The Business of Content with Simon Owens

My newsletter: https://simonowens.substack.com/ Robbie Daymond is best known as a prolific voice actor, the kind of performer whose work spans anime, video games, and animation without ever putting his face front and center. After slowly breaking into the industry in the late 2000s and early 2010s, he built a rare, multi-disciplinary voiceover career—one that includes everything from audiobooks to major gaming franchises. He also spends up to 30 weekends a year attending fan conventions where he engages directly with audiences in what has quietly become one of the most lucrative and meaningful parts of his business. That creator-first ethos has increasingly shaped his ambitions beyond acting. In recent years, Daymond co-founded Sassy Chap Games, an independent studio that turned a quirky concept into one of the fastest-selling dating sims ever, fueled largely by viral user-generated content rather than traditional marketing. The project offers a window into how modern creative careers are evolving by blending IP ownership with direct-to-consumer distribution models. In a recent interview, Robbie explained how fan conventions have quietly become a major revenue engine for creators, why you don't always need a huge social media presence to build a large audience, and how revenue-sharing models can unlock top-tier creative talent.

My newsletter: https://simonowens.substack.com/ For most of his career, Scott Brown has operated at the crossroads of Hollywood and the creator economy. After first breaking into digital media during the early days of web series, Scott went on to work across a wide swath of the modern media ecosystem. His résumé includes producing hundreds of hours of Larry King programming for streaming platforms, helping Dwayne Johnson launch a YouTube channel that quickly surpassed a million subscribers, and even producing large-scale stunts for MrBeast. Throughout that journey, Scott developed a front-row seat to how digital platforms were steadily reshaping the economics and creative possibilities of entertainment. Today Scott believes the next major shift is already underway: the rise of microdramas—short, vertically shot scripted series designed for smartphones and often monetized episode-by-episode inside dedicated apps. In our conversation, Scott explained how he stumbled upon the emerging format, why he believes it represents the first truly native form of scripted storytelling for phones, and how his own microdrama projects are helping push the medium toward higher production quality.

My newsletter: https://simonowens.substack.com/ Pat Walls didn't originally set out to build a media company. In 2017, he was simply interviewing founders as a side project while working a full-time job, hoping the conversations might spark his next startup idea. But those interviews—published as detailed case studies on a blog called Starter Story—slowly evolved into something much bigger. Over the next eight years, Pat bootstrapped the site into a media business built around thousands of founder stories, growing its audience through a series of distribution pivots that ranged from Reddit to SEO to YouTube. That journey culminated recently in a major milestone: the sale of Starter Story to HubSpot Media for what Pat describes as a "life-changing" amount. In a recent interview, Pat explained how Starter Story transformed from a scrappy side project into a profitable media brand, why video ultimately became the company's biggest growth engine, and his decision to shift away from advertising toward higher-priced products and boot camps.

My newsletter: https://simonowens.substack.com/ Founded during the pandemic, the The News Movement set out with a simple but radical premise: what if journalism were designed entirely for the platforms where younger audiences already consume information? Rather than trying to pull readers back to a website, the company built a newsroom that publishes directly to TikTok, Instagram, and YouTube Shorts, translating the conventions of traditional reporting into vertical video, carousels, and other native formats. In a recent interview, editor-in-chief Rebecca Hutson explained how the outlet approaches platform-first journalism, why its reporters function as "triple-threat" video journalists who can shoot, edit, and publish their own stories, and how the company tailors coverage differently for each social platform.

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 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/ 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/ In 2011, as the golden era of glossy newsweeklies was fading, former Time correspondent Nathan Thornburgh made a bet that serious journalism didn't have to look the way it always had. Alongside food writer Matt Goulding, he launched Roads & Kingdoms as a scrappy Tumblr experiment, using food as a gateway into geopolitics, history, and culture Over the next decade, Roads & Kingdoms evolved from a bootstrapped digital publication into a creative hub for Anthony Bourdain—who invested in the company and used it as a base for ambitious editorial and branded projects. After Bourdain's death in 2018, the outlet was forced to reinvent itself. Nathan and Matt shrank the operation and rebuilt it around high-end culinary travel experiences. Now, they're relaunching the media arm with a membership-driven model and an annual print magazine In a recent interview, Nathan reflected on the collapse of legacy media, the perils and possibilities of brand-funded journalism, and why he believes independent, reader-supported publishing offers a more durable path forward.

