Afleveringen
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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, itâs a buyerâs market.
AB breaks down the market for digital publishing assets â broadly those with page-based models â into three types of buyers:
HarvestersCAC jockeysVanity projects/rich person playthingsâIf you're a publisher with a mostly ad-supported site, odds are your business will be worth less next year than it is now,â 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 âwhen the going was good.â
âAny content they invest in has to be ROI positive within 30 days,â AB said. âYouâll never see them spend $20 million hoping advertisers show up. Those days are done.â
Other topics we covered:
How AI uncertainty is creating overhang that depresses valuations and makes long-term modeling nearly impossibleWhy the most resilient media businesses are lead-generation machines or conversion front-endsWe debate whether the Chernin Group content-to-commerce thesis was wrongHow Substackâs recommendation engine is the most efficient user acquisition channel in mediaWhat 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
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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 HubSpotâs 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.
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Zijn er afleveringen die ontbreken?
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Janice Min joins to talk about building The Ankler into a focused, profitable media brandâand 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.
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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.
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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 journalismânot just distributionâis the long-term differentiator.
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Stakeholder media is how a media company can stay influential and build a real businessâespecially 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. Itâs 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 transactionsRachel 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.
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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 â and still be nicely profitable. And so on. Itâs 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.
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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 Brewâs early growth strategies wouldnât work today.
Check out The Rebooting's new audience development research report, in collaboration with Omeda.
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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. Itâs a platform like any other, subject to change. Appleâs 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 thereâs 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 Lennyâs Newsletter all extend beyond just newsletters.Newsletters are a starting point, not a business. They are an MVPâa way to build an audienceâbut real success comes from expanding into new distribution and monetization channels.
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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 âsemi-retirement.â
Iâve 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. Thatâs because the people arriving werenât the âright people.â B2B isnât about reaching everyone.
Know who youâre 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.
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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 publisherâinto 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.
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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. Thatâs 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.
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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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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 â 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 Saraâs Media Trends newsletter. Axios CEO Jim VandeHei has spoken of the need to elevate âstars,â particularly as AI does Smart Brevity by default. The market will drive this as unique talent has more options than ever â 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 â leaving an opening for nonpartisan news, as hard as that is to pull off.Thanks to EX.CO for sponsoring this series.
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On this weekâs 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 administrationOpenAIâs wonky economicsAlexâs bet on AI âcompanionsâWhy X has proved doomsayers wrongThe bright spot of individual creators amid a lot of media industry gloomCheck 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.
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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 thatâs actually useful, as opposed to churning out affiliate content to arbitrage their brandâs 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.â
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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.
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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, Metroâs director of audience Sofia Delgado told me in a conversation at WordPress VIP Innovation Showcase in London.
âWe had a newsroom that came of age in the era of Facebook,â she said. âWe had a lot of bad habits and we were used to doing things quickly. Suddenly that wasn't working anymore.â
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.
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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.
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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."
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