The Rebooting Show

Lisa Hughes, CEO of the Philadelphia Inquirer and former New Yorker business chief, transformed the paper toward reader-funded revenue and AI-powered local coverage. The conversation covers AI tools that monitor municipal meetings and drive high-open hyperlocal newsletters. It also highlights a consumer-first revenue mix, reinvented sales and branded content, weekend and regional expansion, and the case for keeping seven-day print.

Robin Thurston, media and product executive who scaled MapMyFitness and now leads Outside, explains how he fused magazines with mapping apps, SaaS and events to build a media-as-flywheel. He discusses combining content, utility and commerce. He walks through technical integration, revenue shifts to subscriptions and SaaS, and the creation of Outside Days to grow and diversify the audience.

Dmitry Shishkin, media strategist and former BBC and Ringier exec who created the User Needs framework, argues journalism should adopt a product mindset. He discusses why newsrooms overproduce low-value updates. He explains the BBC research that mapped six user needs, how to match format to need, and what leadership and AI mean for future newsroom structures.

Adam Singolda, founder and CEO of Taboola, built a business around open web publishing and ad recommendations. He discusses AI-driven features like Deeper Dive and how conversational models change site search. He explores shifting monetization models, why GEO matters more than traditional SEO, and how publishers can adapt to AI-driven product and revenue shifts.

The industrial logic of media, premised on scarcity, has been replaced by a platform logic that is no less centralizing.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.

Helena Bottemiller Evich, founder of Food Fix and former Politico reporter, built a sustainable subscription food-policy newsletter. She discusses leaving legacy media to launch a paid model, pricing and conversion guesswork, balancing simplicity versus scaling, optionality between lifestyle business or expansion, and how to adapt reporting and operations for growth.

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.

James Capo, CEO of Omeda and veteran media executive, explains the shift from traffic to a connection economy where audience relationships are the core asset. He discusses operationalizing audience-first strategies, consolidating audience data, the convergence of B2B and consumer media, and practical AI uses that add real utility rather than repeating past mistakes.

Andrew Perlman, CEO of Recurrent — a publisher of niche brands across auto, military, home, and science. He talks about shifting revenue from affiliate search to events and experiential offerings. He explains scaling niche conferences, tying events to editorial, expanding into video and creator-led formats, and growing licensing, merch, and AI-driven operations.

Doug Leeds, digital media executive and CEO of RSL, explains why the traffic-for-content bargain is breaking as AI delivers answers without clicks. He discusses RSL’s open standard plus collective licensing, why pay-per-crawl fails, how licensing can scale like music royalties, and how collective leverage could help publishers and creators get paid.