For two decades, the economics of the open web rested on a simple bargain: platforms indexed content, publishers got traffic, and monetization happened downstream. AI breaks that loop by delivering answers without the click.

This week, I’m joined by Doug Leeds, former head of IAC Publishing and now CEO of RSL, to unpack what comes next. We talk about why the old traffic-for-content deal is collapsing, why pay-per-crawl is a dead end, and how collective licensing could create a new economic layer for publishers and creators. A conversation about leverage, incentives, and whether the web can adapt to AI without losing the ability to fund original work

In the second round of our TRB Conversations powered by EX.CO, I spoke to EX.CO CEO Tom Pachys about why the streaming landscape is even more chaotic than online advertising; Manas Mittal from Uber discussed why mobility advertising has become a new category; and Vayner Media executive Andrea Sullivan talked about why Gay Vaynerchuk’s group is expanding into professional development network, Vyve. 

This episode features two conversations I had at CES as part of TRB Conversations, powered by EX.CO. First, a discussion with Vox Media CRO Geoff Schiller on the company’s bet on talent-led franchises, and why podcasts have become the proving ground for individuals over institutions. Vox has leaned into shows like Pivot with Kara Swisher and Scott Galloway and A Touch More with Sue Bird and Megan Rapinoe, treating talent development less like scale media and more like a studio model. Then, a conversation with Mark Floreani, CEO of FloSports, on the rise of niche sports and the power of owning IP end to end—from registration and ticketing to broadcast and fan experience.

In this episode, I talk with CJ Gustafson, the former CFO behind Mostly Metrics. CJ didn’t come from journalism or media. He came from operating. He started writing to document the playbooks he’d built as a finance executive. That side project turned into a $3 million business with no full-time employees, built around a narrow, high-value audience of CFOs.

We talk about why subscriptions are a useful base but not where the money is in B2B, how sponsorships actually work when sales cycles are long and considered, and why CJ has deliberately avoided becoming an events company. Mostly Metrics is now largely sponsorship-driven, sold out well into the future, and optimized for cash flow and leverage.

Semafor's recent $30 million funding round at a $330 million valuation is a needed jolt of confidence in the media sector -- and an endorsement of its events-led media model. CEO Justin Smith joined me to discuss why putting events first allowed Semafor to get to $40 million in revenue and profitability in 3.5 years, why corporate affairs is growing in importance and value, and using a global orientation to expand the addressable market.

CEO Sarah Personette is blunt that she has no interest in becoming an events company, warning that "over-rotating" to events is how media brands lose their identity. Puck runs a limited slate—two premium ticketed summits, insider breakfasts in DC and Hollywood, and partner-driven dinners—but only when they reinforce franchises and margins. The goal is to use convening power strategically, not let it become the business. Sarah joined me to discuss this and other topics, including why podcasting is more about relationships than revenue, how Airmail now brings Puck to over 100,000 paying subscribers.

Axios media correspondent Sara Fischer and Breaker founder Lachlan Cartwright are two of the best reporters who are attuned to the daily changes to the media business. They joined me for a year-end episode that covers key themes of the year, including the rise of personality-driven reporting, the pressure on legacy newsrooms, and the politicized dealmaking that’s reshaping Hollywood.

This week I spoke with Washington Post CTO Vineet Khosla about the collision between a legacy shaped by perfection and a future shaped by iteration. We get into why the Post is pushing beyond the one-size-fits-all article, how conversational and personalized formats change the relationship between readers and reporting, and what it takes for a newsroom to think like a product organization without losing its editorial core. Vineet walks through the shift toward voice as an interface, the role AI will play in expanding how journalism is packaged, and why publishers need to stop viewing themselves as content suppliers to platforms.

Jason Wagenheim has lived the full arc of media’s transformation, from the late-stage magazine era to the current scramble to build durable franchises in a post-pageview world. We talk about how the shift to mobile foreshadowed the AI disruption now hitting publishers, why Football Co is leaning hard into creator-led video and social distribution, and how the World Cup has created a rare commercial tailwind for a sport that has finally broken through in the US. Jason breaks down the decline of the website as a business model, the rise of branded content and experiential, and why soccer’s cultural moment offers a template for what modern storytelling businesses can still be.

The AP is quietly becoming a core supplier to the AI economy. I talk with Kristin Heitman, the Associated Press CRO, about how a 178-year-old cooperative built on serving newspapers is shifting to a business where newspapers now account for under 10 percent of revenue and tech companies already make up 15–20 percent, with that share expected to double over the next few years. We get into how AP prices its data, why recency has become the new battleground, the long-tail demand from companies building their own models, and what this shift signals for the future of licensing across the media industry.