The Business of Content with Simon Owens

Available Episodes

5 of 260

How a local newsletter company is leveraging AI to cover hundreds of counties across the US
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.
--------
55:56
--------
55:56
Why BroBible's staff bought the website back from the media company that had acquired it
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.
--------
1:01:00
--------
1:01:00
Why the founder of a popular cycling blog sold it and then left to launch a competitor
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.
--------
56:02
--------
56:02
How a failed horror movie director co-founded one of the most popular yoga channels on YouTube
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.
--------
48:14
--------
48:14
How Big Cabal became one of the fastest-growing media outlets in Africa
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.
--------
42:29
--------
42:29