Escape from Hell World

Reflections on a relationship with a writer who loved and then fell out of love with Substack

Photo by Chris Barbalis on Unsplash.

In the summer of 2018, I met a freelance journalist named Luke O’Neil at an exposed-brick bar in Boston. I was there to convince him to start a newsletter. Luke’s friend Judd Legum, who had recently started Popular Information, thought Luke could do well on Substack because of his distinctive voice, cracked sense of humor, and livewire Twitter presence. Luke wore a fitted baseball cap and smoked cigarettes as if it were 1994. Tattoos crawled over his arms. 

Over cocktails, I gave him my best pitch: 

Stop taking on freelance assignments that you don’t like.

Write what you want to write.

Get paid directly by your readers. 

The timing was fortuitous. “As luck would have it,” he later wrote in the introduction to a book of collected writings from his newsletter, “I happened to be at one of the lowest points of my writing career and my life lol and quickly running out of money.” Since he started on Substack, Luke relieved himself of the burden of using commas.

I had been writing for a lot of fancy publications for years and that was pretty cool because when you say you write for a place people have heard of they think you are smart and good except it wasn’t making me happy it had been making me miserable for a long time to be a part of the content generation cycle and besides that the industry was crumbling around me and still is.

It was a shitty time to be a writer. If you weren’t at the New York Times, Bloomberg, or the Wall Street Journal, your prospects weren’t good. Newsrooms were shrinking, consolidating, or disappearing altogether. The book publishing industry was doing the same and author advances were getting smaller and smaller. Freelance journalists were especially hard hit, competing for assignments in an increasingly crowded market (on account of all the laid-off journalists) for pitiful rates from publications that were sickly or dying. It was common to be ghosted by editors and paid late, or not at all.

Hardly anyone was publishing on Substack at the time. One of the most common questions we heard back then was: “Is anyone going to pay for newsletters?” But Luke, who somehow lives at the intersection of Twitter shitposting and “poetry MFA,” was willing to give it a shot.

A few months later, Luke was earning enough money from Welcome to Hell World (“weekly dispatches from the pit of despair”) that he could afford to start turning down freelance assignments. Within a year, he quit his gig as a columnist for the Boston Globe after the newspaper’s publisher pulled a piece in which he expressed regret for not pissing in Bill Kristol’s salmon. I published a defense of Luke on the Substack blog at the time, pointing out that, all politics aside, a world in which “billionaire owners [can] get out the ban hammer is bad for anybody who values press freedom.” (Kristol, via The Bulwark, now frequently appears on Substack, along with an incredibly wide range of political viewpoints).

Luke would go on to make more from his newsletter than he ever earned from freelancing. We’d email back and forward about his progress. He was impatient about wanting to get to 1,000 paid subscribers, and then to $100,000 a year. He blew by both goals in short order. 

BuzzFeed featured Luke in a story about the surprising success writers were having with paid newsletters, which led him to write a piece encouraging others to follow his lead. Later, when he got a deal from OR Books to turn a selection of his Hell World posts into a book, I provided a blurb. “Luke O’Neil is like no other journalist working today,” I wrote, “fusing original reporting with memoir and frequently-profane observational humor to create what feels like a new type of truth-telling: precise, fucked-up, infuriating, and, somehow, beautiful.” 

I was proud. Substack was working for Luke. He was no longer vulnerable to the volatility of the freelance life, and he got to write what he wanted, in the style he wanted, on a schedule he controlled. When we interviewed job candidates, I would bring up Luke as an example of why Substack was important. If all we ever did was allow a writer like him to make a living on his own terms, we could count Substack as a win. 

Chris and I flew Luke to New York for a night of drinks. He almost couldn’t believe how well it was all going. We had a good night together, but he retained his fierce independence. A few IPAs in, he told us that if Substack ever fucked up, he’d be letting us know. He hoped we wouldn’t ever let “bad people” on the platform. I pressed him on what he meant, and he said if Ben Shapiro ever turned up on Substack we’d be going in the wrong direction.

