Be bold.

Few ad campaigns survive the sizzle of the moment. They tap into a narrative of humanity, and we remember them long after the ad dollars have evaporated. Think Apple, Volkswagen, Coca-Cola. Here’s a story about a different kind of ad. Now obscured by nearly thirty years, the effects of this one ad campaign single-handedly created a brand you likely still know. In fact, few probably ever remember seeing this ad. Taking wild chances on his future, Tommy Hilfiger was relentless. Against his family’s direction he pursued an interests in fashion, but the thought of decades apprenticing with “the greats” didn’t appeal to him. Mid-thirties, broke, the young Hilfiger took a leap so bold that it cut the line thin between brilliance and idiocy. With nearly every dollar Hilfiger was able to cobble together from investors, he bought a giant billboard on Times Square directly across from Ralph Lauren. The board was simple, it read, “The…

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