Why sports are winning

The Rebooting Show

#Business News #News #Brian Morrissey

33:19

What’s the secret to lasting friendships? How does queer community show up through the ebbs and flows of life? And what’s the REAL story behind the “YMCA” song? In the first episode of Silver Linings, The Old Gays dive into an essential part of queer life: chosen family. They discuss the vital love, support, and sense of belonging that community provides, especially during life's toughest moments. They open up about what “queer” means to them, how chosen family has impacted their lives, and how to maintain close bonds over time–including their love for each other! “We’ve come a long way, baby.” Family isn’t just what you’re born with; it’s the people who show up, shape you, and stick around. See omnystudio.com/listener for privacy information.…

about a year ago 50:34

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Adam Mendelsohn operates at the nexus of sports, media, business and culture. Adam is a longtime advisor to LeBron James and his business partner Maverick Carter. He’s a communications advisor to many athletes and companies. And he’s recently rolled out his own sports platform, OffBall, which is something of a throwback to a pre-algorithmic era where Drudge report and other curators reigned supreme.

We discussed:

The genesis and vision behind OffBall, a new sports media venture
The long-term impact of "The Decision" on sports media and athlete communications
The shift towards human curation in content discovery
The evolving landscape of sports journalism and brand partnerships
The rise of women's sports and international leagues in the U.S. market
The importance of storytelling and character development in sports media

167 episodes

The Rebooting Show

Why sports are winning

The Rebooting Show

published about a year ago

MP3•Episode home

We discussed:

The genesis and vision behind OffBall, a new sports media venture
The long-term impact of "The Decision" on sports media and athlete communications
The shift towards human curation in content discovery
The evolving landscape of sports journalism and brand partnerships
The rise of women's sports and international leagues in the U.S. market
The importance of storytelling and character development in sports media

167 episodes

#Business News #News #Brian Morrissey

All episodes

The Rebooting Show

1
How the WSJ goes beyond ads and subscriptions 51:00

2 days ago51:00

51:00

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 is using the trust its journalism engenders to make money in new ways that aren't related to either ads or subscriptions, including events, executive communities and as a brand halo for Dow Jones information products.…

The Rebooting Show

1
Google Zero 33:07

10 days ago33:07

33:07

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 in a shifting landscape.…

The Rebooting Show

1
Henry Blodget on the media business in 2025 1:03:42

16 days ago1:03:42

1:03:42

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 recent research report about AI and personalization Attend The Rebooting's Online Forum with Recurrent and WordPress VIP on how Recurrent migrated its tech stack…

The Rebooting Show

1
Dynamo's Nicholas Carlson's pivot to video 1:06:42

23 days ago1:06:42

1:06:42

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 storytelling, distribution, and unit economics from day one. We talk about what it takes to start fresh in a mature platform ecosystem — and why the future of media might look more like TV than a homepage.…

The Rebooting Show

1
Anonymous Banker's bleak view of the media M&A market 1:06:09

29 days ago1:06:09

1:06:09

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: Harvesters CAC jockeys Vanity 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 still getting done, but the buyers are different. These are no-name PE firms above ice cream shops in the outskirts of Miami. We go through the list, which ranges from Valnet to Static Media to Savage Ventures to Regent. The playbook is to buy undervalued media properties, slash costs, and milk the programmatic revenue with hyper-lean models that rudely dispense with the nostalgia of “when the going was good.” “Any content they invest in has to be ROI positive within 30 days,” AB said. “You’ll never see them spend $20 million hoping advertisers show up. Those days are done.” Other topics we covered: How AI uncertainty is creating overhang that depresses valuations and makes long-term modeling nearly impossible Why the most resilient media businesses are lead-generation machines or conversion front-ends We debate whether the Chernin Group content-to-commerce thesis was wrong How Substack’s recommendation engine is the most efficient user acquisition channel in media What kinds of content investors still believe in (hint: high-intent verticals, not general news) Check out The Rebooting's new media product research report Sign up for The Rebooting's Online Forum on May 21 at 1pmET featuring a case study on how Recurrent migrated its CMS across a portfolio of sites without disruption…

The Rebooting Show

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Inside HubSpot's go-direct media playbook 50:56

5 weeks ago50:56

50:56

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 companies are better off thinking long-term rather than treating marketing like a vending machine. HubSpot's go-direct playbook offers a glimpse into how companies are rethinking owned media as a strategic asset, not just a marketing channel. Thanks to Marigold for sponsoring this episode. See how Hearst UK uses Sailthru by Marigold and Marigold Liveclicker to connect with millions of readers daily using personalization that feels one-to-one. From onboarding to retention, read to learn their winning strategy .…

The Rebooting Show

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The Ankler's Janice Min embraces more with less 1:04:00

6 weeks ago1:04:00

1:04:00

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 matters, and reflects on the changing power dynamics in Hollywood.…

The Rebooting Show

1
Spin's IP strategy 56:20

7 weeks ago56:20

56:20

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 monetizes) beyond its pages.…

The Rebooting Show

1
The Daily Upside's niche strategy 45:56

8 weeks ago45:56

45:56

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.

