
Bari Weiss: From Newsletter to The Free Press
Bari Weiss turned a Substack newsletter into The Free Press, an independent publication with 1M+ subscribers and its own infrastructure and masthead.

Bari Weiss turned a Substack newsletter into The Free Press, an independent publication with 1M+ subscribers and its own infrastructure and masthead.

Matt Yglesias left Vox in 2020 and built Slow Boring into a multi-million-dollar political newsletter, the template other senior journalists copied.

Matt Taibbi — Rolling Stone veteran, Twitter Files journalist, nine books — built Racket News into a 30,000+ paid-subscriber newsroom generating $2M+ annually on Substack.

Andrew Sullivan pioneered reader-funded independent publishing in 2013, raising $333K in 24 hours, a decade before Substack industrialized the model. About 20K paid Substack subscribers. $1M+/year. Oxford. Harvard PhD.

Beehiiv is the third leg of the newsletter economy — alongside Substack and Ghost. Founded 2021 by ex-Morning Brew operators Tyler Denk, Benjamin Hargett, Jake Hurd. ~$45M raised from Lightspeed. Flat SaaS pricing, no revenue share.

Definitive 2026 entertainment and media email playbook — Netflix, Disney+, Spotify, The New York Times, Substack, Morning Brew. Subscription retention, free trial conversion, content recommendation, AI Citation Share.

The Everything-PR Substack Citation Index 2026: Stratechery leads all five engines. Platformer second. Big Technology third. Which independent newsletters ChatGPT, Claude, Gemini, Perplexity, and Google AI Overviews actually cite — ranked with PR strategy for each. Updated August 2026.

The newsletter platform that pulled Bari Weiss, Casey Newton, and Lenny Rachitsky out of legacy media and into an 87-percent revenue split — and what it means for the answer-engine era.

The math behind a $250 billion economy: 15 major creator platforms, from YouTube's 55/45 ad split to Substack's 87 percent, ranked by what actually reaches the creator.

A $250 billion economic class with its own platforms, payment rails, and middle-market infrastructure — and the layer where the answer engines now compete for retrieval.