It wasn’t until October 2019, several months after the BuzzFeed story, that the first major conservative voices arrived on Substack. They came in the form of The Dispatch, a center-right publication started by veteran journalists Steve Hayes and Jonah Goldberg. We were thrilled, but some writers on Substack complained publicly about The Dispatch’s arrival. 

“Well, this is disappointing,” said one commenter on our blog post announcing The Dispatch’s launch. “Sad to see Substack partnering with someone as odious as Jonah Goldberg.” 

As the culture wars started to creep into Substack for the first time, however, Luke stayed quiet.

“You’re fucking up” 

We didn’t really start getting hated by some writers on the left until early 2021.

By that time, hundreds of writers were making their full-time living on Substack, with the top earners making more than a million dollars a year. We had seen journalists, bloggers, academics, and analysts go independent and thrive in ways they didn’t think was possible. We wanted to make that happen for many more people. We had already experimented with paying advances to writers such as Judd Legum, Emily Atkin, and Lindsay Gibbs so that they could afford to pay the bills while they got their Substacks up and running, and the results were encouraging. We wondered if there were more we could do to remove the financial risk for writers.

Eventually, Chris and Jairaj struck upon a formula that could appeal even to writers with big-time jobs. We would offer a substantial minimum guarantee, and in return we’d keep 85 percent of the writer’s subscription revenue for the first year. At the end of that time, they’d revert to the standard agreement, keeping 90 percent of the revenue. 

It was a pretty good formula. We could attract great writers, get them set up with thriving businesses, and sometimes we’d even make money on the deals. Some of the earliest deals were huge successes – including for Matt Taibbi, Matt Yglesias, Roxane Gay, and Anne Helen Petersen – giving us the confidence to invest more into the experimental program, which we would come to call Substack Pro. 

Inevitably, word got out about these Pro deals. We had been holding off from saying anything publicly about Pro while we were still figuring things out. Early on, we decided not to disclose who got deals. We wanted that decision to be the writer’s – it was their business, not ours, to share if they wanted.

Of course, in the absence of public details, interested observers started speculating about which writers got deals. On Twitter, I saw some wildly off-base guesses that were prompting anger among some people who felt that objectionable writers were being paid directly by Substack. I had already been working on a blog post to explain what Substack Pro was and why we were doing it. In an attempt to cut off the speculation, I rushed to finish the post.

A few hours before the post went live, a writer who had seen the Twitter speculation published a piece on their own Substack based on wrong assumptions about who was getting deals. The writer criticized us for financially supporting writers they felt were antagonistic to trans people. By that point, we had done more than 30 deals with writers who covered a range of issues, none of whom could reasonably be construed as anti-trans. It didn’t matter. The post spread rapidly on Twitter, provoking a strong negative reaction against Substack. In a case of unfortunate timing, my Pro explainer piece inadvertently gave the outrage more momentum. 

In the ensuing days, Substack and I faced intense criticism online, particularly on Twitter. In another widely shared piece, a different writer called the Pro deals a scam and said the recipients were effectively secret staff writers for Substack, further fueling the drama. We published a follow-up post to provide more detail about Pro and express support for trans writers, but it didn’t make much difference. The meme was already on the move. 

During this time, I spent many days and hours on phone calls and in emails with writers to apologize for our bungled communication around Pro and the difficult position it had put them in. I reassured them that we were not using Pro to fund abusive content, but I was not always successful. It was a difficult period. One phone call stood out. 

“I always said I was going to tell you if you were fucking up,” Luke said over the phone. “Well, you’re fucking up.” 

We had a strong relationship and had always spoken frankly with each other. I appreciated that he was airing his criticism with me directly and privately. But two things he said on that call have stuck with me. One was that he was “almost embarrassed” that my endorsement was on the cover of his latest book, Lockdown in Hell World, a second volume of his Substack writings. The other was that he thought that Chris, Jairaj, and I were just chasing money, evidenced by us raising funds from venture capitalists and then embarking on the Pro program. 

“You just want to get rich,” he said. “Admit it.”

