The Rebooting Show (Brian Morrissey)

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.” 

This week on The Rebooting Show, I spoke to The Juggernaut’s founder and CEO Snigda Sur. We discussed the need she saw for a publication focused on South Asians, going through Ycombinator as a media company, using subscriptions as a base of a business model and more. Listen on Apple, Spotify and other podcast services.

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 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 News
• 01:00 Challenges Facing the Washington Post
• 02:20 Industry-Wide Transitions
• 03:51 Engagement and Product Strategy
• 05:49 Podcast Introduction and Format
• 06:12 Will Lewis's Turnaround Plan
• 09:29 Subscription Models and Audience Segmentation
• 22:13 Historical Context and Missed Opportunities
• 28:06 Peak Subscription Debate
• 31:47 The Paradox of Choice in Consumer Behavior
• 35:52 Volume vs. Value in Subscription Models
• 42:09 Challenges of Subscription Tiers
• 46:40 B2B Opportunities for News Organizations
• 51:59 Microtransactions in Media

Semafor, backed by $25 million in private investment, has (finally) launched, marking possibly the most ambitious attempt in recent years to build a new global news brand. At the heart of the effort is an attempt to restore trust in media by rethinking the journalistic product. Despite the long history of failed attempts to "reinvent the article," Justin sees a glaring need to unbundle the article to clearly delineate factual news from analysis and opinion, while providing the context of the news along with countervailing views. 

Matt Reustle, CEO of Colossus, a business-focused podcasting network that’s home to Invest Like the Best, Business Breakdowns and Founders, sees podcasting as an antidote to many of the ills of algorithmic media.

“To me, it's the highest trust media. I think everything else now lacks nuance. And I actually still care about nuance. There are shorter attention spans, which I completely understand. Where do you actually get time to hear someone talk about opinions that aren't scripted? Is it proper back and forth conversation, not just a bunch of us talking at one another on Twitter and replies aren't really constructive conversation?”

We spoke about why podcasts excel at nuance, the business models underpinning the business, and why subscriptions haven’t yet become as widespread in podcasts as other digital media formats.

The Bitter Southerner began as a passion project for a group of natives to the South who were, well, a bit bitter about how it was often caricatured or reduced to its historical legacy as the birthplace of American slavery. That’s a past that is unfortunately still alive and is an indelible part of the American story. The Bitter Southerner confronts such issues head on but while telling a more nuanced and expansive story of this unique and yes complicated part of the world. 

Kyle Tibbs Jones, a co-founder of The Bitter Southerner, joined me to discuss the decade-long effort to build a sustainable, independent publication.

Bloomberg Media CEO Scott Havens sees AI as both challenge and opportunity for publishers, who at this point are used to rapid changes to how their content is distributed. The challenge is how AI is poised to have the biggest impact on search since Google's rise to be the dominant distributor of internet traffic. The opportunity is to use the AI tools to create better experiences and more resilient business models. "There's no use in crying over spilled milk," Scott advises.

Substack’s Reid DeRamus talks about growing newsletter audiences. Reid and I have spoken for the past two years on this topic, going back to before Substack bought his company Yem, which was focused on building a growth engine for newsletter writers. The thing about growth, at least I’ve found, is it takes a long time for most people. It’s taken me over two years to get 12,700 subscribers. I always tell people to take with a grain of salt the overnight success stories of newsletters that amass 250,000 subscribers in less than a year. They are remarkable because they are unusual, and the people running them are likely experts in marketing while most of us writing are not.

Recommendations is Substack’s No. 1 feature it has rolled out. It needed to provide that distribution function to publishers. Otherwise it would just be a newsletter CMS with Stripe integration. Recommendations are now responsible for 40% of new free subscriptions to Substack-hosted publications. Reid and I discussed that dynamic and other features Substack is rolling out to increase the number of people who covert to paid subscribers.

The crypto winter has pitched the giddy excitement over the endless possibilities of Web3. The drumbeat of negativity hasn’t shaken Time president Keith Grossman’s confidence in Web3 providing a new path to sustainable business models. Time, now under the ownership of billionaires Marc and Linda Benioff, has become the most aggressive large publishing brand in exploring the possibilities of Web3. To date, Time has:

• Minted iconic covers as NFTs and generated nearly $500,000 in proceeds
• Collaborated with artists to reinterpret Time covers as part of the Timepieces Web3 community
• Dipped its foot in the metaverse with a Galaxy Digital deal to create a metaverse newsletter and a metaverse category of the Time 100.
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“I started to see collaboration. I started to see Web 2.0  is about the audience, but Web3 is really about community,” Keith told me on this week’s episode of The Rebooting Show. “I started to see a different way in which brands could evolve. “

Flying, a 95-year-old magazine publisher focused on amateur pilots, is on this path. Craig Fuller, CEO of Freightwaves, bought Flying in July 2021 and a key part of the growth plan he and COO Preston Holland have begun is a massive bet on so-called air parks, basically resort communities with ample space to park your plane at your home. The Fields is a 1,500-acre development in Tennessee’s Sequatchie Valley that’s due to open next year. Plans call for 800 homes, 180 “vacation villas,” a runway and many private hangars for people to park their aircraft. The Fields is billed as “a luxury fly-in community for pilots, by pilots.”

The approach is somewhat akin to how Freightwaves uses its media arm in order lower the acquisition costs of its data business. Done right, this allows for taking a longer view of the value of different content products. For instance, Flying’s new management decided to keep the print edition and double the production cost to improve the quality.

“Marrying [editorial] with some other monetization strategy allows for you to make some decisions on the media side that you wouldn't necessarily make if you're trying to make all your contribution [margin] on the media side," Preston said.

Ari Paparo is a longtime ad tech veteran, not to mention holding the disputed title as Funniest Person in Ad Tech. Some highlights from our conversation:

Innovation requires fragmentation. Ad tech’s complexity is a longtime talking point. And it is undeniably a convoluted supply chain that’s given the veneer of plausible deniability to all kinds of corner cutting, at least in my experience as an observer for many years. But Ari points out that “innovation requires fragmentation,” and besides, many of those pushing an anti-complexity narrative just happen to have “anti-complexity solutions” to sell. Go figure.

Small publishers can opt out. Google is the simple ad tech solution. Most small advertisers can just default to Google and Facebook. But larger enterprises gravitate to more complexity simply because they have more complex businesses.

Apple overturned the industry. Cynical or not, Apple’s use of privacy to restrict data flows has upended how the industry operates and will operate going forward.  It’s of course no coincidence that these privacy restrictions hurt their rivals in Meta and Google. “There's no love lost between those companies, so hitting them in the kneecaps was kind of fun,” Ari said.

The Rebooting recently wrapped up its second research project in collaboration with BlueConic. Patrick Crane, vp of sales at BlueConic, joined me on The Rebooting Show to discuss the state of subscriptions at publishers and the maturation of the market. 

“One of the reasons I call it a forever business is to call out the fact that there is going to be ongoing work,” Patrick told me, “but also that it sets you up to play a very sustainable game.”

Among the topics covered:

• The shifting role of steep discounts in subscription programs
• Why ad avoidance is really more bad UX avoidance
• The wisdom of making subscription products for specific slices of your audience
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Check out "The State of Publisher Subscriptions" report.

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.

My former colleague Mike Shields of Next in Media joins me to discuss what to make of Advertising Week, which is mostly a PR vehicle but a useful gauge of the prevailing winds of the media and advertising worlds.

Stephanie Kaplan Lewis founded Her Campus in 2009 with Annie Wang, and Windsor Western as college undergraduates. They saw a need for college women to have a publication made for them by other college women.

