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.

(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.”

• Medium
• Tony Stubblebine
• Tony’s Medium profile
• Mark Suster
• Cal Newport
• Flow: The Psychology of Optimal Experience, Mihaly Csikszentmihalyi

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Thanks for listening!

– Walter.