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Will AI Models Ever Compensate Creators? Tony Stubblebine (Medium CEO)

May 6, 2026 · 53:35

Tony Stubblebine, CEO of Medium, argues the creator economy is ending as AI slop floods public channels, but a writing renaissance is emerging where authentic expertise and private communities hold value. He details Medium's turnaround from losing $2.5M per month and $37M in debt to profitability, achieved by restructuring investor relationships and refocusing on human-written content. Stubblebine warns that AI companies like OpenAI created a 'prisoner's dilemma' by scraping content without compensation, pushing high-quality writing into walled gardens. He introduces Medium's new AI-assisted writing app TK and private blogging groups as responses to the era. The episode explores how creators must diversify revenue streams and reinvent themselves, while per-inference pricing standards like RSL slowly develop.

This Is HOW Newsletters Can Make MILLIONS

Sep 14, 2025 · 1:02:25

Tyler Denk, co-founder of newsletter platform Beehiiv and writer of Big Desk Energy, reveals how Morning Brew's conversational tone and email-first strategy built a $75 million acquisition, then how he applied that experience to create Beehiiv as a 'Morning Brew in a box' for creators and businesses. He explains that email distribution wins because platforms like Facebook and Google cut traffic 40-50% via algorithm changes and AI summaries, while newsletters let creators own their audience and monetize through ads, subscriptions, and affiliates. Denk shares Beehiiv’s early days: 150 of 400 signups from a single tweet, a $99 all-inclusive plan that was a no-brainer, and a 'holy shit' moment when GoDaddy shut down all user websites during his bachelor party. He argues that newsletter M&A will return as companies like HubSpot acquire distribution to their ICP, and predicts waves in hard tech (robotics, energy) and preventative health—citing 50% less alcohol use among teens and the rise of wellness clubs—driven by founders needing peak mental performance to build billion-dollar companies.