Some brands do this well, but not enough of them are true to the brand purpose they carved out for themselves in the beginning. One of the reasons brands struggle with this challenge is they try so hard to remain relevant over time by trying to be everything to everybody, they often lose site of what made them relevant in the first place.
They strip themselves of what made them unique and stand out from other brands offering similar products or services, and end up getting dropped (like any break-up, sometimes you wipe it off your shoulder and other times it leaves a big mark) for the next big brand by those who used to be loyal.
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For example, consider Adam Levine's recent tweetcusation of MTV only caring about music once a year during the VMAs. Regardless of whether or not it was vindictive because he did not receive a nomination, he made a good point. MTV has evolved far from their original brand purpose, bringing far less music to our televisions in the last few years.
Brands should nurture a unique purpose that lasts over time, something that resonates across generations to foster the kind of brand loyalty that will keep them relevant. And they should especially think about tackling this challenge now as it pertains to one generation in particular, because Millennials:
Some tips for brands to gain loyal Millennials:
Confused by your reference to "The Gap". The first Gap store sold Levi's brand jeans, records and tapes - that's it!
Although they have used music in their marketing campaigns for some time, they were not interested in even discussing a mutually beneficial partnership with the largest record company and music publisher in the world. Sure, CD sales may be down, but music sales are up.
Yet despite the fact that Gap started out selling music and has consistently used music to target market to its younger consumer demographic - they had no interest in discussing a partnership that would have aligned them with the largest music company on the planet and all of the associated artists.
The real kicker is that it would not have cost anything for Gap to partner. Rather, they were offered several new revenue opportunities.
So, not sure how how your example of Gap focusing on their beginning to look toward their future is relevant?