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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

01:02:14

Inside Time's practical AI playbook

The Rebooting Show ·

2025/06/09

Jessica Sibley, CEO of Time, joins to talk about how the 101-year-old media brand is approaching AI with a clear-eyed strategy rooted in business fundamentals. We discuss Time’s shift toward B2B, why it phased out speculative bets like NFTs and no-code platforms, and how it’s building AI features that serve users without compromising editorial integrity. Jess shares how Time is keeping close to AI power players like Scale and OpenAI, while remaining disciplined about where it integrates AI into its

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51:00

How the WSJ goes beyond ads and subscriptions

The Rebooting Show ·

2025/06/03

The Wall Street Journal has many advantages at a perilous time for news publishers. It has a massive paid subscriber base (4.3 million across print and digital). It caters to an affluent audience. It has a storied brand. While AI is threatening to overwhelm swathes of the industry, the Journal has benefited from advertising from flush AI companies. Yet it isn’t immune to the pressures facing publishing overall and news in particular.WSJ CRO Josh Stinchcomb joined the show to discuss how the Journal

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33:07

Google Zero

The Rebooting Show ·

2025/05/26

The landscape for digital publishing is shifting. At the center of this is Google search, the backbone of the open web. Google's embrace of "AI mode" last week was a sign that it will overhaul its approach to search with vast implications for publishers. Earlier this month, I spoke with Dotdash Meredith CEO Neil Vogel for the keynote session at the Media Product Forum, an event put on in NYC by The Rebooting and WordPress VIP. Neil laid out the pragmatic playbook Dotdash Meredith is using to thrive

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01:03:42

Henry Blodget on the media business in 2025

The Rebooting Show ·

2025/05/20

Henry Blodget built Business Insider into one of the few breakout successes of the traffic era. Now, with his new project Regenerator, he’s taking a different path—one that reflects the broader shifts in digital media. We talk about the collapse of platform-driven distribution, why subscriptions are a more durable model, how venture capital never quite fit the media business, and what it takes to build in the current environment of fragmented attention and AI disruption.Check out The Rebooting's

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01:06:42

Dynamo's Nicholas Carlson's pivot to video

The Rebooting Show ·

2025/05/13

Nicholas Carlson spent nearly a decade building Business Insider into a video powerhouse to complement its webpage model. Now, with his new venture Dynamo, he’s making a clean break from the old model. No articles. No CMS. No pageviews. Dynamo is a video-first media company focused on YouTube and LinkedIn, with a flagship show called Business Explains the World. In this episode, Nich explains why he’s betting on evergreen content, what he learned from Insider’s rise, and how Dynamo is approaching

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01:06:09

Anonymous Banker's bleak view of the media M&A market

The Rebooting Show ·

2025/05/07

I spoke with Anonymous Banker, an M&A advisor with a front-row view into the market for buying and selling digital media companies. Needless to say, it’s a buyer’s market.AB breaks down the market for digital publishing assets – broadly those with page-based models – into three types of buyers:HarvestersCAC jockeysVanity projects/rich person playthings“If you're a publisher with a mostly ad-supported site, odds are your business will be worth less next year than it is now,” he said.Deals are

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50:56

Inside HubSpot's go-direct media playbook

The Rebooting Show ·

2025/04/29

Kyle Denhoff, head of audience development for HubSpot Media, joined me to talk about how HubSpot has built one of the most effective media operations inside a tech company. We discuss how HubSpot’s practical, non-ideological approach to inbound marketing evolved into a full-fledged media business spanning newsletters, podcasts, and creator partnerships. Kyle shares how HubSpot balances editorial independence with business goals, the economics of building durable audience relationships, and why

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01:04:00

The Ankler's Janice Min embraces more with less

The Rebooting Show ·

2025/04/22

Janice Min joins to talk about building The Ankler into a focused, profitable media brand—and why she believes the future belongs to lean operators, not her past life helming glossy franchises. We talk about her transition from the high-gloss days of The Hollywood Reporter to the scrappy Substack era, the limits of venture capital in media, and how The Ankler is growing through high-impact events and B2B subscriptions. Janice shares lessons from Y Combinator, explains why editorial quality still

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56:20

Spin's IP strategy

The Rebooting Show ·

2025/04/14

Once a music magazine that competed with Rolling Stone to define cool in the pre-internet era, Spin is no longer really a magazine. Yes, it has brought the magazine (and Bob Guccione Jr) back, but Spin is an IP company now. It puts on Spin Sessions events, sells t-shirts at Urban Outfitters, licenses its archive for streaming projects, and runs a record label with Randy Jackson. CEO Jimmy Hutcheson explains how a magazine brand has moved on to become a cultural brand that exerts influence (and

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45:56

The Daily Upside's niche strategy

The Rebooting Show ·

2025/04/08

Inn this episode, The Daily Upside's Patrick Trousdale explains how niche products like Advisor Upside and ETF Upside are helping the company move up the value chain. We also talk about paid growth, building a newsroom, and why journalism—not just distribution—is the long-term differentiator.

