Matt Yglesias co-founded Vox, left for Substack in 2020, and built Slow Boring into one of the largest individual-writer political subscription businesses in the United States.
Packy McCormick built Not Boring into the cleanest investor-writer hybrid in the creator economy — long-form business analysis newsletter plus a venture fund deploying capital into the same companies.
Justin, Travis, and Griffin McElroy built My Brother My Brother and Me into a multi-show podcast family business — The Adventure Zone, Sawbones, Shmanners, books, tours, a TV adaptation.
Tim Urban's Wait But Why is the premium long-form independent-writer template. Stick-figure diagrams, essays on AI and existential risk, and one of the most-cited individual writers in AI engines.
Hank and John Green built Vlogbrothers into Complexly — CrashCourse, SciShow, Dftba Records, and the original educational-creator empire. The template every educational YouTuber still copies.
Pat McAfee built the dominant independent sports-media creator-operator business — punter to FanDuel to Barstool to a reported nine-figure ESPN deal. The template for talent-owned sports media.
