The Business of Content with Simon Owens

Like a lot of people on the political Left, Geoff Sharpe grew frustrated by how successful conservatives were on Facebook. For years, he watched as right leaning conservative groups built huge Facebook followings, which allowed them to promote their highly partisan views to millions of Canadian citizens. So Geoff and his colleagues decided to do something about it. They initially launched their own left-leaning Facebook page, growing it to hundreds of thousands of followers. But they then wanted to pivot to something even more ambitious: a standalone website that published original content from leading progressive voices. To do this, they launched a crowdfunding campaign, and over the last year they’ve rolled out a membership offering that helps generate recurring revenue. I interviewed Geoff about why the political Right does so well on Facebook, how he designed the membership program, and what impact his site has had on Canadian politics.

There’s a common misperception that many non-lawyers have about how legal contracts are written. Most people probably assume that a lawyer writes each contract from scratch, but in reality the lawyer is most likely copy and pasting clauses and sections from already-existing contracts and modifying them for their particular client. One of the resources lawyers often turn to for this is Law Insider. Founded in 2010, Law Insider indexes the millions of contracts that have been uploaded to the SEC website by publicly traded companies. It generates over 4 million monthly pageviews and has over 250,000 registered users, about 5,000 of which pay $30 a month to access its archives. I recently interviewed the site’s co-founder Preston Clark about how he and his partner came up with the idea, what they did to build up its massive audience, and why they’re expanding into a full-fledged media company that produces everything from articles to YouTube videos.

Over the past year, dozens of writers have left their mainstream media jobs to launch their own standalone newsletters and publications. In almost every case, the writer monetized his content through paid subscriptions, usually with a tool like Substack. Rick Ellis never bothered with paid subscriptions. Instead, his website AllYourScreens.com generates so much traffic each month that he’s able to make a good living mostly through programmatic advertising. Ellis has been operating AllYourScreens.com off and on since the early 2000s, but a few years ago he decided to abandon traditional media completely to focus on the site full-time. I recently interviewed him about how he found his audience, what his weekly writing schedule looks like, and why he has no interest in building out a paid subscription business.

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Max Rofagha didn’t have a background in media prior to launching Finimize. He also didn’t have a background in finance for that matter. It was while conducting research on how to manage his own investments that he saw an opportunity for a daily newsletter aimed at helping millennials become more literate in finance. Flash forward four years and Finimize now has over 1 million subscribers, a staff of financial analysts, and a worldwide community of young professionals who often meet up for in-person events. I recently interviewed Max about his early audience development strategy, how his subscribers organize their own in-person events, and why he decided to launch a subscription-funded mobile app.

Per Grankvist had the kind of media career most journalists only dream of. He was a high-profile columnist for a leading newspaper and a regular face on one of Sweden’s top broadcast networks. But over time he grew disillusioned with mainstream media and its tendency to dumb down coverage of complicated policy issues. So Per quit his traditional media jobs and launched his own outlet. It started with just an Instagram account that explained thorny election issues, but from there it blossomed into an entire media outlet that spanned across social media, podcasts, and newsletters. I recently interviewed Per about how he built the company, his approach to monetization, and whether he misses working for mainstream media publications.

Peruse a newsstand full of men’s magazines and you’ll probably notice a few common themes. The cover either features a bikini model or a suit-clad male celebrity. Inside, you’ll find stories meant to appeal to what many in the mid-20th century would have considered the “ideal” man -- articles about scotch, cigars, and custom suits. You won’t find many of those kinds of features in MEL Magazine, a digital-only publication that launched in 2015. Owned and operated by Dollar Shave Club, MEL aims its content at the under-40, educated, likely-urban male...a man less inclined to traditional gender roles who is much more in touch with his feelings and spends an inordinate amount of time on the internet. I recently interviewed editor-in-chief Josh Schollmeyer about how he came to define this 21st century male, where his staff sources its article ideas, and how Dollar Shave Club will profit from its investment in the magazine.

Lon Seidman didn’t launch on YouTube with the goal of becoming a top gadget reviewer. In fact, he stumbled upon that aspect of his career while struggling to run a video local news startup in Connecticut. Almost on a whim, he recorded a video review about one of the cameras he bought for his startup, and to his surprise, the video blew up. Flash forward a decade, and Lon now has tens of millions of views across YouTube and Amazon. He managed to carve out a niche among a crowded field of gadget reviewers, and he’s now making a pretty good living through a mixture of YouTube advertising, affiliate sales, and Patreon subscriptions. We walked through how he accomplished all this in our interview.

If you had to make a list of technologies that are most important to the average person’s day-to-day life, data centers would sit near the top of that list, and yet chances are you know very little about them. There are a few reasons for this. For one, they’re not sexy in the way that an iPhone or a cutting-edge drone is sexy. But also the people and companies who run data centers are fairly secretive, mostly to protect their machines from any sort of attack. This combination of secrecy and obscurity has made Rich Miller’s expertise very lucrative. He’s spent the last two decades covering data center tech for various news outlets he’s owned. His current site, Data Center Frontier, is a must-read for anyone working in the $60 billion+ industry. I interviewed Rich about how he accidentally fell into the beat, why he sold his first data center site, and what made him want to start a brand new one from scratch. 

Back in late 2019, nearly all the writers for the beloved sports site Deadspin resigned en masse after butting heads with the private equity executives who owned the website. After they left, there was lots of speculation about where those writers would turn up. Would they simply get new jobs, or would they band together to create their own site? And then in July 2020 we got our answer: they launched Defector, an employee-owned publication that would be monetized mostly through paid subscriptions. To build the site, they turned to a guy named Austin Smith. Austin is the founder of an agency called Alley Interactive, and over the past decade he’s helped build and maintain the websites of many of the most well-known news publishers in the world. I sat down and interviewed Austin about his career in media, what goes into building a good publishing platform, and why he’s recently begun working with news startups like Defector to help them get off the ground.