What happens when an influential hip-hop star proclaims that a certain brand of boots is suddenly out of style? Is it bad for business?

That very thing occurred when Jay-Z said, in a song, that he was "off Timbs." In response, Timberland CEO Jeff Swartz says: "Would we like to do business with the hip-hop consumer?  Boy, young people with the energy of that movement, music and culture they’re a deeply important part of the fashion scene. We’re going to work humbly and hard to earn their trust." But how will he pull that off?

Swartz stopped by Big Think to talk about more than just the company's push to appeal to the hip-hop generation. The Timberland brand, which was originally geared toward dressy women, didn't evolve until an Italian man named Giuseppe pinpointed the heart and soul of the company.

Even now, it's a quirky family-run business that continues to evolve: Bottled water is now banned. Each time Swartz lays someone off, he adds that person's name to a list he keeps in his desk drawer. And the biggest ethical dilemma he faces on a daily basis? Dealing with the push-pull of making sure overseas employees aren’t forced into illegal working situations.