Dos Equis revived its 'Most Interesting Man in the World' campaign but had to update the slogans for a Gen Z audience unfamiliar with the original. By swapping classic lines for tech-centric jokes like 'his phone is addicted to him,' the brand adapted its nostalgic asset for a new generation's cultural context.

To connect with Gen Z, Coach shifted its brand positioning from simply being an affordable luxury good to being a tool for self-expression. This move addresses a core tension for this generation: the desire to express their true selves while navigating the pressures of constant social media visibility.

Chipotle focuses its marketing on being relevant to 20-somethings, believing this demographic defines what's cool in culture. This strategy ensures the brand never goes out of style, as both younger teens and older adults often look to this age group for cultural cues, creating a halo effect across all segments.

Nutter Butter, a 55-year-old brand, successfully engaged a younger audience by embracing absurdist, meme-style humor. This risky strategy, while potentially alienating some, is effective for generating deep brand love because it requires taking a bold, creative stand.

Enduring 'stay-up' brands don't need to fundamentally reinvent their core product. Instead, they should focus on creating opportunities for consumers to 'reappraise' the brand in a current context. The goal is to make the familiar feel fresh and relevant again, connecting it to modern culture.

Stuckey's, a nostalgic snack brand, wants to appeal to a new generation. The counterintuitive advice is to first double down on its existing, older customer base that already has brand recognition. Tapping out this core market is a more efficient first step than building awareness from scratch with a new demographic.

After its Quencher cup went from a viral status symbol to a ubiquitous item, Stanley is pivoting to men. This reveals that for trend-driven brands, market saturation erodes the exclusivity that created initial demand. The challenge is not just launching new products but rebuilding a sense of an exclusive "club" for a new demographic.

Tim Ellis argued the NFL's loyal 35+ male fanbase was secure, and future growth depended on attracting new, previously neglected segments like youth and women, even if it made core fans uncomfortable.

Maintaining a brand's core positioning over decades requires evolving tactics. As cultural meanings shift, what once communicated "cool" or "sporty" can become outdated. Brands must adapt their execution to stay consistent with their original promise.