Her Campus has grown since then as a profitable, growing media business with 85 employees. Stephanie says Her Campus expanded revenue by 50% last year – and did it with an entirely ad-focused business model. Stephanie credits the growth in large part to building a long-term business that works in any environment rather than a specific environment, such as the easy-money era that’s now in the rear-view mirror.

The twist is that Her Campus is part agency, part publisher, with campaigns leaning on experiential and influencer marketing. This is a path many publishing models will go, as the economics of relying on putting ads on webpages or newsletters grow more difficult. Stephanie and I discuss:

The forced discipline of a bootstrapped model. Her Campus has been profitable for all 15 years of its existence. Imagine.

Not aging up with the audience. Her Campus turns its audience over by design, as it stays focused on college women. When it started, Her Campus was for millennials, and now it’s for Gen Z. 

Being part agency, part publisher. Her Campus ends up with other media companies as customers. 

Doing the basics well. In the media business, strategy is overrated. Execution tends to play a bigger role in separating winners and losers. That means doing the boring things well: Setting achievable sales goals and hitting them, excelling at client service, collecting receivables and such.

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.

Last Thursday, I spoke to Substack CEO Chris Best to get a better understanding of where the company is going. We recorded the interview before Elon Musk threw a temper tantrum over Substack's coming Twitter competitor. Chris and I spoke about a couple of important issues to me: ads and bundling. On ads, Chris explains that Substack is trying to occupy a part of the market on an opposite pole from the attention grabbing part of digital media defined by platforms like Facebook and TikTok. But he allowed that ads could be done in a way that makes sense for the space Substack wants to occupy. On bundling, Substack is opposed to a "subscribe to Substack" option that obviates the direct relationship with individual publishers. Instead, he's more interested in "writer federations" and reader-directed bundles that get the upside of bundle economics but don't tradeoff the direct relationship between the audience and publishers.

Scott Brodbeck got into local news a dozen years ago, after working in local broadcast news in Washington DC. “I looked at the direction of the industry and didn't love where local was going and ended up leaving and just on a total impulse to start my own site,” he said. “it was like a one day thing.” After this prototypical shower inspiration, Scott launched a local site to cover Arlington, Virginia.

Since then, Scott has built Local News Now into a clutch of local news sites for the Virginia suburbs near Washington, including ARLNow (Arlington), FFXNow (Fairfax) and ALXNow (Alexandria). The opportunity Scott saw was to make local news products that were different from the typical local news efforts from those coming from the newspaper industry. “The local news outlets that were focused on Arlington were meant for people middle aged and up, living in single -family homes and the more affluent parts of Arlington, Scott said of the time when he was in his 20s. “I wanted to launch something that was gonna speak to people my age.”

The business of hip hop is often overlooked, even though it's a massive business with outsized cultural influence. Dan Runcie saw this as an opportunity, starting Trapital in 2018. I wanted to talk to Dan about his approach to building an independent media brand. He’s already established himself and Trapital as an authority on the hip hop business. Trapital now has over 16,000 subscribers, with the publication supported almost entirely through sponsorships. Dan had earlier done a paid model, but pivoted to free when realizing he could reach far more people without the friction of a paywall – and a value proposition that appeals to sponsors like Moonpay, Convertkit and Alts..

Some takeaways from our conversation:

Hip hop punches above its weight. There’s a school of thought that niche business publications are best in “unsexy” areas, as Industry Dive showed in its focus on big nuts-and-bolts business sectors. But cultural industries have influence beyond their size. 

Trapital isn’t about news. Dan has made a point of saying what he does is not journalism but business analysis. Part of that is to be clear the product isn’t a tool for keeping up to date on the ins and outs of the industry. Instead of the play-by-play, Trapital focuses on the context with Stratchery-like essays on topics like “how The Weeknd mastered his brand” and “Beyonce’s streaming strategy, explained.”

The pivot from subscriptions. For the past couple years, all roads have led to subscriptions in publishing as the travails of the big digital publishers have cast a pall on the ad model. But as Industry Dive, Axios and others have shown, advertising can be the great focal point of a publishing business model – if the audience is a group that’s hard to reach and valuable. In 2018, Trapital scrapped its initial paid model. Often subscriptions are painted as a set-it-and-forget-it option, but making money is hard no matter the model, and subscriptions require constant selling and marketing. Dan saw as a one-person operation this was cutting into his focus. Instead, Trapital focused on an “influence” model that initially treated the newsletter and podcast as lead gen for consulting, while adding in advertising and moving into investing.

Going beyond solo. Trapital is working as a one–person business, but Dan wants to expand beyond just himself. The challenge is how to do this without losing the personal touch since Trapital’s brand is very tied into Dan’s perspective. 

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.”

Emma Tucker was named the editor-in-chief of The Wall Street Journal (and Dow Jones Newswires) in early 2023. She was brought in with a mandate to shake up the Journal in a media market that Emma describes as changed “beyond recognition.” The Journal itself has its own challenges: an aging subscriber base that’s pushing 60, a stodgy internal culture and often convoluted editing process that’s exacting yet hard to square in the current realities of publishing. Like other publishers (and companies), it also has a restive workforce.

Emma and I discuss the changes she’s instituted since joining, from the small bore like doing away with honorifics (RIP, messrs) and putting a cat on a front page to the more substantial changes in top personnel and overhauling the WSJ’s DC bureau. Her moves even led to a New York piece that wondered, “Who is going to get Tucked next?” (Her deputy is apparently known as an “angel of death,” which is a catchy LinkedIn endorsement.)

Some key takeaways from our conversation:

Transitioning from a “print ethos.” Print still gives publications heft, and I suspect that will become more valuable in a world filled with synthetic content, much of it utter crap. But that role is more of being a “shop window,” Emma told me the Journal needs a “definitive move away from print” to serving digital audiences rather than seeing the newspaper as a central distribution channel.

Adopting an audience-first mindset. It sounds obvious, but the challenge for many publishers is adopting audience-first strategies rather than trying to be all things to all people (and all algorithms). That was the main takeaway from a content review Emma commissioned soon after taking on the top role. Those exercises are usually preludes to organizational change. The main theme highlighted in the review: being an “audience-first publication for people that mean business.” Translation: more investigative pieces, less filler content, more “constructive journalism” that serves audience needs instead of winning Twitter/X.

Engagement is the new uniques. The traffic era of publishing has ended. Nobody brags about their ComScore uniques anymore; engagement is the new North Star. That’s particularly true in subscription models, which are natural outgrowths of audience-first strategies. With subscriptions, churn is the boogeyman. I found it telling Emma didn’t cite traffic numbers but highlighted that the Journal had decreased churn by 6% in the past year. The Journal has a newsroom dashboard that measures KPIs like guest visits, conversion rates, female readership, and young readership. 

Other topics we discussed:

• Why American journalists are prone to navel gazing
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• Balancing the need to attract younger readers without...

Christine Cook joined Bloomberg Media in March as global chief revenue officer. We spoke about reasons for media optimism, how AI is an opportunity (and a threat), and how Bloomberg is approaching programmatic as the data landscape changes.

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 pendulum always swings. Media regularly oscillates between periods of bundling and periods of unbundling. Bundles tend to rub people the wrong way because they feel they pay for stuff they don’t want. The downside is unbundling can be a complete hassle and the supposed savings quickly evaporate. Just look at what you’re paying now for various streaming services (themselves mini-bundles) instead of cable service. Inevitably, whether it’s the proliferation of newsletters or the many streaming products, we’ll see rebundling take off.

“The bundle was the absolute worst form of entertainment delivery, except for every other one,” said Human Ventures executive chairman Joe Marchese. “Consumers are looking for a rebundle and these streamers are gonna have some sort of rebundle coming. News and Substack has some sort of rebundle coming. Everything that's old is gonna be new again over the next couple of months.”

