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The vast majority of writers who launch newsletters on platforms like Substack do so with a single business model in mind: paid subscriptions.
And that makes a certain level of sense, since subscriptions incentivize quality over quantity and can generate sustainable revenue without massive scale. They allow the creator to focus entirely on the core product -- the newsletter itself -- and establish a direct relationship with their readers.
But any business built on a single revenue source is subjected to a certain level of risk, and I think a lot of writers are missing out on opportunities to diversify their income because they’re so singularly focused on the subscription model. There are lots of other ways to monetize your newsletter without compromising its quality.
Josh Spector’s For the Interested newsletter is a great example of this diversification in practice. He launched it in the Summer of 2016, describing it as a “weekly dose of inspiration and proven strategies from the world’s most successful creators to help you produce, promote, and profit from your creations.” Every Sunday, the newsletter curates five items that illustrate some specific idea or strategy. A recent edition, for instance, shared everything from “Eight Writing Tips From Roald Dahl” to “How To Build An Online Presence Without Being Fake.” The newsletter now has over 25,000 subscribers.
All together, Spector monetizes the newsletter five different ways. He didn’t roll out all these business models simultaneously, but instead gradually introduced them along with extensive testing and iteration. Here’s how he approached each model.
For the first two or three years of For the Interest’s existence, Spector didn’t monetize it directly, but it still contributed to his income by generating leads for new consulting clients.
Spector has spent most of the last decade providing freelance marketing services for businesses that range from individual creators to large organizations like the Oscars. Though his services vary depending on the client’s needs, his main expertise is helping people grow their online audiences.
So how does For the Interested generate leads? There’s actually no hard sell within the newsletter itself. “Every week the newsletter is curated, but the first article I curate is usually a blog post I’ve written that’s sharing experience from my own work,” said Spector. “So my guess is people would read the newsletter, then they would read those blog posts, and that's probably how they put together, ‘Oh, this guy consults.’”
In some cases, the potential client will contact Spector via the email address on his website, but often they simply reply to the newsletter itself. “The newsletter is almost like a Trojan horse to attract people who would funnel into the blog posts and then want to reach out to talk about hiring me.”
Spector was an early adopter of Medium and started cross-posting his articles there long before the platform debuted its monetization program. “Initially I was on Medium using it just as another audience growth platform, basically.” Each article ended with a call to action for readers to sign up for his newsletter, and occasionally he’d see a bunch of new signups when one of his articles went viral on Medium.
Given his already-existing following, Spector was extremely well positioned when Medium rolled out its metered paywall in 2017. “In those early days getting featured by Medium’s editors could generate a lot of traffic,” he said. “I was publishing at least once a week, and I got some stuff featured and it did well.” In some cases, a Medium article would generate hundreds of thousands of views.
So how well did this convert into actual revenue? “My biggest month on Medium ever was maybe $2,000,” said Spector. “I'd say for about a year, I was pretty consistently between like $500 to $1,500 a month.” For a brief time, he began linking within his newsletter to the Medium versions of his articles rather than his own website.
Of course, Medium has constantly changed its distribution strategy over the years, and Spector’s income has come down considerably. “For the past few months I’ve only received a couple of hundred dollars a month.” While he’s happy to continue cross-posting his articles to Medium, Spector has reverted back to linking to the website version within his newsletter.
Yes, Spector eventually launched a paid subscription product, but it took several iterations before he settled on a format that actually worked.
The first iteration was called For the Interested All Access, and instead of receiving additional newsletters, subscribers were sent a premium edition of For the Interested that contained 10 curated items instead of the requisite five that were included in the free version. “The response was OK, not great,” said Spector. “It wasn't a complete failure -- about 30 or 40 people signed up -- but it wasn't really growing. It didn't really feel like it was clicking.”
It slowly dawned on Spector that many paid newsletters were built under the flawed assumption that consumers wanted more of the same -- i.e., that if you subscribed to a free newsletter you would then pay to receive additional newsletters that looked just like it. “I had this idea that you can’t just offer more, you have to offer something different,” he said.
So he launched something he called the Creator Accelerator. “It was a separate email, not anything like my free newsletter,” he recalled. “Each week, I would send subscribers an exercise or something you could do in 15 minutes to help grow your audience or your business.” Subscribers also got access to an exclusive Facebook group. Rather than launching the newsletter from scratch, he transferred over his existing subscribers from For the Interested All Access.
This new experiment was more successful than his first, but it still struggled to gain traction. The Facebook group, for instance, failed to provide much value because there were too few members to generate organic discussion. “When you don't have a lot of people [in the group] and you're starting out, it’s like you're walking into a ghost town, basically,” he said.
