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  1. Big Technology Podcast
  2. How AI Is Changing Writing — With Tony Stubblebine
How AI Is Changing Writing — With Tony Stubblebine

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast · Oct 29, 2025

Medium CEO Tony Stubblebine on battling AI slop, championing human writers, and fighting for creator compensation in the age of AI.

Future Productivity Tools Will Use AI to Embrace Messiness, Not Enforce Structure

AI will revolutionize personal productivity by eliminating the need for rigid organizational systems. Instead of complex methods requiring meticulous tagging, users will be able to dump unstructured notes into a single "bucket." AI will then enable powerful, natural language queries to retrieve and synthesize that information on demand.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

Writing's True Value Is Clarifying Thought, A Process AI Cannot Replace

Medium's CEO argues that writing's future is secure because its core function is the process of structured thinking, not just content output. The act of articulating ideas reveals flaws and deepens understanding for the writer—a cognitive benefit that delegating to AI would eliminate.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

Platform Health Depends on Reader Experience, Not Total Spam Volume

Medium's CEO argues the true measure of success against spam is not the volume of "AI slop" received, but how little reaches end-users. The fight is won through sophisticated recommendation and filtering algorithms that protect the reader experience, rather than just blocking content at the source.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

Medium Pivots to Serve Occasional Writers, Ceding the Creator Economy to Substack

Medium is no longer competing for professional content creators building media businesses. Instead, its CEO states the platform is focused on being the best place for "real people"—practitioners and individuals—to share valuable life and work lessons without the pressure of becoming a full-time writer.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

AI-Driven Search Risks Pushing Public Discourse into Private Channels like Discord

As AI-powered search reduces referral traffic, the incentive for creating public content diminishes. This could accelerate a trend already seen with the "Twitter exodus," where users retreat from the open internet into more private communities like Discord, fragmenting public discourse.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

ChatGPT Referral Traffic Converts to Paid Subscriptions 4x Better Than Google Search

Although ChatGPT drives only 1% of the referral volume Google does for Medium, its users convert to paid subscribers at a 400% higher rate. This indicates that AI-assistant-driven traffic is extremely high-intent, making it a surprisingly valuable, albeit small, acquisition channel for subscription businesses.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

Medium's Prolific Em Dashes Inadvertently Poisoned Early AI Language Models

Medium's platform automatically converted double hyphens to em dashes for years, a stylistic preference of founder Evan Williams. This saturated its content with the punctuation mark, causing AI models trained on its vast corpus to replicate this quirk, effectively becoming a "tell" for AI-generated text.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

Publishers Treat AI Data Scraping as a Prisoner's Dilemma, Forcing Retaliation

Medium's CEO frames the AI training data issue as a classic prisoner's dilemma. Because AI companies chose an "antisocial" path of scraping without collaboration, platforms are now forced to defect as well—blocking crawlers and threatening data poisoning to create leverage and bring them to the negotiating table.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

Data Provider in Negative "Wired" Story Pitched Its Services to Subject, Medium

Medium's CEO revealed the company providing data for a critical Wired article about "AI slop" was simultaneously trying to sell its AI detection services to Medium. This highlights a potential conflict of interest where a data source may benefit directly from negative press about a target company.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago

Google's Gemini AI Summaries Create a 100-to-1 Click Loss for Publishers

Medium's CEO estimates that for every referral click the platform receives from a Google Gemini AI summary, it loses 100 clicks it would have gotten from traditional search. Unlike high-converting ChatGPT traffic, these visitors show no higher intent, making the trade-off purely destructive for publishers.

How AI Is Changing Writing — With Tony Stubblebine thumbnail

How AI Is Changing Writing — With Tony Stubblebine

Big Technology Podcast·4 months ago