The Business of Content with Simon Owens

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.

Ben Cohen isn't the world's biggest fan of Facebook. The founder of a political news website called The Daily Banter, Ben worked hard to build up his reach on Facebook, and for a few years he made a decent living selling advertising against his content. But after the 2016 election, Facebook pivoted away from news, and virtually overnight The Daily Banter lost 90% of its traffic. Not only could he no longer pay his own salary, but he was also struggling to keep his stable of writers on board. Out of desperation, he moved the Banter over to Substack and doubled down on paid subscriptions. That was in early 2019. I recently checked in with Ben to see how his efforts are going and how a presidential election year affects subscription growth for a political newsletter.

Alexis Grant didn't start her career with the goal of building several media businesses. She simply wanted work as a reporter. After college, she got a job at the Houston Chronicle and then later accepted a role editing the careers section at US News & World Report. But something about the business of media intrigued her, and while at US News & World Report she launched a side hustle running social media and blogs for corporate clients. Eventually, she drummed up enough business to quit her day job and focus on content marketing full time. In fact, she launched an entire marketing agency that specialized in producing branded content. One of her clients was a personal finance website called The Penny Hoarder, and she was so successful at growing its audience that the company eventually acquired her agency and installed her as its editor in chief. By the time she left The Penny Hoarder a few years later, it was generating tens of millions of dollars in annual revenue. I recently interviewed Alexis about how she helped scale these companies and what she plans to do next.

Because I write and podcast so much about the business of media, I regularly get emails from founders of niche media companies who want to tell me about their successful ventures. A few months ago, I received an email from a guy who identified himself only as Meathead, and after reading only a few paragraphs I knew I wanted to have him as a guest for my podcast. Meathead, who's been writing about food on the internet since the days of dial-up AOL, started the website AmazinRibs.com almost as a lark. Flash forward 15 years, and it's the preeminent authority on all things barbecue. It generates a healthy mix of revenue from advertising, affiliate sales, books, and paid subscriptions, and it grew its business without help from any venture backing. I recently interviewed Meathead about writing for AOL when it was the biggest game in town, running the third most popular wine magazine, and stumbling into a website venture that made him one of the most famous people within the barbecue scene.

If you wanted to become a professional standup comedian in the 1990s, the path was pretty straightforward. You started by going to amateur open mic nights, where you would hone your act. Eventually, you'd develop five to 10 minutes of solid material and maybe get a slot opening for a bigger comedian. From there you'd work yourself up to bigger and bigger gigs, and if you were really talented and lucky, you'd land a slot on a late-night talk show, or, even better, get signed to an hour-long special for HBO. These days, the path for the aspiring comedian is completely different. Sure, there's still the open mic nights and the club gigs. But there's also a bevvy of online platforms that you can leverage to sharpen your craft and build a following. You might collaborate with other comedians and write sketches for a YouTube channel. You can practice your one-liners on Twitter. And you'll definitely want to launch a podcast. As a full-time standup comedian, Joel Byars has employed several of these strategies. I interviewed Byars about how comedians market themselves in this golden age of standup comedy and asked him why he decided to self-produce his own comedy special.

Let's say you're a writer who wants to publish your work to the web and eventually monetize it. These days you have plenty of options. You might open a Medium account and join the platform's partner program. Or maybe you launch a Substack newsletter. If you're really ambitious, you could throw together a Wordpress website and integrate it with a payment tool like Stripe. Or you could just launch an account on Ghost, a publishing platform created a few years ago by a guy named John O'Nolan. Before founding Ghost, John was the deputy head of design at Wordpress, and though he was always a fan of the open source CMS, he thought he could create something a little bit better. So John launched a Kickstarter campaign, and after raising tens of thousands of dollars, he developed Ghost. Today, it's used by some of the world's largest brands, and his hope now is that independent writers will use it to monetize their content. I spoke to John about the platform and why he thinks a writer should choose it over a competitor like Substack or Patreon.