The Rebooting Show

1
Semafor's Rachel Oppenheim on stakeholder media 55:53

9 weeks ago55:53

55:53

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 ecosystems Focused media, intentionally not for everyone Ability to convene stakeholders with the brand as glue Business model geared to long term relationships vs transactions Rachel Openheim, CRO of Semafor, discussed with me how Semafor is centering its business on stakeholder media, and why that moves events to the center from the periphery.…

The Rebooting Show

1
Inside Dude Perfect’s highly profitable business model 45:24

10 weeks ago45:24

45:24

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 that can be monetized in various ways. Dude Perfect is a great example of this. The four dudes from Texas A&M went from viral trick-shot videos on YouTube to building a very profitable media franchise with diverse revenue streams Beyond YouTube ads, Dude Perfect developed business lines in merchandise, licensing and live events. It is a testament to the benefits of bootstrapping. According to an investor deck I saw, Dude Perfect grew to $35 million in revenue with over 50% EBITDA margins. That attracted a $200 million valuation in a funding led by Highmount Capital to expand the business. Andrew Yaffe, the Dude Perfect CEO who joined in October 2024 from the NBA , spoke to me on The Rebooting Show about how to build enduring franchise value in this kind of creator-led media business.…

The Rebooting Show

1
Morning Brew's Robert Dippell on moving into B2B 50:10

11 weeks ago50:10

50:10

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.…

The Rebooting Show

1
Adam Ryan on why newsletters are a channel, not a business model 53:32

12 weeks ago53:32

53:32

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 has broken open rates, AI tools like Superhuman summarize newsletters without opening them, and inboxes are being segmented, reducing visibility. Paid growth is a weak foundation. Many newsletters rely on paid acquisition and cross-promotion. The moment that engine turns off, engagement often collapses because there’s no real audience connection. Winners are thinking beyond email. The most successful publishers are building businesses around community, events, and services. Morning Brew, Workweek, and Lenny’s Newsletter all extend beyond just newsletters. Newsletters are a starting point, not a business. They are an MVP—a way to build an audience—but real success comes from expanding into new distribution and monetization channels.…

The Rebooting Show

1
B2B lessons for B2C 52:58

14 weeks ago52:58

52:58

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 recent years that the worlds of consumer and business publishing are coming together. It used to be they spoke differently and had different priorities. Now, you have publishers like Punchbowl and Puck executing B2B strategies. Semafor relies on events as the bulwark of its revenue model. Publishers are more likely to talk up their newsletters than ComScore numbers. Some of the lesions we discussed: Focus on a specific audience . Industry Dive would turn off ads if it had a story picked up by Reddit that led to a flood of viral traffic. That’s because the people arriving weren’t the “right people.” B2B isn’t about reaching everyone. Know who you’re writing for. A trick of B2B that narrows the focus: Write for a specific job title. Media properties nowadays can be messy, but they need to have a person in mind (and know enough similar people exist). Get receipts . Industry Dive focused its business model on marketing services and lead generation. In B2B, budgets are far greater for demand generation than branding or thought leadership. Do more with less. Industry Dive operated dozens of publications in verticals like wast management, retail, marketing and Tk. But it operated a single platform. That allowed it to quickly move to create new brands, even if it sacrificed unique branding elements. Go direct. Media companies have three core areas: creation, distribution and monetization. Sean criticizes consumer publishers for relinquishing control over distribution by chasing search and social traffic and monetization by relying on programmatic advertising middlemen. B2B media markets have developed differently, allowing companies to avoid those kinds of dependencies.…

The Rebooting Show

1
BuzzFeed's Jonah Peretti on where social media went wrong 55:29

15 weeks ago55:29

55:29

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 social media, as platforms have turned to adversarial algorithms that addict users and prey on human weaknesses. It's a different social media than the heady days of 2012-2015, when BuzzFeed mastered the art and science of creating shareable content. Jonah and I discuss the media landscape and why it's not too late to come up with an alternative social network built around joy.…

