When a Power User Becomes CEO: How Medium Found Its Way Back

When Tony Stubblebine took over as CEO of Medium in 2022, the platform was burning $2.5 million a month, bleeding subscribers, and was overrun with content that left founder Evan Williams cringing.  Tony pitched Ev a turnaround built on small teams with access to data, customers, and the freedom to rebuild Medium like a startup from the inside out. He wasn’t just another executive parachuting in — Tony had worked with him as head of engineering, later as a power user and publishing partner, and eventually, the person who convinced Ev that he could get things on track. In this episode of Fund/Build/Scale, Tony explains how Medium became profitable for the first time, why the platform banned AI-generated content from its partner program, and how his long history as a user and advisor uniquely prepared him to lead the company through a delicate transformation. RUNTIME 50:14 EPISODE BREAKDOWN (3:41) “ I have a long track record of being associated with Medium for just strange reasons.” (7:16) “ Maybe I'm crazy, but I thought on day one, ‘oh, this is a guaranteed win.’” (9:52) “ I think CEOs are delusional, and some amount of delusion is probably healthy.” (12:34) “ Precision is not possible without a combination of data science and user research or words.” (14:30) Creating customer feedback loops in a 13-year-old company (19:49) “ I would almost say there's no product to manage yet because we’re making it, and we’re making it together.” (20:17) The two mandates Evan Williams gave Tony when he hired him as CEO (24:23) “I  knew even if we could grow subscribers, it would be on the back of this content that we weren't proud of.” (25:45) Why Medium banned AI-generated content from its partner program: “ We're a pro-human product.” (30:11) “ We love human moderation. We love our trust and safety team.” (36:28) “ We're trying to be a place where a different set of writers will win on Medium than will win on these other platforms.” (40:46) “ One hundred percent: Medium is for experience, not for influencers.” (42:35) “ I really like to be a champion for what I would call ‘white hat content marketing.’” (46:45) “ It's wild to me that the art of blogging has not been perfected this many decades into it.” (48:17) “ It's impossible to understand how many niches there are.” LINKS Medium Tony Stubblebine Tony’s Medium profile Mark Suster Cal Newport Flow: The Psychology of Optimal Experience, Mihaly Csikszentmihalyi SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening!   – Walter.