How Medium finally pivoted its way to profitability
CEO Tony Stubblebine reined in spending and figured out how to actually reward high quality writing.
For Jason McBride, the nervous breakdown came very suddenly, but it was also years in the making.
If asked to tell the breakdown’s origin story, he’d trace it back to his sophomore year in high school, which was when he decided to become a lawyer. By then, he’d grown obsessed with politics, government, and political history, to the point where he found himself reading texts like the Federalist Papers during his free time. “I was a weird kid,” he told me recently.
Things started to feel awry soon after McBride enrolled in law school. “During the first semester, I'm like, oh, this sucks,” he said. “This is horrible. I don't think I really want to be here.” His classmates were hypercompetitive, and the curriculum discouraged the kind of intellectual curiosity that drew him to the law in the first place. “That really wasn't the point of law school. The point was to teach you to think in a very structured way, to get you into this groove. It’s all just about getting you ready so you can pass your bar exam.” Before the end of his first year, he realized that what he should have done was pursue a PhD in political science with the goal of becoming a college professor, but by that point the sunk cost fallacy had firmly set in. “I was like, yeah, law school's expensive. I've already got a semester in. The only way out is through, so I guess I'll just plow through.”
By the time McBride passed the bar exam, he knew he didn’t want to work for anyone. Two clerkships during his second year had disabused him of the idea of a career in government, and he didn’t want to spend 80 hours a week doing grunt work at a law firm. He knew several solo practice attorneys and decided to rent out office space in the same building as another lawyer he was friendly with. For those first few years, he mostly took on overflow work from other firms — a grab bag of cases across civil and criminal law. He enjoyed helping clients, but he didn’t like interacting with judges and other attorneys, so he’d dread appearing in court.
About four years into his career, McBride began to zero in on a combination of immigration law and IRS tax defense, two areas that he found somewhat interesting and weren’t well covered by other firms in the area. He was still young, but he’d already come up with an idea for an escape: “I thought that if I can bring in other attorneys, teach them the stuff I knew, maybe they can just buy me out, or I can have a very limited managing role.” Though it sounds ludicrous in hindsight, he thought building out a law firm would provide him with a shortcut for exiting the law.
McBride’s mistake soon became apparent, and he only compounded it with more mistakes moving forward. He tried to hire lawyers with similar skillsets to his, but they often dropped the ball, leaving him to clean up after their messes. He was reinvesting everything he made back into the firm, and each new hire put it in an even more precarious position, to the point where he always felt like he was on the brink of financial ruin. “I ended up finally with a really good office manager, and she helped out quite a bit, but I'd already dug too deep of a hole with all the staff that I had hired without any kind of strategic growth plan.” At some point he started seeing a therapist who diagnosed him with two anxiety disorders that stemmed from a combination of depression and ADHD. That certainly explained why he was throwing up every day before work.
The breaking point came in 2012 when McBride found out that an attorney he’d hired was running his own law practice out of an office McBride had rented for him. After all the risk and stress he’d endured over the years, finding out that he was paying a guy a salary to compete with him was a bridge too far. To make matters worse, after McBride fired the attorney, he discovered the guy had been taking on clients who were really bad fits for the firm, so McBride had to pay out tens of thousands of dollars to refund their money. That’s when he snapped. “I was really freaked out,” he recalled. “I was just a basket case.” It wasn’t long after that when he closed his law practice for good.
That didn’t exactly stop the spiraling. While McBride was relieved to have his legal career behind him, he had no job lined up to support his family and no other work experience to fall back on — or at least so he thought. While scrolling through Reddit one day, he came across a post from a guy who detailed how he’d replaced the wages he made as a barista by taking on freelance copywriting gigs. McBride had consumed plenty of how-to-make-money-online content, but this felt like something different. “This wasn’t somebody promising the moon,” he said. “He wasn’t promising the glory of making millions of dollars from a beach in Thailand or whatever.” The guy had simply set a recognizable goal — to replace his barista wages — and then chipped away at that goal until he achieved it.
McBride had no experience with freelance copywriting, but he was confident that his legal career had afforded him enough writing practice to handle most projects. He started by taking on bottom-of-the-barrel gigs, some only paying pennies per word, before seeing success on freelancer platforms like Upwork and Fiverr. Through online research, he learned how to craft cold pitches that he’d send out to small-to-medium sized businesses via their contact forms, and several came on as regular clients. Two months after he started, he had his first month where he billed over $1,000. “And I remember thinking, well, that's a big deal. Obviously not quite a livable income, but within six months, I was making a very comfortable full-time living.”
Over the next several years, McBride carved out a niche for himself writing web copy for law firms. The work wasn’t glamorous, but he also wasn’t puking every morning. He got to spend time with his kids. He went on weekly hikes. He made it a goal to visit the ocean once a month and stuck to it.
