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.

Born in Barcelona, but currently living in Madrid, Oscar Gimenez is an extremely talented illustrator who has worked for a broad range of clients including Adobe, Audi, Playboy, Rolling Stone, Schweppes, TGV France and Zara. Gimenez's works have been exhibited internationally and featured in several publications, such as Big Book of Fashion Illustration: A Sourcebook of Contemporary Illustration, Essential Fashion Illustration: Color and Medium, and What is Illustration?

With that said, it brings us immense pleasure to have the opportunity to speak with Oscar and provide a glimpse into his background, his inspirations, and just what makes him tick.

www.oscargimenez.com

Your father and uncle were both artists, but for years, you refused to follow in their footsteps and went on to study languages. At what point did you start to become interested in pursuing illustration for a living?

When I realized the job I was doing made me completely miserable. By then, and that'll be about 8 years ago, I was working as a language teacher, a job I thought would bring me stability and comfort. I was wrong. The work we do takes so much time and energy off of our lives that it's worth at least trying to do what makes us happy. So I decided to risk it and give it a go. It was hard at the beginning (and it still is sometimes) but I still believe it was worth it.

Did growing up in a creative family influence your art in any way?

It definitely has. In a way, and although being very young when I was exposed to that atmosphere, it taught me some valuable do's and don'ts. Be as professional as possible, even when you are starting. Avoid working nights whenever possible. Learn to say no. Save up (still pending). Be bold. Work to live.

Let's briefly talk about inspiration.

Inspiration comes with work. At least in my case. I love working on commission. I know others don't, but I like facing new challenges all the time, being put to the test. I find it very stimulating.

What music are you listening to these days?

Music is essential when I'm working. Lately I've been mostly listening to The Phenomenal Handclap band, The XX, Bill Withers, Crystal Castles, Koop, The Horrrors, M83, Team9 and Yeah Yeah Yeahs.

Your work spans so many industries, from music to fashion to film to corporate. Are there particular industries you like illustrating for most?

Right now I really like doing music illustration and want to do more. It's just so creative. Recently the Canadian band, Creature, asked me to do some t-shirt designs for them, and I'm loving it. Doing some more film stuff would be great as well. I used to be quite keen on fashion work but I got bored with it at the end.

Do you keep a sketchbook?

I don't... shame on me. Truth is I don't like drawing in my spare time. My regular work takes already enough of my time.

Do you feel the projects that give you the most creative freedom wind up being the most successful, or do you like having some guidelines in place?

As I mentioned before, I don't mind being directed at all. If a client gives you both guidelines and creative freedom, that can add up to resulting in a very successful project. They give you the exposure and you can show your best.

You were commissioned to illustrate scenes for an online animation about the Audi Q5. What was that like, creating all of these illustrated elements and then having them all come to life? Tell us about that process.

It was the first time my work was to be animated and I was thrilled. I worked closely with an animation studio. They would give me a detailed storyboard of all the scenarios, elements and moves and I would draw all of them separately. I had to be very careful with keeping everything coherent though. We would do one scene at a time and then move on to the next one. It was a tough, very intense process.

In your artistic career to date, what would you say has been the most challenging experience for you? And which has been the most rewarding?

Probably the animation job I just told you about. I ended up doing three different animations in three different styles all located in different cities of the world. It required a lot of documentation and a whole lot of dedication.
The most rewarding, I hope, will be one I'm doing now. I'm working on a series of music illustrations based on concerts I'm attending together with a journalist from a Spanish TV channel. He writes the reviews and I illustrate them. Thanks to them, I got a commission for Rolling Stone magazine and the Canadian band I told you about. 
I hope it will all bring a lot more of this type of work.

What's in store for you in 2010? Exciting projects? Travels? Anything?

Hopefully more and well-paid challenges! I recently moved from Barcelona to Madrid and that was enough excitement for a while. I do expect to travel to Argentina and NY within this year.

Illustration is a highly competitive industry. What words of advice would you give to anyone thinking about illustrating for a living?

To me, it's a combination of dedication and talent. If you're talented and are willing to work hard for it, you're half way there. Be persistent but also realistic. And don't be envious, it might just be you are not trying hard enough.

One final question... from The Proust Questionnaire: What is your favorite motto?

"When you think it's bad, it's probably already been worse."

Steffan Postaer is the Chairman and Chief Creative Officer of one of the world's largest advertising concerns, Euro RSCG Chicago, where his clients include Barilla, Kraft, Valspar Paint, Beam Spirits and more. Steffan is responsible for their overall creative leadership and quality of the creative product.

A copywriter by trade, he is perhaps best known for his provocative work on behalf of Altoids, The Curiously Strong Mints. Other moments in his career include co-authoring the famous "Not your father's Oldsmobile" campaign for General Motors and penning a commercial for Heinz featuring a teen-aged Matt LaBlanc. He is the recipient of advertising's most prestigious awards including a Kelly Award, Best of Show at the Addys, and a gold and silver Lion from Cannes.

