Permission, Cringe, and Brand Risk-Taking

Welcome to episode #1020 of Thinking With Mitch Joel (formerly Six Pixels of Separation).

At a time when technology listens more closely than people realize and advertising feels less predictive than presumptive, understanding how culture, data and human behavior collide has become essential. David "Shingy" Shing has spent his career at that intersection, shaping how global brands think about creativity, relevance and the emotional consequences of digital systems. Know as the Digital Prophet at AOL (and then Verizon) and a very influential voice in modern branding and innovation, Shingy has advised companies, leaders and creatives on how emerging technologies reshape not just markets, but meaning itself. His work has consistently challenged organizations to move beyond optimization toward empathy, imagination and cultural intelligence. He argues that the most important signals in a data-saturated world are often the quietest ones. That perspective now finds a more personal, reflective outlet in his Substack, Shingy, a newsletter focused on branding, culture, AI and the human side of technology. He explores how conversational data, algorithmic inference and attention-driven business models are altering the relationship between consumers and the systems designed to serve them. Shingy examines why ads increasingly feel intrusive rather than helpful, how conversations themselves have become raw material for targeting and why consumer fatigue is less about frequency than about lost agency. Shingy's work surfaces a growing tension between personalization and privacy, usefulness and surveillance, convenience and control. He argues that as machines become better listeners, brands must become better stewards of restraint, intent and respect... or risk eroding the very relationships they're trying to monetize. Grounded in curiosity and creative provocation, his thinking offers a necessary counterweight to an industry too often obsessed with what can be done instead of what should be done. Enjoy the conversation…

• Running time: 1:02:31.
• Hello from beautiful Montreal.
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• Here is my conversation with David "Shingy" Shing.
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Chapters:

(00:00) - The Evolution of Digital and Consumer Behavior. (05:01) - Generative AI: A New Paradigm. (10:02) - Creativity in the Age of AI. (20:11) - Marketing in a Changing Landscape. (32:10) - The Shift from Influence to Interpretation. (35:03) - The Evolution of Content Creation. (39:00) - Niche Markets and the New Mass. (44:07) - The Complexity of Advertising and Intent. (51:03) - Power Dynamics in the Age of AI. (57:02) - The Future of Creativity and Connection.