Inside Medium’s decade-long journey to find its own identity

When Medium launched in 2011, it did so with a promise to make “sharing information virtually effortless.” As its founder, former Twitter CEO Ev Williams, would quickly discover, it was not effortless. And for 13 years, the blogging platform has struggled to find its way.



And yet it could be said that our brave new world was created in its image. The creator economy is an estimated $250 billion industry . Every journalist has some kind of newsletter now. And we’re finally at a moment when users are once again seeking out human curation . Somehow, seemingly against all odds, Medium might be perfectly suited to this moment. 



But first it will have to navigate what is quite possibly the biggest upheaval in the basic foundation of the internet since the invention of the smartphone.



A tidal wave of AI tools has hit the internet in the past few years, each aimed to replace the humans and human-powered algorithms we’ve relied on for more than a decade. Whether it’s chatbots like ChatGPT or Gemini summarizing what we used to use search engines for, or machine-learning-based feeds like TikTok bombarding us with video content, a new layer of automation is forming between us and the internet. 



And Medium’s new CEO, Tony Stubblebine, who was actually running a Medium partner publication up until he took over the CEO role from Williams in 2022, believes he’s figured out how to compete: by not leaning into AI at all. And, more importantly, by taking things a lot more slowly than Medium has in the past.



“We turned ourselves around and we’re knocking on the door of profitability,” he tells me with a slightly weary optimism. “We’re not, like, rich. . . . We used to be rich; we could do whatever we wanted.”



Under Stubblebine’s direction, Medium, a site known for its many pivots, is finally being strategic about what it wants and where it’s headed. Last year, it launched a Mastodon server for premium users, and in March it demonetized AI-generated content on its platform. It is solidly on the side of team human and is finally starting to see that pay off. 







When Williams created Medium, he hoped to solve what he saw as the problem with his old company: Back then, Twitter users were limited to a 140-character count per tweet (it’s since jumped to 280). More space, Williams reasoned, would allow for more nuanced thoughts.



Arguably, it’s this close relationship with Twitter that stopped Medium from ever developing its own identity. It has, as a platform, evolved aggressively over the past decade due to the cutthroat demands of the ever-changing social web, frantically hopping from one content strategy to another. It launched paywalls, rolled out (and subsequently scrapped) professionally staffed editorial verticals, introduced a user-approval metric not unlike Reddit’s upvotes (called “claps”), and, most recently, waded into the increasingly crowded world of paid subscriptions.



It had a brief—and slightly problematic —resurgence at the beginning of the COVID-19 pandemic in 2020, after armchair experts and amateur epidemiologists figured out that they could use Medium’s crisp content management system, or CMS, to lend their health-centric thoughts the veneer of authority. But it was quickly overtaken by Substack as the de facto home for independent writers online. 



As Platformer correctly concluded back in 2022 , “Medium had no obvious advantage. With its owned and operated publications gone, it became a general-interest web magazine staffed by freelancers and dependent on Google.”



Then, in April 2022, Elon Musk began his monthslong march toward buying Twitter. And, fittingly enough, three months later Williams stepped down as CEO of Medium. Suddenly, for the first time, Medium was not being run by a Twitter founder—and neither was Twitter.



Replacing Williams was Tony Stubblebine, who may have seemed a little random to anyone scanning the headlines at the time. At that point he was running Coach.me , a personal life coaching platform, and heading up Better Humans, a Medium partner publication dedicated to personal development. But his roots in Twitter and, thus, in Medium, go all the way to, well, before the beginning. In the mid-2000s, he was the director of engineering at Odeo, the podcasting startup that would become the launching ground for Twitter. 



Stubblebine says he used to brag that he was the sixth user of Twitter. “And I used to think that was a cool thing. I don’t think that anymore,” he says.



The direction that Twitter (since rebranded to X) and Medium have gone over the past two years could not be more different. X is all in on automation, rolling out a nonchronological TikTok-like For You tab, leaning hard into video, and even claiming that it’s built a generative AI product that might rival OpenAI’s ChatGPT. Medium, meanwhile, has only become more human.