The Rebooting Show

1
Ad tech comes to TV 45:19

17 weeks ago45:19

45:19

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 world. That’s led to a stampede of the Lumascape to TV, which has always had better ad options than what was on offer on webpages. The promise of streaming with programmatic ad mechanisms is to marry the sight, sound and motion of TV commercials with the targeting and efficiency of programmatic. In this spotlight episode of The Rebooting Show, EX.CO CEO Tom Pachys discusses the transition of the TV ad model that is underway in streaming, the similarities and differences between TV and digital advertising, and why out-of-home is now a fast-growing ad category. Learn more about EX.CO's new CTV product .…

The Rebooting Show

1
The outlook for AI and publishing in 2025 59:45

18 weeks ago59:45

59:45

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.…

The Rebooting Show

1
Axios' Sara Fischer on the alternative media's growth 54:12

19 weeks ago54:12

54:12

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 conclusion. Some of the most popular and influential independent creators present as curious. Speaking truth to power is not enough. Build around trusted voices . Later this month, Axios will roll out a membership program built around Sara’s Media Trends newsletter. Axios CEO Jim VandeHei has spoken of the need to elevate “stars,” particularly as AI does Smart Brevity by default. The market will drive this as unique talent has more options than ever — and the risk:reward ratio is often scrambled in the Information Space as the solo path is less risky and offers greater potential rewards. Pick a lane. The current news market is geared to ideological publications The Free Press, The Daily Wire, etc – leaving an opening for nonpartisan news, as hard as that is to pull off. Thanks to EX.CO for sponsoring this series.…

The Rebooting Show

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Big Tech in 2025 50:11

20 weeks ago50:11

50:11

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 administration OpenAI’s wonky economics Alex’s bet on AI “companions” Why X has proved doomsayers wrong The bright spot of individual creators amid a lot of media industry gloom Check out the Big Technology newsletter and podcast . Learn more about TRB partner EX.CO 's expansion of its award-winning ad server to upgrade programmatic auctions in CTV and digital-out-of-home environments.…

The Rebooting Show

1
The end of affiliate arbitrage 56:14

21 weeks ago56:14

56:14

Mike Mallazzo, writer of the reliably excellent Zero Clicks newsletter from Martech Record and a veteran of digital publishing and marketing, joined me on The Rebooting Show to discuss the state of affiliate and what to expect in the category in 2025. The hopeful view: The efforts to stamp out affiliate arbitrage will ultimately reward those who put in the work to create high-quality content that’s actually useful, as opposed to churning out affiliate content to arbitrage their brand’s high ranking in the search results pages. As Mike points out, "Without huge arbitrage opportunities, affiliate is a bad business model... We had a 10-year golden era of arbitrage that made affiliate a great business model.”…

The Rebooting Show

1
How Gannett is adapting for an AI era 46:44

25 weeks ago46:44

46:44

In this live podcast, I spoke to Imtiaz Patel, chief consumer officer; Kristin Roberts, chief content officer; Jason Taylor, chief sales officer; and Renn Turiano, chief product officer. We discussed rethinking the article page, the imperative to provide a better user experience, why Google is so frustrating, using AI to drive subscriptions, and how AI answer engines are like Uber.…

The Rebooting Show

1
How Metro increased traffic by publishing less 13:48

26 weeks ago13:48

13:48

At Metro, the free London newspaper, the comedown from the traffic era was jarring. At the end of 2022, with Facebook turning off the traffic taps to news and a Google update hitting, overall traffic dropped in half, Metro’s director of audience Sofia Delgado told me in a conversation at WordPress VIP Innovation Showcase in London. “We had a newsroom that came of age in the era of Facebook,” she said. “We had a lot of bad habits and we were used to doing things quickly. Suddenly that wasn't working anymore.” The publisher pulled off a feat: By focusing on what was working, it has managed to increase its traffic by 50% by producing 25% fewer pieces of content.…

The Rebooting Show

1
Mark Penn on the state of the news business 33:34

28 weeks ago33:34

33:34

Stagwell CEO Mark Penn is a veteran of politics. In this discussion, he examines how shifting audience behaviors and trust patterns are reshaping where Americans get their news. The conversation delves into the thorny challenges of advertising on news content and why brand safety concerns are usually overblown. Penn outlines how news organizations can build sustainable businesses by adopting lessons from political campaigns, while warning that chasing ideological audiences risks further eroding media's broader cultural influence.…

