Welcome! I'm Simon Owens and this is my media industry newsletter. If you've received it, then you either subscribed or someone forwarded it to you.

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Let’s jump into it…

The state of this newsletter

Most creators don’t like to let their audiences see them sweat, and that’s why most of you had no idea that I entered 2022 supremely unconfident in the state of my media business.

I was closing in on my two-year anniversary of working on this newsletter full-time, and I didn’t feel like I had much to show for it. Growth in free signups was anemic, and I couldn’t achieve any sort of momentum. For every good week in which my newsletter attracted lots of attention and signups, it was often followed by multiple weeks of attrition and slow growth.

The situation was even more dire on the business side. Back then, I monetized exclusively through paid subscriptions, and churn had eliminated pretty much any monthly gains. I just couldn’t find a formula for what would motivate a free subscriber to convert into paid. Simply sending out extra premium newsletters didn’t really cut it. After nearly two years of relying on my spouse’s salary, I was desperate to contribute to our family’s finances, and yet my business was still only generating revenue in the low five figures.

But that’s the thing about creator businesses: it’s incredibly difficult to monitor your own progress when you’re still building a foundational audience. It’s only once that foundation has been laid that you can start observing real momentum.

Flash forward to today, and I can confidently say that my media business has a solid foundation on which to grow. That’s not to say that I’m no longer riddled with self-doubt, and that I don’t constantly agonize about ways that I could improve my product. But I also no longer wonder if I can actually make a living as a full-time creator.

So what changed? I’m going to devote this final issue of the year to examining the major turning points from 2022. I also want to talk a little bit about where I see this business headed in the next few months.

Let’s jump into it…

Looking back

The nature of being creator is that you’re constantly tweaking your product to see if you can make incremental improvements to your business, and I’ve probably made hundreds of changes to both my work process and content over the past year, but I think there are probably three major turning points that radically changed the trajectory of this newsletter:

The introduction of the Recommendations tool

At this point, you’ve probably read about Substack’s Recommendations tool (in fact, I dedicated an entire newsletter to it), but thus far I’ve only vaguely hinted at its effects on my own audience growth. Take a look at this chart depicting free signups to my newsletter:

As you can see, there’s an unmistakable jump in subscribers starting in April 2020, right around the time Substack introduced the tool. While many Substack creators benefited from it, I probably saw higher-than-average adoption. Right now, over 68 Substack writers have added me to their recommended lists, and it’s driven over 4,000 signups thus far.

Why? Probably because I devote a substantial amount of time to writing about the business of newsletters, and so I have a disproportionate number of active Substack writers in my audience. While the vast majority of these recommendations have only driven a handful of signups, I’ve been lucky that a few really big-name writers added me to their lists.

The lingering question is how valuable these subscribers really are. Are they just as likely to open and read my content? Do they even remember signing up for my newsletter in the first place?

Here’s what I’ve seen in the data so far: I’m definitely experiencing a huge increase in the number of free signups who are unsubscribing from my list. I view this as mostly a good thing, since I don’t want anyone receiving my newsletter with no intention of reading it.

As for open and click-through rates, they’ve mostly remained steady. I have grown more vigilant in recent months in removing inactive subscribers, though Apple’s recent iOS privacy changes make this more difficult to achieve. So far, I’m reasonably convinced that the Recommendations tool has produced a net benefit for my newsletter.

Accepting sponsorships

When I first turned the paid subscriptions functionality on for my newsletter, I assumed that advertising was off the table as a viable business model. Not only did I not have the scale that brands sought, but I wasn’t willing to spend my time cold pitching them to buy an ad. I’m not a salesperson.

But over time, I came to realize that brands really are eager to reach hyper niche audiences, even at small scale. Many companies have also come to understand that newsletter audiences, in particular, are highly engaged, much more so than social media users and website visitors.

What’s more, I came to understand that many of the brands who wanted to reach my newsletter audience were actually among that very same audience, and that if I could craft a sales pitch just right, then I wouldn’t have to cold email any of them. 

So I set about composing a sponsorships page that was 100% transparent. It included audience size, demographics, pricing, ad format, and availability. My goal was to make it so a potential sponsor wouldn’t need to ask me a single question before booking an ad. I simplified the entire process as much as humanly possible.

And then in March 2022 I began regularly plugging that landing page within my newsletter, and in less than a week I had booked out several months’ worth of ad slots. Thus far, that demand hasn’t let up, and advertising now makes up a substantial portion of my monthly revenue.

The launch of Office Hours

For the better part of two years, I struggled to find something of value to give my paid subscribers. Did people really just want to read extra newsletters from me? Not really. I kept spinning my wheels trying to launch various editorial offerings, but most of them either weren’t very enticing or too time-consuming to produce on a regular basis. 

The light bulb moment came to me sometime around April or May of this year. I had teamed up with the University of Oregon’s journalism department to sell an online course, and over the span of 10 weeks we held weekly Zoom sessions that featured some of the top media operators that we could find.

Up until that point, I had been extremely skeptical as to the value of live virtual events, but during those weekly sessions I was amazed by the level of interaction and discussion that we generated. It eventually dawned on me that, through my newsletter and podcast, I had built up a network of the world’s most successful media entrepreneurs, and that many of those people spent thousands of dollars each year to attend in-person conferences. Surely they would see some value if I started hosting live video panels where they could interact with both me and each other?

So starting in June or so, I began hosting bi-weekly Office Hours. For each session, I’d pick a topic in advance — e.g., how to grow your newsletter audience, how to convert more paid subscriptions, or how to build a local news business — and then recruit experts on that topic to attend the call. Rather than structuring it like a webinar, I conducted a live discussion, one where anyone could pipe in and contribute at any point.

