How a finance blog started in a garage scaled into a financial media empire

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-content pages across different niches. That collection of accounts eventually evolved into Doing Things, a social-first entertainment company behind shows and brands like Recess Therapy, Bob Does Sports, and Breezy Golf. I recently spoke with Hailey, now the CEO of Doing Things, about how the company uses audience data to test and refine new shows, how it structures deals to keep creators invested in long-term success, and how it decides which properties have the potential to expand beyond content into products and other businesses.  

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 for mainstream newsrooms? And as AI becomes a routine part of the writing process, does it even make sense to require disclosures every time it lends a hand? To talk through those questions, I brought back Jason Krebs, a media veteran who has held senior roles at Disney, The New York Times, and Google. We discussed whether using AI to write an op-ed is really all that different from the decades-old practice of executives relying on ghostwriters. We also explored why fashion and lifestyle influencers have flocked to tennis — and why the U.S. Open in particular has become such a major cultural event for brands and creators. Then we unpacked the Good Good Golf controversy and what it reveals about the growing risks brands take when they move beyond simple creator sponsorships and build entire products and businesses around internet personalities.  

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 the digital-media era end up shrinking so dramatically? Was the underlying business model always flawed, or did a series of strategic mistakes — from costly acquisitions to overreliance on platforms like Facebook — turn these promising companies into cautionary tales? To help answer these questions, I brought on Jason Krebs, a longtime media executive who has worked at some of the industry's biggest companies, including Google, Disney, The New York Times, and Condé Nast. He's spent decades watching media business models rise and fall, which makes him an especially useful person to talk to about an industry that keeps cycling through new theories about distribution and scale. We also discussed two very different approaches to building subscription businesses. Jason weighed in on The New York Times' experiment with an AI chatbot trained on its own archives and whether the reputational risks are worth it. And we dug into MS NOW's new subscription product, debating whether personality-driven hosts like Rachel Maddow and Chris Hayes can convert their audiences into paying members.  

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 own in-house sales operation, and even an original sports league called Warehouse Games. Much of that growth accelerated after Courtney Hirsch joined the company in late 2020, first to build out its advertising business and eventually to become CEO. In a recent interview, Hirsch explained why the company now builds around creators rather than individual shows, how Warehouse Games could evolve into a major entertainment franchise built on IP Jomboy owns outright, and why she believes apparel could become one of the company's biggest businesses.

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 publication altogether. But how much should readers actually care if an author uses AI for research, editing, or polishing prose? And are publishers genuinely concerned about the technology, or are they simply trying to avoid the backlash that comes with it? To talk through those questions, I spoke with media veteran Jason Krebs, whose career has spanned some of the industry's biggest companies and smallest startups. He's worked across media, advertising, and content at companies including Google, Disney, The New York Times, and Condé Nast.  We also spent a large portion of the conversation digging into YouTube's evolving strategy. The platform is making it harder for smaller creators to qualify for ad revenue, setting an especially high bar for Shorts monetization, and increasingly positioning itself as a competitor to traditional television and streaming services. Jason and I debated what these moves say about YouTube's advertising ambitions, why Shorts may function more as a hedge against TikTok than a standalone creator business, and what happens as YouTube and Netflix increasingly encroach on each other's turf.  

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 few dollars for a single article or a short period of access. But previous experiments have often struggled with payment friction, weak economics, and fears that cheaper options would cannibalize subscriptions.  The Washington Post has spent the past two years trying to solve those problems, running more than 30 tests to determine which products, prices, and audiences make flexible access work. The person leading this experimentation is Anjali Iyer, the Post's global head of subscription marketing. In a recent interview, she discussed why the Post believes technology has finally made micropayments viable, how it discovered that anonymous visitors are the ideal audience for flexible access, and why offering a cheaper short-term option can actually improve both subscription conversion and retention.   

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 much interest in turning that audience into a full-fledged media business. He eventually walked away from YouTube, studied physics, math, and computer science, worked on AI at Amazon, and then teamed up with his brother to build DittoDub, an AI-powered dubbing platform designed to help YouTubers reach audiences in dozens of languages. In a recent interview, Stone explained how his frustrations as a teenage YouTuber helped inspire DittoDub, why the company focused on winning over large creators through product quality and word of mouth, and how multilingual audio can trigger enormous audience growth on YouTube.

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 to men while overlooking millions of potential female fans. What began as a side project built during evenings and Sundays has since grown into a sports media brand with more than 1 million newsletter subscribers, hundreds of thousands of social followers, a podcast, paid community, proprietary games, and partnerships with major advertisers. In a recent interview, Hyslop explained how scrappy marketing helped attract The Gist's first subscribers, why social media became an important source of revenue, and how the company is expanding into a paid community and launching its own games.   

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 directly to retail investors and major brokerage apps like Robinhood and Fidelity. Following a majority acquisition by private equity firm Beringer Capital in 2021, the company entered a new era of growth, hiring former Bloomberg editor Brad Olesen as its first Chief Content Officer to bring its news, video, and data teams together under one roof. In a recent interview, Olesen broke down what it takes to run a modern, multi-channel financial news operation, why Benzinga treats social media as a brand-building tool instead of a website traffic driver,  and how the company balances free, ad-supported news with premium subscription products.  

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 with little more than an iPhone, she began posting unscripted TikTok videos about the experiences of single women. Within months, she had built an audience of hundreds of thousands of followers and expanded into a media business that now includes a Substack publication, YouTube channel, and consulting. In a recent interview, Bentil-Dhue explained how she built a large audience despite having no prior social media experience, why she believes consistency matters more than high-end production, and how she's turning her growing platform into a sustainable business.