Since printing the first Staple shirts, what have been the biggest challenges you’ve faced? What have been your biggest learnings?

The biggest challenge over the last two decades of Staple is probably trying to maintain an edge while growing bigger as a brand. How do we maintain excitement, brand loyalty and “hype,” while also trying to just grow the business to a larger audience? Those two things are inherently polar opposites. So finding that fine line in between is a constant challenge.

Biggest learning? Probably that giving away all the information and trade secrets I’ve learned is the best thing I’ve ever done. It just continuously comes back 100 fold. Whether it’s my 1-2-1 series, or the various lectures I do, or Skillshare, or th-oughts; I pride myself on sharing the experiences I’ve learned. And in turn, I’ve learned so much more than if I just kept it all to myself.

What do you think about the state of streetwear culture and what do you see as the biggest issues it faces today?

I think we’re still at level 1! We’ve only just begun! It’s an amazing time. The breadth of the culture is wide enough to encompass something for everyone. I think there’s very little downside right now; I honestly don’t think it faces any challenges. I think there’s some people and brands that don’t care enough about the culture, but the irony there is of course that street culture is built off this feeling of indifference and apathy. It’s that “I don’t give a fuck” attitude that makes street culture street culture.

Do you have any expectations for where the fashion industry is heading?

One rule has held true for centuries: the fashion industry runs in cycles. So if that continues we’ll be leaving this era of luxury/streetwear and going back to something more basic and simple. That’s my prediction.

What’s been your highlight of 2017?

Fuck. 2017 marked the 20th anniversary for Staple! That shit boggles my mind. I printed the first Staple shirt in 1997. I have employees that were BORN in 2000! So everything we’ve done this year has been a dream. The whole entire year and just still being able to thrive in our 20th year IS the highlight!

What are your short-term and long-term goals for your brand, and personally?

I don’t really divide goals into long and short-term. To be honest, the only thing that matters to me is that I continue to love what I do each and every day and create an environment at work where others can do the same. As soon as that stops, I will make a dramatic change. But life is too short to plan 5, 10, 20 years ahead. If you can be happy today and be relatively sure you’ll be happy tomorrow… you are winning.