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/ For today's episode I spoke to Jim Louderback, the writer behind a newsletter called Inside the Creator Economy Jim is a longtime media veteran who started out in magazine publishing and then eventually made his way over to the Creator Economy. He spent several years running Vidcon, the annual event where the world's biggest YouTubers connect with their fans, and he now helps organize creator economy events all over the world, including the 1 Billion Followers summit in Dubai. In our discussion, we covered a wide range of media topics. We discussed whether media companies were overreacting from the threat of Google Zero, why athletes are the new super creators, and how YouTube will slowly devour Hollywood.

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.

My newsletter: https://simonowens.substack.com/ In some ways, it's never been a better time to be a standup comedian. In previous eras, aspiring standups had to slowly make their way up through the industry by performing in open mic nights and small venues, but now a few viral video clips on Instagram or TikTok can instantly thrust a new comedian into the spotlight. But even if a standup has millions of followers on social media, it can be difficult to monetize their fanbase. There's no easy way to alert followers in a certain geographic area that you're performing at a local venue, and social media moderation algorithms consistently throttle reach, especially if a comedian talks about controversial topics. Danny Frenkel and a co-founder launched Punchup in 2023 to solve these problems. His platform allows comedians to place their video content behind a gate that collects users' email addresses and locations. It also allows venues to sell tickets to events directly through Punchup. Comedians can even directly sell their standup specials on the site. Punchup has already attracted several big name comedians to its network, including Shane Gillis and Tom Segura, In a recent interview, Danny walked through the economics of standup comedy, explained how his experience selling ads on Meta informed Punchup's service offerings, and outlined his longterm ambitions for the platform.

My newsletter: https://simonowens.substack.com/ In today's episode, we're speaking to Suryansh Tibarewala, the co-founder of Essentially Sports. EssentiallySports began in 2014 as a bootstrapped passion project started by Suryansh and his co-founders while they were college students in India. It started as a simple WordPress site focused on tennis and Formula One. The site ran for four to five years with virtually no revenue, relying largely on volunteer contributors. But then in 2018, the site's founders decided to quit their day jobs and go all in. They expanded the sports coverage, found reliable advertising partners, and eventually grew EssentiallySports into one of the largest sports sites ranked by Comscore – all without raising outside capital. In a recent interview, Suryansh walked through the site's early days, its expansion into US sports, and its B2B live events strategy.

My newsletter: https://simonowens.substack.com/ Roca News was founded on a simple premise: so much of news now is consumed on social platforms, with fewer and fewer internet users clicking through to article pages. After launching in 2020, it gained its initial success on Instagram, where it amassed hundreds of thousands of followers by distilling important news stories into swipeable images. It then launched a daily newsletter that's since grown to over 200,000 subscribers. Most recently, the company has invested heavily in its YouTube channel, sending its on-camera hosts to far-flung locations to interview everyday people about their unique experiences. Each video racks up hundreds of thousands of views, and the channel has grown to close to 600,000 subscribers in a little over a year. In a recent interview, co-founders Max Towey and Max Frost recounted Roca's origin story, walked through its initial Instagram strategy, and explained how they invented a unique documentary format for their YouTube channel.

My newsletter: https://simonowens.substack.com/ When Shane Greer took over the magazine Campaigns & Elections in 2011, it was in a sorry state. Founded back in 1980, the outlet had once been the gold standard for reporting on the political operatives who help candidates and corporations influence elections. But by 2011, the magazine was limping along, with its print edition and events struggling to break even. That year, it was acquired by a private equity firm, which installed Greer to run it. In a very short period of time, he killed the print edition, expanded its online reach, and revived its events business. Then in 2015 he and his business partner Shane D'Aprile acquired Campaigns & Elections, and they immediately set about expanding the company into new niches and regions. Today, there's not only Latin American version of C&E, but the company also bought a B2B media outlet that covers the cannabis industry. In a recent interview, the two Shanes walked me through their initial strategies for righting the C&E ship, explained why they acquired the magazine, and outlined their plans to build out a B2B media empire.

My newsletter: https://simonowens.substack.com/ The Kyiv Independent launched in 2021, and its timing was in some ways fortuitous, since it was only a few months later that Russia launched a full-scale invasion in Ukraine. Suddenly, the entire world was paying attention to the country, and the Kyiv Independent happened to be the most authoritative English-language outlet to be reporting on the ground. This attention not only resulted in a massive amount of traffic, but also a surge in membership donations as sympathetic Westerners sought out ways to support Ukraine's cause. In a recent interview, Chief Operating Officer Zakhar Protsiuk discussed the early days of getting the Kyiv Independent off the ground, its shift from one-time donations to recurring memberships, and why the outlet has begun producing longform documentaries.

