The Business of Content with Simon Owens

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.

The audiobook market is massive, with sales projected to hit $3.5 billion this year. What used to be a niche, expensive product is now one of the fastest growing mediums. In fact, The New York Times recently reported that audiobooks are one of the only book formats still growing in sales during the current pandemic-induced recession.  But what does it take to launch a hit audiobook? How does the choice in narrator influence sales? And are book publishers worried about the market dominance of Amazon-owned Audible? These are all questions I put to Scott Dickey, the CEO of a company called Podium Audio. Podium is an audiobook studio that specializes in signing deals with self-published authors. It was the studio that produced the audiobook version of The Martian, the book that was made into a hit film starring Matt Damon.

In the mid-2000s, Digg was one of the most powerful websites on the internet. Powered by its army of users, the platform would send gargantuan amounts of server-crushing traffic to any content featured on its front page. Millions of people visited it each day and it turned its founder Kevin Rose into an internet celebrity.   But you probably know what came next. A misguided redesign triggered a user revolt, and its audience abandoned it for Reddit and other platforms. Before long, it seemed destined to follow in the footsteps of Myspace and Friendster. Its story didn’t end there. In 2012, the site sold to the startup studio Betaworks, which immediately went about trying to revive the Digg brand. In 2018, it was purchased by a company called BuySellAds. I recently interviewed Todd Garland, Digg’s new owner and CEO. We discussed its current editorial operations, its monetization strategy, and his plans to restore Digg to its former glory.

I first discovered Gil Assayas, the musician otherwise known as GLASYS, when one of his YouTube videos made it to the front page Reddit. His amazing keyboard set up and sophisticated musical adaptations of well-known video game soundtracks caught the attention of several gamer subcultures, who then shared his videos widely across social media. I recently sat down with Gil and asked him about how he grew his fanbase and in what ways his viral videos have translated into career success.

The New York Times gets a lot of credit within the media industry for the blockbuster success of its podcast The Daily,  but The Los Angeles Times was also an early pioneer within the medium. Its narrative true crime podcast Dirty John generated over 30 million downloads and was adapted into a TV show for Bravo. The newspaper has since gone on to launch ambitious shows chronicling the criminal trial of Bill Cosby and the famous murders committed by Betty Broderick. I recently interviewed Clint Schaff, VP of strategy and development, about the paper’s podcast productions. He walked me through how shows get made, their monetization strategy, and his views on selling IP to TV studios and Spotify.  

Jono Dry is the type of artist whose work is sold in European galleries by art dealers. He only finishes a few pieces a year, and most of his purchased pieces likely reside in the private collections of rich people, closed off from the public. But that hasn’t stopped millions of people from viewing his work. That’s because Jono films himself drawing each piece and uploads gorgeous time-lapse videos to platforms like Facebook, Instagram, and YouTube. On YouTube alone these videos have generated over 8 million views, and his success on social media has transformed him into a world-famous artist. I recently interviewed Jono about how he built his following and in what ways he’s been able to leverage that following to advance his career.

We’ve seen several media companies launch over the past few years that specialize in sending out newsletters that summarize each day’s news. Newsletters like theSkimm, The Hustle, and Morning Brew speak to their readers in a conversational style and have been embraced by millions of loyal subscribers. The folks behind 6AM City took that model and applied it to local news. Operating out of cities like Greenville, SC and Chattanooga, TN, each newsletter mines local newspapers, businesses, and social media accounts to produce a daily snapshot of the goings on in that urban center. To date, it’s grown to over 230,000 subscribers and monetizes primarily through custom, native ads. I recently interviewed co-founder Ryan Johnston about how each newsletter operates and whether he thinks his company is producing quality local news.