The Business of Content with Simon Owens

Hosted by Simon Owens

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299

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Aug 2026

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About the show

The show about how publishers create, distribute, and monetize their digital content.

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60 recent

August 13, 202659 min

The world's largest YouTubers use his AI language dubbing platform

My newsletter: https://simonowens.substack.com/ Nate Stone was still in high school when he built a YouTube channel with hundreds of thousands of subscribers by filming science and engineering experiments in his garage. But unlike many creators who stumble into a large audience, Stone never had much interest in turning that audience into a full-fledged media business. He eventually walked away from YouTube, studied physics, math, and computer science, worked on AI at Amazon, and then teamed up with his brother to build DittoDub, an AI-powered dubbing platform designed to help YouTubers reach audiences in dozens of languages. In a recent interview, Stone explained how his frustrations as a teenage YouTuber helped inspire DittoDub, why the company focused on winning over large creators through product quality and word of mouth, and how multilingual audio can trigger enormous audience growth on YouTube.

August 5, 202655 min

This newsletter for female sports fans reached 1 million subscribers

My newsletter: https://simonowens.substack.com/ When Ellen Hyslop and her co-founders launched The Gist in 2017, none of them had worked in media or the sports industry. They were young professionals in financial services who had grown frustrated with a sports media ecosystem that largely catered to men while overlooking millions of potential female fans. What began as a side project built during evenings and Sundays has since grown into a sports media brand with more than 1 million newsletter subscribers, hundreds of thousands of social followers, a podcast, paid community, proprietary games, and partnerships with major advertisers. In a recent interview, Hyslop explained how scrappy marketing helped attract The Gist's first subscribers, why social media became an important source of revenue, and how the company is expanding into a paid community and launching its own games.

July 23, 202658 min

How a finance blog started in a garage scaled into a financial media empire

My newsletter: https://simonowens.substack.com/ Founded in a Detroit garage in the early 2010s, Benzinga started as a scrappy finance blog for everyday stock market enthusiasts. Over the next decade, it grew into a major digital media platform, carving out a niche by sending detailed stock analysis directly to retail investors and major brokerage apps like Robinhood and Fidelity. Following a majority acquisition by private equity firm Beringer Capital in 2021, the company entered a new era of growth, hiring former Bloomberg editor Brad Olesen as its first Chief Content Officer to bring its news, video, and data teams together under one roof. In a recent interview, Olesen broke down what it takes to run a modern, multi-channel financial news operation, why Benzinga treats social media as a brand-building tool instead of a website traffic driver, and how the company balances free, ad-supported news with premium subscription products.

July 16, 202646 min

This corporate consultant grew to 260,000 TikTok and YouTube subscribers in only 8 months

My newsletter: https://simonowens.substack.com/ For most of her career, Ashanti Bentil-Dhue didn't have a social media presence. But after spending a decade running a consulting business, she moved from the UK to New York and decided to start sharing her ideas publicly for the first time. Armed with little more than an iPhone, she began posting unscripted TikTok videos about the experiences of single women. Within months, she had built an audience of hundreds of thousands of followers and expanded into a media business that now includes a Substack publication, YouTube channel, and consulting. In a recent interview, Bentil-Dhue explained how she built a large audience despite having no prior social media experience, why she believes consistency matters more than high-end production, and how she's turning her growing platform into a sustainable business.

July 14, 202651 min

The playbook behind Spotify's audiobook expansion

My newsletter: https://simonowens.substack.com/ For years, the audiobook industry was defined by a single dominant player and a purchasing model that asked listeners to commit to an entire book before they knew whether they would enjoy it. Spotify is betting that there's a better way. By folding audiobooks into its subscription service and using the same discovery engine that powers its music and podcast recommendations, the company is trying to transform audiobooks from a niche product for avid readers into a mainstream entertainment format. Duncan Bruce, Spotify's director of audiobooks partnerships and licensing, has been at the center of that effort, working with publishers to build the company's licensing strategy and expand its catalog from 150,000 titles at launch to more than 700,000 today. In this interview, Bruce explained how Spotify convinced publishers to embrace a radically different distribution model, why casual sampling is unlocking new audiences for authors, and how the company is using AI and product innovation to make audiobooks more accessible without replacing human creativity.

