Two years in

A progress report on The Rebooting

This week, I’m taking a look back at two years of building The Rebooting and some ideas on what’s next. First a message from Outbrain, which has a new monetization platform for publishers called Keystone.

There’s more to discover across the open web. As publishers build for the long-term, Outbrain is a total business partner to help them drive sustainable revenue and deeper editorial engagement.

Our latest innovation, Keystone by Outbrain™, uses Outbrain's optimization technology to support every publisher business initiative — driving better outcomes across subscriptions, podcasts, events, and more. Learn how we’re empowering publishers to diversify revenue across their unique business goals while providing the best user experience for consumers who depend on them.

The independent path

One of the nice parts of newsletter independent publishing trend is that it has coincided with this idea of “building in public” that trades the tradition of secrecy for transparency. I never understood why publishing businesses were so secretive about what they do and the results. There aren’t many secrets; it’s mostly a game of execution.

Back in October 2020, I was leaving my job of a decade and figuring out what I wanted to do next. I knew I wanted to take an independent path and start a new publication focused on building sustainable media businesses, using my experience both covering the industry for many years and as president of Digiday Media. I found it a good match for my experience and also something that’s societally important. What I wanted to find out was:

  1. Could I make a product I found rewarding and needed?
  2. Would the people operating media businesses find it useful?
  3. Is there a business model in doing this?

Two years in, I’m confident the answer is yes on all three. Here’s the progress report:


I started with a newsletter because it’s a perfect minimally viable product. Substack makes it simple to set up, for free, and then it’s just a matter of making something people want and doing it consistently. The good part about doing this from “the content side” is you can make the product yourself and how you want it to be.

I’ve found newsletters works differently than other media formats. I know people want to declare peak newsletter, and email has many downsides, but I see newsletters as less about email and more about independent publishers, often solo but not always, who are developing more human media products that are audience-focused and focused on primary engagement. So much of the scale era was fake. It was an era of over-optimization in which distribution trumped everything else. Much of the content produced was done at the behest of those algorithms. The direct connection of newsletters creates a different relationship. The numbers are smaller – The Rebooting has 11,300 subscribers – but the level of interaction is far higher than what I experienced working at Digiday or Adweek. That’s why niche media is having a moment. That’s also why it makes sense to sometimes write about the media business through the lens of washing dishes or delivering newspapers.

The Rebooting Show podcast, started in Nov. 2021, has similar dynamics. The voice is inherently human, and the podcast format is very dependent on the host-guest rapport. I’ve podcasted for several years at this point, in addition to hosting innumerable on-stage interviews. What I like about the podcast format in particular is that, when done right, these are real conversations. I’ve tried to make the approach very conversational to differentiate from the many PR-driven podcasts where guests are trying to hit their talking points.

I don’t pay a ton of attention to analytics to dictate what I write or discuss. I look for signals in the analytics, but I’ve found the dynamics of this type of media are different. What works best is to have a coherent view of a particular area, borne from experience, and use that to offer differentiated insight. I don’t try to break news with The Rebooting – that’s very hit and miss, and something I was never good at, particularly after a decade layoff from reporting – and instead want to give perspective of possible paths for building sustainable media businesses.


Growth is the hardest part of starting from scratch. I had an “unfair advantage” starting out thanks to simply having existed for a period of time in the industry and developing a reputation. That helped in starting from zero, but I always tell those building newsletters or any media product that it takes time. I’m in awe of the rocket-ship growth I regularly read about in these reviews. I haven’t experienced that. Most of the growth has been steady, even halting at times. The topics I write about aren’t exactly the fodder for virality.

So far this year, The Rebooting has averaged 8% month-over-month growth. Total subscribers will end the year with 120% growth. Open rates have stayed at 50%, although that metric is less important. I’m more encouraged that the right type of people are signing up and engaged.

One thing I decided early on is not to not focus on distribution hacks like ads and even insufferable Twitter threads. This could be because I don’t understand the dynamics of growth hacking. I feel like you can get the wrong signals early on if you engineer the numbers. Signals, particularly early on, often aren’t on spreadsheets.


For the first year of The Rebooting, I didn’t focus on revenue. I wanted to put off subscriptions, despite that being the dominant Substack model, because I wanted to better figure out the product. In retrospect, that was probably a mistake. A more personal media product is one way to get out of the adversarial trap of subscriptions that you see with paywalls. Individual publishing brands have an advantage of not being a faceless corporate entity, which helps as the number of subscriptions becomes overwhelming. That means many subscribers don’t see it as a basic transaction. This is why Substack subscription appeals typically use language around “support.”

The business model the first year was mostly around consulting jobs with a few sponsorships here and there. For the past year, I’ve been more focused on sponsorship sales. This has been a great learning experience. First, and I’m not saying this just because they’ve paid me money, but I’ve been very fortunate to work with some great people at the 25-odd sponsors I’ve had. They've been patient beyond reason with my natural disorganization and the reality that a solo operator is going to be stretched thin. Second, it’s only in talking to clients that you can understand what problems you can help solve. I’ve tried to make sponsorships additive to the product. I believe B2B media products operate differently in that an essential role is connecting buyers and sellers.


