The Rebooting Show

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:

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On this week’s episode of The Rebooting Show, Bob Guterma, CEO of The China Project, to discuss how to maintain credibility while catching flack from many sides, The China Project’s decision to leave Substack, adopting a subscription-first model and its crowdfunding efforts to raise capital from its audience.  

More perspective:

Semafor did a deep a piece on The China Project that highlights the criticisms leveled at it in a whistleblower complaint that alleges it slants coverage to favor Chinese interests. (Bob dismisses this coverage as innuendo and cover for Semafor’s own indirect ties to the Chinese government through a partnership with a Chinese think tank.) 

The China Project published a lengthy rebuttal, claiming it is “a target of racist, populist, anti-China sentiment.”

Unlike most small publishers, The China Project has published an annual report as part of its earlier crowdfunding capital raise. 

⁠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 industries. It didn’t wait until it perfected its playbook in one industry, because as Sean told me, you will perpetually put it off because you’ll never feel like you’ve gotten there. Building a leading publication in a single industry is hard but also has a fairly low ceiling, if you’re trying to build a big company. (I tend to think more people should be OK building a great company that’s smaller and skip the lure of massive exits.) Industry Dive was able to pull that off.

And finally, I think there’s something to be said about how Sean and his team went about building their work without all the PR nonsense. I hope of the many things that are left behind from the previous era, it’s the out of whack ratio between sizzle and steak. Fake it till you make it always struck me as a terrible strategy. Ask Ozy. 

Will Hayward, the CEO of Private Media, an independent publishing company in Australia that publishes several titles, including politics-focused Crikey, recently faced the intriguing and likely slightly terrifying experience of being the subject of a defamation lawsuit filed by Lachlan Murdoch over a Crikey opinion column that held the Murdochs were “unindicted co-conspirators” of the Jan 6 attack on the US Capitol. Murdoch withdrew the lawsuit in the aftermath of Fox settling its case with Dominion, much to Will’s relief. 

We discussed the case, the decision to stand firm against a powerful and angry individual, and how Crikey made lemonade out of lemons by using the case to rally support for the politics publication through subscriptions. We also touch on the impact of Australia’s news bargaining code that has wrung payments from platforms and is the model for similar laws worldwide, including in the US, as well as lessons learned from the social publishing era, since Will was in the thick of it.  

The Messenger is coming next week and… counterintuitive: “I don't believe that there is an audience that's salivating out there for straight-down-the-middle news,” Peter said. “Anyone who says that is lying to themselves or to the public.”

After the streaming wars comes the winnowing: “You’re going to have fewer of these big subscription services, more of these free ad-supported services, and streaming will continue to dominate more of the time that people spend in terms of consuming television,” Sara said. “No longer is it plausible that everyone can just launch a subscription service and think that they're going to take meaningful market share.”

The AI “tsunami of bullshit” is coming: “We're still relying on Google for referral traffic and the idea that people might find our articles there,” Peter said. “Whether or not you use AI, you are going to be swamped by the tsunami of bullshit, whether it's good or not, content made by robots. And even if every publisher and every trade group in America agrees to not do it, it doesn't matter because it'll come from all over the world.”

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.

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.

Axel Bard Bringéus is co-founder of Informed, a Berlin-based company with $5.3 million in backing that’s building a service for subscribers to pay for access to paywalled content from top tier publishers like Bloomberg, The Economist, The Financial Times and more. Informed is focused on people in non-English speaking countries who graze on English-language news content yet not enough to consider a subscription. This is a smart approach. Publishers always struggle to make money from international audiences. Most advertisers do not sell globally. And international visitors, in my experience, are far less likely to convert to paid. Axel and I discuss the Informed approach, and how his experience as a Spotify exec informs how he sees the news market.

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.

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.

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.

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.

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.

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.

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.”

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:

Producer: Jay Sparks of PodHelp.us

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

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

Casey Newton, a former writer at The Verge, started Platformer to cover the societal impact of the most powerful tech platforms. He’s used a subscription model, charging $100 a year. With 75,000 free subscribers and what he’ll only call “thousands” of paid subscribers – Platformer is the No. 2 most popular paid newsletter in tech on Substack – Casey has built a successful solo business that’s he’s expanding by bringing on Zoe Schiffer as Platformer’s managing editor. (He’s also got a new podcast coming out in partnership with The New York Times.)

Going direct. “The one thing I've learned from covering these social networks is you've got to stop yourself from having a middleman in between you and the audience. I’ve got to go get that direct connection. And there is no more direct connection than having your own business and selling a product for money.”

Subscriptions make the solo path easier. “It's ridiculously plug and play. It’s  amazing to think that just by adding a subscription component to a blogging platform, you can enable hundreds, maybe thousands, of people to start their own successful businesses.”

Newsletters are more nimble: “The thing I love about new newsletters, in particular, is that they can evolve so quickly. If you go back to the five years that I've been writing a daily newsletter, now there are whole sections that used to be there that just aren't there anymore. And it's totally fine. Whereas like you work for a website, if you want to redesign it, give yourself two years. My newsletter can just evolve.”

The indie path is niche. “My hope was that two years on so many more people were going to do this. I spent that first year that I was independent talking to so many boldface name reporters at The New York times, The Atlantic, you name it, because they were all thinking about doing the exact same thing. I was trying to encourage them to do it because I was having so much fun with it and it was succeeding, but so very few people pulled that trigger. I think individually, they all had good reasons. But I have been shocked at how few people, relatively speaking, have followed. Most people have really wanted the comfort, the stability of that standard media job.”

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.

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.

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

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. 

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:

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.

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.

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.

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.

“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. “

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.

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.