According to Stubblebine, Medium currently uses two stages of human curation, which it calls the “boosts.” Almost half the content on the site goes through it. The first stage is a network of users who have been selected because they have specific expertise in a certain subject. They nominate interesting content that then goes to the second stage, which is an internal curator working at Medium. 



Stubblebine doesn’t mince words about the influx of AI content that’s hitting the site right now: “It’s probably doubled or quadrupled the level of work.” But he says that dual-staged curation does stop a lot of garbage from getting through.



“Our view on spam is essentially that there’s a cost benefit that every spammer is making,” he says. “You can’t ever perfectly stop a motivated spammer, but you can push the cost up high enough that the benefit drops.”



The implosion of Twitter didn’t just send Medium on its own walkabout for a new identity; as Stubblebine sees it, it fragmented the whole internet. “Twitter . . . fragmented and a lot of Twitter communities moved to Discord, right? And the fediverse is this too” (more on that in a minute).



Twitter was never a particularly popular or even profitable website, but it functioned as the tip of the iceberg that is the rest of the social web. As that dynamic has faded post-Musk, it’s fragmented online communities, which are also being squeezed by AI at both ends. Chatbots like ChatGPT and Gemini want to absorb the content online communities produce and also allow users to generate near-infinite amounts of low-effort content to flood those communities.



Or as Stubblebine puts it, “walled gardens that are trying to keep the zombies out. And the only thing that I’ve seen to be effective is human curation.”



Medium has not just demonetized AI content, though. Stubblebine says that OpenAI actually offered to license Medium content—for a million dollars a year. “It’d be like a penny per piece or something,” he says.



Which puts Medium in stark contrast to the other user-generated content platforms that did take a deal. Reddit signed a licensing deal with Google earlier this year. And Automattic, the parent company of both WordPress and Tumblr, is selling user data to OpenAI and Midjourney. It seems like Reddit’s deal with Google was better than what OpenAI was offering Medium, for what it’s worth. The social network has already made more than $200 million.



“I just feel like we’re giving up,” Stubblebine says. “’Where should I go on vacation this summer?’ Right? It’s a question. You could ask ChatGPT. And I’m just like, ‘Is the bar for how you want to live your life so low?’”



So far, Stubblebine says Medium hasn’t been affected by Google’s AI summary search or new March core update, which is devastating other publishers—its search referrals are actually up right now—but that doesn’t mean the company isn’t beginning to invest in other networks. Which is why last year Medium launched a Mastodon server (officially called an “instance”).



To understand why this is a big deal, first you need to wrap your head around a protocol called ActivityPub. The simplest way to think about it is if you took everything that social media encompasses—your feed, your replies, likes, shares—and bundled it all together, running it like your email or the RSS feeds that power your favorite podcast. You can make your own apps that look and feel whichever way you want and there isn’t a company like X getting between you and the other users you follow. The nickname for this decentralized network is the “fediverse,” and it’s small but growing. 



Meta’s Threads integrated with the fediverse back in March. And platforms like Flipboard and Ghost are beginning to experiment with totally integrating their apps with ActivityPub. It’s exciting because if it actually catches on, it would mean an entirely new way of using the internet—one that couldn’t be jammed with AI products by massive tech conglomerates. At least, in theory. 



Medium did not fully integrate with ActivityPub, like Flipboard or Ghost. But it did find a nifty way to support it. “When Twitter really started to implode, you know, a year and a half ago, we wanted to do something with the fediverse,” Stubblebine says. “It wasn’t going to be technology because I don’t have an extra engineering team to put on this.” 



Starting last year, Medium added a perk for premium users. Now you can get a username on Medium’s Mastodon instance. Basically, you can use Mastodon, the most popular fediverse platform, via your Medium account. “I thought, Oh, we could at least give clout to it ,” Stubblebine says.



It’s hard not to want to root for Medium. The assumption for more than a decade has been that the way the internet has to work will be determined by what makes the most money for a handful of companies. They wanted us to post content, then they wanted us to share content, then they wanted us to watch it endlessly, and now they want us to use their AI, which will create a bubble we’ll live in forever. 



Medium is one of the last sites left that’s been in the game long enough to remember that none of this—the internet—works without people at the center of it. “The goal is to have authenticity so that we can have real human connection again,” Stubblebine says.



At the very least, Medium is doing much better than X these days.