Spector still wasn’t satisfied with his paid offering, and he continued to brainstorm ways he could pull together a more valuable product. Last year, he debuted the third and most recent version of a subscription newsletter: This Is How I Do It. Unlike his free newsletter, This Is How I Do It focuses on a single topic each week and goes deep into a specific aspect of Spector’s own work. “In my mind, this is almost like an inexpensive version of consulting; I'm going to tell you exactly how I do things with the goal that you can then do them similarly.” Recent topics have ranged from “This Is How I Analyze The Performance Of My Newsletter” to “These Four Tweet Formats Work For Me Every Time.”
After launching This Is How I Do It, Spector constantly experimented with pricing. He initially offered both a monthly ($20) and annual ($120) subscription. That means a subscriber would save 50% by opting for the annual option. “I really wanted to push people to annual,” he said. “When people started signing up for it, it was about a 50/50 split between people choosing monthly and annual.”
Spector eventually did away with the monthly subscription option entirely, but only after stumbling across a new business model…
One of the biggest selling points for This Is How I Do It is that all of its article topics are evergreen. This means that by becoming a subscriber, you not only get new articles landing in your inbox every week, but you’re also granted access to an ever growing library of articles that were already published.
Eventually, it dawned on Spector that there actually might be a market for individual This Is How I Do It articles, and by selling them as standalone ebooks he could generate revenue from readers who weren’t ready yet to commit to a paid subscription. So he began packaging them as PDFs and selling them on Gumroad for $15. He promotes the ebooks one at a time in the For the Interested newsletter.
After launching the ebook versions of This Is How I Do It, Spector did away with the monthly subscription offering for the newsletter. Now, customers can either buy an individual PDF or pay for an annual subscription.
For most of his newsletter’s existence, Spector was determined to keep it free of advertising. “I feel like the incentives are misaligned,” he said. “In most cases, advertisers don't really serve the audience, and if you're monetizing that way, then you wind up doing things that aren’t in the audience's best interests in order to please the advertisers and drive more clicks.”
That opinion changed in the Summer of 2020. A reader who specializes in providing therapy to creatives reached out to ask Spector if he knew of any newsletters that accepted classifieds advertising. “She said she had run an ad in Ann Friedman’s newsletter, and the results were amazing; it was the best marketing she’d ever done.”
The conversation opened Spector’s eyes to the idea that, rather than selling to large brands, he could source ads from his own readership. “A relevant classified ad placed by a reader of my newsletter would help that reader/advertiser attract more business and help my readers find products or services that helped them,” he said.
Spector decided to send out a survey to his readership with one question: “Should For The Interested have classified ads?” Respondents were given three possible answers: "Yes, I'd be curious to see them," "Yes, and I might want to purchase one," and "No." The vast majority chose either the first or second option, confirming to him that his audience wouldn’t consider the ads an intrusion.
Spector then set about building a system for buying classifieds ads. He didn’t want to have to juggle emails from dozens of prospective buyers, so he set up a very simple ecommerce landing page on Squarespace that would allow advertisers to purchase up to five ad slots per each upcoming issue. Once an issue was sold out, Squarespace would automatically mark it as such. He then reached out to the 100 or so survey respondents who indicated they might be interested in purchasing an ad.
By the time he officially launched the classifieds section, he had already sold out several weeks worth of slots, and so he was able to generate a sense of FOMO for those who might want to advertise. “When I announced it I wanted to be able to say the first couple of issues were sold out,” he explained. “I wanted people to perceive this as valuable and in demand right off the bat.”
Spector initially priced an ad at $50 but gradually increased it to $80. The vast majority of advertisers -- around 90% -- are either individual creators looking to promote their own projects or small businesses. Many will actually purchase several slots at a time, making it easier for Spector to ensure that every issue is sold out far in advance of its publication.
Overall, Spector’s classified experiment has been so successful that he dedicated an issue of How I Do It to explaining his process and also sells it as a standalone ebook on Gumroad.
The majority of Spector’s annual income still comes from his one-on-one consulting, but he told me that his direct newsletter revenue is quickly growing. Today, it represents about 30% of his total income. “That has allowed me to be pickier with the clients I take on,” he said. “It's also allowed me to take on fewer clients and charge higher rates.”
Spector will probably never stop consulting completely, but he’s set a goal for direct newsletter revenue to one day generate the lion’s share of his earnings. Given the newsletter’s current growth trajectory, that day likely isn’t too far off in the future.
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