The Rebooting Show

On this week's episode of The Rebooting Show, I spoke with Vox Media president of revenue and growth Ryan Pauley about how the publisher has become a podcasting juggernaut, with Pivot, Decoder and Today Explained franchises. Ryan discusses the “Lego approach” that snaps together different business models, with some podcasts as owned and operated and others as partnerships. We also get into the rebundling and how media companies like Vox can link with creators to provide the sales and distribution infrastructure most independent media operators will not build.

We held a live recording of The Rebooting Show from the Hearst House in Cannes. I spoke to Cosmopolitan editor-in-chief Willa Bennett and Hearst global CRO Lisa Howard about how Cosmo is evolving from a magazine and website into a multiplatform brand that aims to establish itself with a new generation as its guide to love and relationships. In this phase, a brand like Cosmo's social handles on Instagram (4 million followers) and TikTok (890k followers) are just as important as the print magazine, which is now published quarterly.The days of “50 Ways to Drive him WILD in Bed” are long gone. It's taking a more nuanced view of love and relationships with projects like the video series Blind Date and Cosmo Sports, a new franchise spotlighting women athletes. We also discussed doing more with less, how Cosmo's next phase is more about creating IP, custom projects like the resale collab with DePop and events like its partnership with Bumble for the Valentine's Day Love Ball.

On this crossover episode, Semafor's Ben Smith and Vox Media's and Business Insider's Peter Kafka join me to discuss the quickly vanishing divide between institutional media brands and independent upstarts. This is the second part of three part conversation. To listen to part one, visit Semafor's Mixed Signals. Part 3 is available on Vox's Channels. Mixed Signals with Ben Smith and Max Tani - https://link.chtbl.com/SemaforMixedSignalsChannels with Peter Kafka - https://pod.link/recodemedia

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 products.

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 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.

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 personalizationAttend The Rebooting's Online Forum with Recurrent and WordPress VIP on how Recurrent migrated its tech stack

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.

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 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 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 Substack's 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 reportSign 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

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.

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.

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.

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.

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 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.

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.

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.

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.

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.

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 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.

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.

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.

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 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.

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.”

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.

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.

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.

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."

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 affinityNews as a credibility driverPulling back on B2C events to focus on B2BUsing media to drive “negative CAC” for information servicesImplementing a “house of brands” strategy

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.

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.

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.

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.

This week, I was joined by one of my favorite media entrepreneurs, Adam White. Adam has built Front Office Sports from a college project to the $10 million in revenue mark, with backing from Jeff Zucker's Redbird IMI.Some of the topics we covered:Why investing in creative strategy is critical to break through with big brands. The “faces and franchises” approach. The limits of built-if-sold projects. The decision to put off subscriptions.

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 ventureThe long-term impact of "The Decision" on sports media and athlete communicationsThe shift towards human curation in content discoveryThe evolving landscape of sports journalism and brand partnershipsThe rise of women's sports and international leagues in the U.S. marketThe importance of storytelling and character development in sports media

This week marks an important moment in the history of digital advertising as the U.S. Department of Justice presses its case that Google is a monopolist in ad tech. The seeds of this case were planted in 2007, when Google bought DoubleClick, a critical piece of internet advertising infrastructure that was widely used by advertisers and publishers in running ad campaigns. With DoubleClick in the fold, Google methodically grew to dominate all phases of digital advertising by piecing together a full stack solution for ad tech, supplying the tools used to both buy and sell ads as well as the exchange used for transacting. And Google was the biggest source of demand for the exchange. The go-to comparison of this situation is if Goldman Sachs owned the New York Stock Exchange.On this week's episode of The Rebooting Show, I spoke to Ari Paparo, a former DoubleClick executive and ad tech veteran who now runs Marketecture. Ari, in addition to being the funniest person in ad tech, knows the history. We go back in time to when the Google-DoubleClick deal took place, just as programmatic advertising was becoming a reality, and get into the weeds about why controlling the plumbing of digital advertising created an unavoidable set of misaligned incentives.

Scott Messer is founder of media advisory firm Messer Media and former svp of media at Leaf Group. Scott is in the weeds on the digital ad ecosystem, and he broke down the current state of play for publishers. We discussed why traffic declines are still the No. 1 challenge for publishers, why publishers are shifting from traditional monetization mechanisms, retail media as potential allies, and why “curation” is the latest hot new trend in ad tech, even if it sounds quite a lot like what ad networks have always done.

