The Rebooting Show

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.

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 proceedsCollaborated with artists to reinterpret Time covers as part of the Timepieces Web3 communityDipped its foot in the metaverse with a Galaxy Digital deal to create a metaverse newsletter and a metaverse category of the Time 100.“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.

Since its founding eight years ago, Permutive has bet on privacy being a key consideration in the future of ad tech. Permutive CEO Joe Root  delves into what privacy-conscious advertising looks like – and if it’s possible. Highlights:The GDPR was a harbinger. Most U.S. companies didn’t understand how far-reaching the General Data Protection Regulation would be to them. The landmark move to rein in the collection and use of user data without consent is not without its critics, but it set in motion a focus on privacy that led to Apple’s move to crack down on data collection and the ultimate end of the third-party cookie.U.S. dominance in digital markets is ending. The tech industry has been mostly an American creation, dominated by U.S. platforms and largely operating along the extreme free market proclivities that are a hallmark of American capitalism. But Europe remains a regulatory superpower, and it is determined to use those powers to shape digital markets.Consent – real consent – is inevitable. Clicking out of endless cookie consent pop-ups is a wonder of traveling in Europe, on par with being able to take a train to the airport. The GDPR led to these consent requests as ad tech’s response to the regulation, giving the appearance of consent but not really. That’s going to change.Context is having a moment. The original targeting signal for advertising was context. Someone reading Field & Stream is likely into the outdoors if you’re selling fly-fishing gear. Digital advertising shifted to taking all kinds of signals in order to target ads to individuals. With the collection and application of other signals growing more difficult and expensive, the pendulum is shifting back to contextual signals.Big publishers stand to benefit. The new era of digital advertising will have winners and losers, with many still to be determined. One divide that will likely open is between the biggest publishers that have enough user data of their own to be compelling to advertisers who can’t simply rely on the cookie targeting and the long tail of sites that will likely find competing for ad dollars far more difficult.

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.

Why The Dispatch outgrew SubstackMany 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.

Quick request: Please take this 10-question audience survey that will help me better understand the makeup of The Rebooting’s readership in order to grow it as a sustainable business. I’ve already gotten many useful insights from the first wave of responses. Thanks to all who took the time.This week, I spoke to Anand Sanwal, CEO of CB Insights, about how it uses its popular email newsletter as a customer acquisition tool for a software business. Also: Where Quartz went astray and how access is a subscriptions driver.More companies than ever are intrigued by building their own publishing arms, seeing an opportunity to lower customer acquisition and marketing costs. After all, in an age of “going direct,” why should companies not build media arms?As was once said to me about communism, great on paper, messy in reality. Time and again, companies have talked a big game about building their own media arms only for the initiatives to peter out, flame out or just languish. The latest cautionary tale comes from Netflix, which drastically cut staff last week at its ambitious (relatively speaking) publishing site, Tudum, which only debuted in December 2021.The cuts come six weeks after Netflix CMO Bozoma St. John departed the company – and at a time when Netflix is shockingly talking about reining in spending as subscriber growth hits a wall and goes in reverse. But in truth, Tudum was likely doomed from the start, despite hiring top-flight talent and promising them editorial freedom with tech company pay. One media exec responded to my text of the news of its demise this way: “Who needs this?”That’s a basic media question that marketers often don’t ask. And most of these forays into brand publishing come out of marketing departments. Finding recaps and cultural takes on TV programming is not hard. Sure, you can personalize Tudum with your Netflix credentials. That’s not a ton of added value.Publishing can be very useful for subscription services as both a customer acquisition tool and marketing vehicle. On this week’s episode of The Rebooting Show, I spoke to Anand Sanwal, CEO of CB Insights, which uses its 800,000-subscriber daily email list in order to fuel a high-priced data subscription service that often goes for $60,000 per year. What CB Insights has learned:Be realistic. CB Insights doesn’t claim it wants to take down The Wall Street Journal. It isn’t trying to build out a massive newsroom. (Anand says it has “0.5” employees devoted to it.) Instead, its goal is clearly to introduce people to the CB Insights brand and give them a taste of what its private-company data insights. Compare that with Coinbase claiming it was going to “combat misinformation”

I decided to mix up the days for this newsletter and the format. You’ll now get The Rebooting twice a week, Tuesday and Thursday. The Tuesday email will continue with a new format that is a mix of topics, along with highlights from the podcast. I think this is a better approach than my original podcast-centric approach. But let me know your thoughts: bmorrissey@gmail.com.Human ad productsBuilding a good media product is endlessly difficult, particularly when it comes to advertising. Math gives way to physics when ad products are built, as the complexities get ramped up, trying to satisfy financial goals, performance, audience needs, the overall brand mission, not to mention the challenge of balancing unique ad products with repeatable (and high-margin) ad products. Too often, that’s resulted in an adversarial approach to monetization that seems to operate in a parallel universe to the the stated ethos of the brand. If you’re going to claim to be high end, it’s hard to then turn to bottom-of-the-barrel monetization methods.The shift to primary-engagement media is an opportunity to rethink monetization products. The success of newsletters and podcasts ad products has mostly been due to ignoring the typical monetization methods of other digital media. Running banner ads in email newsletters doesn’t work as well as hand-crafted ads in the voice of the publication, particularly if delivered by an individual. The same holds true for a personal publishing medium like podcasting, which has long relied on host reads. These are more human ad products, playing into the “casualness” that’s eating the world. Litquidity, which is aiming to more than triple the $1 million in revenue it reached last year, has rolled out an interesting new product in which it will co-host earnings calls for companies on Twitter spaces. Litquidity began as a popular finance meme account, and has since expanded into a daily email newsletter with more than 120,000 subscribers, a podcast, mech operation and investment portfolio. Litquidity has signed up RCI Hospitality, operator of dozens of nightclubs and  strip clubs, to host RCI’s investor call on Twitter Spaces. For RCI, this is an opportunity to reach a new class of retail investor and younger finance pros who aren’t the type to dial into the normally dull investor calls where analysts love to repeat “great quarter, guys.”Brian Hanly, CEO of Bullish Studio, which works with Litquidity on growth and monetization,  estimated investor relations to be a $1 billion-$3 billion market, with 4,200 public companies spending on average $800,000 on IR. Those budgets are an attractive target, particularly for smaller public companies that do not generate the equity analyst coverage of more high profile companies. RJI, for instance, has just three equity analysts covering it.“Their last earnings call had 100 people,” said Mark Moran, head of growth at Litquidity who will host the RJI call. “One of my tweets about this [program] reached 200,000. We can confidently say we’ll get more than 100 people.”House of Kaizen brings together leading minds and proven practices to help subscription product teams get ahead, fast. Their SubscriptionWorks program is designed to inspire and upskill your internal team with training, events, best practices and on-call consultation that addresses your current opportunities. House of K

