Ten Questions for Ten Years of Threadless : An Interview with Thomas V. Ryan, CEO of Threadless/skinnyCorp

As part of our ongoing Perspectives Interviews initiative here at Killswitch, we interview everyone from creatives to CEO's in hopes of taking the pulse in the creative business community.

Our latest interview is with Thomas V. Ryan, CEO at Threadless/skinnyCorp, a company that creates online communities and pioneered "crowdsourcing" through their popular art community and e-commerce site, Threadless. Thomas also currently serves on the Board of Directors for Smule, and in the past, has worked at the executive level for Virgin Mobile, EMI Music, and eMusic. Thomas' first company, Cductive, which he founded in 1996 was a pioneering digital music retailer which was among the first to sell mp3 downloads and custom CD compilations. Thomas was kind enough to take some time out of his busy schedule to sit down and answer some questions I had. I asked questions that I thought could benefit a wide range of readers, and I also asked a few on topics that, as a small business owner, I struggle with as well.

Some of these were not easy questions to answer and will shed some light on the real challenges and triumphs of the Threadless brand over the years. This is definitely an organization that should be used as a model of excellent leadership, awesome employee morale and commitment, as well as a brand that achieves great results.

www.threadless.com
www.skinnycorp.com

As the CEO of Threadless/skinnyCorp since 2008, can you reflect back on what this 10 year anniversary means to you and your company?

This year is a huge milestone for our company. Our founder Jake Nickell started Threadless in his apartment in 2000 after winning a one-off t-shirt design contest on the now defunct online designer forum Dreamless. Over the years since then, and thanks to the support of our awesome community, Threadless has become not just a successful business but an important influence in the visual artist, Internet, and business worlds. For example: a Threadless win has become a respected piece in an artist's work portfolio; Threadless has become a posterchild for the web trend Jeff Howe of Wired calls "crowdsourcing"; and universities like MIT and Harvard teach courses based on learnings from Threadless. Having only been here for two of those ten years, I can't take much credit. In fact, when I started here, Inc. Magazine ran a cover story calling Threadless "the most innovative small company in America." I thought to myself "how am I going to help us top this?"

During this tenth anniversary year, we want to celebrate the accomplishments of our community and our company, but we also want to look forward to the next decade of Threadless. To celebrate, we're reprinting popular designs from all ten years, doing a lot of exciting events, releasing a book, and much more. We're also working hard on new initiatives that will drive Threadless forward. We're focusing heavily on international expansion and we're pursuing new opportunities for our artists, such as offering new products (like the iPhone cases we've done with Griffin and the premium tees we've done with Gilt Groupe). We'll have a lot more to announce soon.

As you know there are a lot of people out there that make t-shirts. It seems like the vehicle that has allowed the company to grow, has been the classic t-shirt, but upon further discussion, the design is the real product that Threadless sells to customers. Designers are rewarded by having their designs featured and also get a cut of good ole' hard cash. From your point of view though, what is it about the Threadless concept that set your company apart when it started, and more recently what has been done to make the company successful long term?

It's true that t-shirts are an ideal product for many reasons and that customers come to Threadless first and foremost for the designs. However, lots of companies sell well designed t-shirts. What has always set Threadless apart is the community. From the early days through today, our community members have always been very supportive of one another. Real relationships are formed on Threadless and lots of members are actually friends with one another. Having an authentic community with these types of bonds isn't something that can be forced on people or rushed, so I think it's no surprise that it's been a decade in the making.

As a business owner in the creative space, I find one of the biggest challenges is working within the scope of a client's expectations for a project. In your industry, how do you manage the expectations of both your customers and your content providers, i.e. the designers?

There's a few key things we do that stand out in my opinion.

First, we always try to surprise and delight the community. Another way of saying this, and this is our mission statement, is to "inspire awesomeness." We're always trying to come up with ideas and projects that will inspire awesomeness in each other, in our community, and in the world. Examples are charitable campaigns like our Tee for Haiti which raised over $100K for Red Cross relief efforts in Haiti; partnerships like the ones we've done with RISD; and design challenges with prestigious museums like The Tate Modern or New Museum. These things capture the imagination of artists and customers alike.

Second, we listen to our community and we make decisions and changes to our business based on the things they tell us. An example is our retail strategy. We were getting approached by brick and mortar retailers of all shapes and sizes who wanted to distribute our tees in their stores. Some were really big and we had internal debates as to whether or not we should be selling our tees through them. Ultimately, we felt that the community would be best able to guide us, so we asked them what they thought and got great, immediate feedback from them. That's been informing our retail plans since.

Third, we are always trying to make Threadless valuable to the community. An example is offering a new product that artists can design and that customers will want to buy. Sometimes these decisions can be difficult, since the interests of artists and customers are not always aligned. However, we're making progress and so far the reaction to our new products has been great on both sides.

