THE BUSINESS CHIEF INTERVIEW

IT IS A STRANGE WORD FOR A MAN THIS ZEN. Tony Stubblebine, CEO of Medium and the second in its history, coaches mindfulness in his spare time and prescribes vinyl as meditation. But that serenity holds up until you mention what AI companies did to writers.“ The AI companies chose violence,” he tells Business Chief.“ They continue to choose violence.“ Writers aren’ t going to forget.” Tony learned publishing at O’ Reilly Media, ran engineering at Odeo before it became Twitter( now X) and nowadays presides over one of the internet’ s largest writing platforms. He took over Medium in 2022 with a problem no business school covers: AI models borrowing the content that lives in his servers.“ I think they violated everyone’ s sense of fairness by choosing this adversarial approach, which feels like violence to someone who was writing online out of a sense of generosity,” he says.“ AI doesn’ t know sh * t unless someone writes it down, and very little human knowledge, wisdom, intelligence has actually been written down compared to what’ s actually in our heads.” By OpenAI’ s own accounting, webscraped text made up roughly 82 % of GPT-3’ s training mix. Additionally, research firm Graphite, which analysed 55,000 web articles, finds roughly half of new online articles are now primarily AI-generated. Sam Altman, CEO of OpenAI, made his defence at the New

York Times’ DealBook Summit in December 2024.“ I think the discussion on fair use or not is at the wrong level,” he said, calling instead for“ new economic models where creators can have new revenue streams,” something akin to NIL deals for college athletes. And the productivity case for AI is real enough. Research from the London School of Economics finds employees using AI save around 7.5 hours a week – close to a full working day. So where does online writing go from here, toward rapprochement or open war? Tony has an answer that calls on both sides.

On standing out when others take the easy route Tony’ s writing philosophy is built on visible effort. He points to The Bear, where a chef peels mushrooms so the diner can see the time that went into it, and to his own evidence: an article on making your smartphone distraction-free that took three years of research and became one of the most viewed pages on the internet.“ What if I put way more effort into this topic than anyone thinks is worthwhile?” he says.“ And what will happen is a couple of million views if I showed a person a single life-changing article once a month, that pays for the subscription.”“ I don’ t need a hundred clicks. I need one great one.” That conviction keeps him sanguine in the AI economy, and he refuses to confuse the tool with the threat, since Medium welcomes AI in the writing

46 November 2026