My newsletter: https://simonowens.substack.com/ What if you took Morning Brew's approach to newsletter writing and applied it to local news? That was the original idea behind 6AM City, a company that launched its first newsletter in Greenville, South Carolina in 2016 and gradually expanded into over a dozen cities. For most of its history, 6AM City's approach was to hire a handful of editors in each city and then gradually build up an audience and advertiser base. But in the last year, it developed a playbook for using AI to launch newsletters in smaller, less populated areas, with the goal of eventually hiring human editors once those newsletters reached certain thresholds. In a recent interview, co-founder Ryan Heafy explained how these AI newsletters actually work, where they get their information, and what guardrails the company has put in place to ensure quality control.

My newsletter: https://simonowens.substack.com/ When the media holding company Woven Digital purchased BroBible in 2012, the idea was that the guy-focused publisher would benefit from all the business synergies that come from being part of a larger media network. Instead, BroBible was neglected and undermonetized. So when Woven began unraveling its holdings in 2018, BroBible's staff banded together and bought it back. And what started out as a staff of seven has grown to 16 today, and the business is diversified across programmatic advertising, events, and sponsored social media posts. In a recent interview, publisher Brandon Wenerd walked through Brobible's early blogging days, its transformation into a real business, and how breaking free of its parent company allowed it to adapt to the current media climate.

My newsletter: https://simonowens.substack.com/ In 2008, Wade Wallace found himself living in Australia and laid off from the company that moved him there in the first place. With his visa in limbo, and not much else to do, he launched CyclingTips, a blog that covered both the professional and amateur aspects of the sport. What started out as a hobby eventually grew into a fully-staffed news website, one that eventually sold to the investment firm that owned Outside Magazine. Then in 2022 he quit CyclingTips, raised some investment money, and then launched Escape Collective, which covers the exact same beat. Unlike CyclingTips, Escape Collective is fully funded through paid subscriptions, and when we recorded this interview it was on the verge of profitability. In a recent interview, Wade walked through his early days building CyclingTips, why he grew unhappy at Outside, and how he grew Escape Collective to 15,000 paying members.

My newsletter: https://simonowens.substack.com/ There was a time 20 years ago where if you filmed a horror movie on a tight enough budget, you could plausibly turn a profit from the DVD sales alone. Unfortunately for Chris Sharpe, his entry into the horror genre came just as the DVD market was collapsing, and so his career as a movie director fizzled out after he made only one film. Luckily, one of the stars of that film, Hilah Johnson, had a strong onscreen presence and a penchant for cooking, and together they launched Hilah Cooking, a YouTube channel that eventually grew to over 450,000 subscribers. Then a few years later Chris teamed up with another co-star from that movie, Adriene Mishler, to launch Yoga With Adriene, which now has over 13 million subscribers on YouTube. In a recent interview, Chris walked through how he and his collaborators launched both channels, why Hilah decided to eventually end her channel, and the massive success they've seen building a yoga streaming app.

My newsletter: https://simonowens.substack.com/ When Tomiwa Aladekomo took over Big Cabal Media eight years ago, the company was little more than two promising publications that were read mostly within Nigeria. He stepped in not as a founder, but as someone who had spent years inside every corner of the media world, including music, advertising, brand strategy, and digital publishing. And he saw, even then, that Big Cabal had the potential to diversify its revenue and scale up into one of the most influential media companies in Africa. In a recent interview, Tomiwa walked through how that early instinct turned into a 100-person company that now stretches across multiple countries and several lines of business. He also discussed how Big Cabal is navigating the same headwinds facing publishers everywhere—including shrinking social traffic and the rise of AI—while also confronting challenges unique to African media.

My newsletter: https://simonowens.substack.com/ These days, every audio podcast has an accompanying video podcast, but Jefferson Graham was hosting video podcasts before the term even existed. In 2006, he started co-hosting a show with another USA Today colleague who lived on the opposite coast from him, and they'd physically FedEx the tapes back and forth so they could be edited. Jefferson then went on to host several video series for USA Today, including one where he'd interview celebrities about their favorite tech. In 2021, after 30 years at USA Today, he decided to take a buyout so he could launch PhotowalksTV, a YouTube travel show where he'd visit different cities and instruct viewers on the best spots to take photos. In 2024, he signed a deal with Scripps News to broadcast the show on its FAST channels, and now new episodes air every Sunday at 10 am. In a recent interview, Jefferson discussed what it was like to host a podcast when nobody knew what a podcast was, why he took the buyout from USA Today, and how he generates multiple revenue streams through his YouTube channel.