The Chicago company raised millions to build a social betting app. Its more durable idea was quieter: buy beloved niche sports brands, keep their identities intact and sell useful tools to the fans who already live there.
The company once pitched one enormous digital shelf. Now it is betting that documents, decks, books and book clubs work better in separate rooms - connected by a single subscription strategy and a growing layer of AI.
The Ankler (Ankler Media) is an independent, subscription-driven media company covering the business of Hollywood and the collision of entertainment, media and technology. Founded as a one-man newsletter by Richard Rushfield in 2017 and expanded into a full media company with former Hollywood Reporter/Billboard chief Janice Min as CEO in 2022, it has grown into a multi-platform operation of roughly 15 newsletters, podcasts, video and live events - read by studio chiefs and moguls it covers, raised $1.5M at a $20M valuation via Y Combinator, and reportedly aiming for $10M in annual revenue in 2026.
The Miilk (더밀크) is a Silicon Valley-based cross-border media startup that translates the technology, economy, and investment stories of the U.S. for Korean-speaking professionals. Founded in 2020 by former Maeil Business Newspaper correspondent JaeKwon Son, it runs a subscription news platform at themiilk.com plus the free ViewsLetter newsletter, delivering on-the-ground reporting, analysis, and market intelligence from the heart of Silicon Valley.