Simon Owens Doesn’t Hesitate To Experiment With His Newsletter and Podcast Business

Entrepreneur: Simon Owens

Biz: Simon Owens’s Tech and Media Newsletter

Tilt: Analyzing trends in the creator economy and traditional media

Primary Channel: Newsletter (15K – paid and free)

Other Channels: Podcast (5K monthly downloads), LinkedIn (60K), YouTube (1K), Instagram (256), Threads (844)

Time to First Dollar: 6 years for newsletter media company; 1 month after paid subscription launch

Rev Streams: Subscriptions, sponsorships, consulting

Our Favorite Actionable Advice

• Experiment with revenue streams: Simon went to a paid subscription model, then switched to models with optional patron supporter revenue and sponsor advertising. But he returned to paid subscriptions and doubled down his efforts in 2024.
• Use a platform that helps: Using Mailchimp to distribute his newsletter was fine, but Simon switched to Substack because of its influence in supporting the growth of the audience. (In both options, he owns the audience data.) 
• Get personal: Simon hosts a 30-minute call with every new paid subscriber to learn more about his audience and personalize the experience. It’s reduced churn and increased conversions.

The Story of Simon Owens

Beginning in sixth grade, Simon Owens was a fiction writer at heart. He loved reading novels and tried writing some but never quite finished one. At age 15, after reading a short story collection from Stephen King, he learned he could publish short stories in magazines.

In the 1990s, he also discovered he could reach a wider audience by publishing short stories on newly available internet channels like webzines. 

“It was my first light-bulb moment. I was like, ‘Wow, anybody can post stuff to the web and have just as much access to the global population as The New York Times or any other magazine.’ The internet is really incredible for publishing writing,” Simon says.

Simon got his first dopamine hit when he sold a short story for $10. It spurred him to submit stories weekly to any paying publication.

As a college freshman, Simon blogged to connect with other writers. In 2005, he launched Bloggasm, a blog about publishing on the Internet that marked Simon’s first taste of internet fame and led him to move away from fiction writing.

Fresh out of college, Simon landed a job at a newspaper. He learned journalism skills that he also used to improve his blog, which led to a job offer at a digital marketing agency in 2008.

Simon worked at digital marketing agencies for the next four years before US News and World Report recruited him for an audience development role. There, he gained more experience with social media and audience growth.

Going it alone and finding a home on Substack

In 2014, with the support of his wife (and her secure income), Simon went full time as a writer and content marketing consultant. 

Simon wrote long-form articles for Medium and other outlets and advertised his consulting services in the call to action (CTA). Several companies paid Simon a monthly retainer fee to run their content strategies and produce content, and he was earning six figures for his work.

In 2014, Simon launched his first newsletter on Tinyletter (later acquired by Mailchimp) to create an avenue where he could directly connect with his audience. It rounded up links to Simon’s articles on Medium, LinkedIn, DailyDot, etc.

By 2019, though, he grew tired of using an email platform that didn’t positively influence his newsletter. So, he exported his email list and moved the newsletter to Substack. The free, more robust newsletter platform enabled Simon to engage with his audience better and experiment with monetization strategies, and it didn’t cost him anything.

Around the same time, he launched The Business of Content podcast, interviewing media entrepreneurs and exploring the process of building media businesses. 

Adding revenue with less than 10K in audience

It is hard to pinpoint when Simon made his first dollar as a content entrepreneur. He generated revenue immediately as a consultant in 2014. However, he didn’t add paid subscription options for his newsletter and podcast until 2020.

Simon always planned to monetize his content products, but he wanted 10K subscribers before he started selling. By February 2020, he had 1.2K and needed to bring in revenue.

“I was to the point where I was like, ‘I’m never gonna get here if I’m only working on this stuff nights and weekends. I need to actually build this thing.’ So I launched the paid subscription to try to start replacing some of my income so I could work on it full time.”

The pandemic also intervened, prompting his consulting clients to pause his services and giving Simon the time to build and experiment.

Finding optimal price points and revenue streams

Simon experimented with newsletter monetization strategies. In the debut year, he charged $100 per year for subscriptions and provided minimal extra value. Next, Simon experimented with a patronage model. He asked subscribers to pay $50 a year to support his work without receiving additional content. High churn rates and inconsistent revenue prompted Simon to return to the $100 subscription fee.

In early 2022, Simon started selling advertising in the newsletter at $400 per spot. His entire 2022 inventory quickly sold out. He doubled his rates for 2023, but by the middle of the year, he reevaluated his advertising strategy. Given the challenging economy and his lack of enjoyment in selling sponsorships, he returned to the subscription-only revenue model in 2024.   

Amping up the subscription model

Simon asked himself two questions: “What differentiates me from everyone else?” and “What will people actually pay for?”

His expertise in accessing media operators and analyzing their media businesses was the differentiator. With his content tilt solidified, Simon answered the second question by defining the benefits of subscriptions. These included his growing library of content and exclusive content for paying subscribers. 

The subscriber package costs $10 a month or $100 for a year. New subscribers get a 30-minute introductory phone call with Simon. These meetings allow Simon to learn more about his audience, and the personal touch reduces churn rates (people unsubscribing or not renewing their subscriptions). 

Subscribers also can submit questions that Simon will answer through podcasts, newsletters, and comments throughout the month. (A twice-monthly Zoom Q&A session didn’t work well because having over 30 attendees prevented deep engagement.)

Simon also extended his  The Business of Content interviews to produce a detailed series about aspects of successful media businesses. Subscribers could access them through videos, podcasts, and transcripts, providing valuable, evergreen content for subscribers.

Substack allows Simon to offer free and paid subscriptions. Free subscribers can preview the newsletter’s first 500 words or the beginning of an interview transcript.

Recently, Simon has been scrutinizing his email database to convert free subscribers who open the newsletter into paid subscribers. Each week, he gives 20 of the free but active subscribers a 30-day trial of the paid newsletter. His goal is to double his paid subscriber count and reach 1K by the end of 2024. 

Advice for content entrepreneurs

Among Simon’s tips for content entrepreneurs:

• Mine your audience for content sources. Simon rarely has to reach out for his podcast interview subjects. The CTA for potential guests in his long-form content generates sufficient leads and people he would not have known about otherwise. 

• Make the ask. Your audience subscribes or listens for a reason. Don’t be afraid to ask them to buy your content product or become a paid subscriber. Sometimes, all it takes is the personal ask.

• Double or triple the runway for achieving success as a content entrepreneur. Make sure you have the savings, a supportive partner, or another source of income while you build the content business. 

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