34: Jake Nickell

 
And he tells us that there is a tradition in Sweden where when you meet for the first time, every goes around the room and tells a mini version of their life story.
 
 

From the Episode

About Jake

Jake is an unlikely rebel. Moving around as an army brat, he was on the quiet side and didn’t get a chance to put down roots. Until, that is, he found himself, at 20 years old, in a tiny apartment in Chicago’s Buena Park neighborhood.

This was when the idea for Threadless slowly made its way into his universe.

He was splitting his time between his graphic design classes at the Illinois Institute of Art and part time gigs building ecommerce websites. His girlfriend Shonda was away at Purdue University and he spent the little spare time he had on an online forum for digital artists called Dreamless.

After winning a Dreamless virtual t-shirt design competition, Jake was disappointed that no t-shirt was actually produced. So he and fellow Dreamless enthusiast Jacob DeHart started their own contest with $1000 of their own money, and this time, the winning designs were made. And not only that, they sold out.

It would take another two years before “the two Jakes,” as they came to be known, would drop out of college to turn Threadless into a real company. And the rest, as they say, is history. 

For over 20 years, Threadless has continued to help creators, well, create, providing a platform, tools, and most importantly, a community.

Meanwhile, Jake continues to be a rebel, letting his intuition lead the way. Where many might say that Threadless pioneered crowdsourcing, he just says “we make cool things with our friends.”

Threadless went remote-first during the pandemic, with flexibility to work from anywhere. So when he’s not working, Jake and his now-wife Shondi and their kids Arli and Dash are capitalizing on the great outdoors in a big way, enjoying every moment.

 
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35: Reggie Walker

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33: Shea Hillenbrand