Can media companies ever claw back advertising revenue from big tech?

My newsletter: https://simonowens.substack.com/ Before launching his own media company, Andrew Palermo spent years working in marketing, where he saw firsthand how affiliate deals between brands and publishers actually worked. That experience sparked the realization that many of the sites earning commissions weren't producing especially helpful or original content. In 2018, he decided to test whether he could do it better, launching Prudent Reviews as a side project. He started with products he already owned, with a focus on detailed, hands-on reviews. Flash forward eight years, and Prudent Reviews is not only one of the most authoritative home appliance review websites, but it also reaches a half million subscribers across YouTube, Tiktok, and Instagram. In a recent interview, Andrew explained how his background in affiliate marketing shaped his approach to building Prudent Reviews, why Google's shifting algorithms and the rise of AI forced him to rethink his entire traffic strategy, and how video ultimately became the foundation of a more durable media brand, one that's mostly protected from AI chatbots.  

My newsletter: https://simonowens.substack.com/   Digital advertising has long been shaped by a David-versus-Goliath dynamic, with publishers struggling to compete against tech platforms that control better data, more powerful ad tools, and vastly larger pools of advertiser demand. That raises a few big questions: Why have publishers struggled to close that gap despite the promise of programmatic advertising? What advantages do platforms like Google and Meta have that the open web still lacks? And as AI takes on a larger role in ad buying, could it help level the playing field — or further entrench the dominance of the largest platforms? Rick Erwin, CEO of Adstra and a longtime ad tech executive, has spent decades working at the center of these shifts. In a recent interview, he explained why tech platforms have built such a durable advantage over publishers, how advertisers decide who sees their ads, and why he believes AI could fundamentally change how ad campaigns are planned and executed.  

My newsletter: https://simonowens.substack.com/   Jessica Dante didn't set out to build a multi-platform travel media company—she set out to escape one. After an early career managing social media for corporate travel brands, she quickly grew frustrated with the slow-moving, top-down decision-making that defined the industry. So she struck out on her own, initially experimenting with blogging before discovering a more powerful insight: travelers weren't reading—they were watching. That realization led her to launch a YouTube channel focused on hyper-specific, highly practical London travel advice, a niche that was both underserved and endlessly in demand. Over the next several years, that channel evolved into Dante Media, a business spanning YouTube, Instagram, TikTok, email newsletters, and a suite of high-margin digital travel products. In a recent interview, Jessica explained how she identified a scalable content niche that didn't require constant travel, why a "drive-by" audience can be more valuable than loyal fans in certain contexts, and how the rise of AI-generated travel planning is beginning to erode one of her most important revenue streams, forcing her to rethink what parts of her business can still command a premium.  

My newsletter: https://simonowens.substack.com/   For most brands, TV advertising has long operated as an opaque, high-stakes gamble—an expensive channel dominated by middlemen, limited measurement, and a reliance on blunt audience estimates. That's the system Philip Inghelbrecht set out to disrupt when he co-founded Tatari. Tatari is attempting to rebuild the TV ad stack from the ground up—bringing automation, outcome-based measurement, and software-driven media buying to a medium that has historically lagged far behind digital. In a recent interview, Philip explained how Tatari is turning TV into a performance channel that more closely resembles digital advertising, why the company has rejected the programmatic-heavy approach in favor of direct publisher integrations, and how falling cost barriers are opening the door for a new class of advertisers to enter the TV market.  

My newsletter: https://simonowens.substack.com/   The rise of "sleep podcasts" has quietly reshaped a corner of the audio industry, turning bedtime into a high-engagement listening moment. Few creators have benefited more from that shift than Kathryn Nicolai, whose Nothing Much Happens podcast has grown from a scrappy 2018 experiment into what she describes as the largest sleep podcast in the world. Drawing on decades of experience as a yoga and meditation teacher, Katyrhn built a format that flips traditional storytelling on its head—stories designed not to captivate listeners through to the end, but to gently lull them to sleep. Along the way, she's expanded the concept into books, subscriptions, and a growing ecosystem of products built around relaxation and habit formation.   In a recent interview, Kathryn explained how she accidentally helped define an entirely new podcast genre, why word-of-mouth drove her early growth, and how she's built a monetization strategy around an audience that's literally falling asleep.  

