The Business of Content with Simon Owens

Hosted by Simon Owens

Business News

Website RSS feed

Episodes

292

Latest episode

Jun 2026

Language

About the show

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

Listen to episodes

60 recent

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.

June 4, 202656 min

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.

June 2, 202641 min

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.

May 21, 202652 min

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.

May 19, 202647 min

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.

May 14, 20261 hr 1 min

Publishers are sitting on valuable audience data — many just aren't using it well

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.

May 12, 20261 hr 3 min

This media startup is trying to reach readers exhausted by political noise

My newsletter: https://simonowens.substack.com/ Straight Arrow News was founded around a simple idea: a lot of Americans feel like they're living in completely different realities depending on where they get their news. The company grew out of conversations between founder Joe Ricketts and media executive Jonathan Harding, who come from different political viewpoints but realized they were often consuming very different versions of the same stories. Their goal was to build a digital news outlet focused on politically unbiased reporting and a clearer separation between news and opinion. Over the past year, that mission has increasingly been shaped by chief content officer Derek Mead, the former Vice editor who helped oversee that company's international expansion and also ran its US newsroom. In a recent interview, Mead explained why the company is moving away from high-volume aggregation and investing more heavily in original journalism, how it's using video and social distribution to reach audiences fatigued by partisan news, and why he believes there's still room for a new national media brand built around trust instead of outrage.

May 7, 202654 min

The 30-year-old PDF newsletter with a 98% market penetration rate

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.