The Business of Content with Simon Owens

I think it’s safe to say at this point that digital publishers recognize the importance of email newsletters. In 2016, Facebook pulled the rug out from underneath a media industry that had, until then, relied on it for hockey stick growth, and over the next several years publishers generally warmed to the idea that the decentralized distribution offered by email newsletters would prove more reliable than the fickle whims of social media giants. Today, nearly every media company has a robust email marketing strategy, and some news startups interact with their readerships almost entirely within the inbox. We’ve also seen the launch of platforms that make it easier for individual writers to distribute their own newsletters and monetize them through paid subscriptions. So are newsletters reaching a saturation point? Are they generating real ad revenue? And can newsletters actually replace Facebook as a referral source? These are just some of the questions I put toward Ernie Smith, the creator and editor of Tedium, a fantastic newsletter that almost operates as a kind of Wikipedia of obscure topics. Smith also runs a popular Facebook group for the newsletter industry, and he’s one of the most knowledgeable people I know when it comes to newsletter trends.

Back in 2010, the world was still skeptical of Wikipedia. High school teachers and college professors warned students to never, ever use it for research. If you ever tried to cite it in an argument, your opponent would mock it as unreliable. Late night hosts like Stephen Colbert would enlist their audiences to flood a specific Wikipedia page and vandalize it. Celebrities and major companies would treat it as a vanity project, editing their own pages while making absolutely no effort to disclose their conflict of interest. Flash forward to 2020, and Wikipedia certainly has more respect. The Wikimedia Foundation, which acts as its official steward, has tens of millions of dollars in the bank. While college professors don’t view it as a primary source for research, they’ll sometimes endorse it as a starting point for said research. And nearly everyone recognizes it as one of the most influential websites on the internet. But though tens of millions of people use Wikipedia every day, most only have a passing understanding of how a core group of a few thousand volunteer editors perform the vast majority of contributions to its articles. One of those editors is Bill Beutler. For the past decade, Bill has consulted with hundreds of brands, helping them to edit their Wikipedia pages without running afoul of the platform’s strict rules. I recently interviewed Bill about the problems that have plagued Wikipedia for the past decade and the issues its community will need to address in the decade to come.

Back in June, the Interactive Advertising Bureau released a report estimating that the podcast industry generated $479 million in 2018 and is projected to make $1 billion by 2021. Not only is this a tiny pittance compared to the money generated by other mediums like TV and search, but podcasting has also been limited by its over-reliance on advertising. Unlike, say, Netflix or The New York Times, most podcast companies have struggled to diversify their revenue beyond advertising, and most major podcast apps don’t provide a way for podcasters to directly collect money from their listeners. But several companies, like Spotify and Luminary, are attempting to bundle exclusive podcasts and sell access to them behind a subscription paywall. Other platforms assist individual podcasters in converting their listeners into paying subscribers. The company Glow fits into the latter category. Founded a little over a year ago, Glow developed technology that allows a podcast’s paying subscribers to listen to paywalled episodes on their podcast player of choice. I recently interviewed its co-founder Amira Valliani about how she’s solving the paywall problem and why she thinks paid podcast subscriptions will eventually scale.

In November, a company called Minute Media announced it was acquiring The Players’ Tribune, the website founded by Derek Jeter that regularly collaborates with pro sports athletes on first-person storytelling. Though the name Minute Media might not be familiar to most people, chances are you’ve encountered one of the sites it owns, especially if you follow sports. Over the past few years, it’s slowly amassed an amalgam of sports properties that cover everything from global soccer to esports. It also owns Mental Floss, the quirky trivia magazine that was founded in 2001. I recently sat down with President and CRO Rich Routman to discuss why he thinks Minute Media is different from many of the other venture funded digital media sites out there. We talked about the company’s video strategy, how it approaches advertising, and why it expanded into non-sports content when it acquired Mental Floss.

More than a decade ago, before most people even knew what a podcast was, Macmillan, one of the largest book publishers in the world, launched a podcast network. Called Quick and Dirty Tips, the network consisted of short, scripted podcasts that delivered evergreen, practical advice on a range of topics from grammar to money management. In the years since, Macmillan has continued to invest in its podcast division, expanding into narrative shows and even teleplays. For this episode, I interviewed Kathy Doyle, vice president of podcasting, about where the company has seen the most success and how podcasting allowed it to diversify its revenue.

Jane Friedman has spent almost the entirety of her professional career working in book publishing. In the mid-aughts, she began writing about the industry, both for professional outlets and her own blog. A few years ago, she launched a paid newsletter that now generates the majority of her income. I recently interviewed Friedman about her work. We discussed how she grew her newsletter into a sustainable business, and then we talked about the current state of book publishing. One aspect of this world that’s long fascinated me is self-publishing, so I asked Friedman to fill me in on how this market is maturing and where self-published writers are seeing success.

If you listen to the podcast called Startup, then you’ve heard host Alex Blumberg go into exquisite detail about the trials and tribulations of launching a VC-funded podcast network. In earlier seasons, we got a firsthand look about what it was like to pitch venture capitalists, hire talent, and grow the business. In the final season of Startup, Blumberg walked us through Spotify’s $230 million acquisition of Gimlet. But what about bootstrapped podcast networks that don’t have access to millions of dollars of venture capital money? How do they get off the ground and scale? To answer these questions, I spoke to Jeff Umbro, the founder of the Podglomerate. We talked about his early mistakes in trying to partner with shows for his network and why it can be incredibly difficult to monetize a show with a small audience.

Advance Publications is one of the largest media companies in the world. It owns dozens of newspapers, the Conde Nast magazine empire, and even Reddit. A few years ago, it launched the Alpha Group, a tech incubator that would launch small startups and try to grow them into thriving, standalone businesses. One of those startups was called The Tylt, a platform that allows its users to participate in online opinion polls on a wide range of issues. The Tylt was successful enough that Alpha Group spun it off as its own company. Recently, The Tylt hired Selena Roberts, a seasoned journalist who’s written for The New York Times and Sports Illustrated, to serve as its executive editor. I recently sat down with Roberts to learn about the site’s editorial ambitions and whether online, unscientific polls have any journalistic value.

Agnes Kozera knows a thing or two about helping content creators monetize their content. In 2013, she and a co-founder launched Famebit, a platform that helped YouTubers match with brands that were willing to sponsor their videos. The company was so successful that it was eventually acquired by YouTube in 2016. This year, Kozera and that same co-founder are launching Podcorn, a platform designed to help podcasters monetize their shows. Like Famebit, it will serve as an online marketplace where brands can post RFPs for projects and be matched with participating podcasters. I interviewed Kozera about why such a platform is needed, how the current podcast advertising landscape is flawed, and why podcasters with small-to-mid-sized audiences currently have such a difficult time finding sponsors.  

Clive Thompson has the kind of career that most writers would envy. He’s written two books for major publishing houses. He has a monthly column at Wired magazine. And he writes regular features for The New York Times Magazine and other glossy magazines. But that kind of success didn’t come to him overnight. In fact, Thompson spent years toiling away writing for small publications making very little money. I recently interviewed him to discuss how he made his big break, what it takes to write the perfect magazine pitch, and why book publishers are more likely to award contracts to established journalists.