In some ways, you have to feel for Ev Williams, the founder of Medium, who tried doing something ambitious for an audience that seemed to never get any respect on the internet—writers.
But on the other hand, the challenge with what he was doing was precarious. When he failed, he failed in a way that affected people’s lives. People got laid off; freelance writers that relied on regular paychecks from the company suddenly stopped getting them. That is not a criticism of Williams so much as a reflection of the reality of what his company was doing.
Williams moved away from the CEO position this week, choosing instead to become chairman of the company he founded as a haven for writers. (A longtime associate from his pre-Twitter days at Odeo, Tony Stubblebine, will be taking his place.)
The problem with being a haven for writers, however, is that is not simply a neat, beautiful ideal. When something goes wrong or an idea falls through, real people are affected. And Medium, infamously, went through a lot of them—both ideas, and real people.
To be fair, Williams was attempting to solve a problem that nobody else was trying to solve at the time of Medium’s formation: At a time when most writers had been relegated to living off the scraps of the ad economy (if they could get that), he attempted to find new ways to support publishing that benefited from his learnings at Blogger and later Twitter. Eventually he came upon an important one—offer an alternative to advertising. The problem was, it took him about half a decade to make that call, and along the way, his company burned numerous writers, editors, employees, and publications in the process. It wasn’t like that was his goal, but that was what happened.
“Media is a famously unforgiving business, and Williams is far from the only CEO to struggle to build a sustainable company,” Casey Newton wrote over at Platformer. “And yet over the past decade, few have matched him for the sheer number of changes in direction he inflicted on investors, users, and employees.”
The problem with moving fast and breaking things is that it damages a lot of people’s lives, and it made any future decision-making by the company suspect. It likely inspired other companies to take a more stable approach. Substack has been around for about five years at this point, and its model has stayed pretty consistent the entire time. Same with Patreon. Both of these have their faults but are ultimately better choices if your goal is to build a business as a writer in 2022.
I will admit that while the lean years were pretty lean, I was a beneficiary of some of Medium’s pivots. Over the years, I made some decent money through the network—not enough to be a paid employee, but some of my work found a lot of success there. At one point I was able to sell a Medium publication a completed freelance piece that had been rejected at another outlet, and actually came out a little ahead of where I expected to be with it financially. But at the same time, I knew people who were negatively affected by the wishy-washyness of some of the leadership decisions, good people who did great work but weren’t shown the respect for that work.
My measure of Medium’s success, even after I stopped posting there with any regularity, was whether I made more money from it than my $5 monthly subscription cost, which had generally been true until last year. In the meantime, the content has become lighter and more clickbaity in the very ways that Ev was swimming upstream against. If Medium’s business model only truly benefits polemics, is it really a solution at all?
Nonetheless, I continue to hope that Medium gets out of its doldrums. My suggestion: After years of pivoting and changing directions, I think Medium just needs to find a single direction, stick with it, and hope for the best. That Medium hasn’t makes it feel like every other chaotic part of trying to make a living as a writer.
And that was never the goal.
So no, Ev didn’t nail it. But on the other hand, we probably needed someone with deep pockets, like Ev, to workshop the hard parts of running a media business for people who just love to write. It would have been nice if it had been more clear that’s what Medium was doing, though.
Time limit given ⏲: 30 minutes
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