July 9, 202641 min

Why an NPR reporter left his job to launch a media outlet in Ukraine

My newsletter: https://simonowens.substack.com/ The war in Ukraine has given rise to an entirely new generation of independent media organizations, but few have a backstory as unusual as The Counteroffensive. Founded by veteran journalist Tim Mak after more than a decade covering politics, national security, and investigations for outlets including NPR, Politico, and The Daily Beast, the publication began as a one-man Substack chronicling life inside wartime Ukraine. In just a few years, it has evolved into a growing media company with multiple publications, a team of reporters across Europe, and an expanding portfolio that spans consumer journalism, defense intelligence, and postwar reconstruction. In our interview, Mak explained how an unexpected career pivot led him to launch a newsroom from Kyiv, why he believes text-based journalism—not podcasts or video—remains the strongest engine for paid subscriptions, and how he's building a diversified media business designed to outlast the war itself.

June 18, 202656 min

This platform is powering over 180 local newsrooms

My newsletter: https://simonowens.substack.com/ For more than a decade, Erin Millar has been trying to answer a question that has plagued the journalism industry: What should replace the local newspaper model after it collapses? Her first attempt came with The Discourse, a Canadian media company that experimented with new approaches to community-driven reporting before eventually evolving into a network of local news outlets. But along the way, Millar realized that the biggest opportunity wasn't necessarily building another media chain — it was creating the infrastructure that could help hundreds of independent publishers thrive. That insight led to the launch of Indiegraf, a software and services company that now supports 180 local communities across North America and beyond. In a recent interview, Millar explained why she believes the future of local news will be built around networks rather than traditional chains, how Indiegraf helps publishers generate revenue, and why consolidation may actually strengthen independent media.

June 16, 20261 hr 4 min

This print magazine is thriving by treating itself like a collector's item

My newsletter: https://simonowens.substack.com/ When Mike Rogge purchased Mountain Gazette in early 2020, he wasn't acquiring a thriving media business. For $5,000 and the cost of a couple beers, he bought a dormant outdoor magazine brand whose main assets consisted of a URL, a trademark, decades of archives, and boxes of old issues sitting in storage. But Rogge believed the magazine's legacy — which included contributions from writers like Hunter S. Thompson and Edward Abbey — still carried meaning. At a time when many publishers were chasing algorithms and scale, he wanted to prove there was still a market for a beautifully designed print publication built around passionate readers rather than fleeting clicks. Five years later, Mountain Gazette has grown into a profitable independent magazine with tens of thousands of subscribers who pay for two oversized print issues a year. In our interview, Rogge explained why he rejected the traditional ad-driven media model, how a subscriber-first approach allowed him to invest more into writers and photographers, and why he believes print's resurgence is tied to a broader backlash against an increasingly digital world.

June 11, 202648 min

The software company that's quietly building a media empire

My newsletter: https://simonowens.substack.com/ For years, HubSpot was known as a pioneer of content marketing, building a huge library of articles that helped attract potential customers to its software products. But more recently, the company has expanded far beyond blog posts. It now owns newsletters, podcasts, YouTube channels, and creator-led media brands that reach millions of people every month. Jonathan Hunt, HubSpot's VP of media, has helped oversee this evolution after working at companies like Vice, Vox Media, National Geographic, and Complex. In our interview, he explained why HubSpot is investing so heavily in media, how it turns content audiences into software customers, and why it sees creators as a major part of its growth strategy.

June 9, 202648 min

How a coaching conference turned into a seven-figure media business

My newsletter: https://simonowens.substack.com/ When Aaron Wilbur launched The Coaches Site in 2010, he simply wanted to solve a problem he kept seeing in hockey: the best coaches were constantly sharing ideas with each other, but that knowledge rarely made its way to coaches at lower levels of the sport. What started as a small coaching conference eventually turned into a subscription platform with more than 41,000 coaches across 54 countries and over $1.5 million in annual recurring revenue. In my interview with Wilbur, we discussed how he turned conference videos into a subscription product, why evergreen content works so well for coaching education, and how he's building a platform that allows coaches across all sports to share and monetize their expertise.