My newsletter: https://simonowens.substack.com/ Axios Local began as an experiment in translating a national media brand's playbook into the fragmented world of city-level journalism. After acquiring the Charlotte Agenda, Axios used it as a template to launch a network of local newsletters built around a simple idea: hire well-connected reporters, deliver concise, high-signal updates directly to readers' inboxes, and monetize through a mix of local and national advertising. The model leaned heavily on email as a distribution channel and "smart brevity" as a product philosophy, allowing Axios to build strong brand awareness in early markets while sidestepping many of the traffic and platform challenges that have plagued traditional local news. In a recent interview, executive editor Holly Moore explains how Axios is using AI to shrink newsroom staffing requirements in smaller markets, why the company is experimenting with regional coverage models that stretch a single reporter across multiple geographies, and how its long-term ambition could see it expand into hundreds of cities.   

My newsletter: https://simonowens.substack.com/   Robbie Daymond is best known as a prolific voice actor, the kind of performer whose work spans anime, video games, and animation without ever putting his face front and center. After slowly breaking into the industry in the late 2000s and early 2010s, he built a rare, multi-disciplinary voiceover career—one that includes everything from audiobooks to major gaming franchises. He also spends up to 30 weekends a year attending fan conventions where he engages directly with audiences in what has quietly become one of the most lucrative and meaningful parts of his business. That creator-first ethos has increasingly shaped his ambitions beyond acting. In recent years, Daymond co-founded Sassy Chap Games, an independent studio that turned a quirky concept into one of the fastest-selling dating sims ever, fueled largely by viral user-generated content rather than traditional marketing. The project offers a window into how modern creative careers are evolving by blending IP ownership with direct-to-consumer distribution models. In a recent interview, Robbie explained how fan conventions have quietly become a major revenue engine for creators, why you don't always need a huge social media presence to build a large audience, and how revenue-sharing models can unlock top-tier creative talent.  

My newsletter: https://simonowens.substack.com/   For most of his career, Scott Brown has operated at the crossroads of Hollywood and the creator economy. After first breaking into digital media during the early days of web series, Scott went on to work across a wide swath of the modern media ecosystem. His résumé includes producing hundreds of hours of Larry King programming for streaming platforms, helping Dwayne Johnson launch a YouTube channel that quickly surpassed a million subscribers, and even producing large-scale stunts for MrBeast. Throughout that journey, Scott developed a front-row seat to how digital platforms were steadily reshaping the economics and creative possibilities of entertainment. Today Scott believes the next major shift is already underway: the rise of microdramas—short, vertically shot scripted series designed for smartphones and often monetized episode-by-episode inside dedicated apps.  In our conversation, Scott explained how he stumbled upon the emerging format, why he believes it represents the first truly native form of scripted storytelling for phones, and how his own microdrama projects are helping push the medium toward higher production quality.   

My newsletter: https://simonowens.substack.com/   Pat Walls didn't originally set out to build a media company. In 2017, he was simply interviewing founders as a side project while working a full-time job, hoping the conversations might spark his next startup idea. But those interviews—published as detailed case studies on a blog called Starter Story—slowly evolved into something much bigger. Over the next eight years, Pat bootstrapped the site into a media business built around thousands of founder stories, growing its audience through a series of distribution pivots that ranged from Reddit to SEO to YouTube. That journey culminated recently in a major milestone: the sale of Starter Story to HubSpot Media for what Pat describes as a "life-changing" amount. In a recent interview, Pat explained how Starter Story transformed from a scrappy side project into a profitable media brand, why video ultimately became the company's biggest growth engine, and his decision to shift away from advertising toward higher-priced products and boot camps.  

My newsletter: https://simonowens.substack.com/   Founded during the pandemic, the The News Movement set out with a simple but radical premise: what if journalism were designed entirely for the platforms where younger audiences already consume information? Rather than trying to pull readers back to a website, the company built a newsroom that publishes directly to TikTok, Instagram, and YouTube Shorts, translating the conventions of traditional reporting into vertical video, carousels, and other native formats.    In a recent interview, editor-in-chief Rebecca Hutson explained how the outlet approaches platform-first journalism, why its reporters function as "triple-threat" video journalists who can shoot, edit, and publish their own stories, and how the company tailors coverage differently for each social platform.