How I plan to monetize this newsletter

Welcome! I'm Simon Owens and this is my tech and media newsletter. You can subscribe over here or just click on this handy little button:

October 17th, 2014. According to my records, that’s the date when I sent out the inaugural issue of this newsletter. I’d be lying if I claimed to remember exactly why I decided to create a Tinyletter account that week, but it was around the time that personal newsletters had started to catch on, and I was probably attracted to the idea that I could have a more direct relationship with my readers, one that wasn’t governed by social media algorithms.

Regardless of the reason why I launched it, I was instantly hooked, and I went on to send hundreds of newsletters over the years. On weeks when I was pretty busy, the newsletter would be short, with just a roundup of links. Other times, when my client load was low, I would go really deep on subjects. These longer pieces really helped me grow my subscriber base. For instance, my recent newsletter on why laid off journalists should launch their own media companies was shared by over 100 people. It felt pretty exhilarating to watch that happen. 

In January 2018, I launched The Business of Content, my podcast where I interview media entrepreneurs and executives about how they create, promote, and monetize their content. My audience was tiny at first, but it was cool to watch it grow, week by week, as word of mouth spread. I now get emails on an almost daily basis from people who rave about how much they enjoy the podcast. Sometimes they just want to extend a compliment. Other times they pitch themselves as guests. You’d be surprised by how often I take them up on the offer. In fact, some of the best episodes of the show were interviews with people who reached out.

But here’s the thing: while I get a ton of fulfillment out of creating my podcast and newsletter, I’m severely limited in terms of the amount of time I can devote to them. Because I derive the majority of my income from freelance work, I always have to give it priority, which means that during my busier months I’m hardly able to produce any newsletters or podcasts at all. 

I want to create podcasts and newsletters on a more regular schedule, but in order to do that, I would need to monetize my content directly. Hence why I’m writing this piece you’re reading right now.

As an independent creator, I’m somewhat limited in how I can approach monetization. I don’t publish the kind of content that generates a huge audience that I can sell ads against, and even if I did I’d hate to waste time pitching brands to advertise with me. I don’t have the resources to host live events and nobody wants me to start an ecommerce vertical.

There’s really only one viable avenue for monetizing this newsletter, and that’s through paid subscriptions.

Yep. I’m another guy on the internet trying to get you to enter in your credit card information. But before you roll your eyes, let’s talk a little about the value I create and how it makes your life just a little bit easier. 

Why now?

Not all of my subscribers know this, but a lot of the stuff that I write about in this newsletter gets incorporated into my consulting work. Companies hire me to run their content strategy, and while some of that work involves writing articles, white papers, and newsletters, I also get clients who pay me thousands of dollars to deliver the kind of insights you get from my newsletter and podcast for free.  

Whenever someone signs up for my newsletter, I’ll often Google their name to see where they work, and more often than not, a new subscriber hails from media, marketing, tech, or public relations.While you may get some entertainment from consuming my content, we all know the primary reason you follow me is to glean insights on how to improve your content, grow its audience, and monetize it. 

This point was really driven home for me recently when one of my podcast listeners reached out to me and offered to take me to lunch. Over sushi, he told me how, when listening to my podcast, he couldn’t believe how many industry secrets my interview subjects were giving away, and that he often pinged his work colleagues telling them to listen to a particular episode. It’s pretty common for my readers to forward my newsletters to their coworkers, and one listener to my podcast told me about how she played a portion of an episode to an entire conference room of her work colleagues just to illustrate a point she was trying to make.

These anecdotes were immensely flattering to hear about, but they also confirmed to me that at least some of you derive actionable value from my podcast and/or newsletter. And so I’m simply asking you to pay for that value. And if enough of you do pay, then I can stop the freelance consulting work entirely and you’ll see an even greater output of podcasts and newsletters from me. It’s a win win for everybody. 

What you’ll get

OK, let’s get down to brass tacks and talk about what you’ll get out of the arrangement. 

Free content: While I get you’re not a charity and that to entice you into paying I’ll actually need to deliver subscriber-only content, I hope you at least take my free content into account when making your decision. My goal is to put the vast majority of the content I create out for free, and yes, while this means that some freeloaders will get to benefit from your largesse, that still doesn’t change the fact that your payment helps ensure that you get to read and listen to more of my content. 

Subscriber only newsletters: Ok, now to get to what you’re really here for. So my goal is to produce a paid newsletter for every free podcast and newsletter I send out. So in an ideal week, I’d send out at least one free newsletter, one free podcast, and one subscriber-only newsletter. The more money I generate from subscriptions, the more content I put out. It’s that simple. 

Access to a super secret email address: I don’t want my paid newsletter to just be a carbon copy of my free content, and I’d also like to have a more direct relationship with my super fans. So if you become a paying subscriber, I’m going to email you from a super secret email address. You can submit questions and comments to that email address, and my hope is that I can address whatever it is you send me in that week’s newsletter. Of course, I can’t guarantee that I’ll respond to every comment, but I promise to try to address as many as humanly possible.

What you can do to support me

If you’ve read to this point and you’re super jazzed about the idea of me pumping your inbox and podcast app full of content, then there are three ways you can support me in this endeavor. 

Pay to subscribe: Yeah, it’s not rocket science. Every person who subscribes gets my podcast and newsletter that much closer to sustainability. 

Promote this article: In order to hit my revenue goals, I’m going to need to bring more readers into the fold. Simply sharing this article you’re reading right now to your social media following will expose the newsletter to a greater number of people. Here’s a web version of the article

Interview me on your podcast/newsletter/website: It’s not lost on me that many of you are media geeks like me and create content for your own outlets. I make a pretty good interview guest, and no, we don’t have to spend the entire time talking about my newsletter. I can go pretty deep on all subjects relating to media and content. Now’s the perfect time to feature me!

What it’ll cost

Assigning a price was the hardest part. My natural inclination was to charge as little as humanly possible, but several colleagues talked me out of this, arguing that I needed to price my product according to the amount of value I bring to my audience and their careers.

Still, I want to reward my most loyal readers and listeners, so here’s what I’m going to do.

If you subscribe by March 19th, which is one month from now, I’ll only charge $7 per month, or $70 per year. You’ll be grandfathered in at this price. Here’s the link where you can subscribe:

Get 30% off forever

For those subscribing after that date, I’m charging $10 a month, or $100 a year.

I’ll spare you the for-the-price-of-a-cup-of-coffee analogies and just say this: if you like what I do and want to guarantee that I keep doing it on a regular basis, please pay. If you work at a company, ask your boss if you can expense it. If you’re self-employed, then you can write it off on your taxes as a business expense. If you’re the CEO of a company, buy 10 subscriptions for all of your employees.

Expectations and benchmarks

I’ll be honest: my expectations for this actually generating a full-time income are low. I’ve covered the paid subscription space long enough to know how hard it is to get people to type in their credit card information. 

But in the chance that this really starts to take off and I hit a minimum of 600 paying subscribers, then I plan to put a halt to all freelance client work and start working on this full-time. 600 subscriptions will be enough for me to decide that there’s viable demand for this content and that it’s worth making a go at it. And if I do hit that 600 subscriber mark, you’ll be the first to know.

Until next time…

OK, I’m going to get back to working on the content you’ve come to expect from me. Thanks for your support. Here again is the web URL for this article you’re reading right now in case you want to share it. 

And here again is the discount link:

Get 30% off forever

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