Writing two newsletters a week, doing two podcasts, selling ads and doing client service while still doing consulting projects is a lot. (I’m not complaining, it beats going to an office or using Slack all day.) The reality is the solo path isn’t for everyone. Here’s the areas I’m focused on going forward:

  • In-person events. I’ve dragged my feet on starting in-person events, which I believe are ideal humanist media formats. Connecting people with each other is the test of whether a publisher has an audience or a community. I want to do smaller events than the ones typically done in this industry because I find they have far more value. I have a great partner in Omeda lined up for a lunch event in December, and I’ll soon have details on an event I’m doing with Outbrain at CES in January. I will do dinners and small-scale events more regularly in 2023. Please sign up here to receive invites to future events.
  • A membership program. I plan to keep the majority of The Rebooting free to access. I understand well the tradeoffs of subscriptions, and I feel like business models need to mesh with editorial missions. I’m interested in building a true membership program that goes beyond paywalling every other newsletter. To that end, please take this five-question survey to help me understand better facets of a membership program that would be appealing.
  • Adding new verticals. Solo creators hit a fork where they need to either double down on the solo path like Packy McCormick’s Not Boring or expand into an independent publication like what The Dispatch or The Ankler is doing. I prefer the latter. I prefer working with others. And I see a market need for a new publication that offers a differentiated view of building sustainable media businesses, whether that’s in figuring out your tech stack or in streaming or through commerce. Of course, easier said than done, so expansion will need capital through selling more or partnering with investors. TBD. I’m looking for help in building out the business side of The Rebooting. Successful media businesses are operationally excellent, and I have enough self-awareness to know that I will need help on that front.

The final thing on doing this for two years: It’s probably been the most rewarding work I’ve done. I enjoy interacting with people who share similar views of how the media business works (or should work), and I’ve been forced out of my comfort zone in many ways. Thanks so much for reading, listening and writing back.

When The Dispatch reached the conclusion that they needed to build their own platform in order to continue to grow as an independent publisher, they chose The Code Company to bring its new home to life. We believe in challenging the status quo when it comes to building out the most effective tools for independent publishers. For over a decade, digital media companies have benefited from working with a long-term technical partner. “The Code Company is a strategic sounding board for all of our decisions. It’s had a huge impact on the business,” said Dave Lievense of Her Campus Media.

We know where the landmines and tradeoffs are, and there’s no shortcut to that.


The ad economy has never been weirder. The platform giants have been getting drubbed by the markets after posting disappointing results. But the ad holding companies continue to report robust results. A lot of the discordance is untangling the impact of Apple kneecapping the target ad model relied on by Facebook, Snap et al, from macroeconomic conditions. It’s an issue we discuss this week on the People vs Algorithms podcast, going up tomorrow. Subscribe on Apple Podcasts or Spotify.

Can’t go wrong with following the flow of money and talent. MrBeast is seeking to raise $150 million to expand his media/retail empire. This is the emerging blueprint for a personality-led media business that makes money in several ways.

If you aren’t Semafored out, Peter Kafka has a podcast out with Ben Smith. This part stood out: “When you say, “We want to reinvent the news,” there is an impulse to be like, “Oh, are you putting it on the blockchain? Or perhaps you have an algorithm?” And in fact, I think we are trying to do something very human and literal.”

While publishers are skittish about raising subscription prices, Apple is not at all. It is jacking up prices for its subscriptions significantly – in the case of Apple TV+ by 40% – and blaming higher costs of licensing as Apple sits on $48 billion in cash. Considering how it used “privacy” to kneecap rivals, makes sense to see how far it can go.


I’m starting a new section to point to useful resources, including events, reports and tools. Send me an email with submissions:

Beehiiv is hosting a (free) five-day course from Dec. 4-8 on how to make great newsletters. I’ll be speaking alongside some great newsletter experts, Morning Brew founders Alex Lieberman and Austin Rief, Inbox Collective’s Dan Oshinsky and Contrarian Thinking’s Codie Sanchez. Sign up here before it fills up.

Piano is hosting its Piano Live event virtually on Nov. 2, and it is open to publishers. I’ve spoken at this event previously and will again this year on the topic of taking a more human approach to building direct revenue business lines. Optimization is great, but there’s great leverage in treating humans like humans. Check out the agenda and register.

SparkLoop is hosting a free class on Nov. 3 on paid growth tactics with growth specialist Matt McGarry. The era of cheap acquisition is over, but there’s still ways to use ads to increase list size. Sign up here.

Send me your feedback: (or just hit reply to this email).

If you’re looking to reach over 11,000 people building sustainable publishing businesses, check out The Rebooting’s sales kit and get in touch.

I am in the midst of planning the first Rebooting events. If you’re interested in invites, please fill out this form.

If you this email was forwarded to you, please subscribe for free to receive The Rebooting twice a week.