Tech Meets the T-Shirt at Pistol Lake and Pickwick & Weller

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avoid retail markups, retain control of their brands, and build a direct fan base.

“By not selling through retailers we can keep our prices much lower and offer a boutique-quality product at a price you can’t find anywhere else,” says Donahue. On top of that, “we can own the relationship with our customers…We want to change the experience around buying one’s wardrobe basics.” He adds that the company pays careful attention to all the customer “touch points,” including its website, packaging, and the way customers are treated over the phone.

Sulinski, formerly the founder of Maine startup AccelGolf, makes a similar point. On the Internet, he says, “companies can build meaningful relationships with people who share their values.” This way, there’s a better chance of turning customers into lifelong supporters who can offer the company feedback about designs and manufacturing quality, he says.

But on at least one point, the two startups are different. Pickwick & Weller packages itself as a fashion company and wants to be judged “on the merits of products/designs alone,” says Donahue, who was one of the original user-interface designers at PayPal. He recruited actor Kutcher as a co-founder, evangelist, and investor. To scale up quickly, the company has raised additional funds (it hasn’t disclosed how much) from Andreessen Horowitz, Baseline Ventures, Felicis Ventures, Forerunner Ventures, and Ron Conway’s SV Angel, as well as Warby Parker founder Dave Gilboa and PayPal co-founder Max Levchin.

Pickwick & Weller's Hunt linen/cotton jersey

Pickwick & Weller's Hunt linen/cotton jersey

Pistol Lake, by contrast, steers away from the fashion industry’s limelight. “While we’re operating somewhat close to the fashion industry, we really don’t consider ourselves fashion designers or a fashion company,” Sulinski says. “We are makers and craftsmen, and our goal is building the best product possible. Fashion companies and lifestyle brands have employed tactics of brand building that play on exclusivity, but that just isn’t something we’re interested in.”

Of course, T-shirts have been a staple of online commerce for years, so neither company is breaking ground in that sense. Companies like Threadless, Spreadshirt, CafePress, and Zazzle make it easy to order T-shirts with custom designs. For $15 a month, New York-based Startup Threads will send you a bag containing a startup T-shirt and other assorted swag. And for some consumer Internet companies like CollegeHumor.com, having a T-shirt line is almost a business requirement (that site spun off BustedTees in 2004).

Even famed Silicon Valley startup accelerator Y Combinator is getting into the T-shirt business: one of the companies in its Winter 2013 class was Teespring, which has built a Kickstarter-like site where anyone with an idea for a custom T-shirt design can collect the pledges they need to finance the project. If a project meets its goal, Teespring prints and ships the shirts, keeping a flat fee per shirt.

But what’s new and different about Pickwick & Weller and Pistol Lake is that they’re about image, style, and aspirations, not just e-commerce or cool silkscreen designs. Like Warby Parker, Fab, Houzz, and other style-centric Internet brands, they’re attempting to build new businesses by repositioning old standards for the Facebook generation and its dreams. Says Donahue: “The next billion-dollar company will be started by someone wearing a T-shirt, not a suit.”

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The Author

Wade Roush is a contributing editor at Xconomy.

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