Welcome to this week’s issue of The Rebooting. This week, I’m reviewing progress made in the first year of The Rebooting -- and ahead to my plans for what this can become over time. As always, I appreciate hearing from readers with ideas and feedback. I find the most rewarding aspect of doing this the more personal interactions that come from it vs institutional media. My email is firstname.lastname@example.org. Also, the best way people discover this newsletter is through personal referral. Please consider sharing The Rebooting with others you think would find it valuable. A quick warning: This is far longer than usual. I’ll get back to following my pleas for brevity next week.
A little more than a year ago, when I signed off Slack after nearly a decade at Digiday, my focus wasn’t on what was next. I knew I’d want to take time to figure out what path was best for me, what new opportunities were opened by the unbundling trends in publishing, and the reality that I had a one-year non-compete that would prevent me from taking a job even if I wanted one, unless I pivoted to paddleboard instructor. I spent more time reading, running and going to the beach to think. I don’t regret it.
The Rebooting began as a placeholder, a newsletter I set up in under 10 minutes as an outlet for exploring what’s next in media, processing what I learned over 9+ years as president and editor-in-chief at Digiday, and became an experiment in building a different type of publishing brand that’s more personal. Over the course of the last year, it evolved from a personal project to what I considered a minimally viable product to what I hope now is the seed to grow something more ambitious and my Main Thing.
My goal for The Rebooting is to establish a new publishing brand focused on how to build more sustainable media businesses. I want to develop a place where the focus is squarely on how to execute on business models that can support a new crop of digital publishers built on sturdier foundations. I’ve long felt the promises of digital media -- an explosion of content options, without gatekeepers, backed by good business models -- fell woefully short. Instead, we got the domination of technology platforms, a digital ad system dominated by scooping up as much data as possible for ad targeting, horrific user experiences, a race to the bottom as publishers chased virality, and a business culture that too often excuses corner cutting and dishonesty, giving rise to the shenanigans most recently exposed at Ozy Media but common, to a degree, across the industry. The reason I called the newsletter The Rebooting is I believe the Covid era -- and it’s going to be an era, not a crisis -- will result in much lasting change across our economies and societies. This will take time to play out, but the macro trends are clear.
A crisis of confidence in institutions. It’s been a bad decade for institutions. Government has proven inept from heeding the warnings before 9/11 to the Iraq War to the Financial Crisis to austerity strangling the economic recovery and feeding inequality to the pandemic. The finance industry has lost credibility to the point people are inventing new forms of money. The military has botched several wars in a row. And the media lost its credibility rocked by its own real and perceived bias.
The power of the individual. The Creator Economy is the media industry's manifestation of this macro trend that I think arises from the loss of faith in institutions. We’re more likely have trust and loyalty to individuals rather than faceless organizations.
Unsustainable inequality. Societies are unequal in all aspects. While not at the top of the list, media companies have their own forms of inequality, which I believe are driving the unrest within newsrooms and the trend of people choose the risk of going solo, even if the odds of a true middle class developing are long.
I believe we’re seeing the start of a new wave of changes in digital publishing, reminiscent of the Web 2.0 growth of new digital brands out of the blogging movement. Substack is the canary in the coal mine, as publishing unbundles around individuals, and business models evolve to value direct connections with smaller but more loyal audiences. My focus is on those building these new models. Here are the growth drivers I see:
Of course, vision without execution is worthless, so in the spirit of others on similar journeys, I’ve decided to openly assess progress to date. I’ve come to appreciate the building-in-public ethos because I’ve long felt people were too secretive in the media business. There are few secrets; it’s more of an execution game.
Differentiation is the key to establishing a brand in a crowded area. The world doesn’t need another Substack, another media publication about media, another subscription, etc. I’ve heard it all. And I agree.
I also think the market is missing a place for nuanced, critical thinking about the development of sustainable business models for media. We used to call this coverage “mechanics” content, with the idea that it was focused on going deep into the details on a specific topic. Instead, most publications are focused at 30,000 feet.
The Rebooting will cover the development of sustainable business models from the point of view of having done this myself. I developed a multimillion subscription business, something most writing about media haven’t. I’ve managed product and tech groups. And I’ve led newsrooms. The opportunity I see in the unbundling is in marrying writing skills with actual experience in a topic area, rather than the typical reporter’s position as solely observer. On top of that, I tend to think horizontally even if I focus vertically, so I believe the best way to understand where industries are going is to have a good grasp on the overall political economy, history and culture.
