It's a typical day for the folks at Let's Gift It. Three of the Manhattan startup website's six employees, who include people in Cleveland and Boston, participate in a videoconference held via Google+ Hangouts while working on a proposal over Google Documents. Throughout the day, chief executive and co-founder Ryan O'Donnell communicates with his Gen Y team through a constant stream of Skype keyboard chatting and texting.
Later on, O'Donnell sends several nondisclosure agreements to potential partners using an online service. The 30-year-old likes the fact that this reduces the need for printing, making the practice both green and efficient.
"We operate under the philosophy of 'Do more faster,' " said O'Donnell, whose year-old company, which provides a platform for people to buy gifts as a group, doesn't yet have revenues.
Welcome to the world of the Gen Y startup—Web 2.0 companies founded and populated by members of the millennial generation. There's no hard-and-fast definition for the demographic. It includes people born anytime from 1977 to 2000, according to various experts.
But these young entrepreneurs share some common characteristics and values. Coming of age during a period of great technological change, they live and breathe tech, and take for granted the informal communication the Internet fosters, according to Gary Whitehill, who works closely with the young startup crowd as founder of both the Relentless Foundation in Manhattan, which promotes entrepreneurship, and New York Entrepreneur Week.
Gen-Y types are comfortable working with a distributed workforce, where their officemates are sitting at desks far from New York. (O'Donnell's business partner, for instance, lives in Ohio.)
"Technology is the enabler," said Nick Seguin, manager of entrepreneurship for the Kauffman Foundation, which promotes entrepreneurship. And being as green as possible is almost an automatic reflex for those growing up in a period of dire environmental concern.
"It's just a day-to-day thing," said Brian Cohen, vice chairman of the New York Angels, an investing group.
Many of New York's Gen Y startups have limited impact for now. But as these companies grow and their modus operandi spreads—and some of their alumni eventually leave for other jobs—their workplace culture is likely to have a lasting effect on the business ecosystem. The Kauffman Foundation reported in 2010 that 20 percent of Gen Yers have started a business, and about 40 percent envision doing so.
"Gen-Y entrepreneurs are running their companies in new ways, and they're likely to change the way businesses run for a long time to come," said Jennifer Kushell, president of Young & Successful Media Corp., a consulting firm that advises many New York City companies on how to work with Gen-Y employees. And New York, a hotbed of such startups, could be the testing ground for the future, alongside other hubs such as Silicon Valley.
One of the most obvious differences in how Gen Y startups operate is, of course, in their penchant for digital communication, one that makes the BlackBerry addiction of an earlier generation pale by comparison.
"I can't remember the last time I got a phone call from someone who is Gen Y," said Jeff Stewart, a serial entrepreneur and investor, whose current New York-based company, Lenddo.com, helps provide loans to people in developing countries.
The team at Nothing But Gold Productions, a Manhattan-based multimedia platform for financial news, works in a way that's typical for Gen-Y startups. The 10 employees communicate continually among themselves through a mix of texting, Facebook and Twitter.
"If I need to find one of my team members, more likely I'll find them on Twitter than call them," said CEO Nicole Lapin, 27, whose one-and-a-half-year-old company has "over $100,000" in revenues. They also use an application called HootSuite to manage everyone's Twitter accounts, a tool Lapin keeps open all the time.
The setup is similar at Wanderfly, a 10-employee Brooklyn-based travel site that went live about a year ago. Instead of turning around to ask one of her seven colleagues a question, co-founder Christy Liu, 30, will often send a private message over Facebook chat.
"It's a lot easier than yelling across the room and more conducive to creating a focused working environment," Liu said.
For Gen Y, it's all about a need for instant feedback, said consultant Kushell. "Everything is in real time," agreed Brandon Evans, 34, founder of Crowdtap, a two-and-a-half-year-old Manhattan-based startup with 25 employees, most of them Gen Y, and more than $2 million in annual revenues. "You know what everyone is up to because you're all so connected."
That's not to say face-to-face meetings never happen. At Crowdtap, Evans and his employees communicate online "just about every moment of the day," he said. At the same time, Evans runs regular in-person meetings, although he ensures their brevity by having attendees stand up.
Because of their comfort with far-flung teams, many Gen-Y startups are stretching the definition of what it means to be a New York-based company. Take Wanderfly. Its founders—all are Gen Yers, as are its employees—are based in New York City. Yet three employees are in Quebec City, Minneapolis and Los Angeles. Wanderfly also relies on Google+ Hangouts to connect its workforce. There's a 46-inch TV screen turned on 40 to 60 hours a week, with a quadrant for each developer. When one person talks, the screen enlarges the picture of that individual, enabling everyone, Liu said, "to feel like our team is sitting right here."
Liu expects to continue relying on a distributed workforce even as the company grows—a preference that Kushell says many Gen-Y entrepreneurs share.
Ecofriendly practices are also key for many Gen-Y entrepreneurs, even those who don't see themselves as pioneers of sustainability.
This environmental vigilance can keep older colleagues on their toes. At the Wonderfactory, a profitable Manhattan digital advertising company, which has about $7.9 million in revenues, co-founder Joe McCambley, 55, says his employees have made a fuss more than once when he passed out printouts of proposals or projects. Most of his 30-person team is age 30 or under. "They get genuinely offended," he said. "They're asking me, 'Why are you printing this stuff out when we're capable of viewing this on a 61-inch monitor?' "
"It's a matter of the little decisions everyone makes throughout every day," McCambley said.
Those seemingly small choices are likely to shape a workplace that looks very different in the future.