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In 2000, a college student named Jake Nickell entered a t-shirt design contest hosted by Dreamless.org, a (now defunct) online forum for web programmers and graphic designers. The winning design would become the official t-shirt of a Dreamless event in London. Out of about 100 entries, Nickell’s design won the contest.
Jacob DeHart, another college student with a passion for design, also entered the competition. Though his design didn’t win, he and Nickell (who had met through the forum) began to talk about how much fun it was to participate in the contest. “Dreamless was all about art and design and a lot of artists on there had 'battles' and shared/critiqued their work with each other,” wrote Nickell in a blog post entitled ‘ Threadless.com: The History’. “It was all around a very creative environment for hobbyists and professionals alike to unleash some creativity in their free time.” That got the two thinking: what if they held an ongoing design contest where the winning t-shirts would go on sale? Soon, Threadless was born.