4 lessons I've learned while running a paid newsletter

It's pretty much impossible to grow a paid newsletter as a side hustle.

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I knew I wanted to build a paid newsletter long before I actually launched one. Mainly this is because it’s one of the few business models that caters to my particular brand of journalism. I don’t produce content with enough frequency to generate the scale that would attract major advertisers, and I don’t write about the kind of consumer products that could convert into affiliate sales. 

I also really liked the idea of the value exchange that a paid subscription model brings. By producing high quality, niche content, I’m able to establish a longterm relationship with my audience, and I’m rewarded for the value I create when my readers open up their wallets and pay me. It creates the right balance of incentives in which I’m encouraged to grow a large following without succumbing to clickbait tactics.

But though I knew I really wanted to pursue the paid subscription model and had done a fair amount of research on other successful paid newsletters, I also understood that building such a product would require plenty of patience, experimentation, and learning. And so when I finally launched my paid newsletter in mid-February, I did so with the understanding that my strategy would evolve over time as I learned what worked and what didn’t.

Flash forward six months, and I feel like I’ve absorbed enough lessons from the experience thus far that it’s worth pausing and sharing some of them. I’d consider this to be Part 1 in an ongoing series where I roll back the curtain on my strategies for building a newsletter business.

Here are four lessons I’ve learned while running a subscription newsletter:

The paid version can’t just offer more of the same. It needs to be different.

When designing a paid offering, many writers simply assume that readers will want to pay for access to more of what they’re already receiving. So the writers will publish one free newsletter per week and then pump out a few paywalled newsletters that look almost exactly like the free version in both format and content.

What I think this approach fails to recognize is that your readers are already inundated with too much content. From the very moment they open their inbox in the morning to when they put their phone down at night, they’re bombarded with tweets, photos, articles, videos, and podcasts. Even if they enjoy your newsletter, they’re probably fine with reading it and then waiting a week until the next free issue comes out. Only your biggest superfans will be champing at the bit to subscribe and receive more. 

This is the trap I fell into with my own newsletter. For the first few months, the paid version was indistinguishable from the free product. Once a week I’d spend a few hours writing up some analysis of the latest media industry news I’d read that day. I never felt quite like I was producing all that extra value, and I even felt a little guilty asking people to shell out upwards of $10 a month for content that would quickly become outdated within a few weeks.

Then one day the solution dawned on me. I was keeping a spreadsheet of all my paid subscribers, and in the spreadsheet there were three main fields I was tracking: Name, email address, and occupation. It was while scrolling through that third column that I realized that most of my paying subscribers were successful entrepreneurs and executives within the media industry -- the very industry I covered in my newsletter. I was sitting on a wealth of industry knowledge, and I just needed to figure out how to mine it in a scalable way.

So I began reaching out to my paying subscribers and interviewing them, going deep on their successful ventures. I then took these transcripts and converted them into case studies with actionable intel. Here are a few examples I’ve placed in front of the paywall:

  1. How a blogger sold $72,000 in ebooks over a 3-day period

  2. This barbecue website has 15,000 paying members and a thriving ecommerce business

  3. He built a massively popular newsletter by syndicating it to media outlets

Not only do these case studies provide a lot more value than what I was sending out before, but they’re also evergreen in nature, which means a new subscriber can immediately start diving into my archives. In essence, my subscription bundle generates more value every single week, and a year from now I’ll have 50 of these stored up.

I debuted the case study series about three months ago and I’ve noticed a definite improvement in my free-to-paid conversions.

Change up your calls to action

So many subscription publishers recycle the same messages that urge readers to convert from free to paid subscribers. It’s usually a copy-and-pasted message that they place at the top, middle, or bottom of their weekly free newsletter. 

I think this is a huge mistake. A user who doesn’t convert the first time they see a call to action probably won’t convert the third time they see it. If anything, they’ll simply learn to ignore it and scroll on to the next piece of free content.

Think of your potential subscribers as existing on a spectrum. On the one end of the spectrum you have the person who really just wants to support you and your work. They’d subscribe even if it meant not receiving any paywalled content. On the other end of the spectrum is the person who doesn’t give a crap about you, they just need access to your paywalled content.

Most potential subscribers will exist somewhere between these two points. You should be constantly switching up your messaging so that it appeals to various points along the spectrum.

One of the best ways to convert free users into paying subscribers is by literally showing them what they’re missing out on. Expose them to headlines from your paid newsletter and then couple that with different messages explaining the longterm value of a subscription. Make it nearly impossible for them to scroll past your calls to action without at least pausing to consider whether this is the week they finally hand over their credit card information.

Churn will sting

When I launched my paid newsletter, I understood intellectually that some percentage of my subscribers would cancel their subscriptions or let them lapse, but that doesn’t make it any less painful whenever I receive an email alerting me that someone has ended their subscription. 

There was one particularly bad week a few months ago when three or four subscribers canceled over a period of days. This happened to occur at the same time when my subscriber growth numbers had seemed to stall (notably, before I pivoted my paid offerings to the case study interviews). For me, it felt like I was taking two steps forward and the one step back.

Unfortunately, churn is a fact of life. As any business owner can tell you, the day you start getting customers is the day you start losing them. 

This can’t be just a side hustle

I think there’s this perception that a successful paid newsletter can be built by someone who just writes on their nights and weekends, and while I’m sure it is possible, most won’t achieve the level of consistent quality output needed to scale their newsletter business.

Keep in mind that a successful paid newsletter requires a very steady stream of paid AND free content. Without the free content, you can’t get enough top-of-the-funnel signups that you can later convert to paid. And without enough paid content, your non-paying subscribers won’t see any reason to convert.

In a recent article, I laid out how much time I spend on each category of content every week -- my podcast, free newsletters, and paid newsletters. All together, I spend a minimum of 30 hours every week on my newsletter and podcast. Maintaining that kind of time commitment took real sacrifices; around the time I launched the paid newsletter I drastically scaled back my freelance client work, a move that decreased my monthly income drastically.

Any newsletter strategy should include a plan for how you’ll set aside a sizable chunk of your week so you can work on it, because trying to squeeze your writing in between the time you eat dinner and the time you go to bed is going to lead to burnout pretty quickly.

The subscription business is a long game

Most of the newsletter success stories you read about are outliers. A journalist with hundreds of thousands of Twitter followers quits their media job, they announce they’re launching a paid newsletter, thousands rally around them, and within a month they’re generating a six figure income.

And if you have a huge pre-existing audience, maybe that’ll also happen for you. But for the rest of us, building a subscription business is a slog. When I launched the paid version of my newsletter, I’d already been operating a free version for over five years. I’d been hosting my podcast for two years. I had tens of thousands of social media followers across Twitter and LinkedIn. And yet I was only able to convert a few dozen customers in my first month.

Getting people to turn over their credit card information is hard. Really hard. And there are plenty of competitors out there who have much more resources and reach. You’ve got to be prepared to show up every day and grow your audience one subscriber at a time. It gets easier as time goes on -- my subscriber conversions have definitely picked up recently -- but gird yourself for a years long marathon of steady content production. This is a business that rewards persistence, and the vast majority of paid newsletters will end up abandoned once writers come to understand how much work it truly takes to build one.

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on TwitterFacebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.

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