10 years ago, if you wanted to plan a family vacation to the Caribbean, you likely had to go through a travel agent. Today, there are a slew of travel planning sites like Gogobot, TripAdvisor, Expedia, etc. that help you navigate to warmer waters.

Today the business of buying outdoor advertising space, a 6 billion dollar a year industry, is stuck in the 90s. To buy billboards, wallscapes, transit space or innovative street art campaigns requires lengthy excel spreadsheets, phone calls, and driving from site to site.

Adstruc, a 4-person startup based in New York City is changing the future of outdoor advertising space, by providing an online auction and listing-based marketplace for sellers and buyers. Founder and CEO John Laramie brought his team together last summer under the mentoring of David Cohen’s TechStars program in Boulder, Colorado, to build the entire system in just three months.

Screen shot 2011 03 16 at 12.27.16 PM 520x191 Adstruc disrupts the outdoor ad space with Gary V, Twilio and Shepard Fairey.

Last month, ADstruc released a campaign titled, “Billboards for Everyone.” Their first billboard, which depicts a play on the immigration policy and is aptly displayed in Arizona, was designed by Shepard Fairey’s creative agency Studio Number One. The campaign is supported by partnerships with BA RepsSpread ArtCulture Magazine, and JWT New York. Each month, Adstruc puts out a creative brief to host a similar project in various states. For future campaigns they will work with popular street artists like Ron English and experiment with 3D digital outdoor campaigns.

“What’s fascinating about these projects is how full circle they are,” says Laramie, “The deal starts out online [on Adstruc], then they are produced in the real world, but end up gaining the most visibility back in the online space as they virally spread across blogs and websites.”

Closeup.jpg.scaled1000 520x347 Adstruc disrupts the outdoor ad space with Gary V, Twilio and Shepard Fairey.

In September of last year, Adstruc closed a $1.1 million Series A investment led by DFJ Gotham, with participation from RRE, Founder Collective, Jeff Clavier, David Cohen, Kal Vepuri, David Tisch and Social Leverage. This gained them quite a bit of popularity in the New York area, catching the attention of notable businessman, Gary Vaynerchuk, better known as Gary V.

To promote Gary V’s latest book titled, The Thank You Economy, Adstruc partnered with Twilio to launch an innovative campaign on the streets of New York City featured on telephone kiosks throughout Manhattan from Titan Outdoor and a subway platform ad at 23rd Street and Park Avenue. The campaign engages consumers with a unique phone number on the advertisement that enables people to speak directly about the book with Gary V – all through Twilio, a web app that makes calling and receiving phone calls through the Internet easy. The campaign was created, produced, bought and installed without an advertising or media agency and cost less than $20,000 in total.

“It was a no brainer to work with Gary and Twilio,” says Laramie. “We thought about who Gary V is and that his new book is about 1 on 1 communication and the relationship with your customers and those poeple around you. We said, how can we have some sort of interaction other than QR codes or texting a number? There isn’t enough call to action and outdoor ads are flat. Integrating Twilio into the ads made sense.”

Screen shot 2011 03 16 at 1.21.57 PM Adstruc disrupts the outdoor ad space with Gary V, Twilio and Shepard Fairey.

Earlier today, I tested it out and gave Gary V a call, and he answered! Since the ads went up last week, he’s received only 25 calls, answering all of them unless he’s on a plane or asleep. The first four people freaked out and hung up on him right away and many others asked him questions like “What’s the ROI of your mom? What’s the book about?”

“Dollar for dollar, I’ll have to look if the campaign was totally worth it but I wanted to do it because I think these guys are disrupting media. I’d never have been able to do this without them. I think being creative in outdoor advertising is a very big opportunity,” says Gary.

Adstruc gives buyers the ability to say, “OK, here’s who I want to target, the location, here’s my budget and let’s do this right away.” Adstruc gives buyers the ability to see a space and using photoshop like tools, play with their ad within that space. For sellers, Adstruc scrapes all of their available data on the spot and uploads it to the Internet so they have one place to manage it. On average, Adstruc saves buyers 2-3 weeks of time and 15%-25% off of costs depending on location and timing. For sellers, Adstruc helps sell otherwise remnant ad space.

A smartphone application is also in the works. Imagine being able to see a billboard, and submit a proposal right then and there? Why not? The future is here.