I didn’t like that. I had not got into Substack to make money. In fact, when Chris first proposed starting a company together in 2017, I resisted the idea. I knew that life as a startup founder would be stressful and an unrelenting grind. I never imagined myself as a businessman. I wanted to be a writer. I was plotting a future for myself as a freelancer, with the hope of writing books and perhaps getting speaking gigs to cover living costs. My wife Steph and I were just about to have our first kid and I wanted to be a good, available father, in control of my own schedule and not too bogged down by the demands of work. I also knew that most startups fail – especially media-focused startups. I had covered many such startups as a reporter for PandoDaily in 2012 and 2013 and saw dreams crushed as Silicon Valley tried and failed to “save the media.” In all cases, it was writers who were hurt the most along the way. 

Steph eventually convinced me that I had to do Substack. It was the perfect encapsulation of my interests and experience, and the chance to work with someone as brilliant as Chris was too good to turn down (Jairaj joined us a few months later). Maybe I wouldn’t be working as a journalist, but I could help others. 

Steph and I didn’t have much money at the time. She had an operations job at a startup with a reasonable salary, and I was well paid during my one year at Tesla ($120,000, by far the most I had ever earned), which was enough to pay rent for a one-bedroom apartment in San Francisco. I had also been paid a good advance for my book ($75,000), which, after many stops and starts, would take me three years to write. After rent, most of our money went to a $450-an-hour lawyer that we ultimately couldn’t afford. I was paying him to help me respond to legal pressure from Elon Musk, who did not want me to write about my experience at Tesla. I burned our balance down to zero. 

To start a company in this position, just as our first child was about to be born, was financially irresponsible. I could do it only because my grandmother, who lived a modest life in New Zealand, had recently died in her 90s and left her entire life savings to her children. My dad passed on $20,000 to me and I used it to pay myself for the first eight months of working on Substack. If Substack worked out, maybe one day we could make good money from it. It would be nice if in our late 30s, and as we were starting a family, Steph and I could get into a position where we could have even a little financial cushion after making rent – but I wasn’t counting on it. 

We didn’t start Substack because we were looking to build a giant company that could one day go public and make us rich. We started Substack because we believed it was important to offer writers and readers a way out of the media systems that were serving them poorly. We wanted to show that there can be something better than the attention economy, the incentives of which were leading to the types of content and behavior that corrode trust and comity; that turn readers into mindless doomscrollers; and that strip writers of their financial dignity. 

Our idea was that we could make it simple for a writer to pursue the work they believe is most important while making money from subscriptions. A small number of writers, including Ben Thompson and Luke Timmerman, had been doing this already, and they spent a lot of their time on non-writing work like wrangling the tech and managing customer support (Timmerman estimated that it took up 40 percent of his time). We guessed that those inconveniences were enough to prevent most writers from even trying the model. Our pitch to writers ended up being: We’ll take care of everything except the hard part. 

Our first customer, Bill Bishop, was a smash hit. Bill had been writing his China newsletter, Sinocism, for five years but, save for a couple donation drives, had never made much money from it. We convinced him to be Substacker number one and launched the new Sinocism in October 2017. He made six figures of revenue on the first day. 

Soon after, Daniel Lavery, who had been one of the founders of cult favorite site The Toast, also got off to a flying start. Danny had been publishing a free newsletter through TinyLetter, owned by MailChimp, but had maxed out the subscriber limit. To continue publishing his free newsletter, he would have to pay to upgrade to MailChimp’s main product, which was built to support ecommerce rather than writers. We asked Danny: “Why don’t you come to Substack, increase your publishing frequency, and introduce the option for readers to buy subscriptions to get everything you write?” It didn’t take long for him to be making the equivalent of a full-time income on Substack. 

These two successes, so different from each other, led us to believe that the Substack model was powerful. Bill was writing about China for an audience of business people. They could easily justify the $168 cost of an annual subscription and charge it to their companies. But Danny was doing something different, writing comedic riffs on Victorian literature and retellings of Bible passages in millennial vernacular, for an audience of librarians and literature lovers who were paying fifty bucks a year out of their own pockets. 

If Substack could work for Bill Bishop and Daniel Lavery, then it could probably work for many more writers. We decided to aim high. If we raised money from investors, we could hire great people and build a support structure to help independent writers do their best work. 