Last, but not least, we're authentic. We speak openly, we inject our personalities into how we speak to our community, and we try to have fun wherever possible.

It's been a challenging year for the majority of creative businesses. Whether you are a large agency or a small shop like Killswitch, I know no one likes to talk about this subject, but has the recession impacted Threadless? If so, how? And what are you doing to keep morale up and the t-shirts leaving the loading dock?

It's certainly been a challenging time for creative businesses. Fortunately, we have been growing rapidly through the turmoil, but it hasn't been for lack of effort! When I joined, we decided that we should focus on our core business of Threadless and related ventures instead of launching new projects or concentrating on some of the other businesses SkinnyCorp had launched in the past. Since then, we've gotten even more disciplined, and Threadless is our primary focus. It's tough to balance the desire to launch new creative ventures with focusing on the core business, but over the past couple of years we have channeled our creativity into making Threadless better and that focus has paid off.

Threadless has opened 2 retail locations in the last 2 years. Can you talk a little bit about why Threadless decided to enter the retail space? There has been both praise and criticism for this move, and I'd be interested in your thoughts.

The first retail store, located in the Lakeview section of Chicago, was intended to extend the Threadless community and business into the real world. It's a physical manifestation of the online community - we only have two weeks worth of releases at any one time (like the homepage of our website); we invite visitors to take a picture of themselves so their face appears on the TV which sits atop the shoulders of the mannequins in the shop (mirroring our community-approach to product models on the website); and we reserve a large amount of the space as an art gallery (just as Threadless is largely about showing off art, rather than solely selling products). The second store, in the Wicker Park section of Chicago, was started as a Threadless Kids store, but now serves both kids and adults. We feel the stores are a great extension of our online business, excellent marketing vehicles, and allow people to step inside Threadless in a physical way. We don't see a brick and mortar retail rollout as the best or fastest way to grow the business, but the stores made sense for us to open here in Chicago.

As the CEO and with the help of other advisors, you make a lot of critical decisions for the organization. If you could do one thing over again as the CEO, in any of the sectors you work in on a regular basis (i.e. Management, Thought Leadership, Employee Communication, etc) what would it be and how would it affect the Threadless/skinnyCorp brand?

I haven't been active enough in the community. I'm certainly a part of it: I score designs, submit slogans to Type Tees, I read and comment in the blogs, and I attend our meet ups and events. However, I need to become more active. Most Threadless employees are so active in our community that I defer to them and take a less prominent role than I should. Given how critical the community is to our business, I should stop lurking and get out there more! In doing so, I would get to know our community even better, hear all of their great ideas or criticisms directly, and be better able to help make Threadless even better. I'm not an artist, but maybe to feed my masochistic side I'll even submit my first design under a pseudonym!

There are a lot of tips for designers that want to submit for Threadless on the site and elsewhere. What would be your best advice be to a new designer out there looking to submit a design and win a challenge on the site?

Spend time on the site, see what's working, and go for it. You can only benefit from submitting, even if you don't win, so once you feel your design is worthy, go ahead and submit. Lots of community members give valuable feedback and try to help new members improve their art and improve their chances of winning.

As a business model that clearly has a deep footing within the design community, both from a content as well as customer standpoint, what can companies, including skinnyCorp, do to support art and design in their communities, beyond the monetary rewards offered to designers of Threadless merchandise?

Money is certainly a part of it, but there is certainly more. Artists submitting to Threadless today already get a good amount of constructive feedback on their designs. Those who win a design challenge also make progress in their careers by creating a valuable portfolio piece and gaining notoriety. Additionally, we are expanding the number of products we sell and the places in which we sell them, so that our artists have more and more opportunities to sell their work. Aside from that, we are actively trying to do more for the arts. We introduced a program called Threadless 101 that aims to bring Threadless to schools, and we are working on a charitable strategy for the arts. We'll have more to share on that soon!

I read on your blog you are in the process of making a 10th Anniversary book. Can you tell us a little about it? I'm sure the readers are giddy with excitement on this one!

Sure. This is an exciting project Jake has been spearheading. It's a retrospective of the past ten years of Threadless. The art, the artists, and the community that makes us who we are. It showcases the 400 best designs that we've printed over the years and also includes "think pieces" about Threadless by luminaries like John Maeda, Jeff Howe of Wired, and Seth Godin.

And finally, now that you are in the midst of celebrating your 10 year anniversary, after Threadless, which of the skinnyCorp brands do you see the most potential for growth over the next 10 years and why?

Threadless. Community-driven design is a universally appealing proposition - to the artists who submit, to the members who score, blog and give feedback on designs, to the customers who want to buy an awesome design with a unique story and real person behind it. As we continue to grow Threadless by growing internationally, adding new community-design products, and distributing our products more broadly, we hope to increase our impact on the arts and the world.