The future of work is one of the most fertile topic areas out there. The pandemic caused a reset, when combined with the labor shortage coming out of Covid, and it’s not going back to normal. The Atlantic’s Derek Thompson cited statistics that show basically every industry halted by Covid – from restaurants to cruises – has more or less returned to normal, except ones like movie theaters and offices. I’ve long thought the boss class is kidding themselves about strongarming people back to dreary commutes, fights over who left a coffee mug in the sink, pointless meetings and presenteeism. Work is changing, even if bosses don’t trust people with their cameras off.That’s why I find the scramble to own the future-of-work category fascinating. Jay Lauf, a cofounder of Charter, a new brand exploring the transformation of work, joined me to discuss how this bootstrapped media company is taking a different path than his previous executive roles at Quartz, The Atlantic and Condé Nast.“We've run these workplaces,” Jay told on this week’s episode of The Rebooting Show. “We've thought about these workplaces, and we've served different roles within these workplaces. We've been our own test lab in some ways, both prior in our careers and currently, trying to build this out.”Some takeaways: Start with an idea. Jay talks about how he and co-founders Kevin Delaney and Erin Grau all felt like they were “scratching an itch.” Media born from a legitimate interest tends to be more valuable than engineered media that looks for an arbitrage opportunity.Find a high-value area of need. The upending of the work routine during the pandemic was unprecedented. Human resources issues have gone from the sideline to a central organizational challenge.Embed in a community. Charter is both covering the future of work but also living it as they build their own workplace. Being both a participant and observer is a powerful combination.Ads and subs aren’t an either-or proposition. Charter wants to develop a business model mostly reliant on direct payments. But that doesn’t mean it is averse to ads. In fact, ads are the majority of its revenue as it determines the best direct-revenue model. Check out the full episode on Apple Podcasts or Spotify. Let me know what you think: bmorrissey@gmail.com. Thanks to House of Kaizen for its support.SponsoredHouse of Kaizen is an extension of your subscription revenue growth team. Decades of subscription growth experience are brought to bear to get you where you want to be faster with more confidence and efficiency. House of Kaizen works alongside your team to discover, ideate and execute experiments for sustainable growth.In-House support: When your team needs augmentation, House of Kaizen is there for you. Through collaborative execution and in-depth training, the House of Kaizen team will help improve, expand, and support your expertise and in-house capabilities.Full-Outsourcing:

Check out the full episode on Apple Podcasts or Spotify. Let me know what you think: bmorrissey@gmail.com.The war in Ukraine is now six weeks old, likely to drag on even longer. It’s important to consider how vital an independent and free media is to a free and independent Ukraine. I visited Kyiv in the fall, and I wrote about how the media operates in a far more complicated context there than in a place like the U.S. This challenge got greater in the wake of an invasion that’s mostly ground the economy to a halt. Andrey Boborykin, executive director of news outlet Ukrayinska Pravda, told me on this week’s episode of The Rebooting Show that the independent news media in Ukraine for now must rely mostly on grants from foundations and individual contributions from abroad. (Ukrayinska Pravda is also now publishing in English.)“We are in a very tough position when we speak about reader revenue, because here we are competing with expenses for food and transport and utilities,” he said. “We don’t have the culture of people paying for content.”We spoke about his own experiences being displaced in Ukraine twice, as well as how Ukrayinska Pravda is continuing its operations. I wanted to have Andrey on to bring attention to the threat to sustainable and independent media in Ukraine. Andrey and Eugene Zaslavsky of the Ukraine-based Media Development Foundation have set up a local news emergency fund to help independent media in the country get over to the other side of this tragedy. The institutional-individual divideThe shift from institutions to individuals is happening in many areas of the economy and society. The Economist noted that influencers were “initially dismissed as credulous Gen-Z folk who had mistaken posting selfies for having a job” rather than being the entrepreneurs they are. The same is happening as the media business itself goes through a reorganization that shifts more power to individuals. Dean Baquet’s get-off-Twitter missive to his newsroom can be seen in this light. Reporters should be out reporting, not tweeting all day and having their viewpoints trapped in the Twitter bubble, not to mention the fact that many NYT journalists are “bad at Twitter.” (Starting a Twitter fight is like engaging with a mascot at a sporting event: Impossible to emerge from the encounter looking good.) The Times is in a unique position to be able to set its own expectations as a brand that employs individuals. Other publishers will have a tougher time.The return of Covid (again) and eventsSurprise, Covid is back — well, it never went away. Case numbers have been spiking in Europe, and they’re starting to rise again in many places in the U.S. The Gridiron Dinner, a regular social gathering of Washington powerbrokers, turned into something of a superspreader event<