Other topics:

• Media is often a terrible standalone business but is good support for other businesses. The TV business is now dominated by tech companies, a trend likely to continue. That isn’t particularly new. “Media has historically been owned by non-media businesses,” Joe notes, going back to early radio and then cable systems owning TV networks. “The business of media has outsized influence but undersized monetization.” The result: “I don’t know the media business works at scale without alternative models.”
• The "permission to curate" is powerful. In a world of near-infinite media choices, people need some way to make sense of what’s good and what’s bad. That’s where trust comes into play. People can turn to algorithms like Google’s or Facebook’s to make sense of what’s important to them, or they can turn to publishing brands and individual brands. “Brands matter for the curation of goods and services so that people don't have the paralysis of infinite choice,” Joe said.
• Not everything is performance advertising. With ample data, sophisticated targeting and analytics, it can sometimes seem that brand advertising is an anachronism as the media world shifts firmly to “performance advertising,” or what used to be known as direct response.  “In a world where we have dynamic targeting and we know what each household is watching, the advertising experience is actually worse,” Joe said. “How did we get worse at advertising in a CTV advertising environment than broadcast television 40 years ago?”
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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.

6am City is turning to the newsletter to build out a network of 25 local news publications it says have 1 million cumulative subscribers and an open rate around 50%. After starting in Greenville, South Carolina, in 2016, 6am has expanded to markets like Madison, Wisconsin; Austin; Portland; and Indianapolis. The 6am formula is to keep new publications’ costs under $250,000, staff them with two-or three editorial staffers and four total employees, mostly making money from ads, both local and regional. It looks for markets based on a criteria developed, including income and education levels, inflows and outflows of residents, charitable giving and retail activity. It aims to get to profitability (and healthy 50% profit margins) in a market in two to three years.

Thanks to Jay Sparks from PodHelp.us for producing the episode.

The Guardian has used voluntary reader contributions as a bulwark of its unique model that blends philanthropy, advertising and voluntary contributions. In the U.S., The Guardian now generates 57%, or $33 million, of its revenue from voluntary contributions, either one-off or recurring. 

On this week’s episode of The Rebooting Show, I spoke with Steve Sachs, The Guardian’s U.S. managing director and veteran of non-profit news models, about this approach and how extensible it is for news publishers.

Forbes is a unique brand that has global cultural cachet that’s managed the transition from being a magazine business to a mostly digital business, with an emphasis on building its direct revenue as well as its brand extensions. Now, it's looking to plot a future business in which consumer revenue take a far larger role.

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.

Claire Atkinson, chief media correspondent at Insider, has long experience covering the ins and outs of the media industry. In this episode, we discuss the state of affairs as different parts of the media business are between eras. 

• What’s next for Vice and the other ailing big digital publishers? The usual answer would be more consolidation, but this time might call an bundling of assets to realize more value.
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• Streaming’s next phase. Disney’s shifts after Bob Iger’s return indicate a new era of sustainability after the free-spending ways of the streaming wars.
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• CNN and Fox News’ identity crises. As what is sure to be a bonkers presidential election campaign nears, the twin poles of the cable news universe are in their own forms of disarray.
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• The sports rights question. Sports programming continues to fetch higher rates as it basically props up many cable broadcasters. Tech platforms continue to tiptoe into this arena, but Claire explains why rights holders are unlikely to cast their lots entirely with subscription streaming platforms.
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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, 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.

This episode is sponsored by Kerv, which uses artificial intelligence to identify objects within video and match them to databases, enabling for, among other uses, the creation of interactive “shoppable video” that embeds commerce in entertainment

Kerv CEO Gary Mittman sees AI leading a sea change to the creative process, allowing for a movie franchise, for instance, to create sequels to the original without starting from scratch. For advertising, the changes are poised to be broader, with AI detecting ads that are not performing and automatically "fixing" them without much in the way of human involvement. “This is another revolution, and we're at a precipice of the creation of something new,” he said. Other highlights:

• Subscription fatigue. The land rush phase of the streaming wars is over. The pendulum is shifting from subscriptions to advertising. “People are not going to pay for 100 different channels at $5-$10 a month,” Gary said. “ It's just not going to happen.”
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• The “Jennifer Aniston’s sweater” moment. In ancient days – think 2005 – a staple of what were then called internet conferences was the idea that you’d be able to watch “Friends” and tap to buy a Jennifer Anniston sweater set. Much of the tech wasn’t ready, much less the consumer behavior, but that’s changing. “There's a long road of dead bodies to get here,” Gary said.
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• QR codes are changing behaviors. Of all the changes of the pandemic, the comeback of QR codes was among the least likely. Now, it’s the norm to see QR on TV ads, shifting consumer behavior. “The capability of having a one-click transaction off of television with your remote is where we're heading,” Gary said.
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Morning Brew is a breakout success in digital media, turning an email newsletter of business news delivered with a witty tone, into a robust digital media business that now has over 4 million email subscribers, with another 1 million to its growing stable of vertical industry email newsletters.Now, Morning Brew is focused beyond its original product, the daily Morning Brew publication, by building a roster of five B2B offshoots, with two more in the works, in addition to podcasts and video shows. A key growth area: individual creators. The bet: Morning Brew can use its infrastructure – editing, production and, crucially, monetization – to partner with creators who don’t want to do it all on their own.

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.

This week, I caught up with Larry Fitzgibbon, the CEO of Tastemade. I think of Tastemade as an original digital video brand, ahead of its time in many ways since it was founded back in 2012, before streaming was even a thing. This was an era when online video was still mostly about webisodes nobody watched and YouTube’s famed dog on a skateboard videos. Tastemade has been at the forefront of many trends, as it is now with its focus on everything from IP to subscriptions with Tastemade+ and recreating the modern version of the cable channel. 

Brian Hanly, CEO of Bullish Studio, is creating media brands from memes, working with a stable of finance meme accounts in particular to build media properties. I got to know Brian over the pandemic, and quickly became fascinated by Bullish’s business. No doubt much of the fintech media segment was helped along by ZIRP and crypto craziness, but the use of memes as the starting point for lightweight media businesses is a good template as we enter into what’s sure to be another crazy cycle for the media business.

Begun as a meme account in 2017, Litquidity has amassed 1 million social media followers across Instagram, Twitter, LinkedIn and TikTok, specializing in the dark arts of “dank memes” that poke fun at the weird world of finance. The account, run pseudonymously by a former trader who goes by Lit, has spawned a daily news summary email (Exec Sum) with 160,000 subscribers, podcast (Big Swinging Decks), investment fund, merch and more, as part of a $2 million business. Some key takeaways:

• Find underserved audiences. The world is not short on finance news. But what Lit found as a young investment analyst is that little of the coverage captured the experience of being in the (well-compensated) rank and file of finance. “One thing that I felt was lacking was real insider baseball-type humor,” Lit said. “You look at CNBC or Bloomberg, it's probably people who aren't insiders that are reporting on the news or talking about the stock markets.”
• Memes are top of the funnel. Litquidity began as a meme account, attracting advertisers as its revenue source. But Lit felt that could only go so far –  “I don't think they're like the highest value monetization paths to go through because you'll saturate your audience with ads, and people hate ads” – so he spun off Exec Sum, a newsletter that pithily summarizes the days finance and markets news. And more importantly, provides valuable surface area for high-value ads. “I really thought of how can I provide value to my audience in a way that would also make sense monetarily.”
• Publishing and investing mesh. Like Packy McCormick and Anthony Pompliano, Lit sees the opportunity to use his publishing reach as a way to expand his investmenting by raising a fund. Eventually, he sees Liquidity as more of an investment fund with a publishing arm rather than vice versa. “That's how I want that to be viewed going forward as I continue to build out the credibility and the track record.”
• Expanding beyond a personal brand is hard. Recently, Litquidity lost its “only employee” – there are a handful of part-timers – when Mark Moran split to focus on an investor relations play, Equity Animal. Expanding a media company tied to a person, even one who uses a pseudonym, is tricky. “One of the things that I found difficult was having the entire brand being ied by my humor and my voice,” he said. “If you start to introduce other creators or elements who don't fit that, then it starts to dilute that brand.”
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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.

