The venture capital life bleeds into the subject matter of the art that these people collect as well. Mike Brown of AOL Ventures, the company’s investment arm, is an avid collector who visits Art Basel Miami Beach every December and finds himself drawn to the playful. He collects street artists like Shepard Fairey and Swoon, and owns works by William Powhida, Barry McGee and the tattoo artist Scott Campbell. Prints by the established conceptual artist John Baldessari wouldn’t seem to fit, aesthetically, until you hear Mr. Brown explain it.
“There’s a lot of the whimsical in his approach, which I think is very unique,” he said of Mr. Baldessari. “It feels like he’s having a lot of fun when he makes these pieces.
“For the work I collect, I tend to be an optimist,” he said. “And obviously as a person who takes incredible risk in his professional life, I’m not as big a fan of darker and more underground stuff.”
Mr. Brown’s involvement in the art world extends beyond collecting. Years ago, he became friends with Christina Ray, founder of the Conflux art festival, which blends technology and street art, and Mr. Brown now serves as Conflux’s finance director. Mr. Brown even reached out to Ms. Ray, who runs an eponymous gallery in Soho, when soliciting artists to decorate the offices of AOL, now a fairly prominent sponsor of public works like Friends With You’s sprawling artwork-cum-carnival Rainbow City at the High Line.
In New York, the line between start-ups and other creative endeavors can get blurry. Dennis Crowley, co-founder of Foursquare, was drawn to Conflux when he was in the graduate Interactive Telecommunications Program at N.Y.U.’s Tisch School of the Arts. In 2004, when he started following the festival, Conflux included “Yellow Arrows,” a Lower East Side street-art project that allowed users to slap yellow stickers on personal landmarks with a code that could be sent via S.M.S. for a secret message left there by the sticker-placer. It naturally caught the attention of Mr. Crowley, who was already at work on an early version of Foursquare called Dodgeball, for his I.T.P. thesis.
“I always look at it from a tools perspective, but these were people who were doing performance art on maps,” he told The Observer. “It was more like what can happen after the check-in that was our big revelation around that period.
“Conflux was pushing a lot of people to think about those specific issues in different ways, like how can technology change your notion of being in a specific place in a specific time, and the context around that,” he said.
On weekends, Mr. Crowley regularly takes gallery walks with friends, to get a better sense of how people use Foursquare as much as anything else. He favors Soho, and buys infrequently, but the walls of his apartment feature a cut-out by Swoon, prints from Lori Earley and Lyle Owerko, and original pieces by Williamsburg painters Nic*Rad and R. Nicholas Kuszyk, among other works. “I don’t consider myself a collector by any means,” Mr. Crowley said. “But my apartment is full of interesting stuff as opposed to posters that I bought online.”
This isn’t to say that the intersection of art and technology in this city make it easy to enter the art world. John Borthwick, CEO of technology incubator Betaworks, began his flirtation with the art world back in 1994 with a web project called äda ’web that partnered with artists to explore the possibilities of expression online (“Flashing text was exciting back then,” he told The Observer). Their first project was with Jenny Holzer. Mr. Borthwick’s brother Mark is a photographer so his own modest collection includes many photographs, along with artists who worked with äda ’web—among them John Simon and Lawrence Weiner. He’s now on the board of Rhizome, a New Museum project that aims to do much the same thing as äda ’web and that recently partnered artist Ryan Trecartin with Tumblr founder David Karp for a video project.
Despite all this, Mr. Borthwick, who lives in Chelsea, still feels he’s at the very fringes of the art world.
“The New York art scene is a little bit overwhelming at times,” Mr. Borthwick said. “It has a whole culture of its own and what I’m more interested in is the edge of the digital arts, the invasion edge where people are really pushing the boundaries of what’s new, what’s possible.”
If one attempts to think about the art market through the eyes of a start-up entrepreneur, it suddenly becomes obvious why a host of recent start-ups have sought to improve it. Mr. Brown, who frequently probes the secondary market for finds, called the process of calling around to friends in galleries and auction houses—the usual way in which people look for art to buy—“a joke” in terms of efficiency. “That process doesn’t really scale,” he said.
Biotech entrepreneur Aditya Julka, a co-founder of one such art start-up, Paddle 8, which hosts online exhibits and connects users to gallery inventories, said the site came out of his own desire to enter the world of collecting.
“It was driven by very personal reasons,” Mr. Julka said. “I wanted to start collecting, I wanted to keep in touch with what’s happening with Indian art and I also at the same time wanted a way to learn more about contemporary Western art and start collecting contemporary Western art in a way that’s easier.”
Carter Cleveland, founder of art.sy, said at the General Assembly panel that he was motivated by similar reasons, and Laura Martin, founder of Exhibition A, told The Observer she started her prints site because she found herself desperate to buy a certain Rene Ricard painting she had no hope of affording. She pitched the site idea to her former boss Cynthia Rowley, who provided the seed money, and after it launched Ms. Martin snagged a print of the Richard she desired. Then she bought an original Ricard.
“You catch the bug,” Ms. Martin said. “Since then I bought an original Leo Fitzpatrick.”
One element that has yet to establish itself in the start-up world is a strong social model that encourages collecting, which you are likelier to find in the world of finance thanks to ambitious and influential collectors like Steve Cohen (the best offered by the tech world is Eric Schmidt). Zachary Aarons, an angel investor in a handful of mobile-based apps with a focus on travel, says that he rarely finds himself discussing art with colleagues, despite the fact that he’s a Lower East Side gallery regular who collects, among others, Brian DeGraw.
“When I talk socially to people I know in the tech world, it tends to be more about restaurants and things to do,” he said. “Because of the nature of my portfolio, the conversation tends to be about cuisine, travel, events and sports more than about contemporary art.”
The Observer found Josh Abrams, co-founder of the start-up Tutorspree, through his membership in a gallery walks Meetup group and his savvy answers about the art market on the questions forum Quora. Tutorspree boasts around $1 million in funding—a figure that still lands them in “bootstrapping” territory. While Mr. Abrams says he often sees pieces that interest him on his visits to Chelsea, he’s content to buy from the Brooklyn Flea for now.
“I’m just trying to live in the moment right now,” Mr. Abrams told us. “If my goal is to own a Warhol one day, maybe that will happen, but my goal right now is to build a company and not have the external stuff happen until later. It happens when it happens.”