The Rebooting Show

The Philadelphia Inquirer is a typical big city newspaper that's been in retreat for a generation. Now under a unique nonprofit ownership structure, the Inquirer grew revenue last year and turned an operating profit. CEO Lisa Hughes, the former New Yorker chief business officer who took the role in 2020, has focused on shifting to a consumer revenue model — 70% of revenue now comes from readers through subscriptions, events, and donations. She discusses what's working: an AI tool called Scribe that monitors 30 municipal meetings to power hyperlocal suburban newsletters getting 75% open rates, a reinvented sales operation built around branded content and corporate reputation, a content strategy organized around being "useful, revealing, and responsive" rather than chasing prizes, and an aggressive regional expansion into South Jersey and beyond to grow the addressable market. Plus: the case for still printing a seven-day newspaper, why weekend content was a hidden growth lever, and what it means to "feed your Philly bias."

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. 

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.

Defector is one of the clearest test cases of what comes after the scale era. Born out of the Deadspin walkout and structured as a worker cooperative, it has achieved something most digital media operations haven’t: five years of stability with zero staff turnover. I talk with Defector COO Jasper Wang about the upside of that model, the limits it imposes, hitting a subs ceiling, and why Defector is comfortable with the tradeoffs.