Clothing design is in Scott Sasso’s blood. His mother was a designer, and she not only introduced him to the wonders of creating clothing, but to hip-hop music, as well. Sasso, however, didn’t have much interest in designing when he was younger. Maybe it was his way of rebelling or trying to carve his own path, but Sasso preferred dabbling in everything from graffiti to DJing instead. This, as he describes it, was his “training ground,” set against the illustrious backdrop of New York City.

Fast-forward to today. Sasso is now the founder and CEO of the clothing brand 10.Deep, and just celebrated the milestone of having 20 years in the design biz.

So, how did he get here?

Well, perhaps the best way to put it is: Gradually. During his first decade of designing, Sasso was hesitant to fully commit to the craft, dabbling only in T-shirts and smaller time stuff. But for some reason, after hitting the 10 year milestone, he decided to completely invest himself in designing, and finally went all in on 10.Deep as a bonafide business venture. That increase in dedication paid off, as the brand’s popularity skyrocketed very quickly.

Now, with 10 more years in the rear view mirror, Sasso reflects on how special it is to have remained relevant for two decades in a business where people usually wash out in a matter of months. “When I think of how many brands come and go,” he says, “and how fast culture and style, and youth culture moves in general, for me to still be doing this 20 years later—that’s crazy.” 

“Crazy” might not be the word we’d use, but after 20 years of making amazing clothing, Sasso has earned the right to call it whatever he wants. Here’s to another two decades of enjoying Scott Sasso’s designs—and, for Sasso, to the many more milestones that lie ahead.

For more from Scott Sasso, be sure to watch the new installment of “Then/Now” above, brought to you by Honda.