There’s the understandable urge to “do something” to fix the difficult situation the news business finds itself in. Government intervention in markets has historically been less common in the U.S., but we’re in a time of aggressive industrial policy becoming the norm with measures like the Chips Act and the climate bill.

Enter the Journalism Competition and Preservation Act, a bill that was attached to the defense bill winding its way through Congress. The JCPA would force big tech platforms to pay local news publishers for the privilege of sending traffic to these publishers.

The measure, which at the moment has been removed from the defense bill although it could always get added back in upcoming the back-and-forth, has proponents who claim that it is a “lifeline” to local publishers by sweeping aside antitrust restrictions to allow them to collectively negotiate terms with big tech platforms like Google and Facebook parent company Meta. Detractors see a cash grab by local news chains that are often run by deep pocketed private equity firms. For its part, Meta has threatened to exit exit news altogether if the measure passes.

On this week’s episode of The Rebooting Show, I spoke to Chris Krewson, executive director of the Local Independent Online News publishers group, to understand the possible unintended consequences to the bill, which Chris sees as mostly benefiting incumbents, many of which continue to cut journalists as a result of bad business decisions. It doesn’t help that many legacy chains are owned by private equity firms that probably shouldn’t need government assistance.

For Hearst global chief revenue officer Lisa Howard, the shift to focus mostly on subscriptions at many publishers obscures the reality that advertising will continue to be the dominant monetization form for most media, including Hearst. Lisa discussed the power of ads and the resilience of legacy media during a live podcast recording at The New Attention Economy on Tuesday.

Joshi Herrmann is the founder of The Mill, a newsletter focused on Manchester – England, not New Hampshire, for those who call it “soccer” – as well as sister publications in Sheffield and Liverpool. Joshi started The Mill in June 2020, and across the three newsletters, the company has 45,000 email subscribers and has converted over 7% to paid subscribers. The Sheffield Post has 12,000 email subscribers and has managed to convert an impressive 950 to paid, according to Joshi. The company is near profitability with a small full-time staff augmented with freelancers.

The common knock on the newsletter model applied to local journalism is that it can’t scratch much beyond the surface, and it tends to be mostly aggregation of original reporting still done by local newspapers, however depleted they are. The Mill and its sister titles are leaning on original reporting and in-depth features as opposed to just aggregation or fluff about local events.

The Dispatch is a three-year-old publication focused on bringing fact-based politics news and analysis from a center-right perspective. Steve Hayes, CEO of The Dispatch, joined the podcast to discuss how it's managed to climb to near 40,000 paying subscribers with a healthy 17 percent conversion rate from its free email list. Steve discusses the importance of aligning the editorial mission and business model, occupying the middle ground between the institutional media brands and the so-called creator economy, and its approach to introducing ads to The Dispatch. 

Last week, at The New Attention Economy in Cannes, I discussed the notion of “influencer journalism” with Semafor co-founder and editor-in-chief Ben Smith and Puck co-founder and COO Liz Gough. Some highlights from the session:

• The creator economy is a long term shift: “Every other media industry, starting with Hollywood 80 years ago, made this transition to a connection with individuals. Journalism, because it is the worst of the media businesses, is the last one to get there.” – Ben
• 
  
• The legacy brand challenge: “Any new brand coming into existence, with Puck, Semafor or The Ankler, the balance to the individual needs to be more present. The legacy brands are struggling to figure this out.” – Liz
• 
  
• No influencers, please, we’re journalists: “When you’re recruiting a star reporter at The Wall Street Journal, the last thing you want to tell her is you want her to be an influencer.” – Ben
• 
  
• The journalist entrepreneur: “We are actively recruiting entrepreneurial journalists. They want to be commercial partners to my team. We spend a lot of time sitting down with our writers talking about commercial strategy, how we grow their subscriber base, how we do events, and how we do more advertising, who we’re going to call on. Our journalists are business partners.” - Liz
• 
  
• The Riviera is filled with Dylan Byers doppelgangers: “One in three men here look like Dylan.” – Ben
• 
  
• 
  

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.

Bridget Williams is a veteran of the industry. I first got to know Bridget when she was at Business Insider prior to heading to Food52 before landing at Hearst Newspapers in tk, where she is chief commercial officer. On this week’s episode of The Rebooting Show, we spoke about the progress toward a sustainable business model for Hearst news outlets like The Houston Chronicle, The San Francisco Chronicle and others around the country. All told, Hearst newspaper properties have 400,000 digital subscribers.

Bridget and I discuss how a "thoughtful mercenary" approach to local news means looking to non-news products to provide utility to communities to subsidize the critical impact journalism that is disappearing from many places.

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.

The Athletic started in 2015 with a simple proposition: It would produce the highest quality sports journalism with a subscription model that would align incentives with producing quality work vs chasing traffic. The approach wasn't without its flaws -- The Athletic consistently lost money -- but it did produce a differentiated, high quality product.  In January, The New York Times bought The Athletic for $550 million. Nine months later, the Times, which has proven that advertising can co-exist in a subscription-first model, introduced advertising on The Athletic. Sebastian Tomich, chief commercial officer at The Athletic and a Times veteran, joined me to discuss the advantages of building an ad model from scratch and how The Athletic is seeking to align brands with sports affinity.

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.

This is a preview of a new weekly podcast I’m doing with Troy Young. The People vs Algorithms podcast will focus on patterns in media, business and culture. Each episode will revolve around themes. This week, we tackled the theme of whether media is better now than in the past, along with an exploration of the type of media that’s winning in this kind of environment. It’s narrower, more focused, more niche. Subscribe to People vs Algorithms on Apple or Spotify.

Matt Cronin is a  founding partner at House of Kaizen, a consultancy that works with publishers and other companies on recurring revenue growth.

House of Kaizen, which is a sponsoring partner of The Rebooting, uses research-backed experiments to foster audience-first engagement. This allows clients to turn total reader revenue into cumulative gains.

We discuss how publishers can become truly audience centric, what publishers can learn from other consumer companies and more

This is a bonus episode of The Rebooting Show, featuring a conversation I had on the People vs Algorithms podcast. We discuss why the conventions of media are giving way to new formats that dispense with the artifice in favor of something approximating real conversations.

On this week’s episode of The Rebooting Show, I spoke to Darren Samuelsohn, a longtime politician reporter who was most recently head of Insider’s ill-fated DC bureau. Darren and I spoke about his new newsletter devoted to journalism, the decision to take an independent path, and the topsy-turvy career that’s journalism.

Alex Kantrowitz is the founder of Big Technology, an independent publication focused on he immense impact of tech companies on business, politics and society. A reporter covering tech for BuzzFeed News, he wrote a book on the tech industry called “Always Day One” and became one of the early trailblazers to decamp to Substack in 2020. Since then, Big Technology has amassed nearly 100,000 subscribers.

