The Business of Content with Simon Owens

The Business of Content with Simon Owens

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

Episodes

December 5, 2025 56 mins

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 eventua...

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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 th...

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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 ...

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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 sever...

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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 s...

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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 ...

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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 nex...

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If Stuart Schuffman were in his early 20s today and building an independent media career, he'd probably be a TikTok influencer, but when he launched Broke Ass Stuart in the early 2000s, the natural medium was a print zine, one he printed out and stapled together himself. It was a San Francisco travel guide of sorts, and he trucked it all around the city and convinced coffee shops an...

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By the time Eric Coffie launched his YouTube channel in 2016, he was already one of the most successful federal government contractors in the US and employed an entire team that specialized in erecting steel buildings. The YouTube channel came out of his frustration of having to repeat the same advice over and over again to those wanting to break into the industry; he f...

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The Coppell Chronicle isn't your average Substack newsletter. For one, the headlines are incredibly boring. Secondly, there's really no free version of it, since every issue that's sent out includes a paywall. But perhaps the most remarkable thing about it is that it's managed to convert upwards of 40% of its email list into paid subscribers, which is a conversion rate at least 10 t...

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If you ask Dave Anderson what he does for a living, he'll probably tell you he's retired, but that's not entirely true. While he did leave his last full-time job at Amazon back in 2020, he still writes a weekly newsletter on Substack about tech leadership. And even though he only works on the newsletter part time, it currently has over 2,000 paid subscribers. It turns out a lot of p...

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Andrew Fogliato never set out to be a marketing consultant. He was simply trying to succeed as a real estate agent and began creating local online content to promote his listings. His colleagues at RE/MAX quickly noticed that his marketing savvy gave him an edge, and soon he was training other agents across Canada. Eventually, he left RE/MAX to launch his own marketing ...

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SailGP is only a little over five years old, and yet the competitive sailing league has already built out a substantial fan base all across the world. Not only are its competitions broadcast on linear TV channels, it also produces an impressive amount of content that includes YouTube videos, social media clips, and podcasts. In 2022, it hired Melissa Lawton, a longtime sports broadc...

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When Eli Woolery and Aarron Walter launched the Design Better podcast, they did it on behalf of InVision, a tech platform used by designers and other creatives. Aaron was the head of content at the company, and the goal of the podcast was to educate the designer community while also raising awareness of the InVision brand.

 

But when InVision decided to win...

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When Kevin Raposo launched KnowTechie in 2014, he had no idea it would grow into a thriving tech news outlet – he just wanted journalists to answer his emails. He was working as a PR consultant and figured reporters would be more receptive to his pitches if they considered him to be one of their peers.

 

But after three years of running the site, its audien...

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By the time Amy Wilson and Margaret Ables came together to launch a parenting podcast in 2016, both had already achieved some mainstream success in traditional Hollywood. Amy landed multiple roles in TV sitcoms and Margaret had worked for several years as a senior writer at Nickelodeon. They teamed up on the podcast, which is called What Fresh Hell, because it offered them more crea...

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Spencer Macnaughton doesn't believe there's a lack of LGBTQ-focused journalism in the mainstream media; as a former producer for both 60 Minutes and the Wall Street Journal, he saw a willingness from these outlets to cover anti gay and trans hate movements. He launched Uncloseted Media last year, though, because he thinks there's a need for more concentrated, investigat...

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You've probably seen headlines by now declaring 2024 to be the podcast election. It certainly did seem like a breaking out point that established podcasts as important messaging vehicles for any future presidential candidates. 

 

But back in 2015, podcasts had far less clout, and most of the political shows that did gain traction were produced in DC and New...

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Jonathan Skogmo has been working with user generated content since before the term "user generated content" even existed. Back in the 2000s, he moved to Hollywood and worked for what were called "clip shows," where viewers would physically mail in funny home videos to have them compete for cash prizes. As it turned out, Jonathan's entry into the industry coincided almos...

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If you work in the live music business, there's a decent chance you know of Josh Weidling, even though you probably wouldn't recognize his face. That's because he's almost always been behind the camera as he interviewed literally thousands of musicians touring through the midwest. Josh launched his YouTube channel Digital Tour Bus in 2009, and over the next 15 years he ...

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