In a spotlight episode of The Rebooting Show, I spoke with Affinity Global CEO Lavin Punjabi for his view of how publishers adapt their affiliate operations. Affinity operates NucleusLinks, an affiliate operations platform that serves as something akin to Google Ad Manager for affiliate operations. Some takeaways:Many publishers are playing catch up. Affiliate marketing is one of the oldest internet business models, with its growth turbocharged by the ease and rise of e-commerce. Many legacy publishers were behind in adopting affiliate models, seeing performance ads as scraping the bottom of the barrel compared to impression models. “The biggest publishers in the world are scrambling to compete in this area that they kind of ignored for a generation,” Lavin said.Affiliate stresses silos. The entire idea of affiliate runs contrary to the notion of church and state. At one of The Rebooting's dinners focused on commerce, I heard a large publisher lament how the editorial team would battle to control personal finance reviews rather than the commerce team. They were basically working against each other internally. "Some publishers it's the main thing, but for a lot of marquee publishers, it's a department, and they have to figure out where it fits because it's not really editorial, but it's not really sales."Dotdash Meredith is an anomaly. Dotdash Meredith is the manifestation of these worlds colliding, with the internet-native Dotdash taking over the legacy Time Inc publications. It's telling that as publishers sound the alarm over AI, DDDM has weathered this storm and returned to growth. "They came from a commerce first angle, which is operated with CPS for a large degree. And then eventually with Meredith, which was CPM, they tried to find middle ground."

On this week's episode of The Rebooting Show, I was joined by Ana Andjelic, a veteran brand executive and writer of the Sociology of Business newsletter. I wanted to try an episode with Ana because we focus on different ends of the media ecosystem. Among the issues we discuss:The internet's impact on brands. “It forces you to compete on everything other than on brand. You compete on price, convenience, product recognizability, speed of your supply chain."​Product-led branding. “It's starting with that iconic original product, using different wear stories, wear scenarios, different subcultures, to give it identity."Why DTC brands were really performance marketing companies. “A lot of brands, especially in the DTC era when money was free, thought they would build demand by buying Facebook ads, Instagram ads, search and so on."The limits of performance marketing. "Performance marketing is not going to build your demand. There needs to be something else that tells people to search for it or click on the ad.”

This week, we are wrapping up a series on The Rebooting Show that examines the role of product at a time of distribution and monetization shifts. The twin themes that emerged are that publishers are increasingly focused on direct relationships with audiences and are in a back-to-basics mode of focusing product resources on critical business objectives, which often rely on loyalty. And the looming question: How will AI be used to make these businesses more effective while not losing their distinctiveness in a sea of artificial slop.Brian Alvey, CTO of WordPress VIP, discussed with me how AI's impact on publishers' day-to-day operations will be felt first and foremost on mundane tasks that end up eating up a lot of resources. The early efforts to embed AI within the publishing process were predictably ham-handed. Using ChatGPT to create AI slop is hardly innovative – and unlikely to be very effective. I'm very skeptical of creating much value out of using AI to churn out tons of aggregation newsletters, for instance.The most immediate opportunities in the content process lie in areas like tagging, inserting links to related articles, testing headlines and the like. As Brian warns, there's no point in using AI in a way that eliminates the competitive advantage of having a distinct voice.Some highlights from our conversation:On the site as a requisite for an independent path: "If you want to be around in five years, I think so. Don't you like why would you has nobody ever learned that building up and like no offense to any of these, you know, what I call bastard gatekeepers that take your audience away from you."On where AI's impact will be felt: "People probably overestimate the amount of things that AI is going to help them automate of what they do today. They underestimate how many things they're just not doing because it's so hard that AI is going to let them do."On AI's use within the content creation process rather than creating content: "Some parts of that [process] can absolutely be handled by modern generative chat, GPT-style, LLM AI."​On distinctiveness in an AI era: "Be remarkable, No. 1. That's how you'll stand out from a sea of junk."On being product-minded vs a tech company: Publishers “should be product minded. They are creating a product for people to consume. They should have product talent. If you are the New York Times, you have a thousand product people. If you are somebody else, you have 10. But no, they shouldn't be a technology company."​

At the Media Product Forum earlier this month, I spoke with Gannett head of product Renn Turiano, Hearst Newspapers chief commercial officer Bridget Williams and Millie Tran, chief digital content officer at the Council on Foreign Relations. The conversation revolved around the shifting product priorities at publishers at a time when the weight of most publishing businesses is shifting from catering to the whims of platforms to a more independent path. That requires a change in focus to satisfy user needs, as well as the need to identify and serve various audience segments. We spoke about how all three organizations are tackling this. Thanks to WordPress VIP, which partnered with The Rebooting on the Media Product Forum.

