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PODCAST

The Rebooting Show

Brian Morrissey

The Rebooting Show gets into the weeds with those building and operating media businesses, giving an open view into how the smartest people in the media business are building sustainable media businesses. https://www.therebooting.com/ (www.therebooting.com)

news business news

All Episodes

41:32

Content and community

The Rebooting Show ·

2026/02/02

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.

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53:30

The open web needs a new economic model

The Rebooting Show ·

2026/01/27

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

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27:39

The messiness of streaming advertising

The Rebooting Show ·

2026/01/22

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.

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20:08

Inside Vox’s talent-led franchise strategy

The Rebooting Show ·

2026/01/20

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

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01:14:12

The B2B indie opportunity

The Rebooting Show ·

2026/01/16

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

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52:54

Semafor's big bets

The Rebooting Show ·

2026/01/13

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.

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55:48

Why Puck isn't all-in on events

The Rebooting Show ·

2026/01/06

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

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44:35

What we learned about media in 2025

The Rebooting Show ·

2025/12/18

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.

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51:48

Inside The Washington Post's product strategy

The Rebooting Show ·

2025/12/16

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

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43:49

The post-pageview media model

The Rebooting Show ·

2025/12/11

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

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41:10

The AP's pivot to tech

The Rebooting Show ·

2025/12/09

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

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51:41

Building a post-scale media company

The Rebooting Show ·

2025/12/04

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.

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56:57

Caliber's Ramin Beheshti on Gen Z news

The Rebooting Show ·

2025/12/02

Caliber CEO Ramin Beheshti says younger audiences who aren’t typing URLs into browsers and aren’t interested in being talked down to. We get into why the traditional news product is mismatched with how people actually consume information, why platform-native formats have beaten the homepage, and how Caliber is trying to build news that fits into people’s lives rather than demanding the reverse. Ramin explains the logic behind The News Movement, The Recount, Capsule, and the new SaySo app, and why he

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41:51

How Tangle became a $4m+ revenue, profitable news...

The Rebooting Show ·

2025/11/25

Isaac Saul started Tangle in 2019 without a platform job, a big name, or the institutional head start many Substack-era independents enjoyed. He describes himself bluntly: “When I started Tangle, I was a nobody.” In this episode, we talk about how he hustled his way from zero readers to a 450,000-person list and 70,000 paying subscribers, and how he’s trying to make the shift from a creator-led project to a durable media company. We get into his decision to add new voices, the limits of solo output,

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44:17

The Schneps Media local news playbook

The Rebooting Show ·

2025/11/20

The Schneps Media story is a blueprint for how local publishing can still work when it’s treated like a real business, not a civic charity. Josh Schneps explains how he and his mother built a diversified local empire by combining print, digital, and events into a single ecosystem that feeds itself. He talks about why print still drives more than half of their revenue, how they use events to build relationships and coverage, and why proximity—not scale—is the true advantage in local media. We also

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54:15

Inside The Economist’s Ferrari strategy

The Rebooting Show ·

2025/11/18

The Economist’s president Luke Bradley-Jones looks to Ferrari as an example of a brand that’s been able to use scarcity to drive value. Ferrari has avoided the trap of many luxury brands in chasing scale and in the process diluting their brands. While The Economist won’t limit the amount of people who can subscribe, it follows the less-is-more strategy in sticking to its legacy values and hand-crafted journalism while modernizing its distribution and presentation.

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54:08

How the NYT makes subs and ads work together

The Rebooting Show ·

2025/11/11

The New York Times has become the rare publisher proving that subscriptions and advertising can strengthen each other. Chief Advertising Officer Joy Robins explains how a subscriber-first model creates the engagement, trust, and data that fuel a thriving ad business. She also discusses how the Times’ bundle — from Games to The Athletic to Cooking — opened new surface areas for news-averse marketers, and why video is the big test for the NYT as it strives to become the Netflix of news.

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01:00:01

The Bulwark's anti-neutrality approach

The Rebooting Show ·

2025/11/05

Sarah Longwell, publisher of The Bulwark and founder of Republican Voters Against Trump, discusses why neutrality no longer works in political journalism. Longwell argues that legacy media’s “studied impartiality” has become a liability in a polarized, low-trust world—and that audiences now crave conviction over detachment. She explains how The Bulwark grew out of the ashes of The Weekly Standard to become a mission-driven newsroom defending liberal democracy, why she sees “no conflict, no interest”

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01:00:51

How Axios segments its audience

The Rebooting Show ·

2025/11/04

Axios CRO Jacquelyn Cameron breaks down how Axios thinks about audience segmentation in an age when every publisher says they’re “audience-focused.”Jacquelyn explains why Axios organizes around five core personas — influencers, C-suite executives, dealmakers and investors, communicators, and smart local professionals — and how each connects to a product, event, or revenue line. We get into how “no opinion” coverage is a competitive advantage in Washington, how local works when it’s “localized

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01:01:13

How TechCrunch rebuilt its email strategy

The Rebooting Show ·

2025/10/29

TechCrunch’s new owner faced a familiar challenge: modernizing an old tech stack built for a different era. Matt Gross, vp of digital initiatives at TechCrunch owner Regent, joins Beehiiv CEO Tyler Denk to discuss how they untangled years of tech debt, rebuilt email from the ground up, and reframed newsletters as core editorial products rather than traffic drivers.Note: This episode is part of a commercial partnership between The Rebooting and Beehiiv. Learn more about how Beehiiv works with

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208 results

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