The point of view I want to continue is that it’s past time to develop sturdier business models in order to support a vibrant and largely independent media ecosystem. This is critical to the functioning of democracy and open societies. Why wait for governments to break up tech companies? Why hope for another pivot to actually lead to somewhere? Why wait for a benevolent billionaire, or hope that the demise of the third-party cookie is some gamechanger? I believe the publishing industry can be rebuilt -- and must be -- in order to thrive. I was asked this week by a subscriber if I’m optimistic about finding sustainable media business models, and I am. Doesn’t seem to be much choice.
Building a product set
The Rebooting started as an email newsletter because email has always been a workhorse for business content. We obsessed over email because understanding your audience, or ideally community, is everything. It allows a publisher to develop loyalty and understand more about their audience. In a world where user data is harder to come by, this is obviously critical.
Email is also an ideal MVP because it’s so easy to spin up. I didn’t want to waste time or money on building out and designing a Wordpress site, getting up and running a podcast, reports, events and other things before I truly understood the editorial mission and my own version of product-market fit.
The focus I wanted to bring is less on commentary about media trends, but on the why and how of building sustainable media businesses. Here are the posts that resonated the best:
- Revisiting the Digiday plan. I started The Rebooting with an examination of the plan I had starting at Digiday and how things turned out (mostly as hoped, just took a long time).
- The unbundling of publishing. I broke down the major forces I see reshaping the media business. There’s also a part 2.
- The rise of DTC media. I explained my hypothesis around why the media business's future lies in niches.
- Houses of brands. I went into some detail about different brand architectures and the merits of having a systemic approach to brands.
- The media business has a larger Ozy problem. This piece tried to place the Ozy story into the context of an industry where smoke and mirrors and corner-cutting are too often seen as the normal course of business.
I didn’t get the podcast up and running. That was frustrating and all my own fault. The eventual podcast, The Rebooting Show, will feature breakdowns with those building sustainable media businesses. I’m excited to get into the details -- the first episode is with Adam White, CEO of Front Office Sports, one of my favorite modern B2B brands -- and I promise not to have on people who are reading nonsense talking points. I endured enough of that already when guests of the Digiday Podcast would bring out a sheet of talking points prepared for them. Talk about a red flag.
My plan for the next year is to introduce a second weekly newsletter, probably a recap of the week in sustainable media, and experiment with both in-person and virtual events. On the events side, I have ideas on how to make valuable peer-focused events where attendees are truly participants and learn from each other. I’m interested in experimenting with other ways, although I have a gut-level doubt about the long-term viability of Slack channels and Discords as effective in the long run.
Developing the right audience.
Starting from scratch is humbling. By far the biggest lesson to data -- an unsurprising one -- is that audience growth is the biggest challenge. (I went into this more in a discussion I recently did with the HeyDay community.) The advantage of having a fair-sized Twitter following and two decades of experience and the network that comes with were tremendous advantages. But, as I wrote in June, everyone hits a wall.
Before even publishing a newsletter, I had nearly 1,500 subscribers. By the end of the first month, I topped 2,500. Plug that into the compound growth calculator, and I had “goals” of reaching 15,000 subscribers after year one. Let’s say I came up a bit short: 5,300. By the end of 2022, I hope to reach my original year-one goal of 15,000 subscribers. Growth is hard, particularly if you have an aversion to nonstop shilling on Twitter, which as Casey Newton of The Platformer notes in his one-year-in review is the biggest growth lever for newsletters.
But beyond the numbers, I was encouraged by having the right types of subscribers. The Rebooting’s subscribers include many top executives from top publications like The Financial Times, The Guardian, The Wall Street Journal, The New York Times, Vice, Insider, Politico. Many subscribers come from top brands and agencies, as well as, of course, lots of tech companies, venture capital firms and other key players in the media business. I hear from a lot of people, my open rates have remained near 50% and many posts get over 10,000 views. That’s a good base.
The challenge on this front is to find more reliable growth levers than trying to angle for a viral hit or devoting a chunk of my life to Twitter threads. Word of mouth/passalong remains the workhorse of growth for newsletters. Without much in the way of search authority and a focus that isn’t about glomming on the latest Twitter controversy, search and social aren’t going to be the big drivers they are for many. Of course, the biggest growth bump I got -- a quarter of all new subscribers -- came from carving out a spot in the Ozy Media maelstrom. The lesson I took: There’s room for both evergreen content and differentiated viewpoints and analysis tied to the news cycle.
