GroupOn Scores $1.35 Billion Valuation; Continues to Dominate

Groupon, a Chicago-based social shopping and deal-finding site (and whose name is derived from group coupon) just raised a remarkable $135 million in venture funding from Russian behemoth Digital Sky Technologies (with Battery Ventures tagging along). Nice work. This is just four short months after it raised $30 million in expansion capital from top-tier venture capital firms Accel and NEA, and a swift year and a half after the site was launched. DST, which purportedly likes to scare away competition by offering huge valuations, plans to spend an additional $1 billion on social media investments in the next five years. Groupon joins Glam Media ($750 million valuation), Twitter ($1 billion) and Yelp ($475 million) as social media sites that have received massive funding rounds and valuations in the past couple of months.

None of these developments seem to have fazed Andrew Mason, the young CEO of Groupon. When asked by Kara Swisher of Boomtown about what it’s like running a big company and moving to the valley, Mason replied humbly and introspectively. “Life is just as depressing and hopeless as it was when I wasn’t doing this, or lack thereof. I never thought of myself as an entrepreneur before I started this, and I don’t really now. I just like to build things.”

Groupon, which operates in 40 cities and offers its members a deal a day on restaurants, spas, theaters, Segway tours and a plethora of other services, will be expanding to Canada this month, and globally after that. When Mason was asked to verify the reports that suggested Groupon will generate $350 million in revenue this year, Mason declined to elaborate, saying “money is so boring.” He told the San Francisco Chronicle that he’d rather talk about Groupon’s new publicity stunt, for which a Groupon user will try to live off of only Groupon coupons for a whole year. “he’s probably going to die,” Mason said. “It’s going to be awesome. Once you’ve had success on the level of Groupon, it’s very hard to become stimulated in any way. Some people come up with weird sexual fetishes. I thought it would be interesting to be involved in someone’s death.”

As for Mason, he is not planning on any lavish purchases in the near future. “I’m not a fancy, flashy guy,” he said. “In life, you either have money or you don’t. When people came with a lot of money to buy a very small percentage of Groupon and it was enough to permanently solve the money problem, why would I not want to do that? Now I can focus on making Groupon great.”

Mason’s casual irreverence and sincerity is rare, refreshing and make him easy to root for. If you haven’t already checked it out, go to Groupon and sign up.