Meet the Man Behind the Tees

Gettin' The Skinny with Jake Nickell

Welcome to Gettin’ The Skinny 2.0! A proper GTS reboot just wouldn’t feel right without chatting with the one person I should’ve interviewed during the GTS 1.0 era. Without further ado, here’s my conversation with Threadless founder/CEO, Jake Nickell.

(Image courtesy of @skaw)

GTS: Jake – Welcome to Gettin’ The Skinny! Thanks so much for being the first guest for GTS 2.0.

JAKE: I am excite.

GTS: How has your involvement with Threadless evolved since your started the company?

JAKE: Well, I’ve always worked on it all day every day since day one, 15 years ago! The first couple years I was supposed to be working at another job, but mostly just worked on Threadless all day (don’t tell anyone). In the beginning, I did everything from shipping orders to writing code to working with our manufacturers. Later on, I slowly began hiring people to help with the more painful things. I took a bit of a hiatus from 2008-2013 when I stepped down as CEO and worked on new initiatives out of a satellite office in Boulder. But I’m back in the saddle again, here in Chicago, driving the company forward!

GTS: What do you enjoy most about being a CEO? And alternatively, what’s your least favorites aspect of the job? 

JAKE: There’s nothing that I particularly enjoy about being a CEO, haha. However, having founded my own business, I really enjoy working on something that I built, really believe in, and love doing. It just so happens that when you start a business, you also have the opportunity to run the business going forward, and I like having the ability to continually mold and shape the business as it grows. My least favorite aspects of the job are being responsible for all of the more serious parts like legalities, accounting, etc… but I’ve hired an amazing team of folks who love that stuff.

GTS: What’s been the biggest challenge and/or change for the company in your view?

JAKE: It’s an exciting and challenging time right now. We were lucky to have very little competition for the first decade we were in business. Now we are seeing a lot of other options online for artists to monetize their work (which is likely connected to the advancement of on-demand printing technology). Separately, we have discounted our product pretty heavily in the past and we’re working to reduce that to make more room for artist payments. We aim to be the best place online for an artist to share and monetize their work.

GTS: Can you share a rough ballpark of how many shirts Threadless sells each year?

JAKE: Millions and millions.

“Funkalicious” by Christopher Golebiowski continues to be one of Threadless’s top-selling tees

GTS: Do you think it’s fair to say that vote totals and comments have declined in recent years? Is this something you’re concerned about?

JAKE: They have declined on a per-submission basis but not in total. We’ve been receiving a lot more submitted designs. That said, we definitely want to see more users voting. We believe the best place for this to happen is on mobile. Just last week we announced 1-5 scoring on our app and we’re already seeing 30% of total votes coming in through the app now.

The Threadless app now includes 1-5 scoring!

GTS: Awesome. When can Android-based users expect to have the app?

JAKE: Man I wish it was sooner! We might be kicking off the development of it here shortly.

GTS: I can’t speak for everyone, but I’m definitely keeping my fingers crossed for sooner rather than later.

JAKE: Let’s get a petition going.

GTS: And now for the impossible question: What’s your favorite Threadless shirt of all time?

JAKE: That is always a tough one. I get new favorites all the time (weekly?), but the one that has stuck with me the longest is “My Little Pony“… it’s just so bizarre. It did not sell very well though. 

One of Jake’s all-time favorite designs, “My Little Pony” by Kenneth Lavallee

GTS: Do your kids have a fave Threadless tee?

JAKE: They like Mr. Mittens’ Big Adventure because they both have one and I have one, so we can all match, haha. But my daughter is super stoked about the Peanuts challenge. We collaborated on a Snoopy design submission. 

“Mister Mittens’ Big Adventure” by Joe Van Wetering

GTS: Can you share some insights as to what the future of Threadless will look like?

JAKE: Future Threadless! Mainly we are looking at two big areas. First, Threadless’s presence in offline retail will be expanding like gangbusters. We’ll be seeing a lot of product by Threadless artists in stores around the world. Second, we’re working on new ways for artists to monetize their work online. We’ve got some top secret plans that we will be rolling out soon!

GTS: One of my favorite features of Gettin’ The Skinny 1.0 was the community questions. I’ve asked fellow Threadless enthusiasts for some questions for you and they cooked up some good ones.

Jake Friedman wants to know: Are there any designs that you wanted to print but ended up not pursuing?

JAKE: SOOO many. It’s hard, but we have to set our personal tastes aside when choosing which designs to print!

GTS: biernatt asks: What does the design judging process look like?

JAKE: First the community votes. Then, all of Threadless staff looks at the top scoring designs and votes for what they like. Those picks are the distilled down for a smaller group of ThreadStaff to review and determine the finals.

GTS: mohacsy wants to know: Why did Michael Jordan never print?

JAKE: Copyright issues :(.  But, we did sneak some out at the 7th annual family reunion using DTG. ;)

GTS: Now it’s time for PICK ONE. As you might recall, this is the in-depth, highly technical segment where I give you two things to choose from and you pick one. Here we go…

GTS: Kayaks or canoes?

 JAKE: Kayaks!

Jake battles the waves kayaking in Lake Superior (Image courtesy of @skaw)

GTS: Milky Way or Snickers?

 JAKE: Snickers

GTS: Banjo or mandolin? 

JAKE: Bnajo (typo included)

GTS: Sunrise or sunset?

JAKE: Sunrise

Screen Shot 2015-03-03 at 11.10.16 AM
Jake prepares for a sunrise paddle on Lake Michigan with daughter Arli (Image courtesy of @skaw)

GTS: IPA or Porter?


GTS: Rick Grimes or Daryl Dixon?

JAKE: Rick Grimes! 

GTS: Crew neck or V-neck?

JAKE: Crew

Screen Shot 2015-03-03 at 11.12.34 AM
Turns out Jake’s been rocking the crew tee since the beginning of time (Image courtesy of @skaw)

GTS: C-3PO or R2-D2?


GTS: Puzzle or board game?

JAKE: Puzzle

GTS: Trombone or trumpet?

JAKE: Trombone

GTS: Jake – Thanks so much for taking the time to chat today. Before we burn this mother down, are there any words of wisdom you’d like to share with the Threadless community?

JAKE: Thanks man, stay weird everyone!

“Stay Weird” by Perry Beane (aka BeanePod)


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Andrew Gregory

Andrew Gregory (aka lunchboxbrain) is a creative mastermind living and working in Upstate New York. View my work at www.lunchboxbrain.com.