’s a good feeling: “Oh, this did exactly what we hoped it would do and found some people in a way that we hoped it would find people.” That’s really cool.

Correction: This story originally misspelled the name of Luke O’Neil, the writer of the Welcome to Hell World newsletter. It was updated on July 13, 2023, at 11:15 a.m. We sincerely regret the error.