Tactically, the power of referrals means simply more marketing -- God forbid, Twitter threads, I guess -- and finding opportunities like podcast and events appearances that will introduce more people to The Rebooting. (On that note, be sure to check out my guest appearance on “The Media Jungle,” a new video show from Alex Ragir.) Also, asking people to recommend The Rebooting to colleagues. Please recommend The Rebooting to colleagues, friends, family, strangers.
Working out a business model.
The media operator school would put this first. I find many people I speak to are trying to reverse engineer media businesses. This is perfectly logical and also not how my mind works based on my background on the content side. Last year, in an experiment using Clubhouse (remember that?), Charter founder Kevin Delaney was asked by a participant how he sized up the market for Charter’s mission to build better places to work. Kevin, who started his career as a reporter, honestly answered that he didn’t and instead focused on the need for self-taught managers like himself. This resonated with me, because I want to first and foremost build something new that I want to see exist. I know if I’m able to do that, the business model will follow.
I want The Rebooting to be a resource for everyone building sustainable media businesses, at all levels and in all geographies. While I believe very much that direct revenue models are powerful parts of many sustainable media businesses, I don’t see this as a religion. There’s a room for other models, including sponsorship, consulting, even investment. I decided to focus the business model in the first stage of The Rebooting around sponsorship and consulting. This will enable free access, removing friction from building the audience and expanding the product set. Down the road, late next year or in early 2023, I can see developing a membership component.
So far, I’ve executed sponsorship campaigns with a handful of companies as well as several consulting arrangements. (Big thanks to my initial crop of sponsors: Mediaocean, Hashtag Labs and One Day University.) In addition, I’ve done several consulting stints that have helped improve the core product of The Rebooting by getting first-hand views into publisher challenges from the inside. (I also work with non-publishers looking to use media as a brand-building and customer-acquisition tool. In the unbundling, media takes many forms.) For the first year, these were mostly separate, although I see the opportunity to merge the two. With a small audience, the key is to provide services that others with bigger audiences cannot or will not. That’s why I work directly with sponsors on their messaging and approaches. For Mediaocean, I hosted their Omnichannel Imperative event. My hypothesis is that a more personal brand enables more flexible and effective partnerships than the tried-and-true approaches of trade publications, with their endless partner emails, dry webinars and cookie-cutter banner ads.
The good part of operating in a business-focused niche is the name of the game on the business side is connecting sponsors with the right people, so absolute numbers are only useful so much. I know from experience the reach most publishers market in their big email lists includes a lot of chaff with bits of wheat. I’m confident that so long as The Rebooting continues to reach more of the right people, and I execute smart integrations, I can run campaigns that are more effective than others with far larger distribution that simply comes from being around a long time.
I’ve been encouraged in my discussions with potential clients that there’s a demand for new approaches. On that note, please get in touch if you have a product or service that helps create sustainable media business models. Here’s a rundown of the types of programs The Rebooting offers, although most engagements tend to be customized. Get in touch to learn more.
An important part of the shift we’re seeing post-pandemic is people rebalancing how they want to live. I realize like many I put too much of my identity into a job, fooling myself that it was the way to win the Squid Game. Many are rejecting this as the only way to live. They have a point.
I realized over the past year that I don’t need all of the false privileges of a corporate job. In the end, none of it truly matters. That’s a privilege, of course. The pandemic exposed vast inequalities in our societies, particularly between the Zoom Class and those we labeled “essential workers” as a fillip while we refused simple steps like a $15 federally mandated minimum wage.
The downside is working solo can be a grind. I miss talking through ideas, coming up with solutions and the simple upside of having teams that can cover up for your own weaknesses. On that front, I’ve partnered with different people to help on different aspects, like Reid DeRamus on growth approaches and Alex Ragir on podcasting and video. As Alex Kantrowitz of Big Technology noted in his one-year-in review, partners are key because this can be lonely and overwhelming.
But with that said, I realize I find more fulfillment in building from scratch than managing and optimizing more mature businesses where the focus of people tends to shift from what’s best for the business to what’s best for them playing the corporate game. Let’s just say I’m not surprised how big of a global hit Squid Game is -- most of us can painfully relate. For me, starting something new and small is right. I know if I stay focused and execute on all the details, I can make this work, ideally well beyond a one-person enterprise. But you need to go from zero to one, and that was accomplished in the first year.
Thanks for reading this much. Send me a note with idea, disagreements and sponsorship inquires: email@example.com.