How much this newsletter grew in 2020

I want my newsletter and podcast to be considered the gold standard in media industry analysis

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

Heading into the year 2020, I had no intention of launching a paid newsletter. Sure, it was on a list of goals for the future, but my thinking then was that I’d continue tinkering away at the free newsletter in my spare time, growing both it and my podcast until it reached some tipping point that triggered runaway success. Only then -- once I’d hit 10,000 or even 20,000 signups -- would I make the plunge and monetize my content directly.

But by February I had reached two realizations. The first was that I’d grown immensely unhappy with my work. Since 2014, I’ve made a living as a freelance content consultant. Sometimes this meant writing fun journalism pieces for places like Scientific American, New York, and What’s New in Publishing, but I derived most of my income from corporate content marketing. Companies hired me to create content for their blogs, publications, newsletters, and social media accounts. The pieces often focused on subjects that didn’t particularly interest me, and in many cases my name didn’t even appear anywhere on the content.

For the first few years, I found this work fulfilling. Not everyone has what it takes to quit their job cold turkey and still manage to land on their feet. I was immensely proud that I could repeatedly drum up new business, all without any cold pitching. I had no boss and made my own hours.

So why did I sour on this career trajectory? I grew tired of building up other people’s brands at the expense of my own. I started feeling resentment every time I’d ghostwrite an op-ed for a CEO because it meant time away from creating content for my own media properties. This was especially frustrating whenever I’d see substantial growth in my newsletter and podcast, only for that growth to stagnate when I hit a busy month that tore me away from them.

By February of 2020, I finally acknowledged to myself that I would never be happy creating my own content as a side hustle. I was coming up on my 36th birthday, and if I ever was going to make a significant career shift, it needed to be when I was still relatively young.

The second realization I reached that month was that there’d be no tipping point that would allow me to achieve escape velocity. If I wanted to have a successful paid newsletter, I needed to build it one subscriber at a time. I was not a Matt Yglesias or a Glenn Greenwalld or any of these other star Substack writers who could generate a thousand paid subscribers in just a few days. I’d need to spend months, or even years, just putting in the work.

And so I announced the debut of the paid newsletter on February 19 with very little planning. It ended up being fortuitous timing, as the pandemic-induced lockdown caused a slowdown in my client work. I had a few-month period in which I was able to work on my newsletter and podcast on pretty much a full time basis. Once clients did start reaching out again, I became much more circumspect in what work I took on, as I was determined to keep the momentum going.

In preparation for writing this article, I reviewed the spreadsheet where I record my weekly audience stats. In 2020, my free newsletter list grew by 100%, which means it grew as much this year than it had in the previous five. And the level of engagement stayed steady; my last 10 newsletters averaged a 34% open rate, which is slightly higher than what it was at the beginning of the year. I also saw substantial growth across many of my other marketing channels -- my private Facebook group doubled in size and my Twitter following grew by about 10%.

My podcast also grew significantly. My 2020 downloads were 93% higher than they were in 2019. I now regularly get emails from listeners, many of whom have ended up as guests on the show. With its B2B focus, the podcast’s audience growth may have been impacted by layoffs and the elimination of the work commute, but plenty of people still found the opportunity to listen.

As for the paid version of my newsletter? Growth was painfully slow and worrying at first, but I saw a clear acceleration after rolling out my case study interview series. It now generates what I’d describe as a healthy side income, but I still have a ways to go before I hit my “1,000 true fans.” As I anticipated from the very beginning, the only way to reach that number is by just putting in the work. 

So what do I hope to accomplish moving forward? Well, in the immediate future I’m laser focused on reaching those first 1,000 paying subscribers. My hope is that I can hit them by the end of 2021, though I’m prepared to keep chugging along beyond this year until I achieve that goal. While 100% growth in 2020 was a great accomplishment, I definitely need to accelerate expansion of my free list significantly if I want to convert enough non-paid signups into paying subscribers. Thankfully that acceleration does seem to be occurring; my free list growth in the second half of 2020 was 133% higher than it was in the first half.

And what about my longterm goals? I want my newsletter and podcast to be considered the gold standard in industry analysis, known as widely in media as Ben Thompson’s newsletter is known in tech. And by “media,” I mean everyone from top Hollywood executives all the way down to indie podcasters and YouTubers. If  you make a living in digital content, I want you to consider my work a must-read.

Once this newsletter becomes financially sustainable, then I’ll have the luxury of contemplating whether I want to expand into other mediums and/or business models. Perhaps I could pursue a book deal or try to partner with a larger media organization. I could maybe even launch a media startup of my own.

But for now, I’m keeping my head down. There are no shortcuts in this line of work, and if I want this to become my full-time career, then I need to continue publishing high quality content at the highest frequency possible. It’s as simple as that. 

If you’ve read this far, then hopefully that means you’re at least partially invested in my success. If that’s the case, consider becoming a paid subscriber. Not only will it support all the work I do here, but it also gets you exclusive case study interviews with some of the top media executives and entrepreneurs working today. I’m running a special New Year’s discount where you can get 20% off for the first year. Just click on the button below:

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You can also recommend this newsletter to others. If you plug it on social media, be sure to tag me so I can thank you publicly.

And finally, I love collaborating with other content creators, so if you ever want to interview me on your podcast, newsletter, YouTube channel, or other medium, then I’m almost always game. I typically promote my interviews in my newsletter and social media, so you’re guaranteed at least a small audience boost. Don’t hesitate to reach out if interested.

Either way, thanks for sticking with me on this journey, and I hope you continue reading and sharing my work far into the future. Happy New Year!

My favorite work this year

Before I sign off completely, I wanted to share some of my favorite pieces from this year, especially since many of you have only signed up for the newsletter recently:

Favorite articles:

  1. Why Andrew Sullivan’s new paywall experiment will outlive his last one

  2. Why Crooked Media is succeeding where Air America failed

  3. Why Ira Glass is the godfather of modern podcasting

  4. How I ran an NPR-style pledge drive to grow my newsletter

  5. Why Medium is succeeding where other “platishers” failed

  6. Why Patreon’s business model is under threat

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

  8. Quibi could have succeeded. Here's how

  9. How The Daily Show reinvented itself for the social media age

  10. Did theSkimm try to expand too quickly?

  11. Is Patch actually producing quality local journalism?

  12. What The Athletic’s success teaches us about monetizing local news

  13. How Complex Media became one of the most innovative digital publishers

Favorite podcast episode:

  1. Why a Fortune Magazine writer left her job to focus on her newsletter

  2. This sports podcaster's listeners pay him for text messages

  3. FreightWaves is building a media empire around the logistics industry

  4. How Jesse Singal built a 6-figure income through Patreon and Substack

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

  6. This media company scaled ad-supported newsletters to 7 cities

  7. How Alexis Grant grew several successful media ventures from the ground up

  8. How a hobby website about barbecue amassed 15,000 paying subscribers