The Business of Content with Simon Owens

Simon Owens
  • 5.0 (2)
  • News Commentary
  • Updated Weekly

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

  1. 6d ago

    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.

    56 min

  2. Jun 16

    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.

    1h 4m

  3. Jun 11

    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.

    49 min

  4. Jun 9

    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.

    48 min

  5. Jun 4

    How a niche newsletter about startups evolved into a data business

    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.

    57 min

  6. Jun 2

    How a weekly PDF became one of Africa's most innovative news products

    My newsletter: https://simonowens.substack.com/ When Sipho Kings and his co-founder Simon Allison launched The Continent in 2020, they wanted to rethink how journalism is distributed online. Instead of chasing search traffic and social algorithms, they created a weekly PDF newspaper designed specifically for smartphones and distributed it through platforms like WhatsApp, Signal, Telegram, and email. The idea was to bring back the simplicity of a curated newspaper while adapting it to how people actually consume information today. Six years later, The Continent reaches tens of thousands of readers across Africa and around the world. In a recent interview, Kings explained how the publication grew entirely through word of mouth, why its unusual PDF format created a deeper relationship with readers, and how it's building a sustainable media business outside the traditional web ecosystem.

    41 min

  7. May 21

    This former TV writer now produces prestige audio dramas for Audible, iHeart, and Spotify

    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.

    52 min

  8. May 19

    This independent magazine publisher doubled down on print

    My newsletter: https://simonowens.substack.com/ After spending several years helping launch food and travel magazines in London, Krista Faist returned to Toronto with a simple idea: replicate the free magazine model that was thriving across the UK transit system. In 2015, she launched Twenty Two Media Group and started building two media outlets into lifestyle brands focused on food, travel, and culture. What began as a one-person operation has since grown into a media company spanning print, digital, events, and now shortform video. In a recent interview, Faist explained how she landed major advertisers before the first print issue even launched, why she still believes premium print magazines have real value in a digital-first media landscape, and how Twenty Two Media Group is expanding into vertical video and creator partnerships while keeping print at the center of the business.

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

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