Oct 30, 2025 · 1h 1m · big-technology
Medium CEO Tony Stubblebine: Here's How Writing Evolves In The AI Era
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Medium CEO Tony Stubblebine joins Alex Kantrowitz to discuss the future of online publishing in the artificial intelligence era, detailing how the platform moderates AI spam, protects creator compensation, and champions human-centered writing.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 33.3% of the talking time here. How this is scored →
Alex as informed peer 5.3 Guest teaching 4.2 Guest disagreement 3.6 Alex pushing back 3.3
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:19 Threatening data poisoning against antisocial AI crawlers
Stubblebine calls AI labs antisocial and explicitly warns Medium will quietly feed poison data into crawlers if they refuse fair compensation.
Hardest push from Alex ▶ 41:28 Defending publisher crawler access over platform blockingKantrowitz directly challenges Stubblebine's crawler-blocking strategy by asserting that independent writers gain valuable distribution and paying subscribers when scraped.
Biggest teaching moment ▶ 16:04 How Ev Williams' typographical preference shaped ChatGPT's styleStubblebine educates Kantrowitz on how Evan Williams hardcoding em dashes into Medium's editor ended up dominating LLM training data and output formatting.
Alex holds their own ▶ 52:46 Challenging Medium's non-creator thesis with Amazon NYT news sagaKantrowitz demonstrates detailed recall of digital media history by outlining the Jay Carney versus Dean Baquet Amazon clash to contest Stubblebine's anti-news positioning.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| Addressing the Wired AI Slop Article and Medium Moderation | 6 | 4 | 5 | 5 | Kantrowitz opens by grilling Stubblebine on a Wired report about Medium being flooded with AI slop. He pushes back when Stubblebine claims 'AI slop' was a meme coined by that article and challenges Stubblebine on the real SEO incentive for spammers posting on Medium. | |
| Why Writing is Thinking: The Enduring Value of Human Narrative | 5 | 3 | 1 | 1 | Both host and guest align warmly around the fundamental principle that writing is thinking. Kantrowitz contributes industry examples like Amazon's six-page memos to reinforce Stubblebine's thesis. | |
| AI Scraping, Typographical Em Dashes, and Data Retaliation | 4 | 7 | 6 | 4 | Stubblebine shares insider history showing how Medium's early typographical formatting forced em dashes into LLM training sets, and aggressively warns that Medium is prepared to poison AI training datasets if companies continue uncompensated scraping. | |
| Medium's New Writing Tool and AI as a Workflow Assistant | 5 | 2 | 1 | 1 | Stubblebine previews Medium's forthcoming writing app and 'bucket' concept. Kantrowitz draws from personal experience trying complex PKM tools like Roam to validate the need for unstructured note-dumping. | |
| Incentivizing Lived Experience and the Web's Shift to Private Spaces | 5 | 4 | 3 | 3 | Stubblebine explains Medium's Partner Program stance prioritizing lived human experience. Kantrowitz and Stubblebine discuss how dying public web incentives are driving online discourse into private channels like Discord. | |
| Blocking Crawlers, the RSL Standard, and Creator Compensation | 5 | 5 | 6 | 3 | Stubblebine discusses Cloudflare and the RSL standard, taking sharp aim at platforms like Reddit for pocketing AI licensing deals rather than remitting 100% of proceeds to creators. | |
| The Independent Publisher's Dilemma: AI Referrals vs Google Losses | 7 | 6 | 4 | 6 | Kantrowitz pushes back against blocking crawlers, arguing independent publishers benefit from chatbot summaries and referral conversions. Stubblebine responds with hard platform metrics showing Gemini summaries destroy 100 Google clicks for every 1 returned. | |
| Medium's Distinct Identity: Non-Professional Domain Experts vs Substack | 7 | 5 | 4 | 5 | Kantrowitz probes Medium's niche versus Substack, citing engineering newsletters on Substack and historical news moments like the Jay Carney versus NYT Amazon dispute. Stubblebine defends Medium's focus on non-professional practitioners sharing domain knowledge. | |
| Medium's Return to Profitability, Writer Surge, and Conclusion | 4 | 2 | 2 | 2 | Kantrowitz brings up his own Medium creator contract getting canceled after Stubblebine took over, but graciously validates Stubblebine's strategic turnaround and return to profitability. |
Statements from this episode (22)
Pangram Labs Pitched Medium Using Ongoing Wired Investigation Data
“There was something just suspect about the service provider that they use where it's like they, that at the same time, this article is coming out, that service provider is using the article to try to get me to hire them.”