We spoke about his independent journey – and plans to start a paid tier to his newsletter – as well as the state of the tech industry at this pivotal time. Some highlights:

• Why a lot of the meltdown in tech valuations is a function of the Federal Reserve
• How Apple got away with kneecapping tech rivals under the guise of privacy
• Mark Zuckerberg’s ballsy bet on the metaverse
• Generative AI as a legitimate contender for the New New Thing
• Betting on yourself after seeing journalism businesses struggle
• 
  

Producer: Jay Sparks of PodHelp.us

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 Introduction
• 01:43 Panel Introduction and Discussion Overview
• 02:07 Ad Challenges in the News Business
• 06:31 Impact of Keyword Block Lists
• 08:19 Brand Suitability and Safety
• 23:23 Performance Marketing Trends

I had a conversation with Krystal Olivieri, global chief innovation officer at GroupM, about whether advertisers would conveniently forget all those promises they made during flush times to support local news. The takeaway: Advertisers will cut here and there, and that’s outside of the control of publishers, but news publishers can help themselves by having better ways of showing the value they’re creating for advertisers. Check out the full conversation on this week’s episode of The Rebooting Show, followed by a discussion of the year ahead with Outbrain co-CEO David Kostman. Thanks again to Oubrain for the support. Appreciate it.

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.

Adam Ryan, former president of The Hustle and cofounder of Workweek, wants to rethink the B2B model. Workweek is banking on finding individuals – creators, if you will – to build audiences around. The bet is that individuals, particularly but not exclusively those who are practitioners in the field, can build deeper connections with audiences while benefiting from the infrastructure, services and halo effect of a parent media brand. Some highlights from our discussion:

Don’t raise too much money. Adam spent part of his career at Spiceworks, a professional network for IT professionals. The company identified an underserved community and executed on the opportunity, only to have an unsatisfying outcome. “It was a great company, bad cap table,” Adam said. “They actually made a ton of money. They didn't need to raise that much money. And then because they did, they made terrible decisions, long term.”

You can be professional and have personality. Workweek is leaning on its network of 19 creators to be front and center. It doesn’t have an editor-in-chief and instead relies on its newsletter writers to chart their own path that hews closely to what motivates them. Nicole Casperson, for instance, writes WTFintech and focuses often on diversity and inclusion issues that are important to her personally.

Sector expertise is critical. Not all Workweek creators worked in the fields they cover, but many do. Workweek writer Nik Sharma, for instance, is a DTC marketer. This hands-on familiarity with the issues in these fields in invaluable, so long as it is also married with the ability to clearly communicate and consistently produce valuable pieces.  “The reason why [B2B content] is kind of boring is because you have a lot of people that have never done those jobs,” he said . “They're just like listening and regurgitating. They're not like coming from a point of action.”

Paid acquisition is more than a shortcut. Publishers used to have an aversion to admitting to buying traffic. I can remember BuzzFeed making sure to point out it only bought ads for its sponsor content, not editorial. But Adam saw how an effective paid audience development strategy can accelerate growth. For instance, Workweek’s The Marketing Millennials property grew by 7,000 newsletter subscribers organically in seven weeks while paid acquisition added 20,000. So long as a company is confident in its cost per subscriber number, and is focused on quality of acquired subscribers, paid acquisition is an important tool. Overall, Workweek pays to acquire nearly half its overall list at an average cost of $10 per subscriber.

You need connective tissue. Workweek has cast a broad net in its first eight months of existence, with newsletters focused on everything from cannabis to fin tech to memes to franchises to marketing. It has since refined the model around “pods” of core categories. Workweek has clusters around areas like startups and investing, health, marketing and fintech. “​​It just allowed the business to focus on marketing allows our business to essentially have more efficiencies,” Adam said.

Patrick Trousdale started The Daily Upside in 2019 after working in investment banking at Guggenheim. Patrick saw the success Morning Brew and The Hustle had with newsletters that produced business, finance and entrepreneurial news for younger audiences. He started The Daily Upside with the idea there was space for a newsletter that catered more to investors as a lens instead of general business and finance.

The Daily Upside is now at the point where it can incrementally expand. It started that in January with the acquisition of a specialist newsletter called Patent Drop that trawls  patent registries for updates on what tech companies are filing patents that will expand into a publication focused on “technologies like blockchain and AI, how policy is impacting tech innovation, and conversations with the thought leaders and entrepreneurs building the future.” The Daily Upside will also launch Power Corridor, a publication at the intersection of Wall Street and Washington with longtime Institutional Investor journalist Leah Goodman.

The opportunity Patrick sees is applying The Daily Upside growth playbook to these new properties – and using them to move beyond aggregation. Making the shift from aggregation to original content is a time-honored and tricky path in digital publishing. I can remember when Business Insider was mostly aggregating the reporting of others.

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."​

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. 

In 2014, Bonnie Kintzer was named CEO of Readers Digest Association, becoming its fourth CEO in three years as it emerged months earlier from its second bankruptcy.

After renaming the company Trusted Media Brands, recently shortened to TMB, Bonnie set out to decisively shift the company to a digital model while diversifying its focus to include its other lifestyle brands, such as Taste of Home and the Family Handyman. TMB added Jukin Media, bringing its streaming and video capabilities as well as brands like FailArmy and The Pet Collective.

“I had multiple steps that I shared with the entire company. Did we have the right people? Did we have the right culture? Did we have the right assets? Were there assets that we should bring into the company? What did we need to stop doing? Because I think when you're doing a turnaround, you have to really have an incredible amount of focus.”

Here’s Bonnie’s three principles for a turnaround:

Enjoy the process. Turnarounds can be grinding affairs, filled with their fair share of downs along with the ups. “You have to be a certain kind of person to like turnarounds, and you have to surround yourself with those kinds of people,” Bonnie said.”

Be decisive. Tough decisions are inevitable. Putting them off isn’t going to make them any easier.

Over-communicate. Change is hard and understandably unsettles people. “When I first got back, people didn't believe that we could do it,” she said. “It was about constant communication and proof points that all of a sudden people [believe] we can do it.”

The Rebooting Show is produced by Jay Sparks at Pod Help Us. 

In 2016, Max Kabat and Maise Crow moved to Marfa, a small arts town in west Texas, and a couple years later made a bold call. They bought the local newspaper, The Big Bend Sentinel. Ever since, they've been building out their take on a sustainable local news model by pairing the weekly newspaper with a cafe and events space. Max and I discuss the model, the challenges of operating entwined but separate businesses, and whether this could be a blueprint that could work in towns with similar characteristics as Marfa, a tourist town that attracts a flood of visitors every year. After all, most towns in America aren’t featured in Vogue.

Digital media veteran Scott Messer discusses the structural changes to the publishing business, from the deprecation of the third-party cookie to the critical role search plays in many publishing businesses. Scott is a longtime digital media exec who understands the mechanics of the digital ad industry as well as anyone I know.

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.

CJ Gustafson is one of the rare people who is both immersed in his field but does not suffer from the tyranny of knowledge. CJ uses memes and a conversational style with Mostly Metrics to address what those outside corporate finance would consider dry topics. But most importantly, he completely understands the challenges of being a CFO because he’s a CFO. In this episode, we discuss how he built Mostly Metrics, as well as getting into the weeds of why media is often a terrible business and what are the drivers of a sustainable media business.

Blockworks, founded as a crypto events company in 2018, has rode these ups and downs. It began in the face of a crypto pullback with the thesis that crypto would become a major asset class and as it grew, institutional investors would need a credible source of information, analysis and research beyond an anonymous Twitter account with a monkey avatar shooting lasers from its eyes.

As crypto recovered and headed into a bull run that accelerated during the pandemic into what I’d consider a bubble, Blockworks expanded from events into podcasts and news. With $12 million in VC raised in possibly the hardest time to raise for a crypto media company, Blockworks is building out a research arm.