Then came the 2016 presidential election, and the stress of Donald Trump’s win nudged McBride into finding a creative outlet to channel his energy. He started writing poetry, at first with no intention of publishing it anywhere, but then in 2018 he created a profile on the publishing platform Medium and began posting to it. “I kind of tried everything I could,” he recalled. “I would write about content marketing and freelancing, but I also wrote some personal essays as well.” Part of his motivation was to find more clients for his freelance business, but he was also attracted to Medium’s partnership program, which allows writers to place content behind a paywall and generate revenue based on the amount of engagement it receives. “I wanted an additional stream of income, so I almost always put everything behind the paywall.” He liked the elegance of a subscription business model that eschewed internet advertising.
Pretty quickly, though, McBride realized Medium wasn’t producing a great experience for either writers or readers. “The algorithm was kind of unpredictable, and I felt like it really needed more humanity to it,” he explained. The payouts were partially determined by the amount of engagement an article received, and several writers had figured out how to game the system by pumping out dozens of articles a week and then reciprocally sharing each other’s stuff. This meant the homepage was cluttered with clickbaity headlines for articles that were dashed off in less than an hour. An essay he wrote about a bad encounter he had with the police as a kid went quasi viral and eventually earned over $1,000, but otherwise his writing didn’t really take off, and he wasn’t particularly proud to have it nestled next to the “bro-tastic,” self-help clickbait that thrived on Medium.
In late 2019, McBride launched a Substack newsletter and stopped publishing to Medium entirely. During the pandemic, he used his free time to teach himself how to draw, and from there he started combining his poetry writing with illustrations. Over the next few years, he self-published several illustrated poetry books with names like Pirate Haiku and Horror Haiku and produced a series of zines called Surreal Haiku.
But while Substack provided a clean publishing experience, he struggled to grow an audience. McBride had never been good at playing the social media game or promoting his personal brand, hence why he had once been so hopeful that the Medium algorithm could surface his writing to a wider readership. Though he no longer posted to the platform, he’d continued shelling out the five bucks a month to remain a Medium member, and in early 2024 he started to notice a change in quality for the articles being recommended to him. Gone were the clickbaity headlines and growth hack content, and in their place he was seeing more essays that had obviously required actual research and effort.
As an experiment, McBride cross-posted one of his essays to Medium, and right away it received a “Boost,” which is when a human editor who works for the company officially endorses an article, thereby enhancing both its reach and monetization. “I thought, oh, this is interesting,” he said. “This is the piece that had been missing before.” Because humans were making the recommendations, the algorithm had become much harder to game. What’s more, a Boost increases the amount a writer earns for each article view, so it further incentivizes high quality work.
So in October 2024, McBride made a commitment to posting at least one article to Medium every week. Much of the work he publishes there combines his illustrated poetry with personal essays. For instance, in a recent piece titled “Finding Pockets of Joy in an Angry World,” he discussed growing up as an overly sensitive kid and how he copes with that sensitivity as an adult. “You must train your brain to see wonder,” he wrote. “Once you choose to look for wonder, you will see it everywhere. Even the most mundane day holds tiny pockets of joy.” The piece generated 1,400 “claps” — Medium’s version of a like — and over 40 comments.
McBride told me he hasn’t hit $1,000 in monthly payments from Medium yet, but he’s quickly approaching that number. All together, he’s now generating almost as much revenue through what he calls his “creative” endeavors as he does from his freelance copywriting. More important, however, is what this creative writing has done for his depression and anxiety. “My mental health is a million times better.”
I asked McBride why his experience with Medium now — as both a reader and writer — is so different from when he started posting there in 2018. “It feels cleaner to me,” he said. “The algorithm is serving me better. I enjoy reading it more now than I did back then, by a lot. It rewards quality in a way that it didn't before.”
McBride’s improved experience wasn’t an anomaly. In July 2022, Medium’s co-founder and longtime CEO Ev Williams announced he was taking a step back from the company and passing the reins to Tony Stubblebine, a longtime friend and advisor to Williams and also a prolific Medium writer himself. Over the next few years, Stubblebine implemented a number of changes to both the company and platform — changes that included paring down staff, reining in server costs, and tweaking the way the Medium partnership program works. In early 2024, he surprised the world by announcing Medium had reached 1 million paid subscribers, and a few months later he shocked us all again by revealing it had reached profitability.
By that point, many of us in the media and tech world had written Medium off as a failed experiment, a rare miss from a founder who had helped build Blogger and Twitter, two of the most influential communication platforms of the 21st century. So why had Stubblebine managed to find the product-market fit that had eluded Williams for 10 years? And how did he get writers to trust Medium again?
That’s what I sought to find out.
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