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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.

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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.

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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.