Substack could have remained an indie project. We could have avoided venture capital and aimed for profitability from the outset. If we did that, we could have built a nice business and some writers would make a great living. But any success would likely have made us a target. It would have been trivial for a competitor to come along, replicate our model, and then buy up all the writers, making us vulnerable to acquisition or obsolescence. We didn’t want to risk losing Substack to Facebook or Amazon.

We twice took advantage of historically favorable conditions for startup funding, raising $15 million in a Series A in June 2019 and then $65 million in a Series B in March 2020. The money would help build an incredible team and create a legal support program (Substack Defender), a healthcare program (Substack Health), and fellowships (like Substack Local), among other initiatives to support independent writers. All the while, we stuck to Substack’s fundamental promises: it is free to use; we only make money when the writers make money; and writers retain total ownership of their content, mailing lists, and payments relationships. 

Some analysts have said our approach to writer ownership is a weakness because it makes us vulnerable to our top customers leaving and taking their revenue with them. But we put ourselves in this position by design. For the entirety of the social media era, writers have been treated like content mules and penned into systems that reward them with nothing other than internet points. In such a system, writers and readers have no agency. The platforms have the power. 

With Substack, the dynamic is flipped. The vast majority of revenue captured in the platform goes to the writers. Substack can only succeed if the writers, our customers, are happy. We have to prove that we are providing them more value from the tools and the network than what they pay us in return. And writers have to prove to readers that the work they’re doing is worth paying for. The people have the power. 

“I gotta get out of here man”

From the start, we intended for Substack to be a place where a broad array of views could find a home, including and especially those of writers with outsider perspectives. The model, where readers subscribe directly to writers and content isn’t foisted on people in addictive news feeds, makes it possible to take a strong stance for freedom of the press and freedom of expression.

In the first two years of Substack’s life, the most prominent writers on the platform were lefties, including Judd Legum, Nicole Cliffe, Daniel Lavery, Jamelle Bouie, Tressie McMillan Cottom, Emily Atkin, and Luke. What we lacked were voices from the right.

For a while, we worried that Substack’s left-wing lean would make the platform an unwelcoming place for people with different points of view. We weren’t for any one particular ideology; we were for writers. Our concerns intensified as the culture wars spread during President Trump’s term. People from both the left and right were in no mood to be charitable to each other. The Steve Bannon Way ruled as the MAGA right relentlessly trolled “the libs” and left-wing student groups sought to prevent undesirables from speaking on their campuses. 

Everything got so much worse in 2020, with the arrival of the pandemic, and then the social justice protests, and then the US elections. Life on social media became increasingly fraught. Twitter in particular became a digital war zone and many of us were trapped there in our own addictions, witnesses and contributors to social horrors. The fights on Twitter spilled into traditional media. 

In the space of a few months, Bari Weiss jumped from the New York Times, Andrew Sullivan left New York Magazine, and Glenn Greenwald quit The Intercept, all in strained circumstances after falling out of step with their progressive peers. Weiss, Sullivan, and Greenwald subsequently moved to Substack and massively increased their income and influence. 

Around this time, the tone of some of the news coverage and Twitter chat around Substack took a negative turn. The criticisms of Substack Pro and the increasing political division playing out on Twitter put the PR honeymoon we had enjoyed for three years to an abrupt end. Some writers who once loved Substack started to feel uncomfortable being associated with our brand. Luke O’Neil was probably in this crowd. A group of writers with whom he was seriously at odds started to gain more prominence on the platform.

At some point, a small group of antivax writers started showing up, realizing that while they might not be welcome on Twitter they could at least publish posts through Substack. We don’t have the same content moderation policies as Twitter or Facebook because our system is fundamentally different to those amplification machines. Our decision to not take strong action against the antivax writers opened us up to criticism. 

There are lots of writers on Substack for whom even the words “free speech” provoke an allergic reaction. It has become a culture war issue, with some on the right adopting it as a central cause and some on the left seeing it as a facile excuse for allowing hate speech. When Elon Musk announced that he would try to buy Twitter in an attempt to protect free speech on the platform, the free speech culture war found a new level of intensity, especially on Twitter itself. Our head of communications joined the fray with a “We’re hiring!” tweet that poked fun at Twitter and inadvertently went viral, provoking praise from the free-speechers and rage from their opponents. My inbox filled up with complaints. 