Additionally, Steffan is an avid writer and blogger. His blog, Gods of Advertising, is considered one of the best places on the web for candid, expert commentary on the advertising industry. Steffan has published two novels, including his most recent, The Happy Soul Industry, a book that explores themes of religion and materialism by asking the question, "What if God needed an advertising agency?" Steffan's short stories have been included in the 1994 and 1995 editions of New Voices in Poetry and Prose. His first novel, The Last Generation, was published by the Inkwater Press. Touchstone Television later optioned the story for TV.

Prior to joining Euro RSCG, Steffan was Executive Vice President and Chief Creative Officer of LBWorks (a Leo Burnett company), overseeing creative for their full client roster including Altoids, Handspring, Lexmark and Maytag. Prior to this position, he served as Executive Vice President and Executive Creative Director at Leo Burnett USA, and was a member of Leo Burnett USA's Creative Management Board.

How did you get into writing novels?

I started writing short stories in high school, where I worked for my high school newspaper (I went to Lane Tech, a public school on Western and Addison here in Chicago). At the University of Wisconsin I wrote for both the conservative and super-liberal papers, unbeknownst to either of them. I also wrote for the music newspapers. I took my classes and did reasonably well, but I really spent a lot of my time writing for newspapers and interviewing the bands that came through Madison. My dream was to be a writer for Rolling Stone.

The epiphany I had--I think that this is a fun story--came about from something that all critics are guilty of, which is when you review someone who is terrible and then find clever ways to eviscerate them. As a young, young man I was totally guilty of that. One night, a day or two after I published some rip on a band, I'll never forget what they were called: Whiz Kid. They had tights and long hair and sang 80's rock like Lover Boy and they were terrible. I made fun of them and then this guy in the band came up to me several nights later, he didn't want to fight or anything, he came up to me and let me know that he didn't want to play those songs. He told about how he had a kid and had to pay rent and said that he couldn't play his songs and expect these college kids to come to the show. He let me know that I had really hurt his feelings.

That was bothersome to me. I didn't want to be that guy anymore. At that point I went away from wanting to be a Roger Ebert or a Rolling Stones writer or any of that. Who was I to knock this guy for following his dreams? That's a true story, and I don't think I'm embellishing it. I don't think that I wrote another review after that conversation. That was the change, and that's what led to my becoming a copywriter and an author.

But I do all of it now. When I go home at night, I don't watch TV. Whether it's with writing for work or my blog or my other writing, I'm always writing or trying to either make content or sell the content I've made. That's what interests me now. Until I see my book at the airport in LaGuardia or I'm sitting on the couch next to Oprah Winfrey, I'm not going to stop. That's the way I channel ambition and keep my work ethic going. Writing isn't a chore for me. It can be at first, but it is sort of like a pool. Once you jump in it's chilly but once you're in it and enjoying it, it's the best.

So what compelled you to start blogging?

The first few months I was primarily doing it to learn about blogging and to sort of communicate to my troops without sending memos, which nobody does anymore. So for the first few months I had about 40-50 people, mainly from around the office. Then 70. Then 100. Then I wrote a controversial piece, it got linked and picked up and spiked to 450. Then 700. Now, my record is 1200 in a single day and I average about 400 knuckleheads daily that visit my blog.

Then I launched the Rogues Gallery, my second blog, which is a collection of art and writing from advertising people. It's what we make when we aren't making ads. And so the Rogues Gallery is a place for people to submit anything: their photography, art, poetry, fiction, and essay. It's not a beauty pageant. No prize. There isn't any editorializing. As long as it's not commercial and you are in the industry, I'm going to publish it.

So here you are, an advertising creative that has found this outlet in writing literature that has recently launched a website for other ad creatives to post their non-advertising art. Do you count yourself lucky to have been published and is this your way of providing others with an avenue to get their work noticed?

I had the idea about ten years ago to do a copywriters anthology; I wanted to call it "The Book," because we call our portfolios "books." I couldn't get a publisher interested, for obvious reasons....it's not very commercial or lucrative. We're a small business. Advertising and creative services isn't a big audience. Publishers would say, "Who the hell would buy that?"

So I let this fantasy go dormant. And then as I was blogging I had a minor epiphany, which was "Forget this format, I can do everything I wanted to do in the 90's but couldn't and I can do it all by myself." I didn't need underwriters or anything like that. It's pretty cool. I started out with some artwork by my brother and I worked out all the legal disclaimers.

I just started it and it's doing better then I thought. But it's never enough. When I read about some dumb-ass viral video getting a million hits, I'm thinking about how I think I'm a big deal when I get a thousand. There are a thousand people in that building over there, you know? It's nothing in terms of how many human beings are out there. I mean it isn't really about the numbers, if it was I would've been out of business a while ago.

Everything we've talked about is a passion, a labor of love; the numbers don't necessarily support it. But you do it and you don't worry about things you can't control. I need these outlets. I don't relax well, and I like to be busy doing things that bring me satisfaction.

What part about being a Creative Director do you enjoy most?

