I’m going to take a little risk. It’s a tame one; there’s no jagged cliff or potential pregnancy involved, but it does involve a bit of assumption on my behalf. The thing is; I think you know about Threadless. I think you’ve visited Threadless, I think many of you own shirts you bought from Threadless, and I think many of you have submitted designs to Threadless. Some of you may have even been among the posse that packed out the first Threadless store in Chicago earlier this month. I can say this because, if you do fill that criteria, you are just another example of the kind of design-savvy, creatively driven reader we are blessed to have*. Taking that into consideration, I’m not going to thrown down a long introduction babbling about the magnificence of the of the site’s founders (particularly Jeffrey Kalmikoff, to whom we owe this interview) and the wonders of screen-printed cotton. In fact, all I’m going to say is that this interview is glorious, mainly because it is, but also because it’s Friday, and you need time to get your drink on. So read it, then drink (or drink, then read it, or drink while reading it).

*If you suffered from the sort of monastic upbringing that deprives you of the familiarity I presume you possess, click here before forging onward.

Joshspear.com: Where did the idea for Threadless come from?

Threadless: Jake and Jacob were part of an online design & development community called Dreamless. There was a tee design competition held on Dreamless to create the event tee for the New Media Underground Festival in London in 2000. Many entered, one man won. That man was Jake. Jake and Jacob had so much fun participating in this competition for a purpose, they decided to hold their own without a purpose… a free-for-all open-to-all-ideas tee design competition. And thus, Threadless was born (as a THREAD on DreamLESS… get it?)

JS: Correct me if I’m wrong, but it seems like you (all) have more of an entrepreneurial background than a design background. You must have had some history in design to come up with such an awesome concept…?

T: It’s actually quite the opposite. We all come from design or development backgrounds. The only real experience we all had with business was watching the people who ran the ones we worked for. Though I suppose that was more of a road map of what not to do. Our current so-called business savvy was learned by tripping over our own feet. A lot.

JS: Speaking of history, can you quickly walk us through Threadless’s humble beginnings up to where you are now?

T: Who doesn’t love a timeline? (I’ll be speaking in the third person)

2000: Jake and Jacob come up with the concept of Threadless, and in late 2000, it becomes its own website. A side project.
2001: Threadless remains a side project, Jake and Jacob work together at a small web dev shop in Chicago. Jeffrey is working at an agency. Jake, Jacob and Jeffrey meet when Jeffrey orders a poster from Threadless which is rolled up, and shipped in a triangular tube. Jeffrey’s poster shows up triangular, and in figuring out where to return the damaged goods, he discovers Threadless is also in Chicago. Friendship ensues.
2002: Jake, Jacob & Jeffrey work together as separate businesses out of the same small office designing and building websites for other people. Threadless remains a small, yet steadily growing, side project.
2003: Holy hell, Threadless ain’t doing half bad! We move into a 4300 sq. ft office. Part-time people are brought in to help ship shirts. Client work is picking up and so is Threadless’s business. Hey, we could actually live off Threadless!
2004: We decide to live off of Threadless. skinnyCorp (our parent company) now has about 8 people. We fire all our clients and devote every waking second (no joke) to Threadless. 2004 is a big year.
2005: Threadless is outgrowing our space! We move into 10,000 sq ft. and have probably 15 employees. We’re also working on other projects such as Naked & Angry, ExtraTasty, I Park Like An Idiot, and decide to put our beloved 15 Megs of Fame to eternal rest.
2006: Bananas. Having outgrown our 10,000 sq ft space over the course of one year, we move into 25,000 sq ft. Last year was kinda a blur. We got a lot done. We also took a minority investment from the amazing Insight Venture Partners to help us not collapse upon ourselves due to our growth on the logistical, back-end, fulfillment-and-all-that-other-stuff of Threadless.
2007: Threadless gets domestic and international. Domestic because Jeffrey and Jacob get married (no, not to each other!) and Jake’s wife gives birth to a beautiful baby girl. International because we set up a partnership to have a mirror warehouse just north of London to better serve our European customers. We haven’t launched that, but the year ain’t over yet!

