The exact time commitment it takes to run a paid newsletter

It's impossible to run a Substack as a side hustle.

Welcome! I'm Simon Owens and this is my media newsletter. You can subscribe by clicking on this handy little button:

About six months ago, I made two decisions that were aimed at changing my career trajectory.

The first you’re likely already aware of. I launched a paid version of this newsletter. I had been sending out the free version of the newsletter since October 2014 and hosting my podcast since January 2018. By this February I felt that I had built enough of a following for both and it was time to monetize them directly. There were several motivations behind this, including my desire to build a scalable business that placed my personal brand front and center. But mostly I just love writing and podcasting about the media industry. It’s a true passion of mine.

The second decision I made is one I haven’t talked about much publicly. Since mid-2014 I’ve derived most of my income from freelance content marketing. I’ve ghost-written dozens of “thought leadership” articles for executives that ran in places like Forbes and Inc. I wrote white papers, blog posts, and newsletters for companies. I ran the digital marketing for a trade association. I wrote native advertising pieces for places like Politico.

During good years, this produced a pretty good income for me. But in February I made the conscious decision to scale back my freelance work. I started turning down new projects from one of my most consistent clients. I stopped advertising my services on my newsletter and social media. I didn’t pause this line of work completely, but I became much less aggressive in pursuing new business. Because of this, I saw an immediate and drastic decrease to my monthly income.

So why do it? Because I knew that I could never convince my audience to convert into paid subscribers if I was only publishing content occasionally, and I didn’t want to lower the quality just so I could have more consistent output. When the client work got heavy, my podcast and newsletter definitely suffered. In the month of December 2019, for instance, I only sent out one newsletter. And it didn’t matter how good my articles were; nobody was going to convert into a paid subscriber when they were only exposed to my stuff once a month.

And so I took a gamble. Six months later, I feel like I have a pretty good handle on my workflow and can provide some insight into what it takes to operate a podcast and newsletter operation that’s monetized through paid subscriptions. 

Here’s a look at what that entails.

Industry news curation

No matter what I have on my to-do list, I try to set aside a minimum of one hour each day for simply reading media industry news. Whenever I see a piece of content that I might want to read later, I save it to Instapaper, and so during what I call my “news roundup” time — which usually takes place in the morning — I open that Instapaper account and begin combing through the articles one by one.

There are a couple reasons behind this. For one, a lot of the industry news I read ends up getting curated on my social media accounts and within the newsletter itself. This is how I provide incremental value to my audience in between publishing my longform articles and podcasts.

More importantly, this news curation serves as the springboard for the vast majority of my articles and podcasts. The ideas for most of my articles almost always stem from something I read somewhere else, and I discovered many of my podcast guests in a similar fashion. It’s only through this constant curation that I’m able to lock on to industry trends that I can later flesh out with more research or incorporate into a question for one of my podcast guests.

Longform articles

I play around with a couple different formats with my newsletter, but my favorite kind (and the one most likely to be shared on social media) is the longform piece that provides in-depth analysis on a company or trend. Here are a few examples.

1. Why Patreon’s business model is under threat

2. Tinyletter was one of the greatest missed opportunities in tech

3. How Snapchat repaired its relationship with publishers

These articles take a fairly long time to research and write. They start with a germ of an idea -- usually only a headline. I then begin Googling to find nearly every article I can find on the topic. Sometimes I’m looking for information that was reported several years ago, which requires some creative use of keywords and Google Advanced Search. 

I then move on to more observational research. For that Snapchat article linked above, I spent a few hours on the app itself, combing through the Stories for dozens of Discover publishers to get a feel for how they were using Snapchat on a daily basis.

That research usually takes a minimum of four hours. Then I sit down to write it. I’m a slow writer, averaging about 300 words per hour, so that takes a minimum of five hours. Add in the time to edit and format the article, and I’m looking at 10 hours from start to finish.

I’m not going to pretend this is the equivalent to the research and writing that goes into a feature article for The New Yorker, but it’s the most time-consuming piece of content I’ll produce in a given week. 

“Quick hit” newsletters

In addition to the longform pieces, I also send out newsletters that will jump across several topics. I might spend 400 words responding to some sort of news that broke that week, then answer a few questions from readers, and finally end it with a round up of links. Here are a few examples:

1. Audible is becoming more like Amazon Prime Video

2. Why Wirecutter might go behind The New York Times’s paywall

3. Do news consumers want to pay for an ad-free experience?

I like these because they allow me to cover a wider spread of topics and are less research intensive. I can also be a little more casual in my writing. All together, these take about four hours to write.

