Robin Thurston raised $150 million to turn Outside into more than a magazine. He explains how the company married media brands with mapping apps, SaaS platforms, and a festival to reach profitability at $125 million in revenue.

Dmitry Shishkin, a veteran of the BBC and former CEO of Ringier International, has a back-to-basics suggestion: Journalism needs to adapt more of a product mindset. Too much of what newsrooms produce is basic news updates rather than acting as a utility for the audience. His User Needs framework seeks to shift journalism to be more useful to the audience. We talk about why newsrooms overproduce content nobody values, how the BBC tripled its audience by doing less, why Dmitry thinks the next editor-in-chief should come from audience development, what happens when AI can handle all the commodity news, and whether your publication would even be missed if it disappeared tomorrow.

Taboola CEO Adam Singolda has built his company on open web publishing. He sees the dynamics of the open web changing, as the battle for AI surpremacy acclerates the shift from traditional web search, putting in motion a cascading series of second-order effects that will remake the publishing landscape. We discuss why GEO is the new SEO, the need for publishers to match changed consumer expectations, the collapsed marketing funnel and why creators are the new long-tail publishers.

The industrial logic of media, premised on scarcity, has been replaced by a platform logic that is no less centralizing. Meet the new boss. Entertainment industry veteran Darren Cross breaks down what platform logic is, and how it dictates what's made, who has power and where our attention goes.

Food Fix's Helena Bottemiller Evich has achieved sustainability. She has a recurring revenue business that exceeds her salary at Politico, with a 10% free-to-paid conversion rate. This gives her the option to continue as is as a solo operation or expand into adjacent verticals. Our conversation ranges across the choices that independent media operators need to make around complicating a simple business model, the guesswork that goes into subscriptions pricing, and how to maintain enthusiasm while on a content treadmill.

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.