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55:53

Semafor's Rachel Oppenheim on stakeholder media

The Rebooting Show ·

2025/04/01

Stakeholder media is how a media company can stay influential and build a real business—especially now, when scaled ad models are in a full race to the bottom. Everyone wants to move from passive audiences to active communities. Stakeholder media is a variant. It’s defining features:Elite audiences operating in interconnected, complex ecosystemsFocused media, intentionally not for everyoneAbility to convene stakeholders with the brand as glueBusiness model geared to long term relationships vs

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45:24

Inside Dude Perfect’s highly profitable business model

The Rebooting Show ·

2025/03/25

An enduring challenge of the media business is finding leverage in models. This used to be fairly straightforward. Newspapers had leverage as quasi-local monopolies, Magazines had leverage that allowed Vanity Fair to pay a writer nearly $500k for three articles a year – and still be nicely profitable. And so on. It’s increasingly hard to find that kind of leverage beyond a few exceptions to the rule.The closest is likely in lean creator businesses that have created valuable intellectual property

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50:10

Morning Brew's Robert Dippell on moving into B2B

The Rebooting Show ·

2025/03/17

Morning Brew CEO Robert Dippell joins me to break down the fundamental differences between consumer and B2B media, why so many publishers underestimate the challenge, and how Morning Brew has built a thriving B2B business alongside its flagship newsletter. We also discuss the role of events, the shift to creator-led media, and why some of Morning Brew’s early growth strategies wouldn’t work today.Check out The Rebooting's new audience development research report, in collaboration with Omeda.

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53:32

Adam Ryan on why newsletters are a channel, not a...

The Rebooting Show ·

2025/03/10

Adam Ryan, CEO of Workweek, joined me this week to discuss his recent warning that the newsletter sector is overheated. Some points from the conversation:Newsletters are a commodity. The number of newsletters is growing faster than the number of readers. AI tools and cheap platforms like Beehiv have made launching one easy, but most newsletters lack true audience affinity.The inbox is not really a direct connection. It’s a platform like any other, subject to change. Apple’s Mail Privacy Protection

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52:58

B2B lessons for B2C

The Rebooting Show ·

2025/02/25

Sean Griffey, until recently the CEO of Industry Dive, joined me on The Rebooting Show to discuss the big things Industry Dive, and by extension a lot of B2B, got right.Sean was rarely mentioned in the collection of digital media CEOs of the recent decade. Yet Industry Dive achieved one of the standout exits of the category. He led the B2B publishing company to a $525 million exit to Informa. At the end of 2024, Sean left his role at Informa TechTarget to enjoy “semi-retirement.”I’ve found over the

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55:29

BuzzFeed's Jonah Peretti on where social media went...

The Rebooting Show ·

2025/02/17

BuzzFeed has always been a company that plays with the boundaries of media, technology, and internet culture. From its early days mastering viral content to its ill-fated attempt to build a sustainable news division, the company has been in a constant state of reinvention. Now, CEO Jonah Peretti is making perhaps his boldest move yet: transforming BuzzFeed into something more than just a publisher—into a social network.In Jonah's telling, this move springs from a frustration with the direction of

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45:19

Ad tech comes to TV

The Rebooting Show ·

2025/02/03

The worlds of TV and internet publishing operated separately. The platforms, the dynamics and even the language used was completely different. Linear TV was brand focused and driven by scarcity dynamics while the internet quickly became a direct marketing machine. Those divisions have nearly erased, thanks in large part to the rise of streaming.Once TV began to be delivered across IP it was inevitable that the digital ad system would be ported over to be married with what was formerly a stodgy

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59:45

The outlook for AI and publishing in 2025

The Rebooting Show ·

2025/01/28

This week, I'm joined by Pete Pachal, a publishing veteran who writes The Media Copilot newsletter that focuses on the intersection of the news business and AI. Pete and I discuss the recent breakthrough with Deepseek, and what it means beyond Silicon Valley and the stock market. We also get into how publishers are adapting to AI, why many of the product use cases are fairly basic to date, and how news consumption is likely to change as agentic AI takes off.

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54:12

Axios' Sara Fischer on the alternative media's growth

The Rebooting Show ·

2025/01/20

This is set up to be a banner year for alternative media. Axios senior media reporter Sara Fischer joined me on The Rebooting Show to discuss why institutional media has lost power and influence to an assortment of podcasters, YouTubers and independent creators — and steps it will take to adapt. Three key ones:Embrace curiosity. Much of institutional media feels like a set piece. Cable news shoutfests are obviously performative. Fact checks often come off as assembling facts to back up a preordained

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50:11

Big Tech in 2025

The Rebooting Show ·

2025/01/13

On this week’s episode of The Rebooting Show, I was joined by Alex Kantrowitz, who writes the Big Technology newsletter and hosts a podcast of the same name, in order to discuss the year ahead in tech platforms. We covered a lot of ground, including:The slightly unseemly kowtowing to the incoming Trump administrationOpenAI’s wonky economicsAlex’s bet on AI “companions”Why X has proved doomsayers wrongThe bright spot of individual creators amid a lot of media industry gloomCheck out the Big

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