Cracking the Code of Cool: Understanding How to Connect with Gen Z
A legacy brand sought to reconnect with Gen Z—not just through relevance, but by regaining cultural cool. Using AI agents trained on real Gen Z data, we simulated brand actions to uncover the most effective pathways to build buzz, uniqueness, and long-term cultural impact.
The Challenge
In a rapidly shifting cultural landscape, legacy brands with high trust and emotional affinity were struggling to remain relevant to Gen Z. These brands weren’t disliked—they were respected, even loved—but had lost their "cool factor." The central question: How can a brand that’s trusted and loved reclaim cultural relevance and become cool again?
"Cool" was not about popularity or awareness—it was about cultural energy. For Gen Z, cool brands are those that feel like insiders, speak their language, and evolve with their values. The challenge was not just to be visible, but to be vibrantly alive in the cultural imagination.
Our Approach
We combined deep cultural mining with scalable simulations:
300+ Gen Z AI Agents were trained on 5000+ pages of trend data and responses from 300 real Gen Z voices.
Using these agents, we simulated different brand actions to test how they impact trust, love, and coolness.
We broke down “cool” into layers—attention-grabbing moments, cultural depth, and long-term impact—and mapped the most effective activation pathways at each level.
We didn’t ask Gen Z what’s cool. We watched how our AI agents responded when brands showed up in different cultural contexts—FOMO-driven drops, humour-based content, subculture immersion, and more.
The Impact
The simulations uncovered that coolness is not a derivative of trust or love—it’s a distinct, cultural force. Brands must earn it through:
Strategic cultural embedding: Aligning with subcultures like sneaker culture, desi hip-hop, or stand-up comedy—not just as sponsors, but as participants.
Layered brand activations: Pairing FOMO with humour, or innovation with risk-taking, to stack cultural credibility over time.
Precision by place: What worked in metro cities didn’t always land in Tier 2/3 towns. Strategies were tailored by geography and mindset.
The result? A clear roadmap of which pathways unlock cultural buzz, uniqueness, and long-term relevance. Brands could now shift from simply being known, to being talked about—and from being respected, to being aspired to.


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