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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…

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:…

There was a time when HuffPost and BuzzFeed looked like the future of digital media. Both mastered the mechanics of internet distribution, attracted enormous audiences, and convinced investors that scale itself could become a durable competitive advantage. So how did two of the defining brands of…

My newsletter: https://simonowens.substack.com/ Jomboy Media began as a Yankees podcast launched by Jimmy O'Brien and Jake Storiale with a small investment from a friend. Since then, it has evolved into a much larger sports media company, with dozens of channels, a roster of full-time creators, its…

My newsletter: https://simonowens.substack.com/ Over the past year, book publishers have repeatedly found themselves caught in controversies over authors' use of AI. Social media sleuths run books through AI-detection tools, accusations start flying, and in some cases publishers cancel a book's…

My newsletter: https://simonowens.substack.com/ For years, micropayments have been one of those ideas that repeatedly resurface in the publishing industry without ever seeming to gain much traction. The theory is simple: instead of forcing every reader into a recurring subscription, let them pay a…

My newsletter: https://simonowens.substack.com/ Nate Stone was still in high school when he built a YouTube channel with hundreds of thousands of subscribers by filming science and engineering experiments in his garage. But unlike many creators who stumble into a large audience, Stone never had…

My newsletter: https://simonowens.substack.com/ When Ellen Hyslop and her co-founders launched The Gist in 2017, none of them had worked in media or the sports industry. They were young professionals in financial services who had grown frustrated with a sports media ecosystem that largely catered…

My newsletter: https://simonowens.substack.com/ Founded in a Detroit garage in the early 2010s, Benzinga started as a scrappy finance blog for everyday stock market enthusiasts. Over the next decade, it grew into a major digital media platform, carving out a niche by sending detailed stock analysis…

My newsletter: https://simonowens.substack.com/ For most of her career, Ashanti Bentil-Dhue didn't have a social media presence. But after spending a decade running a consulting business, she moved from the UK to New York and decided to start sharing her ideas publicly for the first time. Armed…

My newsletter: https://simonowens.substack.com/ For years, the audiobook industry was defined by a single dominant player and a purchasing model that asked listeners to commit to an entire book before they knew whether they would enjoy it. Spotify is betting that there's a better way. By folding…

My newsletter: https://simonowens.substack.com/ The war in Ukraine has given rise to an entirely new generation of independent media organizations, but few have a backstory as unusual as The Counteroffensive. Founded by veteran journalist Tim Mak after more than a decade covering politics, national…