Hard to believe, but I sent the first edition of The Rebooting four years ago to about 1,500 people. I have a retrospective below, but you’ll need to join the TRB Pro membership. Luckily, I’m offering a 20% discount for the next week. You get a year of TRB Pro, with access to all content and invites to member events, including a live podcast this December at Gannett’s NYC headquarters, for $160. 

The Rebooting is kicking off a new research project with our partners at EX.CO. I’m a believer that the media business is about managing tensions and tradeoffs. What we want to understand is how video is viewed within publishing organizations. The survey only takes five minutes to complete, and all answers are anonymous.

Your gateway to transformative brand experiences

Year after year, we’ve watched the walled gardens dominate the digital space with their innovative formats that engage users. Moments by Outbrain is here to change that narrative by delivering an immersive experience that channels the power of vertical video on the Open Internet. 

Complementing the lower-funnel engagement of social platforms, Moments amplifies a brand’s media mix, extending average attention duration to 23.5 seconds from the 12.4 that social as a standalone achieves – superior to any other digital media combination for better brand recall and recognition. By combining immersive full-screen experiences with advanced prediction technology, Moments creates deeper connections, enhances content engagement, and drives powerful results for both brands and media owners.

AI in the newsroom

On this week’s episode of The Rebooting Show, I have a spotlight episode with Josh Brandau, CEO of The Rebooting’s partner, Nota, which offers AI tools to improve workflow in newsrooms. 

As I wrote about the AI adoption curve last week, publishers have passing through the anger and bargaining for deals phases and are now moving onto practicalities. Companies overall are adopting AI initially in the hopes of becoming more efficient and productive. Publishing is no different. The Rebooting’s recent survey of news publishers found efficiency by far the biggest opportunity they saw in AI.

Josh 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. This is critical in a more-with-less era.

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.

Listen to The Rebooting Show on Apple | Spotify | other podcast platforms

Four years in

Four years ago this week, I sent the first edition of this newsletter to 1,500 subscribers. It was an analysis of the plan I’d set out for Digiday before I joined the company in 2011. My thinking was it would give a sense of how I think of the media business from my experience.

The Rebooting has expanded incrementally since then, adding a second edition (and for an insane few months, a third), a podcast, a second podcast, online forums and research reports, dinners and in–person events.

My high level takeaways so far: 

  • Building anything from scratch is hard. The cliche that it “takes twice as long and is twice as hard as expected” is a cliche for a reason. Persistence pays off.

  • Planning isn’t as important as doing. Most of the time spent sketching out grand strategies is rumination; you’re better off just doing things early on because you need feedback.

  • Funding growth with cashflow is a useful constraint. You have no option but to listen to the market, even if it’s telling you things you don’t want to hear.

  • Fractional is a force multiplier. I now have a team of seven – nine if you count Troy and Alex – but none full-time. I think more companies will look like this.

  • Newsletters aren’t a business model.Many newsletter businesses are email marketing businesses. To build a media property, you need to do more than just email.

Here’s the state of The Rebooting’s business at 4 and what’s next:

As a business, The Rebooting is in good shape, particularly when considering that the business is a media business focused on media businesses. 

The Rebooting has 27,000 email subscribers. That’s far smaller than the numbers I see trumpeted in legacy trade publications. The real test of these businesses is if you can “activate” valuable segments. The amount of business The Rebooting did with partners increased substantially after moving from solely offering ad placements to taking more of a marketing services approach. We work to understand a client’s target customer and design programs to connect partners with decision makers that fit those criteria. 

This means going beyond branding or “thought leadership” in B2B marketing jargon. I’ve found the biggest share of marketing budgets goes to performance, which in B2B means metabolizing a sales pipeline.

One of the big bets I’ve made is around a robust audience database that has critical information on audience members that allows them to be segmented and ultimately “activated.” I view activation as either taking a commercial action in one of our collaborations with The Rebooting’s 18 partners or upgrading to a TRB Pro or TRB Insider memberships. The KPI is not so much the size of the email list but the overall number and percentage of audience members activated.  

In this kind of business, you either deliver the right people or you do not, whether that’s in the form of what I consider “CRM-level leads” or people in a room. 

That was a big driver of my decision this year to leave Substack. Substack is a direct-to-consumer platform model. I decided not to take this path because in B2B there’s a bigger business in connecting a buy and a sell side. The tradeoff, as fellow ex-Substcker Casey Newton wrote in his own four-year report, is you sacrifice Substack’s growth engine – and its underrated leverage of driving more conversions simply because it already has 1 million credit cards stored.

The other tradeoff is simply focus. It’s impossible to fully focus on content while operating what’s in essence a marketing services business.

Client service and delivery has been by far the hardest aspect of the business to get right. Being easy to work with, doing what you said you would do when you said you’d do it is basic but hard to get in place. We’re getting better – and good problems to have! – but this is an area where I underestimate the difficulty.

Events are by far the biggest line item in the marketing budget of most companies in this space. What else could explain Advertising Week persisting for two decades.

I haven’t bet on larger events, possibly because I spent nearly a decade in a mullet model with publishing in the front and events in the back. Events have a lot of upside, particularly for a bootstrapped media company. They can generate a lot of cashflow at one time. The tradeoff is both the risk and constraints of high venue costs and deposits, as well as the reality that events can swallow you whole. I used to joke that you start out running events only to find events running you. 

Instead, The Rebooting has bet on smaller, more focused events, particularly private dinners. These work like mini-events, only without the four-dudes-and-a-woman panels of platitudes. Over a long career of doing so many types of events, I find the smaller and more focused events the best. They’re the way you move people from attendees to participants. They deliver the most value to all sides, in my view. 

The next step is to continue to expand these while retaining the conversational elements, as we did with our New Growth Agenda event in May with a second edition coming up on Nov 13. The idea of this event is to have 45 C-level executives for two hours of conversational programming, cocktails and networking and then roundtable dinner conversations. 

One strategic decision I made was to skip news. I view The Rebooting as operating downstream from the who, what, where in order to focus on the why. I’ve always gravitated towards the more analytical approach. I’d rather win on this level of connecting the dots than be the first to get the scoop. My goal is to focus more on this side by branching into practical information about the mechanics of media businesses. I want The Rebooting to provide the analysis and insights that helps people build sustainable media businesses, whether they’re building from scratch or retrofitting existing models. 

I find at some point during my meetings people ask me for the models I like and also tactical examples. I view what I’ve done so far as being at more of the strategic level, focusing on business models. Where I plan to expand is in zeroing in on the mechanics of execution through case studies and in-depth research. Expect to see more of both in year 5 as part of The Rebooting’s membership, which launched this year. 

Memberships are currently a small part of the overall business, about 5% of revenue. I want to continue to make membership a bigger part of this business (and my own focus). I don’t think subscriptions are the be-all and end-all, but I believe they’re critical for alignment. 

In addition to depth, I want to widen the aperture to encompass more aspects of the emerging Mediaspace, which I divide between the Contentspace and the Information Space. Publishers are one aspect of these universes, which increasingly are filled with all kinds of different entities and individuals. Media isn’t dying, it’s just changing. There will continue to be challenges to legacy models, without a doubt. But there are many vibrant new models that are using the more-with-less era as a competitive advantage with leaner, more productive approaches with better business models. 

Finally, thanks so much for reading The Rebooting and upgrading to a membership. As always, I like to get feedback: [email protected]

Keep Reading

No posts found