The Powers That Be: Daily Ellison’s Weiss Gamble & ESPN App Questions
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Sep 8, 2025 The discussion dives into the potential $100 million deal for Bari Weiss’s The Free Press and what it could mean for CBS News. They explore the shifting landscape of media and assess the implications of Weiss's involvement. The conversation also critiques ESPN's ambitious new app and its challenges in adapting to a direct-to-consumer market. Insights on the struggles of traditional media companies in connecting with modern audiences highlight the broader conversation about innovation and consolidation in the media world.
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Price Reflects Talent, Not Tech
- The Free Press's price will be set by what a buyer values: primarily Barry Weiss as talent rather than infrastructure.
- The Substack-based business has little tech or ops but carries outsized cultural and ideological value.
Revenue Versus Valuation Gap
- Estimated Free Press revenue (under $20M) implies buyers are paying a high multiple for audience and brand.
- Expect payout structures with earnouts to keep Barry attached post-sale.
Contrarian Audience Is The Asset
- The Free Press fills a contrarian, anti-woke lane that appealed to disaffected elites post-COVID.
- Its audience loyalty makes it attractive even without large paid-sub percentages.