Overview of Media Monday: Bari’s Dating Advice & Ben Shapiro’s Haircut
This episode of The Powers That Be focuses on two major media-business stories: The Free Press expanding into events and community experiences, and The Daily Wire’s slowing growth amid subscriber losses, internal mismanagement, and changing dynamics on the right. Peter Hamby and John Kelly frame both as examples of how modern media companies increasingly depend on live experiences, personalities, and alternative revenue streams—not just publishing or podcasting.
The Free Press: Turning Audience into an Events Business
Barry Weiss’s announcement that The Free Press is launching forums, supper clubs, retreats, and excursions sparked a broader discussion about where media monetization is heading.
What The Free Press is launching
- A subscriber forum for discussions around issues, books, music, travel, parenting, dating, and networking.
- Supper clubs designed as small, curated dinner gatherings.
- Retreats and excursions to places like Gettysburg, Normandy, and the Vatican.
Why it matters
- Hamby and Kelly argue this is part of a larger trend: media companies increasingly acting like events businesses.
- They compare The Free Press to outlets like Semaphore, Punchbowl, Fortune, and Axios, which also use events as a revenue driver.
- Kelly notes that live events can be one of the easiest ways to monetize a media brand because they create premium, high-margin experiences layered on top of editorial content.
Critiques and concerns
- They question whether some of the offerings fit The Free Press’s brand, especially:
- Dating forums
- Curated trips with families and children
- They also suggest the operational complexity may be too much for a company whose appeal is rooted in a lean, lo-fi, Substack-era identity.
- A major behind-the-scenes concern is whether Barry Weiss, now at CBS News, should be spending time on this side project at all.
The Daily Wire: Subscriber Slippage and Strategic Drift
The second half examines Ben Shapiro and The Daily Wire, which remains large but appears to be losing momentum.
The numbers and trend
- Shapiro still has roughly 7.1 million YouTube subscribers.
- But the channel has lost about 80,000 subscribers since the beginning of the year.
- The company has also reportedly laid off about 13% of its workforce.
Why the decline is happening
Hamby and Kelly point to two overlapping causes:
1. External pressure from the “new right”
- Shapiro is under attack from more populist or conspiratorial right-wing figures, including:
- Tucker Carlson
- Megyn Kelly
- Candace Owens
- Nick Fuentes
- Shapiro is trying to defend what he sees as traditional conservatism against a more chaotic and anti-establishment right.
- This ideological shift has weakened some of the audience cohesion around The Daily Wire.
2. Internal management mistakes
- The company’s early structure, built by “three buddies,” lacked discipline and investor oversight.
- They made costly detours into:
- Film projects
- Consumer products
- Side brands
- A key example cited is Pendragon, an Arthurian fantasy project that consumed time and money.
- Kelly argues that the company should have stayed focused on the core business: media distribution, ad sales, and audience growth.
Broader Media Takeaways
Media is increasingly a “membership + experiences” business
- Editorial content alone is often hard to monetize.
- Events, retreats, dinners, and community access can produce meaningful additional revenue.
- The tradeoff: these businesses require different operational muscles than journalism does.
Brand fit matters
- A company like The Free Press may be better suited to lightweight community offerings than expensive, logistically heavy global excursions.
- The Daily Wire’s problem was the opposite: it tried to be too many things instead of scaling a coherent media product.
Personality-driven media has limits
- Both companies are built around strong personalities.
- That creates audience loyalty, but also:
- Management complexity
- Ideological conflict
- Difficulty scaling into durable media institutions
Bottom Line
The episode argues that:
- The Free Press is following a real and potentially profitable trend by expanding into events, but may be stretching beyond its natural brand.
- The Daily Wire is still a major conservative media force, but it appears to be entering a more fragile phase due to both market shifts and self-inflicted business mistakes.
- Together, the two stories show how modern media is increasingly about community, monetization, and personality management as much as publishing itself.