At last week's Media Product Forum, which The Rebooting held in collaboration with WordPress VIP, I had a discussion with Dotdash Meredith chief product officer Adam McClean and The Daily Beast svp of product Samantha Winkelman about their respective product strategies. While both owned by IAC, the publishers are at vastly different sizes, with The Daily Beast having three people in product to DDM's 75. The connective tissue of both: A focus on audience needs.

In a session recorded at The Media Product Forum in NYC, Bloomberg Media global head of product Marissa Zanetti-Crume shares how the media organization takes an audience-focused approach to building products. Marissa highlights the importance of understanding user behavior, particularly the shift towards personalized, relevant content delivered efficiently. She shares insights on Bloomberg's recent homepage redesign, the role of AI in enhancing user experience, and the strategic decisions driving their product development.

In a discussion held in Cannes, I sat down with Jason White, chief product and technology officer at The Arena Group, and Johanna Bergqvist, general manager of the managers at The Rebooting partner EX.CO. A part of the conversation that resonated was how White has zeroed in on revenue per session as what he calls the “God metric” that prioritizes session depth over raw page views. This is a recognition that traditionally digital media publishers have focused on eyeballs without understanding the intrinsic value of user engagement."The days of not knowing the value of your audience and your content are kind of gone,” Jason said. “Marketers forever have had CRM experts; they know their audiences, they know the value of their users, the value of their products, their margins, etc. We've played an eyeball game for the past 30 years in digital media."The benefits:Organizational alignment. As highlighted in The Rebooting and WordPress VIP's recent research, internal misalignment bedevils publishers. Different groups pursue different goals. The horror show of many webpages is a sign of internal misalignment and “shipping the org chart.”True personalization. There's no personalization without understanding the person. RPS allows The Arena Group to figure out not just how best to serve visitors – “Is this a younger audience that wants to consume video?” Johanna said. “Let's take them down more of a video path." – but how best to make money from them. Publishing is increasingly a game of finding the high value audiences within a mass of impressions.Resource allocation. The more-with-less era is a reality. It requires making hard choices about where to spend and where to cut. Having alignment on a KPI makes these choices somewhat easier, if no less painful.

In a session recorded at the Cannes Lions, Hearst Magazines CRO Lisa Ryan and Jen Dorre join the show to discuss how the publisher is responding to the shifts in advertising to performance-focused channels, including retail media and platforms. Skip to topic:00:00 Introduction01:36 Realism in Publishing and Growth Strategies04:45 Focus on Audience and Data Utilization07:33 Innovative Ad Products and Consumer Engagement13:03 Challenges and Opportunities in Attribution14:26 The Role of Brand Storytelling16:37 Hearst's Commerce Business18:53 Understanding Consumer Behavior with AI20:39 The Future of Programmatic Advertising24:04 Premium Ad Strategies for Publishers

In this episode recorded at the Dotdash Meredith villa in Cannes, Dotdash Meredith CEO Neil Vogel and Axios senior media reporter Sara Fischer discuss the impact AI is set to have on the publishing business.Skip to topic:00:00 Introduction03:04 Challenges and Opportunities in Publishing05:44 The Role of Algorithms in Media13:02 AI Deals and Legal Considerations22:47 AI's Impact on Business: Myth vs. Reality25:38 The Future of Print and Digital Media31:36 The Role of Credibility and Relevancy in Content37:41 Adapting to the Digital Advertising Ecosystem40:43 The Challenge of Intermediation in Publishing42:58 Embracing Change and Enjoying the Chaos

This episode from Cannes of The Rebooting Show, presented by Outbrain, features David Kostman (CEO of Outbrain), Kate Scott-Dawkins (Global President for Business Intelligence at GroupM), and Johanna Mayer-Jones (chief advertising officer of the Washington Post). They discuss the ad market's growth contrasted with the decline in ad revenue for news publishers. Emphasizing the value of trusted journalism, they explore the importance of advanced audience targeting and AI in creating brand-safe environments. The conversation highlights the need for new strategies and better communication to showcase the value of news audiences to advertisers.Skip to topic:00:00 Introduction01:43 Panel Introduction and Discussion Overview02:07 Ad Challenges in the News Business06:31 Impact of Keyword Block Lists08:19 Brand Suitability and Safety23:23 Performance Marketing Trends