Jason Yanowitz, CEO of Blockworks, discusses the evolution of the company and the benefits of staying focused and being a "mile deep" vs an inch deep.

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.

Defector is a worker-owned media company that was born out of disillusionment with the tradeoffs the digital media ecosystem often requires (or at least incentivizes). Instead of chasing traffic, Defector relies on a subscription model for a small but sturdy business.

On this week’s episode of The Rebooting Show, I was joined by Hearst’s David Carey to discuss the resilience of so-called legacy media businesses. David returned to Hearst in 2019 as svp of public affairs and communications after a stint at Harvard, picking up on an eight-year run as president of Hearst Magazines from 2010 to 2018. He was group president at Condé Nast for many years, as well as the founding publisher of Smart Money.

Some highlights from our discussion:

The broad view of content: Hearst used its media assets to diversify into information services. Fitch Ratings is its largest business, and in 2016 it spent $2 billion on Camp Systems, a software provider for the airline maintenance business. “The company's had a very broad view of what content is, and, boy, is that to the benefit of everyone who works here.”

The end of the shiny object era: “There was a lot of chasing whatever the latest thing was, but those businesses turned out not to be sustainable, or they turned out to be gimmicks, or they turned out to be easily replicated by others. It’s chaos in all directions for all media forms. It very much favors companies with real strategies, deep roots.” 

Media’s always been hard: “Media is much harder to operate than it looks from the outside. That's always been true. It's easy to make a splash and make some noise, but even the latest upstarts are finding it's really hard to build a sustainable business that engages people on a regular basis.”

Media businesses need a bigger price curve: “Whenever I meet a [Wall Street] Journal executive, I tell them, you should come up with a $1,000 a year subscription, because I would pay that. It's that important. to how I operate in the world as an executive. Every brand has these concentric circles of diehard fans and next diehard fans and so on. The problem is there hasn't been effective price discrimination.” 

Print is like a couture fashion show: “What they send down the runway is important but not their biggest business. What happens at Chanel at a couture show, that business is relatively small, but it sets the stage for everything below that. It's the eyewear, the handbags, the accessories. Ultimately they make their money from selling beauty products at Bloomingdale's and in Saks Fifth Avenue. You're starting to see that happen with magazines. They have an opportunity to become multi-tiered businesses. The print piece becomes the standard bearer [to more lucrative businesses like events and data].”

Literally Media -- home to Cracked, I Know Your Meme and Cheezburger -- isn't going to fight creators. Instead, it's partnering with them to do everything from launch channels on new platforms, get access to brand partnerships and be part of live events. Literally Media CEO Oren Katzeff explains the approach, along with Literally's emphasis on IP-based video franchises and more.

Katie Vanneck-Smith, formerly president of Dow Jones, co-founded Tortoise Media, a UK-based publisher dedicated to “slow news.” The problem she and her co-founders diagnosed: “The problem isn’t just fake news or junk news, because there’s a lot that’s good – it’s just that there’s so much of it, and so much of it is the same. In a hurry, partial and confusing. Too many newsrooms chasing the news, but missing the story.”

The slow approach means that Tortoise confines itself to producing one podcast episode a day, one daily newsletter (in email and audio), one multi-part series per month and one book a quarter. Katie discussed the Tortoise approach in an on-stage conversation at the FIPP World Congress in Cascais, Portugal.

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

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.

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 Introduction
• 03:04 Challenges and Opportunities in Publishing
• 05:44 The Role of Algorithms in Media
• 13:02 AI Deals and Legal Considerations
• 22:47 AI's Impact on Business: Myth vs. Reality
• 25:38 The Future of Print and Digital Media
• 31:36 The Role of Credibility and Relevancy in Content
• 37:41 Adapting to the Digital Advertising Ecosystem
• 40:43 The Challenge of Intermediation in Publishing
• 42:58 Embracing Change and Enjoying the Chaos

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.

Founded a decade ago, Team Whistle is a survivor. It sprang to life as a wave of multichannel networks that filled the need of aggregating YouTube properties to make buying easier. The biggest problem of the MCN model is that it takes a difficult business model (advertising) and makes it even more difficult because you’re taking a cut of a cut, after YouTube gets its taste. Most MCNs fizzled.

Whistle shifted its focus to building its own properties, producing franchises like “No Days Off,” a series following incredibly focused child athletes. It still reps other properties, like Dude Perfect. It complemented that with an agency business that relies on the distribution and cachet of the original programming.  Whistle is part publisher, part agency.

The digital advertising system is in the midst of a shift, from an over-reliance on collecting vast amounts of data to crunch to do one-to-one targeting – dog owners getting dog food ads, cat owners get cat food ads – to a new landscape that gives people more say on data collection and pushes advertisers and ad tech companies to operate differently. 

In this episode, I had a conversation with Joe Root, CEO of Permutive, an audience platform that's used to deliver privacy-safe digital advertising. Among the topic covered:

• The shift in publisher incentives to build trust vs build traffic
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• Why direct sold advertising is back in vogue
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• Whether GDPR’s implementation gives real consumer choice or just the illusion of it
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• The surprisingly large carbon footprint of digital ads
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• Why the loss of ad targeting signals has become an advertiser problem
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• The demise of the long tail in favor of top-tier publishers
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• Why the so-called ad tech tax will come down
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increase revenue from first-party data by 46%.

One of the most solid areas of digital publishing is what’s become known as intent media. In the old days, we called this “SEO.” The basics are taking service content and applying it to algorithmic distribution (usually Google) and marrying it with performance advertising models like affiliate marketing programs that pay for sales leads. 

Ad Practitioners is another intent-based publisher in expansion mode.In late 2019, Ad Practitioners bought Money.com from Meredith with the plan to run its intent playbook with the personal finance brand. That means more lists of the best credit cards, best savings accounts and, yes, the best pet insurance companies. The entire company, which is based in Dorado, Puerto Rico, is 160 people and generates over $100 million in annual revenue.

Some takeaways from Ad Practitioner CEO Greg Powel:

Arbitrage works. Paid acquisition is an important part of the Ad Practitioners model – it has spent about $500 million on Google ads in its history. Search for “best credit cards 2022,” and you’ll see why. This kind of high-value intent traffic is very valuable – credit card leads can fetch $100 – that it makes sense. 

Bad sites are a business model problem. Publishers with terrible websites do not have a tech problem; they have a business model problem. The attention-based ad model for general audiences is hard to make work without adopting, well, adversarial tactics. The performance ad model of intent media aligns incentives better since the publisher wants people to get the information they need rather than hijack their attention elsewhere.

Algorithm dependence is a manageable risk. To put it mildly, there’s a checkered history of publishers relying on algorithms for the overwhelming majority of their distribution. Ad Practitioners look to mitigate that dependence with its paid acquisition as well as licensing deals with the likes of MSN and others. While new channels like TikTok could catch on to eat into Google’s search share, Greg sees the biggest threat of disruption coming from Apple, since its devices are the originator of a big chunk of Google searches.

I spoke to Matt Cronin, founding partner of House of Kaizen, a consultancy that works with publishers on their subscription and recurring revenue products. Among the topics we covered:

• fixing misaligned incentives in publishing 
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• whether peak subscription exists
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• subscriptions as a force function to be customer centric 
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• what publishers should and shouldn’t learn from the success of The New York Times
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• The struggles of many streaming services 
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• what publishers can learn from subscription companies outside media 
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Isaac Saul saw knee-jerk distrust in media firsthand as a political journalist at outlets like Huffington Post, where what he wrote would end up being distrusted based on the place it appeared rather than the substance. Three years ago, Isaac started Tangle with the idea that presenting both sides to news stories would appeal to a wide group of people. And that’s proven true. Today Tangle has 8,000 paying subscribers and nearly 50,000 free email subscribers – a 16% conversion rate is amazing. It is launching a new ad program to complement the $30,000 a month in recurring revenue it takes in.

