The Business of Content with Simon Owens

My newsletter: https://simonowens.substack.com/ When Will Richards first started compiling news about startups, he wasn't trying to launch a media company. He was working at a family office and needed a better way to track what was happening across the Australian startup ecosystem. After realizing there wasn't a single place that aggregated all this information, he began sending out a weekly email. That side project eventually evolved into Overnight Success, a newsletter read by thousands of founders, investors, and startup operators. But Richards didn't stop at building a newsletter. He's since expanded Overnight Success into a broader business that includes sponsorships, a startup database, and an investment syndicate. In our interview, we discussed how he grew within such a narrow niche, why a small audience can still attract major sponsors, and how he's turning years of startup coverage into a valuable data product.

My newsletter: https://simonowens.substack.com/ For years, Hollywood writer Aaron Tracy built his career inside the traditional television system, writing for shows like Law & Order and navigating the endless cycle of pilots, canceled series, and development purgatory that defines much of the TV business. But over the last several years, Tracy has quietly carved out a very different kind of entertainment career: producing serialized audio dramas for platforms like Audible and iHeart. Along the way, he's worked with everyone from Aaron Paul to Lizzy Caplan to Glenn Powell, helping pioneer a form of storytelling that sits somewhere between television, audiobooks, and podcasting. In a recent interview, Tracy explained why audio dramas offer writers far more creative freedom than television, how he packages and sells narrative shows to platforms like Audible and iHeart, and the surprisingly lean production process behind large-scale audio series.

My newsletter: https://simonowens.substack.com/ James Capo has spent much of the last decade helping publishers solve one of the industry's biggest challenges: how to better understand and monetize their audiences. As CEO of Omeda, he oversees a platform that powers subscription management, email marketing, audience data, and paywall tools for many of the world's largest media companies. In a recent interview, Capo explained why he believes many publishers have made audience management far more complicated than it needs to be, how AI could soon help publishers better predict churn and improve subscriptions, and why media companies should build more niche products and verticals around loyal audiences.

My newsletter: https://simonowens.substack.com/ There's a certain irony that one of the most influential publications covering Australia's telecommunications industry still arrives each morning as a daily PDF. But that format has become central to the success of Communications Day, the niche B2B outlet founded by Grahame Lynch in 1994. What began as a fax-delivered newsletter covering the early deregulation of Australia's telecom market evolved into an indispensable industry briefing read by executives, regulators, infrastructure providers, and tech companies across Australia and New Zealand. While much of digital media spent the last two decades chasing pageviews, social traffic, and algorithmic distribution, Lynch built a highly profitable subscription business by doing almost the opposite: keeping his journalism off the open web, tightly controlling distribution, and turning Communications Day into a daily habit for nearly everyone working in the sector. In a recent interview, Lynch explained why Communications Day still distributes its journalism as a PDF despite the rise of blogs and social media, how he built a subscription business with near-total market penetration in a niche B2B sector, and why conferences now account for nearly half the company's revenue.

My newsletter: https://simonowens.substack.com/ In 2004, Eric Hochberger co-founded Mediavine, which would eventually become one of the most influential ad management companies on the open web. The company didn't start as an ad tech firm — it began as a scrappy collection of SEO-fueled fan sites, built by three founders chasing traffic in the early blogosphere. While selling $50 sidebar ads and offering SEO consulting services, Eric and his partners learned firsthand how fragile and inconsistent early digital advertising could be. That experience ultimately pushed Mediavine to build its own header bidding system in 2014, a move that quadrupled the company's ad revenue and transformed it from a publisher into an ad management platform. Today, Mediavine represents roughly 17,000 publishers and operates with a 140-person team, primarily serving independent creators rather than legacy media brands. In a recent interview, Eric pulled back the curtain on how programmatic advertising actually works, why "made-for-advertising" sites are siphoning off industry dollars, and how Google's AI Overviews are reshaping traffic patterns — sometimes wiping out entire businesses overnight.

My newsletter: https://simonowens.substack.com/ Michael Fritzell doesn't fit the typical profile of a newsletter writer. Before launching Asian Century Stocks, he spent 15 years inside the machinery of global finance — working in investment banking, buy-side firms, and eventually managing money for a wealthy family in Singapore. A Swedish native who studied Chinese at Peking University, Michael built a career analyzing overlooked equities across China and Southeast Asia. When he struck out on his own to launch the Asian Century Stocks newsletter in 2021, he wasn't experimenting with a side hustle — he was walking away from a traditional finance track to build a niche media business focused on Asian stocks that most Western investors ignore Launched on Substack and now operating independently, Asian Century Stocks sells in-depth, 40- to 60-page research reports to paying subscribers, many of whom are professional investors accustomed to paying banks tens of thousands of dollars a year for comparable research. Michael positioned himself as a bridge between local Asian markets and global capital — offering deeply reported, independent analysis without the conflicts that often accompany sell-side research. In an interview, he explained how he went from anonymous finance professional to six-figure recurring revenue newsletter operator, why he ultimately left Substack for Ghost, and what it takes to monetize serious financial research in a tightly regulated industry.

My newsletter: https://simonowens.substack.com/ For decades, Diane Salvatore helped lead some of America's most recognizable magazine brands, including Consumer Reports, where rigorous product testing and consumer safety were core to the mission. Now, as executive director of the MedShadow Foundation, she's applying that same watchdog mentality to one of the most opaque corners of the marketplace: prescription and over-the-counter drugs. In a recent interview, Diane walked through how MedShadow operates as a nonprofit investigative newsroom, its expansion into social media video, and its plan to build a donor-supported model that funds independent health journalism.

My newsletter: https://simonowens.substack.com/ Kit Chilvers started posting memes on Instagram when he was 14, treating the platform like a video game and obsessing over what made posts take off. A decade later, that experimentation has turned into Pubity Group, a bootstrapped social media company with roughly 170 million followers and hundreds of billions of annual views. In a recent interview, Kit broke down how he cracked early Instagram growth, why wholesomeness turned out to be a massive business opportunity, and how he's trying to turn platform-native virality into durable media brands, original franchises, and real revenue.