Timberland CEO Jeff Swartz didn’t try to win the acceptance of the hip hop generation; it just happened. And now he might be losing them.

Question: How did Timberlands become synonymous with hip hop?

Jeff Swartz: We didn’t know what hip-hop was, what it meant or what it represented and so after the fact. I mean long after the train left the station where people said to us you know young people are wearing the boots. We thought yeah, the young Con Edison guy. No, no, no, 16, 18 year-old kids are wearing the boot as a fashion statement. They’re not lacing it up. What do you mean they’re not? Their feet will get wet if they don’t lace up their boot. I mean I don’t mean to sound like I fell off a turnip truck, but I’m telling you until 1994, ’95 we had no idea. Now I’m not proud of that. I’m just telling you the truth.

How did that consumer decide our brand was valuable? The postmortem says you showed respect because you were in the neighborhoods where we live and work. You made a product without compromise meaning it was tougher than the rest as the Bruce Springsteen song goes and you did fine until you decided you were cool. When you decided you were cool now we’re… We are now an element of hip-hop culture and so now we have to add colors and fancy styles and the consumer said back, “If we wanted colors and styles we wouldn’t have bought you in the first place.” “Stop doing this.” We said, “It’s working.” Our sales were way up and we were rocking and rolling and we were believing that we were cool and the truth is the only thing that isn’t cool is when you try to be, so I’m told. When we were authentically who we are, we make the best damn boot in the whole world. We guarantee it for life and it won’t disappoint you, consumer came to us and said, “That’s respectful and we appreciate it, but if you want to make it cool hey look, look in the mirror.” “That isn’t you.” And we didn’t listen and the last five years has been that cycle of boom and now bust against that consumer, not against that consumer in terms of values, meaning the hip-hop consumer as best I understand it continues to believe in the authentic things we do. They just were put off by our attempt to be topical and cool.

Question: Jay-Z says Timbs are out. Can you win him back?

Jeff Swartz: Now I don’t know about Jay-Z, Mr. Shawn Carter. I don’t know what it would take to get him to wear a pair of Timberland boots again. I don’t know if he wants to. I don’t know what it would do for our brand if he did. He is a very influential guy, but the truth is that’s never been our strategy. Our strategy has been about put your head down and make something so good that they got to have it. Who is they? Well, we think about different consumers all time, men, women, children. 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 and we’re going to work humbly and hard to earn their trust.

Recorded on September 21, 2009