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Tony Stubblebine

Chief Executive Officer, A Medium

Search every verified Tony Stubblebine interview, podcast appearance, and on-the-record quote — each transcript cross-checked by AI and human review to confirm speaker identity. Tony Stubblebine, CEO of Medium, discussed the company's recent financial struggles and turnaround strategy on the Bounce podcast, published August 12, 2026. He stated that Medium was losing $2.5 million per month, had limited cash reserves, and faced a shrinking business, which he described as a situation where doing nothing would lead to bankruptcy. He also detailed challenges related to investor governance, including the need for majority approval from five investor tranches for major decisions and the impact of liquidation preferences on employee equity value. Stubblebine reflected on the psychological aspects of leading through near-failure, noting that he felt able to explain the facts openly because the difficult situation was not of his own making. He also shared his perspective on business strategy, saying he has shifted from a product-first to a business-model-first approach, and he expressed that he often tells entrepreneurs he is less interested in discussing product utility than in addressing business fundamentals. He reiterated Medium's mission as providing a place for people to share their lives and experiences.

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Verified interview transcripts

Notable quotes

“I've always sort of flipped from thinking product first to thinking business model first. I still run into a lot of entrepreneurs who will come up to me and say, 'Oh, I want to talk to you about this new habit tracking thing.' And I always say to them, I'm sure you're going to build something that's useful. I don't even want to talk to you about it. But that's always the thing that they want to talk to me about. That”

“The easiest part of the hole to understand is just the business, right? Like we were losing $2.5 million a month. We only had limited money in our bank account and our business was shrinking, not growing. If we did nothing, eventually we'd run out of money and go bankrupt.”

“I think that what the LLM companies, the AI companies, are just starting to realize is that they kind of created this prisoner's dilemma situation by coming out of the gate defecting on day one. Like they weren't like, hey, let's have an exchange of value. They were like, we're going to take all the value and give you none. What are you going to do about it, right?”

“I think the simplest way to frame it is that this what we call the three C's which actually had been used in other places before we started using it. First is consent. Ask for permission. Allow us to say no. The other is credit. So you know one of the hallmarks of the early AI is that it would tell you something but not credit what it had trained on in order to tell you that the sort of generative AI was all based on”

“You can't have AI without source material. And you can't have the source material be public without traffic and compensation. So by definition, there has to be some equilibrium in there.”

“Medium I think and I think we're the only platform that wants to do do this is we want if we get any money out of these AI companies, we want to give all of it back to the creators. Like so far every other platform has been doing side deals and then just pocketing the money and like I don't that doesn't make sense to me.”

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