The Rebooting Show

1
The new search wars 41:03

30 weeks ago41:03

41:03

AI-powered search engines have clawed a foothold in the critical search market that controls distribution on the open web. Media management consuling firm Activate estimates 15 million people are using these answer engines rather than Google, which is adding AI summarization to its results. By 2028, Activate expects that to rise to 36 million. The open question is whether publishers can stem this tide. Michael Wolf, the CEO of Activate, sees a fundamental shift in the search market, as generative AI can currently handle about 40% of searches as an open web discovery tool. He expects the rest of searches will follow suit over the next five years as the fundamental nature of the open web changes. This will lead to search becoming the front end to what Wolf calls "gated web discovery" and eventually "discovery-led transactions."…

The Rebooting Show

1
The evolution of Blockworks 43:52

31 weeks ago43:52

43:52

Blockworks CEO Jason Yanowitz discusses how Blockworks has evolved the company from an events business to podcast network to news provider to becoming a data and information play with media, events and franchises feeding the core data and research business. This kind of shift is hard to pull off. Among the issues we discuss: Using podcasts for broad reach and affinity News as a credibility driver Pulling back on B2C events to focus on B2B Using media to drive “negative CAC” for information services Implementing a “house of brands” strategy…

The Rebooting Show

1
Defector’s Jasper Wang on slow growth 55:22

32 weeks ago55:22

55:22

Defector Media, the sports and culture publication launched four years ago by former Deadspin writers, is an example of the mixed picture for the future of the media business. On the plus side, it is a profitable, employee-owned publication with 42,500 paying subscribers supporting a $4.6 million business. At the same time, the company saw revenue growth drop to 2.2% from 18% last year and 16% in 2022. Defector's Jasper Wang joined me to discuss Defector’s plans to expand its ad revenue, the inevitable challenges of fast decisionmaking in an employee-owned business, the “lean stack” approach of outsourcing as many publishing and corporate functions as possible, and the growth of its Normal Gossip podcast and diversification of Defector’s audience.…

The Rebooting Show

1
Building independent media businesses 1:10:53

33 weeks ago1:10:53

1:10:53

I was joined by Reid DeRamus to discuss the strategic and tactical decisions that go into building an independent media business. We discuss everything from choosing a business model, using the leverage of individual reputation, the value of consistency and authenticity, the mistake of over-reliance on optimization techniques, and the challenge of growth as tried-and-true methods wane in efficacy.…

The Rebooting Show

1
AI in the newsroom 48:25

34 weeks ago48:25

48:25

In this Spotlight episode, Josh Brandau, CEO of The Rebooting partner Nota, discusses how AI can be a critical tool for newsrooms in a more-with-less era. osh is a publishing veteran having been CRO and CMO at the Los Angeles Times. That informed his decision to create Nota since like other publishers he saw legacy media struggling to adopt technologies that underpin sustainable businesses. We discuss the inefficiencies inherent in a lot of newsrooms that end up taking scarce resources away from the actual news reporting, and how tasks like versioning, content optimization, SEO and tagging can be sped along with an AI assist. We also take a big picture view of where journalism goes in an AI world, licensing as a growing revenue source and how AI could create other new revenue streams as publishers inevitably move beyond efficiency and begin to create new products that improve the customer experience.…

The Rebooting Show

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Fitt Insider's Anthony Vennare on niche media models 54:30

35 weeks ago54:30

54:30

Fitt Insider , a media brand for the fitness and wellness industry, is a good example of the type of media brand that hits on many of the current trends in the industry: Niche. The fitness and broader wellness industry is a growing area that will only expand. B2B. The most robust media models are B2B or targeting influential audiences with similar approaches. Direct. Fitt relies on podcasts for engagement and its 100,000 email subscriber list for audience data and a direct connection. Organic. Too many newsletters are growth hacked. Fitt Insider has traded slower growth for a quality list that has open rates near 75%. Expertise . Fitt Insider’s founders, Anthony and Joe Venare, are fitness industry experts, having owned gyms and invested in the space. Media flywheel. The best media models tend to make most of their money in media-adjacent areas. For Fitt, this is through its recruiting and consulting arms. Anthony Vennare joined me on The Rebooting Show to break down the Fitt Insider model, and how he views media more expansively. That’s led him to forgo the typical ads and marketing heavy approaches to monetization.…

The Rebooting Show

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How Front Office Sports went from college project to $10m in revenue 48:36

36 weeks ago48:36