Substack

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.

Why Hand-Typing Code Will End Your Career in 2026

Mar 2, 2026 · 49:31

Dan Shipper, co-founder and CEO of Every, argues that AI agents like OpenClaw and vibe coding—prompting apps in English—are fundamentally reshaping how companies operate, from internal workflows to product development. Every, a 20-person company running four AI-native products (Quora, Spiral, Sparkle, Monologue), treats failed software experiments as content that builds distribution, and uses a 'two-slice team' approach where each product is managed by one person. Shipper details how he reclaimed the 'founder' title for legitimacy, the four-year 'flatline' period before the AI wave hit, and why over-hiring early is 'crazy—most of the time it doesn't end well.' He advises founders to automate every internal process with AI and build for both humans and agents.

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.