500 T-shirts: Fashion And Culture At Demo Day

Black t-shirts were on sale for $250,000 at 500 Startups' Demo Day on August 16. Kind of.
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Black t-shirts were on sale for $25,000 at 500 Startups' Demo Day on August 16. Kind of.

Dave McClure, founder of 500 Startups, the Internet seed fund and incubator program in Mountain View, jokingly promised that when an investor wrote a $25,000 check to any of the 30 companies presenting at Demo Day, he'd throw in an awesome t-shirt that said, "500 Startups: We're kind of a big deal" on the front and "#500strong" on the back.

Coincidentally, #500strong was the official hashtag for following the event on Twitter. If you've ever been in a fully packed room with Silicon Valley insiders, you'd understand that there's not much that can separate these people from their computer gadgets and twitter feeds. While the presentations were taking place offline, the commentary was happening online. The #500strong twitter stream was moving so fast it was like high school note passing on speed.

When DJ Real, a waif hipster with blonde curly hair and an embroidered graphic sweatshirt, kicked off the event with some bad jokes and awkward dance moves (talk about high school!) someone in the audience tweeted, "I wish I had been late."

At one point DJ Real asked the audience, "Is anyone in love tonight? How about in love with your computers?" And so he droned on. To all of the negative twitter chatter, Dave McClure responded, "Folks we take risks @500startups -- doesn't always work, but we keep rolling."

And so commenced the presentations. From a proofreading marketplace (Kibin) to email marketing (Tout), from fine coffee delivery (Craft Coffee) to last minute event tickets (WillCall), the companies presenting ran the gamut from stuff for tech nerds to apps for common folk. All so different, but all the same in that they were all seeking funds in order to solve #firstworldproblems. And they all had great t-shirts.

"Most people don't have the problem of having to sort the hundreds of emails they receive everyday. I get lots of emails, but that's part of my job," said one venture capitalist in attendance.

A problem with a lot of these founders, with their fancypants resumes and numerous degrees, is that they are living in their own bubble and suffer from myopia when it comes to solving problems that affect most people.

Yes, PicCollage, a photo collage app dubbed the "anti-Photoshop" for its usability, is fun and Snapette, "the app for snap-happy fashionistas," could help you find a pair of heels in SoHo, but these companies aren't about to alleviate any of the grave issues facing society today. Nor are they trying to.

Man Packs delivers underwear and socks (and condoms!) to men who can't buy themselves the bare necessities. Their team t-shirts said, "More time to slay dragons." Now men can have even more time to play video games!

At least Alex Baldwin, the designer at Console with a Justin Bieber haircut, knew what's up. "Who likes free t-shirts?" he asked before chucking a few shirts to the crowd. (Full disclosure: I snagged one.) Console makes it easier to rock out during the workday. "During the day we like to rock out, not fiddle with stuff," Baldwin said during the presentation.

When Ainsley Braun -- the UX designer for website security company Tinfoil - took the stage, she asked everyone in the audience to please put down their computers and smartphones unless they were tweeting about her presentation. In response to this, CNET editor Rafe Needleman tweeted "...How cute. But no." You simply cannot ask computerheads to turn off their monitors or quiet their keyboards.

Braun's plea for full attention may have come up short, but her shiny Tinfoil Security t-shirt turned some eyes because even nerds are distracted by bright shiny things. Braun and her co-founder ordered the t-shirts from a local guy who does silk screening. The companies are not obliged to get shirts made, but all of them do because it helps them stand out and be easily identifiable to potential investors.

Somewhere along the way, t-shirts have become a thing in the startup world, making the savvy SV insider's uniform of choice a pair of jeans, some new Internet company's shirt (the lesser known, the better!) and probably dark rimmed glasses. T-shirts are often sent around the scene as a marketing ploy or traded like soccer players trade jerseys with the opposing team after a match.

So choosing which startups to cut checks for based on the best shirts may be just as practical a method as any other that a venture capitalist uses.

Kibin had some rad yellow t-shirts with an outline of Shakespeare's face and his famous quote, "Be not afraid of greatness."

From.us, a company that improves the gift-giving process, had cool blue shirts with a drawing of a little girl hugging a big present. At the end of his four minutes, the presenter told the audience that his "cofounder is the one in the back wearing the same sweet t-shirt." Clearly they were trying to make a statement with their style.

Shirts aside, Storytree, a website for documenting family history, was quite captivating because it combined human-centered design with storytelling, two things that really can bring greater happiness to the world.

Really all of the companies were founded by bright, passionate people and here's to them all becoming the next big thing. But worst-case scenario, at least they can start t-shirt businesses as a fallback career.

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