Being a Creative Director and critiquing others work....it's not even in my top five things I like about this job. It's like number seven on the list. The "Good Ad, Bad Ad" aspect of the job is the price of entry. Anybody, all my lieutenants, are capable of saying, "That's a good ad. That's a bad ad. Here's how we can make this bad ad better." Everyone that aspires to this job has some kind of talent for that.

What makes this job worthwhile for me is building an esprit de corps, new business pitching, arguing for work, helping people manage accounts and creating momentum for the agency; things which proved critical when I first took this role here. Now we are good at these things and we are trying to be great. The economy has only hindered that, not stopped it.

There are many advertising creatives that had turned novelists: Joseph Heller, Elmore Leonard, F. Scott Fitzgerald, Salman Rusdie, Augusten Burroughs. They share in their writing a common cynicism. Do you think that cynicism is a product of being a Mad Man?

I'm a spiritual person, though I don't define God in the traditional, Judeo-Christian sense. The thing is, in Happy Soul Industry, God isn't searching for an ad agency for cynical reasons, it's cynical because we believe that God shouldn't need an ad agency and that advertising is sleazy. We infer that based on the concept, and that's what I wanted to happen with this book.

Look at the seven deadly sins. Envy, Greed, Lust....all of them, that's what we do! Copywriters merchandise these sins. "I want that! I want to look like her! I want to be like him!" Everything is based on Greed, Envy and Lust. Everything I'm selling for my clients I'm trying to appeal to those sins. We make you want what you don't need.

It's like being in a rock and a hard place, but I don't lose sleep over it, partly because I put it into a story and explore that theme. I think it's a big theme for me personally but it's also an entertaining theme.

There are personal and professional things that happen in your life and create a pattern over time. The pattern for me became a very questioning and introspective look at what I was doing with my life. So I discovered with advertising that I was extolling these sins. Is that the legacy I want to leave behind? The answer? Yes, no, maybe so.

But really, in the book, all characters find redemption. Redemption is a big theme for me, and for all men really. You can't exercise those themes in copywriting; you can only do a really good job writing on behalf of consumer goods and services. But I love advertising! So I love something even though it has these defects.

Where do you stand on the importance of copy vs. art? There are those that believe that rich, well-written copy isn't that effective since the viewer's attention span is so short.

I'm even a victim of having a shorter attention span. I get impatient with my morning newspaper now. I've become so accepting of technology now that getting news from longer formats frustrates me. But with copy, we're just talking about a few sentences. People will continue to read good copy. If they desire what you are trying to sell, if it's feeding them in some way, they will devour what you write.

Advertising is very much popular culture. It's pop culture, but it's culture nonetheless. It defines our society, for better or worse, as much as anything else out there. Advertising is a great common denominator.

This is a difficult time for the advertising industry. How has Euro RCSG managed to persevere through this recession?

I'm a salesman and I'm totally comfortable being a salesman. Maybe not "totally," but more so than my peers, who will talk about anything other than how well their work sold stuff. They'd rather talk about how many awards it won or what their peers think about it, who the director was....anything other than the sales part.

I don't have that problem. I know I can compete against any other agency because of the single fact that I respect the skill set of copywriting as writing words to persuade. My peers try to spin that so that it satisfies their creative imperatives. I have those imperatives, but I have other outlets for that. I recognize that I am a salesman.

With the Altoids "Curiously Strong" campaign, I knew it was good and I knew it would be successful. The best award that came from that is that we established Altoids as the leader in the marketplace. Especially nowadays in a struggling economy, how do you justify winning an award for work that came from a client that went under or is near bankrupt?

Our agency has only been glanced by torpedoes. We haven't taken anything too hard and haven't had any significant lay-offs. We went right through the first year of this recession, I wouldn't say that we have been unscathed because that would be untrue, but relatively strong and secure. That's because I think that we are real about what it is we do.

If you talk to ten people that have my job, I'm pretty certain that, while they wouldn't disagree with what I've said, they wouldn't personally agree with it. They couldn't publically disagree with that because their clients would wonder what they are paying them for. But privately they wouldn't say, "I got into this business to sell cars. I want to make films and shoot pictures." All that vainglorious stuff.

In your creative career, you've seen the emergence of digital communications. I've heard creatives lament that digital is killing advertising creative as we know it. What's your take?

Digital is the latest, greatest screen. But it's still just a screen and we still have to make films that you watch just like the one in your living room. You have to be careful. A lot of clients scream and yell about digital, but they still want the 30-second TV commercial.

I think the best name for a band would be "Skip Intro." Do you want to read this ad or do you want to go to the site? You are going to hit "Skip Intro." Everybody skips the intro to everything. So what? Is that the future? A bunch of annoying ads that get in front of your websites? No. That's junk mail. Banner ads, is that what you mean by digital? Or do you mean branded content? Banner ads are just billboards on the Information Superhighway.

One final question... from The Proust Questionnaire: Who are your favorite characters in fiction?

When I was young, I identified with troubled superheroes, like Spiderman. Of course, that became very vogue later when the movies came out. I sort of identified with those flawed characters.

In college I liked Ayn Rand, there's no question that I was sucked into that. Howard Roark was a favorite character of mine.