Under The Hood
On Tony Stubblebine's Medium turnaround, and the difficulty of running a media business in 2025
I like getting under the hood and seeing what makes the engine of a company run.
That partly explains my recent shift to writing about the media landscape. The future of the industry and its challenges have been the items I’ve thought about most in my spare time. How do you run a media organization successfully in 2025 when seemingly being attacked at every angle by AI, the government, or your competitors? How can you be profitable in an era of declining trust and the changing ways people produce and consume media, seemingly daily? And when the VC money dries up, how do you stay afloat? What’s under the hood matters more than ever.
Medium CEO Tony Stubblebine’s fascinating essay on the turnaround of the company covered all of these items. The platform for independent writers and niche publications has gone through multiple transformations, both in the type of content it promotes and its profitability, throughout the years. In his piece, he outlined the steps the company had to take to get things turned around, and position the company for success in the future. This meant doing all the unsexy things that media and media-tech startup companies would hate doing (or at least hate telling people about), like cutting staff, getting out of a lease for an office no one works in, promoting content with real value, and, most difficult of all, reevaluating what the financial value of the company was.
By his account, Medium is a profitable entity again and has been since August of 2024. But until that point, they were hemorrhaging money, overstaffed, and were working out of an office that was set up for a pre-COVID era media platform.
While Medium may occupy a different sector of the media business than a legacy product like the New York Times, it still faces similar challenges.
As the future of the industry shifts from large publications to independent media, Medium is facing the added challenge of trying to attract the best content creators to its platform. As someone who occasionally writes on the platform, I saw the get rich quick articles and AI content Stubblebine mentioned in his essay.
For a while, the most prevalent content on Medium was how to write successfully and make money on Medium. It was cannibalizing itself through its algorithms, and any writing or content being published by creators worth reading would be lost to a black hole. Writers weren’t getting seen. Combined with a lack of clarity around how payment on the platform worked, it turned into a disparaging place to be as a creator.
Because of the decline in content value, the $5 per month fee readers were asked to pay became yet another subscription that fed into subscription fatigue among consumers. and contributed to a growing sense of distrust that the platform could deliver to writers and readers.
Assuming the changes stick, a $5 monthly flat fee to get access to everything on the site is one of the things Medium did right, and could be a place where it can begin delivering value again. Bundled pricing presents an advantage for readers who have a wide array of interests and want to follow multiple creators, rather than individually subscribing to a handful of newsletters on Substack, all asking for a handout. (I acknowledge the fact that I publish Zone Five on Substack, and, should my readership ever grow to a material number, I’ll probably have a paid tier. But let’s not get ahead of ourselves.)
I’ll also give Stubblebine credit where it’s due - he’s the first media executive in the creator space to admit that to make it through this media transformation, you have to do hard things and change.
Who knows whether Medium can succeed in the long term. It’s still a text-only platform at a time when everything seems to be trending towards audio and video. Its follower function is less attractive to creators than direct email. It still may not be enough to win the war, but they at least did something to win a battle.