At first, these discussions could only be viewed live, but after several requests I started recording them and distributing the YouTube video to my paid subscriber list.

To say that these Office Hours have been well-received is an understatement. I’m constantly flabbergasted and flattered as to the level of expertise that can be found on these calls. I can’t believe that people who are so successful in their careers take an hour of their week to attend these sessions, and the feedback I’ve received from attendees has been tremendous.

The Office Hours also played a significant role in spurring new growth in my paid list. Take a look:

Not only have I created something of real value for my subscribers, but I get genuinely excited whenever I get to host these things. There’s nothing quite as electrifying as getting to interact with your audience in real-time (more on that in a bit).

Looking forward

Now that this newsletter has some real momentum behind it, I’ve been giving a lot of thought to how I can both increase its quality and also ensure that it continues to grow into a sustainable business. Here are a few of the changes I’ve planned:

Raising subscription prices

Starting on January 1, I will be raising the subscription price for new subscribers — but only for new subscribers; all current subscribers will be grandfathered in at the price they’re now paying. 

My reasoning for this is simple: conducting biweekly, live calls takes a lot of work, and I need to charge a price that’s at least somewhat reflective of the value I’m creating in these calls. Right now, the majority of my subscribers are paying only $50 a year, and I think attendance of even a single session — where I and other experts are giving live feedback — is worth more than that. So I’m raising the annual subscription price to $100. For comparison, we charged $800 for that University of Oregon journalism course, and that was only for 10 sessions. 

But again, that new pricing doesn’t kick in until January 1, and anyone who subscribes before then will be grandfathered in. If at any point you’ve considered a subscription, now is the time to pull the trigger. Sign up here:

Get 10% off for 1 year

Raising ad prices

The math here is pretty simple: when I set my current prices, I had 4,000 subscribers to my newsletter. Now I have over 8,000.

So on January 1, I will raise my sponsorship prices significantly. That means if you’ve ever considered sponsoring the newsletter, you’ll never get a better price than what’s being offered right now. Go here for details.

The year of getting out and meeting people

Over the last 2.5 years, I’ve had the pleasure of meeting hundreds of other media entrepreneurs, but these meetings mostly occurred over Zoom.

I’m not satisfied with mere phone calls anymore. One of my biggest resolutions for the new year is to have more face to face interactions with my audience.

Part of that involves accepting more speaking arrangements. Back in November, for instance, I had the pleasure of speaking at an event in Aarhus, Denmark, and in January I’m scheduled to participate on a conference panel in NYC.

But I also want to start organizing regular get togethers, both in my home city and the ones I’m visiting. These will be small gatherings hosted at both my own apartment and in restaurants. I’d love to reach a point at which I’m organizing at least one get-together a month, though that might be too ambitious. If you’re interested in attending these get-togethers, don’t hesitate to reach out, especially if you live in Washington, DC.

Rethinking my content and format

Ok, so this is the topic on which I have the least amount of confidence.

If you’ve been subscribed to this newsletter for a while, then you know it has a pretty consistent format: it starts with a longish essay of roughly 1,500 words, followed by a roundup of industry news. 

For each essay, I try to provide analysis of an industry trend. My goal with each of these is to impart some kind of original idea or observation that hasn’t been shared elsewhere. Sometimes I actually achieve this goal, and there are lots of essays from the past year that I’m really proud of.

But there are also plenty of weeks when I’m really struggling to pick a topic to write about. While I always end up with something decent, I can’t push away this creeping feeling that I’m running out of interesting things to say.

At the same time, I’m beginning to miss the act of original reporting — you know, picking up the phone to interview sources and impart their wisdom. For the past year or so, I scratched that itch through my longform podcast interviews, but the problem is that audience growth for the podcast has completely stagnated, and in the meantime it’s doing very little to contribute to my business.

Don’t get me wrong — I like doing the podcast, and it does bring value to those who listen. But I also haven’t been able to devote the time and effort it needs to continue growing, and so I’ve felt like it’s been limping along for months, always playing second fiddle to this newsletter. At the end of the day, it’s just not my top priority right now, and it took me a long time to admit this to myself.

So here’s what I’m thinking: I’m going to put the podcast on hiatus, and then devote the time that frees up into longform original reporting. To start with, that means taking all the unproduced episodes I’ve already recorded and adapting them into longform case study articles, but once I’m through those then I can spread my wings a little bit and tackle a diverse array of topics.

That’s not to say I won’t publish any more hot take analysis, but now at least I can limit it to the weeks when I actually have something interesting to say. My hope is that by shifting all my focus to the newsletter, I can maximize value for both free and paying subscribers.

As for the podcast…I do want to return to it, but it’ll probably be once I’m generating enough revenue to hire a freelance producer, someone that can give it the care and attention to elevate the show to the next level. 

Anyway, those are my thoughts as of right now. As always, I’m happy to read feedback in the comments, and I’m incredibly grateful that you’ve stuck around this far. Despite all the anxiety and stress of building a media business from the ground up, the last 2.5 years have been the happiest of my career, and I’m genuinely excited for the year ahead.

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Do you live in NYC?

I’ll be speaking at an event there on January 17, and I was hoping to organize a small dinner gathering with my readers the night before on Monday, January 16. If this is something that interests you, please reach out.

I’m pretty much off Twitter

The breaking point for me came when Elon started banning links to competing social networks. I’ll still schedule out tweets to my Substack articles there, but if you’re looking for my day-to-day industry news commentary, then you should follow me on one of these platforms:

1. My private Facebook group: [link]

2. My LinkedIn profile: [link]

3. My Post profile: [link]