How a former USA Today columnist launched his own travel channel on YouTube
The Business of Content with Simon Owens
Release Date: 11/21/2025
How the Kyiv Independent used global sympathy to generate membership revenue
The Business of Content with Simon Owens
My newsletter: 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...
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How a local newsletter company is leveraging AI to cover hundreds of counties across the US
The Business of Content with Simon Owens
My newsletter: 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...
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Why BroBible's staff bought the website back from the media company that had acquired it
The Business of Content with Simon Owens
My newsletter: 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,...
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Why the founder of a popular cycling blog sold it and then left to launch a competitor
The Business of Content with Simon Owens
My newsletter: 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....
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How a failed horror movie director co-founded one of the most popular yoga channels on YouTube
The Business of Content with Simon Owens
My newsletter: 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....
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How Big Cabal became one of the fastest-growing media outlets in Africa
The Business of Content with Simon Owens
My newsletter: 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...
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How a former USA Today columnist launched his own travel channel on YouTube
The Business of Content with Simon Owens
My newsletter: 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...
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Why this business news outlet ditched advertising to focus entirely on paid subscriptions
The Business of Content with Simon Owens
My newsletter: If you attend any media industry conference, you’ll hear lots of discussions from publishers about how they’re trying to diversify their revenue streams, but Todd Scott took the opposite approach. A few years ago, he announced the National Business Review, the New Zealand media outlet he runs, would no longer accept advertising and instead monetize solely through paid subscriptions. NBR now has over 14,000 subscribers paying $499 New Zealand dollars a year. In 2025, it’s projected to generate $4.5 million in revenue and is profitable. In a recent interview,...
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Why a former New York Times editor launched her own women-focused magazine
The Business of Content with Simon Owens
My newsletter: Francesca Donner has had a somewhat unusual journalism career in that she never aspired to be a reporter or have her own bylines; instead, she started out her career as an editor and rose through the ranks of places like the Wall Street Journal and New York Times. But though she wielded some influence at these publishers, she was always frustrated by the lack of female viewpoints, both in terms of who was writing the articles and who was being interviewed for them. So in 2022, she launched the Persistent, a sort of online magazine that’s written entirely by...
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How an IMDB co-founder achieved three successful media exits
The Business of Content with Simon Owens
My newsletter: One day in the 1990s, Alan Jay received a surprising phone call at work from Jeff Bezos’s assistant, who said the Amazon founder wanted to meet with him during an upcoming trip to the UK. That meeting would eventually lead to Amazon acquiring IMDB, the movie database Alan had co-founded. After the acquisition, Alan didn’t rest on his laurels; over the next two decades, he went on to co-found two other media companies – one in entertainment and the other sports – both of which had their own successful exits. In a recent interview, Alan told the origin story...
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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.