Like Semafor, Tangle has its own spin on deconstructing the atomic unit of news, aka the news article. Tangle separates out the factual presentation of the issue, before presenting the view from the left, the view from the left, and then Isaac’s viewpoint. This is hard to pull off, particularly with issues like affirmative action, Covid-era school closures, and, of course, all things Trump.

“I am pretty politically incongruent. I try to go and understand, as a politics reporter, what's happening in the world. In order to get a balanced view of any single story, I would have to read 10 publications that have clear, diametrically opposed  political leaning. I can't just read the New York Times. I have to read the New York Times news section and then go read the Wall Street Journal if I really want to get this full picture. And so I was like, there have to be other people like me out there. I figured if I could put all that stuff in one place, a lot of sort of politically open-minded people would read it.”

I’m joined by Matt Cronin, founding partner at House of Kaizen, which works with publishers and other companies with recurring revenue businesses to align their business goals with audience needs through customer experience frameworks. Some highlights of our conversation:

• Shift to audience-centric approaches: There's a significant shift towards understanding and directly engaging audiences rather than relying on platforms for traffic, which involves a fundamental transition to being audience-centric. A key part of that: Realizing an audience is not a monolith but different groups with different needs.
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• The importance of intentional audiences: Publishing became a (big) numbers game. That’s changed, as every publisher now much compete for “intentional audiences.” These are people  you have a real tie to, who subscribe to a newsletter, follow a podcast, visit your site directly. This is what Business Insider is after with its shift to focus on “digital go-getters.”
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• Looking beyond efficiency with AI: Synthetic content is about to overwhelm the internet. Many publishers are focused now on the efficiency gains of AI, as all businesses are and need to be, but stopping there is a mistake. AI needs to be harnessed to – you guessed it – provide added value to audiences.
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Why The Dispatch outgrew Substack

Many would assume the most popular political publications on Substack are culture war agitators like Matt Taibbi and Glenn Greenwald. In fact, the top two slots are much milder publications: Letters from an American and The Dispatch. Taibbi and Greenwald will be moving up a slot soon, since The Dispatch is leaving Substack.

Steve Hayes, one of the founders of The Dispatch in 2019, said the conservative news and commentary publication has outgrown the tools that Substack provides. Part of this is ideological – not in the political sense – in that Substack has squarely cast its lot with individual creators, doesn’t believe in advertising, and wants to be a platform rather than a backend tool.

“There was a certain point when they were seeing the success that they were having by focusing on individual content creators, and said, we need to do more of this. And there came a point, when their growth, which was just monumental and what they were doing to get that growth, didn't work for us as much as it had in the past.”

Businesses are all about making choices. And ultimately you can’t please everyone all the time. That said, I think Substack is at risk of losing many of its initial wave of successful publishers, particularly as upfront deals end and the pinch of paying 10% of revenue. (The Dispatch had a “handshake agreement” with Substack and didn’t get a special deal, according to Steve.)

The shift to individuals from institutions has been a major catalyst of publishing’s unbundling, but I believe we’ll see more confederations between individuals, sometimes just a gussied-up regular company and other times in new collectives. That’s because working with others tends to be more enjoyable for most people. What’s more, being part of a group means you can have someone to cover up for your inefficiencies or allow you to take a vacation. There’s still strength in numbers. What’s more, bundles are often better for customers.

Steve and I discussed how The Dispatch plans to expand beyond its 30,000 paying subscribers by adding in advertising and events. We also discussed building a center-right political publication at a time of extremes, and I tried but mostly failed to get him to give an optimistic view of what’s to come in U.S. politics.

Check out the full podcast on Apple or Spotify. Thanks to House of Kaizen for its support as presenting sponsor.

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 media business in 2024

To kick off the year on The Rebooting Show, I spoke to Axios senior media reporter Sara Fischer about the main themes of the year ahead. Among the topics we covered:

• The value of identifying patterns from the torrent of news
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• The unrealistic expectations of the ZIRP/scale era
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• Cyclical challenges vs structural changes
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• The wasteland of general interest publications
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• The existential threat of AI to many publishing businesses
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• AI’s impact on the non-content aspects of the publishing function
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• How debt will accelerate the inevitable consolidation of streaming services
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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:

1. Using podcasts for broad reach and affinity
2. News as a credibility driver
3. Pulling back on B2C events to focus on B2B
4. Using media to drive “negative CAC” for information services
5. Implementing a “house of brands” strategy

Mosheh Oinounou, a broadcast news veteran, started posting summaries of the news of the day during the early days of the pandemic. He found they were resonating, and over the past few years, Mo News has amassed 440,000 followers on Instagram for news delivered mostly through Instagram Stories. Mosh has since expanded to a daily podcast, a membership program that’s attracted 6,000 paying subscribers, newsletter and more. We spoke about the prospects of “creator journalists,” why his evenhanded approach resonates with his 85% female audience and the inherent challenges of building a business built around a “personal brand.”

Bill Bishop likes to make clear he’s not a journalist. Instead, he’s a China analyst who brings his deep understanding of the country to an English-speaking language through his newsletter, Sinocism. In 2017, Bill became the “original Substacker” after teaming up with Substack’s co-founders to be the first newsletter on the platform.

On this week’s episode of The Rebooting Show, Bill and I discuss his independent path, and how a subscription model has created different dynamics as opposed to his experiences in the dot-com era as a co-founder of Marketwatch. What’s telling to me is that Bill is also now considering advertising. The Substack model of “only ads” doesn’t make much sense long term for most writers. Even if they convert 10% of their audience, they’re making no money from 90%. Most businesses don’t operate that way.

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."

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. 

Anna Palmer is a journalist turned startup CEO. Along with Jake Sherman and John Bresnahan, she founded Punchbowl News in January 2021, just in time for the assault on the Capitol. Punchbowl’s obsessive focus on the Capitol, and business model that combines subscriptions with high-value issue advocacy ads led it to sprint out of the gates with a $10 million first year. Anna is more reticent about its current pace – I tried – but by all measures what Punchbowl is doing is working in a media environment that's shifted to favor narrower brands focused on high-value audience segments, backed by direct connections and diversified business models.

“I've been in Washington journalism for almost 20 years, and I always laugh when everyone talks about Substack and the rise of newsletters,” Anna said. “It's the new hot thing. I mean, I've literally been doing newsletters for that entire time.”Some things that stand out to me about Punchbowl:

1. It is reporter focused. I believe journalists who start media businesses create different products. Punchbowl is journalism-driven, relying on the daily grind of uncovering new information vs playing SEO or social traffic games.
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3. It has a rich niche. Issues advocacy ads are a lucrative ad category, and one where you not only mostly don’t compete with Google and Facebook, but they’re also your biggest clients. If only more media was like this.
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5. It has stayed lean. Punchbowl started with funding from Liontree, and it has grown quickly, but it has also resisted the temptation to expand quickly by, say, springing up operations in state capitols around the country or joining the fray at the White House. Instead it has focused on high-value areas like its expansion in financial services vertical with The Vault.
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7. It has managed to be a publication about politics without being a political publication. Many aspire to non-partisan news. Easier said than done. See the Chris Licht experiment at CNN for evidence. Punchbowl has managed to thread the needle for the most part with not being pulled into the inevitable political Rorschach test, mostly because they’re obsessed with the legislative process vs the posturing of politics.
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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 Challenges
• 01:02 Welcome to The Rebooting Show
• 01:44 Discussion on Audience vs. Consumer
• 03:38 Key Takeaways from the New Growth Agenda
• 07:22 Challenges in Media Transformation
• 09:37 The Role of Technology and Organizational Structure
• 13:01 Existential Threats and Industry Nostalgia
• 18:22 Adapting to a Consumer-First Strategy
• 25:59 Navigating Data Collection and Audience Insights
• 30:16 The Role of AI in Audience Understanding
• 36:00 The Future of Personalization and Content Delivery
• 38:55 Transparency, Privacy, and Value Exchange
• 44:47 The Future of Advertising and Publishing

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:

1. 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.
2. 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. 
3. 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.