The podcast

My podcast The Business of Content has a lot of moving parts. I usually reach out to lots of potential guests at a time, with the assumption that a few of them won’t answer or will say no to the interview (I get a lot of requests to “circle back in six months,” which is basically a no).

Once a person has agreed to come on the show, I then usually schedule an “on background” phone call with them. On this call I’ll pepper them with questions and take lots of notes. This is so I can ask them really informed questions once we conduct the actual interview. At the end of this call we both open up our calendars and find an hour-long window to record the interview. I’ll also send them pre-written production notes so they can be prepared with the best sound quality (seriously, more podcasters should do this. Sound quality is such an important factor).

On the day of the interview itself, I’ll usually spend about half an hour reading through my notes from the previous call and jotting down 12 to 14 questions. I try to keep my interviews as conversational as possible, so I use these questions as guideposts to keep the conversation on track. The interview itself will take between a half hour and an hour.

From there, I start the editing process. I basically relisten to the entire thing and edit out all the awkward pauses and interruptions. I then write a script for the intro, record it, and then begin splicing all these recordings together. I finally upload the file to my host, which then distributes the file to all the major podcast players.

But that isn’t the end of it. I also make an article version of each podcast that’s optimized for the web. Here are a few examples:

1. How The Water Coolest generated over 50,000 newsletter subscribers

2.  Scott Brodbeck built a thriving local news company in the DC suburbs

3. How Dan Oshinsky developed the early newsletter strategy for BuzzFeed

To do this, I first run the audio file through automated transcription software, which spits out a Word file of the transcript. The transcript is extremely rough and only about 80% accurate. So I start reading through it and pulling out the most insightful quotes, packing them under at least three subheaders. The goal is that someone can read the article and learn from it without ever listening to the podcast. These articles clock in at about 1,000 words.

Adding all this up, I probably spend a minimum of six hours on each podcast episode.

Case study interviews

For the first months after launching the paid newsletter, I struggled with what to actually send to my paying subscribers. At first, I simply sent them an extra “quick hits” newsletter, but this never seemed very compelling to me. Did readers really want just more of the same -- a piece of analysis that’s going to be old and stale by the end of that week?

Then one day I was perusing through my spreadsheet of subscribers and realized that most of them were media entrepreneurs and executives, some of whom I’ve even had on my podcast. There was a wealth of industry knowledge sitting at my fingertips and I was doing nothing to mine it.

So that week I launched an ongoing series of case study interviews. Here are a few I placed in front of the paywall to give you a taste of what they look like:

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

2. His network of newsletters merged local news with content marketing

3. She built a business around helping podcasters solve one core problem

Like with the podcast interviews, I usually get on the phone with the subject to hash out what we’ll discuss in the interview. We then schedule a time for the interview. I actually conduct these via some kind of text chat platform like Twitter DM or Skype. Why? I run them as Q&As, and so doing it over text makes for a much cleaner transcript. But I don’t simply email the person the questions, since that would produce wooden answers and wouldn’t allow for follow up questions. Chatting over DM can provide some wiggle room for more back-and-forth conversation.

Once the interview is completed, I then merely need to write a headline and a few intro paragraphs. Start to finish, these case study interviews take about three hours to complete.

Adding it all up

As I mentioned earlier, I need to produce all the above content on a consistent basis if I ever hope to attract new subscribers. But all of this comes at a cost; in a given month, the time I spend on the newsletter and podcast results in up to a $6,000 loss in freelance revenue.

Sure, the paid subscriptions I’ve generated so far helped replace some of that revenue, but not nearly enough. I’m lucky to have a patient spouse and some savings in the bank, but there will come a day in the not-so-distant future when a potential client comes calling and I won’t be able to justify turning them down. And once that happens, my content output will suffer.

If you enjoy my work and feel that it helps you in your own career, there are three ways you can help:

Subscribe: The best way to support my work is to simply subscribe. It’s the only way I derive direct revenue from my content. For the next month, I’m going to be offering a 20% discount for the first year. You can get it by following this link:

Recommend this newsletter: Almost 100% of my newsletter growth comes from recommendations from readers. This includes people sharing both the newsletter itself and the individual articles I write. Chances are that if you’ve made it this far, you work in the content industry and know others who could benefit from my analysis and interviews. Taking just a few seconds to forward it makes a huge difference.

Interview me: Most the people who read and listen to my stuff are content creators themselves. I love going on other people’s podcasts and am always happy to field questions across a variety of topics including media and tech. If you have a newsletter or a podcast or a blog, I’d love to come on and lend my expertise.

Either way, thanks for sticking with me this far. I knew building a sustainable, reader funded newsletter wouldn’t be easy, and I’m determined to stick with it. I’ve always wanted to run my own media business, and by reading and sharing my work you help make that dream possible.

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