From Ask.com to Tinder to CBS Interactive, Jim Lanzone has spent his career redefining how we connect online. In this episode, he joins Michael to share how he’s reimagining a 30-year-old internet icon for a new era, leading Yahoo through a bold new chapter defined by innovation, trust, scale, and cultural impact.

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Stephen Upstone has spent two decades proving that AI isn’t just a tool, it’s the new operating system for brand advertising. In this episode, the LoopMe Founder and CEO joins Michael to reveal why mobile apps and gaming are marketing’s most undervalued frontiers, how the mid-funnel is becoming the next big battleground, and what it takes to turn disruption into lasting competitive advantage.

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From Disney to Condé Nast, Lisa Valentino has helped shape some of the most iconic media businesses. And now, as President of Best Buy Ads, she’s turning a trusted retailer into a modern media powerhouse. In this episode, Lisa and Michael unpack how scale, data, and creativity are transforming retail media, why storytelling still matters in a metrics-obsessed world, and how AI, culture, and commerce are colliding to redefine the future of media.

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