Everything comes back in fashion. Why not the portal? Yahoo is a true legacy brand of the internet. An OG portal that failed to stem the rise of Google, missed on buying Facebook and for the last four-plus years has been a ward of private equity under the ownership of Apollo. It’s also found the market turning in its favor in many ways.

Kat Downs Mulder, svp and general manager of Yahoo News and home, joined me on The Rebooting Show to discuss the portal’s comeback.

In this episode, I talk with James Capo, CEO of audience data platform Omeda, about why the traffic-driven media model has finally run out of road and what replaces it. We dig into the idea of a “connection economy,” where audience relationships—not page views—are the core asset. We also get into why so many publishers struggle to operationalize audience-first strategies, how B2B and consumer media models are converging, and where AI fits if it’s meant to add real utility rather than repeat past mistakes.

Thanks to James and Omeda for supporting The Rebooting as partners.

Recurrent CEO Andrew Perlman discusses how the publishing company is focusing its niche brands increasingly on events as it retools its model from the traffic era. Affiliate revenue is now a third of what it was at its peak, while experiential has risen from "effectively zero" five years ago to 12% of overall revenue and rising.

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.