Medium Saw a 10x Surge in Submissions Following the AI Boom
“We saw like a 10 X increase in what people were trying to post on medium.”
Google Personally Emailed Medium Asking Why Specific Stories Were Not Indexed
“I think what we've heard from Google actually is sometimes they're confused by what we're saying no index to. And I've gotten emails that are, that have really brought up stories that, that literally ask why these 10 stories aren't indexed.”
Generative AI Will Not Replace Human Writing Because Writing Is Thinking
“Writing is thinking and smart people like to think that's not going away when you have a thought and you put it under paper, put it, you know, type it out. Suddenly this, like all these subconscious, like feelings about that thought, all of your like life less…”
AI Automates Bureaucratic Writing, But Cannot Replicate Genuine Thinking
“Where people are getting confused is it just turns out there's a lot of writing that's only done for bullshit reasons, right? It's like I'm required to give a report or I have to pass some writing up to some bureaucracy, right? And so you're just checking the …”
Medium's Content Corpus Is Large Enough to Poison Any AI Model
“We learned really early on that medium is a big enough corpus of data that we can poison the
the results of any large language model.”
ChatGPT Uses Em Dashes So Frequently Because It Trained on Medium
“I'm saying it's because of medium.
Absolutely.
It's because we've in part, we popularized it in other parts of the internet too, but the medium corpus is very, very deep in those.
And so, right.
So when you hear, oh, this must've been written by AI because…”
Medium Threatens to Poison AI Training Data If Companies Refuse to Pay
“I think that if we can't find some fair exchange of value, if we can't get something going, if they insist on continuing to train and work around our blocks and, you know, continuing to avoid even paying for what they're training on.
I think we're just like …”
Eighty Percent of Articles on Medium Are Written by Non-Professionals
“80% of what gets published on medium is by people that are just using the tool and the medium network for distribution. They're not you know, the vast majority of the internet is non-professional writers.”
Medium Will Only Pay Writers for Lived Human Experiences, Not AI Text
“The thing that we want to pay for to make sure it exists on the internet is your real life lessons. And this idea of paying you to spend 15 seconds generating a ChatGPT transcript, Just not even doesn't even make sense to us as a worthy thing to pay for”
A Large Portion of the Twitter Exodus Actually Went to Discord
“We think Twitter, there was a Twitter exodus and it went to like most people think the Twitter exodus went to blue sky and to threads and originally a little bit to mastodon. I would make the case that a lot of it went to discord.”
Medium Blocks Any Web Crawler That Does Not Drive Referral Traffic
“Medium is a Cloudflare customer and a happy one, and we do use Cloudflare to block basically any crawler that isn't crawling in a way that drives traffic back to us, we're blocking right now.”
Medium Plans to Pass 100% of AI Licensing Revenue to Creators
“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.”
AI Models Will Lack Reliable Information Beyond 2025 Without Creator Compensation
“The information they're pulling in, it is literally going to stop showing up on the internet. And it's like chat TPT will give you good advice for a 20, 25 and earlier, but nothing beyond that.”
ChatGPT Drives Only 1% of the Referral Traffic Medium Gets From Google
“ChatGPT is about one percent of what we see from Google right now.”
ChatGPT Traffic Converts to Paid Subscriptions 4x Higher Than Google Search
“The thing that's really important to us is that it converts into paid subscribers four times higher than Google traffic.”
ChatGPT Referral Traffic to Medium Has Plateaued Since Spring
“ChatGPT was on a tremendous growth curve from the fall of last year to the spring of this year, and then leveled out. And a bunch of people said, oh, it's only, it's all college students, and it'll pick back up when school starts again. We haven't seen that. S…”
Medium Loses 100 Google Clicks for Every One Click From Google Gemini
“I would estimate that we lose about a hundred clicks from traditional Google search for every one click we get back from a Gemini summary.”
Medium's Google Search Click-Through Rate Dropped by Half After Gemini's Launch
“The click-through rate when Gemini launched dropped nearly in half.”
Practitioners Sharing Job Expertise Is the Most Commercially Viable Internet Content
“That idea of I could learn how to do my job because someone else who had, who's better at my job is just happens to be writing about it on the internet. Like that's the most commercially viable content on the internet. Like, I hate to break it to you, to anyon…”
Medium Is Profitable With Active Writer Numbers Up 50% Since January
“We got out of it. We were profitable. And then this, like, we're trying to say, like, we're not competing with the creator economy. And for a while, one of the things that people don't see is how many people are writing on medium. It had been flat during our s…”