The Business of Content with Simon Owens

My newsletter: https://simonowens.substack.com/ So the format to this podcast is pretty straightforward and consistent. I bring on a media entrepreneur or executive and interview them about their craft. But I’m also sort of a media entrepreneur myself, in that six months ago I launched a paid Substack newsletter that I hope to grow into a full-time job. Growth has been slow but steady, and over the six-month period I’ve experimented with a number of strategies to boost signups. Some worked, others didn’t. I’ve still got a ways to go before it’s completely replaced my consulting income, but I think I’ve made enough progress that it’s worth pausing and looking back at some of the lessons I’ve learned along the way. So strap yourself in, because we’re about to dive deep on my paid newsletter strategy.

With the journalism industry in freefall, there’s a good chance that your local newspaper is experimenting with some kind of digital subscription offering. In many cases, this involves some kind of metered paywall where you’re expected to start paying after consuming a pre-determined number of articles. Hundreds of newspapers have installed paywalls like this, but they’ve seen mixed results, with many reporting disappointing revenue numbers. But is content the only thing an audience will pay for? That’s a question Doug Lesmerises, a Cleveland.com sports columnist, sought to answer. A few years ago he co-founded a popular sports podcast but had a difficult time attracting advertisers. Then some executives from his newspaper’s parent company approached him with a new product called Subtext. It provides a simple way to allow paying subscribers to exchange text messages with Doug and other hosts. The service was a surprise hit, and Doug now uses the app to crowdsource questions for the podcast and send his paying subscribers quick-hit analysis when Ohio sports news breaks. I interviewed Doug about how he incorporated texting into his show and what other local journalism outfits can learn from his success.

When Naoise McNally and her business partner launched One Fab Day, neither of them had any experience working for a media company. Naoise didn’t even have much knowledge of the wedding industry outside of planning her own wedding. But the lack of wedding-focused internet resources in Ireland presented a clear market opportunity, so they went for it. Flash forward several years, and the site now has a full time staff and an interesting business model. Instead of relying on traditional advertising, it charges wedding vendors to be listed in an index it curates for readers.  I recently interviewed Naoise about One Fab Day’s founding, how she settled on a business model, and what she hopes the site can accomplish now that it’s owned by a major media company. 

Quick question: how big do you think the global freight industry is? If your guess is in the billions, then you’re aiming too low. According to some estimates, global logistics generate somewhere in the range of $8 and $12 trillion annually. For Craig Fuller, that number represents a massive opportunity. His company Freight Waves covers this industry across text, video, and podcasts. But Freight Waves is a lot more than just a trade publication; it also delivers data and intelligence. In fact, it’s much more analogous to a Bloomberg LP, which in addition to its massive media business also generates billions of dollars a year from its expensive Bloomberg terminals.  I interviewed Craig about how he built his expertise in freight, where the company sources its data, and why it recently took on venture capital investment.

When Terrell Johnson launched on Substack, he had no intention of rolling out a paid newsletter. He was just trying to escape Mailchimp’s expensive fees and liked that Substack would send his newsletter for free. About a decade earlier, Terrell had created HalfMarathons.net, a running focused website that grew so popular that at one point it was generating six figures in revenue just from Google Adsense. His free newsletter served mostly as a form of marketing for the website, but he eventually began to wonder if his most engaged readers would be willing to pay for it. So he flipped on Substack’s payment features, and while it wasn’t an overnight success, he’s gradually grown it into an impressive community of paid subscribers. I interviewed Terrell about where he got the idea for HalfMarathons.net, how he built up an audience, and why he eventually grew to distrust Google as his primary traffic driver.  

Josh Spector was blogging before most people even knew what a blog was. Over the span of a decade, he started and abandoned several of them, often before they had a chance to amass much of an audience. But in 2011 he got more serious about audience growth for a blog he ran that focused on teaching standup comedians how to market themselves, and to help drive traffic to it he launched a newsletter. Pretty quickly, he grew addicted to the newsletter medium, and a few years later he merged a couple of newsletters he was running into a single list and renamed it For the Interested. Since 2016, he’s been sending out new issues each week featuring ideas to help creators to produce, promote, and profit from their creations. For the Interested now has over 25,000 subscribers, and Josh recently launched a paid spinoff newsletter. I recently interviewed Josh about how he grew his audience, the role his newsletter plays in his consulting business, and why he thinks so many writers are approaching paid newsletters the wrong way.

A year ago, Jesse Singal had a very traditional freelance writing career. When he wasn’t working on his book, he’d write articles for places like The Atlantic and New York magazine. The mixture of book advance and freelance revenue provided a reasonably stable income. Today, the economic climate for journalism is much more dire. The Covid-induced recession has led to mass layoffs and a squeeze on freelancer budgets. Some publications have closed up shop completely. But in many ways, Jesse’s income streams are more secure than ever. That’s because he launched a paid newsletter through Substack and co-hosts a hit podcast that monetizes through Patreon. Together, these two sources generate a nice six-figure income for him. I recently interviewed Jesse about why he decided to monetize his audience directly, how he designed his paid offerings, and whether he thinks platforms like Substack and Patreon can replace the income for laid-off and underemployed journalists.

When Tyler Morin was in high school, he dreamed of going into journalism, but his parents convinced him to major in finance instead. After graduating, he went into the financial sector, but he never lost his ambition to work in media, and he became obsessed with daily newsletters like Morning Brew and theSkimm. After experimenting with a group sports blog, he pivoted to launching a daily newsletter called The Water Coolest. The Water Coolest found an audience and quickly grew to tens of thousands of subscribers. I recently interviewed Tyler about the founding of his company, how he found his first advertisers, and why he decided to launch a paid version.

Arlington Country, Virginia is a suburb of DC. It has over 236,000 residents, thousands of local businesses, and an average household income north of $100,000. With those sorts of attributes, you’d think it would have a vibrant daily newspaper, but instead its citizens mostly rely on the Washington Post metro section and a few weekly newspapers to get their news. Or at least that’s all they had up until about a decade ago. In January 2010, a former TV news producer named Scott Brodbeck launched Arlington Now, an online only news site dedicated specifically to Arlington. It quickly grew an audience and revenue base, and Scott has since launched several other sites covering Northern Virginia. I recently interviewed Scott about the founding of Arlington Now, how his journalists approach their coverage, and why he doesn’t consider Google and Facebook to be much of a threat to his advertising revenue.

Dan Oshinsky didn’t apply for an open position to run BuzzFeed’s newsletter operations. He just happened to reach out to editor Ben Smith back when BuzzFeed was hiring a bunch of people with weird internet obsessions, and the company hired him without a clearly defined role.  This dynamic granted Dan a lot of leeway in terms of how he approached BuzzFeed’s newsletters, and he went on to launch several products, including multiple online courses and the newsletter This Week In Cats. A few years later he got hired to run newsletters at The New Yorker, which was focused on building out its paid digital subscriptions. Recently, he left that job to run his own newsletter consultancy. I recently interviewed Dan about how he built out BuzzFeed’s newsletter strategy, the role of newsletters in driving paid subscriptions, and why he left such a prestigious job to strike off on his own.