The Business of Content with Simon Owens
The show about how publishers create, distribute, and monetize their digital content.
- Indexed episodes, last 90 days
- 15
- Latest publication
- Sep 24, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 9, 2026
Latest episodes
This company is building a Substack competitor geared toward B2B creators (opens the original)
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My newsletter: https://simonowens.substack.com/ When Adam Ryan launched Workweek in 2021, the thesis was that some of the most valuable voices in B2B weren't professional journalists or full-time creators, but practitioners who had spent years accumulating expertise inside their industries. Rather than asking those people to quit their jobs and become media entrepreneurs, Workweek would give them the infrastructure to turn that expertise into newsletters and other content — then help them grow a
Will The New York Times lose its top journalism talent? (opens the original)
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The New York Times has become one of the few legacy media companies to successfully reinvent itself for the digital era, but that doesn't mean it's immune to disruption. One of its emerging problems is that some of the journalists it helps turn into stars can eventually make far more money by leaving and building independent businesses. The latest example is the team behind Hard Fork, whose hosts reportedly attracted multimillion-dollar offers to strike out on their own. So does the Times need t
How a high-end print magazine built a modern media business (opens the original)
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My newsletter: https://simonowens.substack.com/ Design Anthology was founded in 2014 around a simple idea: some of the most interesting design work in Asia-Pacific wasn't getting the attention it deserved. The magazine set out to give those designers a global platform, wrapping its journalism in a premium print product designed to be kept rather than discarded. Over time, it has grown into a broader media business spanning print, digital subscriptions, events, branded partnerships, and a YouTube
How an Instagram meme page became a social-first entertainment empire (opens the original)
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My newsletter: https://simonowens.substack.com/ In 2015, Reid Hailey started an anonymous Instagram meme page called Shithead Steve, mostly as a way to joke around with his friends. But once he began creating original memes, the account took off, eventually reaching a million followers and generating meaningful advertising revenue. Hailey soon teamed up with Derek Lucas, who was running his own fast-growing social accounts, and the two began building a portfolio of meme and user-generated-conten
Why fashion influencers love the US Open (opens the original)
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The Wall Street Journal found itself at the center of an AI controversy after publishing an op-ed that billionaire investor Stanley Druckenmiller later acknowledged he had written with the help of AI. What made the episode especially notable wasn't the disclosure itself, but the Journal's reaction: Its opinion editor essentially shrugged, arguing that AI is now a fact of modern life and that what matters is whether the piece accurately reflects the author's views. So is this a watershed moment f
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