Semafor editor in chief Ben Smith sees a fragmenting media landscape and impatient owners running headlong into the peculiarities of newsroom culture, where bosses have never had an easy time. Enter the hard-charing Brits. Also: check out Ben's new podcast, Mixed Signals, in which Ben and co-host Nayeema Raza unpack the real conspiracies of modern media. Skip to topic:00:54 Introducing Ben Smith and Mixed Signals04:14 Podcasting and Media Expertise09:09 Challenges in Modern Newsrooms20:11 Unionization and Media Management23:40 The Washington Post's Third Newsroom26:19 Semaphore's Journey and Business Insights28:37 BuzzFeed News: Reflections and Lessons35:28 AI in Journalism: Opportunities and Challenges41:55 Starting from Scratch: Advantages and Strategies43:22 The Role of Journalists in Modern Media

In the wake of Jeff Bezos buying The Washington Post in 2013 and the heady “Democracy Dies in Darkness” days following the 2016 election, The Washington Post was considered a credible rival to The New York Times. That's no longer the case. New CEO Will Lewis is embarking on a turnaround at the Post, which lost $77 million last year. As Lewis put it, “We are in a hole, and we have been for some time.” On this week's episode, Matt Cronin, founding partner of House of Kaizen, joins to discuss the Post's strategy as laid out by Lewis.Skip to topic:00:00 Introduction and Breaking News01:00 Challenges Facing the Washington Post02:20 Industry-Wide Transitions03:51 Engagement and Product Strategy05:49 Podcast Introduction and Format06:12 Will Lewis's Turnaround Plan09:29 Subscription Models and Audience Segmentation22:13 Historical Context and Missed Opportunities28:06 Peak Subscription Debate31:47 The Paradox of Choice in Consumer Behavior35:52 Volume vs. Value in Subscription Models42:09 Challenges of Subscription Tiers46:40 B2B Opportunities for News Organizations51:59 Microtransactions in Media

Publishing is shifting from prioritizing breadth to rewarding depth. That starts with understanding the audience — and its segments — more granularly in order to create a more sustainable and varied business foundation. Cory Munchbach, CEO of BlueConic, shares her view of the next chapter.Skip to topic:00:00 Introduction and Media Challenges01:02 Welcome to The Rebooting Show01:44 Discussion on Audience vs. Consumer03:38 Key Takeaways from the New Growth Agenda07:22 Challenges in Media Transformation09:37 The Role of Technology and Organizational Structure13:01 Existential Threats and Industry Nostalgia18:22 Adapting to a Consumer-First Strategy25:59 Navigating Data Collection and Audience Insights30:16 The Role of AI in Audience Understanding36:00 The Future of Personalization and Content Delivery38:55 Transparency, Privacy, and Value Exchange44:47 The Future of Advertising and Publishing

Scott Porch, founder of Big IP, which operates the business side of several popular lifestyle podcasts like The John Campea Show, Happy Sad Confused, Star Wars Explained, discusses that state of podcasting, and how it is morphing. He acts as something of a talent manager in expanding these podcasts into more well rounded media companies, with revenue coming from memberships and events. The growth of these businesses will not be driven by ads necessarily. "Podcasters are influencers in a lot of respects and they monetize like an influencer in a lot of respects,” Scott noted.Skip to topic:00:00 Navigating the Complex World of Podcasting and Monetization01:25 Introducing Scott Porch: The Podcasting Pro02:31 The Intricacies of Podcast Production and Distribution07:33 Exploring the Podcast Landscape: Growth, Challenges, and Opportunities15:25 The Evolution of Podcasting: From Audio to Multi-Platform Engagement19:30 The Future of Podcasting: Diversification and Creator Economy26:25 Understanding Podcast Subscriptions and Membership Models35:06 The Realities of Podcast Touring37:52 Monetization Strategies in Podcasting42:14 AI's Impact on Podcasting and Content Creation48:36 The Debate Over Long-Form Podcasts53:23 Challenges and Strategies in Podcast Distribution58:50 Sponsorship and Monetization in the Podcast Industry