I hadn’t spoken to Luke for many months by the time he emailed a few weeks later to say he was taking his newsletter off Substack. He was going to Ghost, he said, and felt “weirdly emotional” about it. Luke’s post announcing the move was entitled “I gotta get out of here man”:

I cannot emphasize strongly enough how little I want to take part in never mind be the subject of one single more conversation about “free speech” on platforms and cancel culture or whatever...

Writers have left Substack in the past, and it has always been hard. I hate that any writer might feel like Substack isn’t a place for them to publish and build. Everything we do is designed to help them thrive – it’s an imperative baked into our business model. But this departure hurt more than others. 

I remember well meeting Luke for those drinks in Boston. I remember him being in that low point, and I remember getting deeply into his odd and beautiful writing as he started publishing on Substack. I cheered him on as his newsletter income grew and as he kept on surpassing new milestones. I almost burst with gratitude when he wrote the piece encouraging other writers to start newsletters too (“It cannot hurt!”); I quietly fist-pumped when he bought a house. And then, on the other side of the honeymoon, I watched as he became less proud to be on Substack, and then increasingly uncomfortable. The gaps in time between our emails and texts grew larger. When I finally got the “goodbye” email, I had the wind taken out of me. But by that point, there was nothing more I could do. He didn’t like the vibes here. 

I remain deeply sad that Luke isn’t publishing on Substack anymore, but I am happy he had the power to leave. That agency has been a crucial missing piece from the systems that writers have worked within for decades. I know, because I’ve lived that life. 

I had a privileged run as a journalist, getting to work on magazines and news sites, as well as being a freelancer and then an author. As a freelancer, I wasn’t as successful as Luke – my annual income from freelancing topped out at $55,000 – but I lived that hustle, chasing anything that could be a story, emailing countless pitches to editors knowing I wouldn’t get a reply, and then taking on corporate side gigs because there weren’t enough $300 paychecks for 1,200-word stories to add up to a living. As a staff writer for consumer and trade magazines, I saw stories killed or promoted because the subjects were advertisers. While working for news sites, I had to prioritize volume over quality in order to get traffic numbers up. Then, I saw the industry shift as my peers and I started to look to Twitter for validation of our work, and then story ideas and contacts, and, ultimately, for status among our peers and editors. The more that we did the volunteer labor for Twitter, the more we got drawn into its impossible game, the more we mistook it for the world. By that point, we had built up big audiences on the platform, followings that helped determine the jobs we would get and how much we were paid. But we couldn’t take those audiences with us; they belonged to Twitter. And so did we. 

Writers have been belittled and demeaned by bad systems for decades now. The gulf between their cultural value and economic value is tragically large. The work that writers do is important: it shapes how we think, how we cooperate with others, and who we are. It is the foundation of a functioning society. And yet, in recent years writers have continued to be shunted down the economic order, forced to sublimate themselves to fickle gatekeepers and algorithms while living with acute financial anxiety. 

I believe, though, that the game can change. The internet can work in favor of writers. The power of free, global-scale distribution is immense. The ability for almost anyone to start a media business in a matter of minutes is revolutionary. That people with even the most esoteric interests can gather in online communities no matter where they are is society-changing. It’s just that the way these forces have been organized in the internet’s first thirty years has given writers a raw deal. We don’t have to live this way. We have to recognize that Hell World is a human construct. 

If writers are given power – true ownership, a direct connection with their readers, and a simple way to make money from the people who value their work – amazing things can happen. You might be a college professor who starts writing daily letters about US politics and suddenly find yourself as one of the most influential and successful political writers in the country. You might be a 20-year-old essayist who has found an income and an outlet away from TikTok, where nothing matters more than image. Maybe you’re a former product manager with no real writing background who starts a newsletter that grows to more than 130,000 subscribers, becoming the top-earning business publication on Substack. 

Or maybe you’re Luke O’Neil, making a good living by saying what you want to say, by writing about what you care about, and earning the freedom to work completely on your own terms.

Luke’s particular case might suck for Substack, but it is good for the world. And I’m proud that he started with us.