Photo by Bloomberg. Illustration by Mike Sullivan.

One of the wonderful things about being a tech reporter for going on two decades is the chance to observe executives in multiple acts. And this week, while the internet was debating Twitter CEO Jack Dorsey’s scraggly pandemic beard, I was chatting with one of Dorsey’s predecessors in that role, Twitter co-founder and now Medium CEO Ev Williams.

Williams defies the stereotype of a tech or media executive. More tech smart than your average media executive and more wise about the media business than virtually any tech executive I know, I’ve always found that he’s someone who looks around corners. Today, as the leader of a tech platform that pays millions of dollars a month to writers, he’s a blend of both worlds.

While its platform is ubiquitous, Medium the company has stepped out of the spotlight in recent years as Williams has retooled (and retooled) its strategy. Created to address some of the perverse effects the internet and the online ad model has had on quality content, Williams in recent years has embraced a membership model and supplemented Medium’s bloggers with a small cohort of professional Medium publications. Needless to say, we had a lot to discuss, ranging from Medium’s business and his thinking about an IPO to his views on politics in the workplace and why the future of media is not newsletters.

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