Outsider is a media and commerce brand focused on a particular view of “the American lifestyle” that, to me, takes its cues from the South, emphasizing college football, hunting, fishing, wraparound sunglasses and the like. Recently, Deirdre Lester moved from CRO of Barstool Sports to become the CEO of Outsider. The goal is similar to Barstool: Use personality-driven publishing – former NFL QB Jay Cutler is chief design officer at Outsider – to build a deep connection with a like-minded community, then complement the media with commerce operations. Some key takeaways from our conversation:

Finding the sweet spot between individuals and institutions is a big opportunity. The unbundling of publishing has put the focus on individual creators, but there are only so many Mr. Beasts in the world. The more tangible opportunity is the Goldilocks approach with institutional brands that can tap into the power of individuals to establish tight ties with an audience. Outsider is doing that with Cutler and popular podcaster Marty Smith.

Lifestyle publishing brands are more about AOV than CPM. Publishing has been stuck in a default mindset that the audience either pays with data and attention to ads or with money through subscriptions. Commerce – real commerce, not just affiliate links – offers a third way to build product companies with media used for efficient distribution and, ideally, premium pricing power based on the credibility established with customers.

Doing both media and products is hard. These are different businesses with different dynamics. The rough patch hit by Food52, a prime example of publishers pivoting to product, shows how difficult it is to manage both publishing and products. Publishing is all about managing conflicts, and that can get even messier when publishing is in the service of moving products.

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.

In a live recording of The Rebooting Show from Cannes, Kirk McDonald, CEO of GroupM North America, seemed to wonder whether we’ve all talked ourselves into a downturn that wasn’t, "For the first half of this year, we saw behavior that anticipated a crash,” he said, even if we’ve had a “pretty smooth landing.”

“The thing we were worried about didn’t happen,” he added. “But I don’t think we’re seeing the kind of fulsome growth [we’ve seen in the past]”

Jeff Selingo spent eight years at the Chronicle of Higher Education, serving as editor in chief and editorial director, before setting off on his own path. Jeff and I have traded notes on the independent path over the years, and I wanted to have him on The Rebooting Show to discuss what we’ve both learned on the independent path. We discuss the transition from editorial to sales, why treating “lifestyle business” as a pejorative is strange, and fighting the pull to rebuild what you left behind.

Last week, I was in Chicago to attend the Omeda OX6 conference, where I recorded a live version of The Rebooting Show podcast. Jessica Sibley, CEO of Time, joined me to discuss her first six months at the 100-year-old publishing brand. Among the issues we discussed:

• The benefits of being a “legacy” brand
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• The importance of a brand clearly standing for something
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• Why taking down a paywall was right for Time’s strategy
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• How Time is building a diversified business strategy
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• Why commerce content needs to sit alongside the newsroom, not in it
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• Why she believes in an in-office culture
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Future is a collection of over 200 specialist titles that range from gaming and tech (Tech Radar) to homes (Homes & Garden) to beauty and fashion (Who What Wear) to B2B (SmartBrief), Future has established itself as one of the UK’s most successful publishers. (Its current market capitalization puts it at 8x the value of BuzzFeed.) But for its future growth, Future is betting heavily on the U.S. market, which CEO Zillah Byng-Thorne noted to me is five times the size of the UK. The U.S. already represents 35% of Future’s audience as well as 38% of its revenue. 

Byng-Thorne is something of a newcomer to the media business. An accountant by training, she joined Future in 2014 as its interim CFO and soon was appointed CEO, tasked with turning around a magazine publisher that, like its peers, was struggling to make a transition from print to digital. Her turnaround plan – she initially cut 40% of employees as the company was recording a £35 million loss in 2014 – has become something of legend, setting the stage for a remarkable financial turnaround as Future became an early adopter of using its niche focus in high-intent categories to drive transactions. The shift to commerce – it is now 34% percent of Future’s revenue – was informed by her previous time at Auto Trader, which made the leap from car magazine to marketplace. 

Zillah recounted how her first year at Future, which was on what she describes as a decade-long decline, the key question to answer was: “What’s our right to exist?” Her conclusion: Put the company on firmer financial footing, double down on the expertise embedded in the brands. Future was struggling with the transition from print to digital when Byng-Thorne took over. Beyond that, the diversification needed to be done on the digital side as well since many publishers were overly reliant on digital advertising. Commerce was a way to make money from audiences without the ups and downs inherent to the ad business. Future’s revenue is now roughly split in thirds among advertising, commerce and direct revenue from the audience. Having an acquisitions playbook. Future has spent over £1 billion on acquiring companies since Byng-Thorne took charge. In the past year alone, it has acquired four companies, including Who What Wear and Dennis Publishing and MarieClaire.com. “We integrate fully. I know some of our competitors don't all integrate fully, but for us, it was really important that it's one Future, one tech system, one sales team, one way of working.” 

This episode was produced by Jay Sparks from Pod Help Us. If you have podcast production needs, get in touch with Jay.

⁠Thanks to Kerv ⁠for sponsoring this episode. To see Kerv's technology at work, ⁠check out Peacock's MustShop TV⁠.

If you’ll be on the Cote d’Azur next month. The New Attention Economy, presented by Kerv, will have speakers from the Financial Times, Uber, Paramount, Havas and more. Let’s talk ‘Active Attention’ Economy at Cannes Join us for three days of exclusive thoughtful conversations and cocktails with the industry’s best to discuss the Attention Economy and the future of publishing, streaming, AI & creativity. Register here.

Last week, I traveled to Washington DC to record a podcast with Sean Griffey, CEO of Industry Dive. I’ve known Sean and Industry Dive a while, mostly because two of its 33 publications – Marketing Dive and Retail Dive – were in areas in which my previous companies had publications. Sean was also the rare media CEO who would come onto my podcast and not rattle off a bunch of talking points. The big numbers he talked about weren’t Facebook video views of ComScore uniques ginned up through traffic assignment schemes. He spoke about revenue and, imagine, EBITDA. 

Industry Dive went on to be bought not once but twice. First in a transaction to growth equity firm Falfurrias Capital in 2019 and then last year in a deal to events giant Informa last year that Axios reported put an enterprise value on Industry Dive of $525 million. That would make Industry Dive’s value at over two Vices and five BuzzFeeds.

What Industry Dive got right is something I covered after the Informa deal. I was long impressed by Sean and Industry Dive’s management ability to stay focused and disciplined in their business model. It helped that Industry Dive didn’t raise venture capital. Constraints can be good. It meant focusing on what was working, notably newsletters and being good at putting first-party data to use for B2B marketers.

In B2B, the pull to do events – have you signed up for The Rebooting’s Cannes events yet? – is strong. That’s because B2B doesn’t have advertisers per se, but marketers. And B2B marketers serve to get their sales teams prospects. That leads many B2B publications to go heavily to events.  Industry Dive skipped events because it was very good at building publications in high value industries with tons of regulation and tech-driven change and acting as a critical marketing partner. That isn’t revolutionary. But it’s hard to execute.

Another aspect that impressed me about what Industry Dive did was it executed its playbook not once but across multiple...