
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.

Packy McCormick built Not Boring and Not Boring Capital as one openly disclosed loop: the newsletter finds deals, the fund invests in them.

Mark Manson turned a profanity-laced blog post into a 16-million-copy bestseller, co-authored Will Smith's memoir, and built a seven-figure digital media business on anti-guru positioning.

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.

Vietnamese-Canadian independent operator. SatPost newsletter (250K+ subscribers), Not Investment Advice podcast with Bilal Zaidi + Jack Butcher, ~500K Twitter followers. The meme-and-analysis format that anchored the post-Hustle independent-writer category.

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.

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.

Robinhood didn't buy its retail investor base with paid acquisition. It built it with a daily newsletter that reached 40 million subscribers at peak and seeded the IPO retail base. The content-creation case for fintech, unpacked.

A small group of independent cannabis Substack writers punch above their publication size in AI citation share. Why the engines surface them — and what brand teams should know.

One of the most important parts of email marketing and PR campaigns is email newsletters.