One thing I didn’t say in each year to avoid being redundant is that we worked our asses MORE off exponentially in parallel to the growth of the business. Who knew that having fun was so much work?

JS: Choosing 7 designs out of 1000 submissions a week seems tough. What helps you narrow it down, and what do you do when you have more than four to six awesome designs?

T: It’s actually not quite like that. We launch seven new designs and two reprints every Monday. And it’s true, we do get about 1000 new submissions every week. However, it’s a lot more organic. Every week we choose new designs to print. Sometimes we choose 20 sometimes we choose five. Those designs then are added to the queue of designs that will be released later on. So it’s not really about choosing seven new shirts for any particular week. It’s more about keeping the queue full of great designs so we constantly have new products to launch each week.

JS: When you submit designs to Threadless, you’re up against some seasoned players. I always notice that a nice percentage of the tees are by already-well-known designers, and subsequently wonder how hard it must be for the little guys to score a winning submission. Is there any truth to this idea, and if so, do you consider it at all problem?

T: Threadless is pretty level, truth be told. “Big name designers” get no special treatment, unless they’re designing a Select tee, in which case they’re circumventing the competition anyway. In reality, a lot of big name designers’ stuff never even sees the light of day because it scores so low. The only real “big names” on Threadless are the ones who have been printed over and over. So we’re talking about niche fame, not like teach-your-stuff-at-design-school fame. Not to downplay our pool of talent. Honestly, it’s better than most “big name” designers out there to begin with. But to answer your question directly, yeah it’s tough. Out of over 50,000 submissions yearly, only 364 become Threadless tees. Hell, I’ve never won!

JS: What do you look for on a new design? I’m sure our designer-readers are dying to figure out how to get their designs picked.

T: We’re really only looking for the “new” part. When we print a new tee, we tend to get a ton of designs that look like the stuff that just came out. A good rule of thumb is that if you’ve seen it recently on Threadless, don’t submit something that looks just like it. We’re more interested in what’s “next” rather than what “works”. Sure we could find a niche style and beat it until it’s dead and then beat it some more, but that’s really lame. However, the truth is that there is no trick to being printed. It’s more about having that fine cocktail of talent, originality, timing, and sheer luck.

JS: You see your fair share of design work- who’s your fave these days?

T: Oh, that’s not fair! I really don’t play favorites…

JS: So the new store in Chicago; what led you make the move (or diversification, I should say) from web to walls?

T: Honestly, there’s really no good reason. And really, there was no good reason not to as well. It’s just something that we wanted to do, and create an environment in real life where people can experience the same things they can online at Threadless. It’s really more about brand awareness and providing a true community space than just opening our doors to sling cotton and ink.

JS: The “upstairs” of the Threadless store seems pretty awesome. Can you explain your idea behind that, and your hopes for it?

T: The upstairs represents everything at Threadless that isn’t buying a tee. It’s really open for whatever it becomes. Its intention is to be a gallery/classroom. We partnered with Digital Bootcamp to provide all sorts of technology classes such as intros to Photoshop and Illustrator. We’ll do lecture series, acoustic band sessions.. anything! And you’re right… it’s pretty awesome!

JS: Any plans for more stores (I know you were considering Boulder for awhile…le sigh)?

T: Yes! We’ll most likely open a kids’ store in Chicago first. But after that, the tentative list is Boulder (yay!), Portland, Seattle, San Francisco, Austin, Minneapolis, Columbus, Savannah, Boston, Toronto. Every new space will be unique to it’s city. We have no intention of creating drag-and-drop stores all over.

JS: And last but not least… anything else in the works that we should know about (or you can hint about)?

T: Well, Naked & Angry (Threadless’ sister site) has a TON of new products launching in October, November and December. Keep your eye out for some design changes and new features on Threadless. Of course, our famous $10 Holiday Sale is right around the corner in November so that’ll serve to turn our world upside down for a while. Other than that, not too much else! Except maybe a ton of stuff I can’t talk about…