Success in business can be a gamble and for one well known Oak Harbor businessman, 2011 is a time for throwing in all his chips.

On Jan. 3, Gerry Oliver decided to overlook a stubborn housing market and months of construction ahead on SE Pioneer Way – a factor that’s driven more than one business to new locales – to open his very first real estate office right smack dab in the middle of downtown.

“It’s a huge risk; I’d be naive to say it wasn’t,” Oliver said. “But it’s a risk that makes sense.”

Oliver co-opened the brokerage, GO Realty, with his wife Cindy. While the move no doubt has some scratching their heads, Oliver claims that both his sales and feedback received from the community over the past month are early indicators that the gamble is paying off.

In fact, he says it’s not only the best business decision he’s ever made but may just be the breath of new life the commercial district has been waiting for.

“It’s what downtown needed if you ask me,” he said.

Having spent most of his life on North Whidbey, the 33-year-old businessman is well known in town. His parents are the former owners of Bargain Center, now Furniture World, on Ault Field Road, and the Oak Harbor High School graduate also serves on the city’s planning commission.

Oliver may have gained his greatest name recognition in 2009, however, when he lost a narrow race for an Oak Harbor City Council seat won by Scott Dudley. But name recognition alone won’t be enough for success, especially considering the challenges facing Oliver and his new business.

For starters, after five and half years in real estate, Oliver is well aware of the volatility of the housing market. He got his start when sales were at their peak only to watch the bottom fall out from under him.

“It tanked, that’s just a fact,” Oliver said.

According to statistics from the Washington State University Center for Real Estate Research, single family homes sales in Island County peaked in 2005 at 5,820. By 2008, they had plummeted to a low of 2,510. Although numbers did rise in 2009 to 2,570, they remained largely stagnant in 2010.

It’s a trend that should continue to hold true over the next year, said Glenn Crellin, the center’s director. The large number of foreclosures is keeping home values down and keeping buyers wary. In 2010, the median price of a single family home in Island County was $259,950.

“That’s going to keep a lot of consumers on the sidelines wanting to wait until they get the lowest possible price,” Crellin said.

Compounding the challenge of the small real estate pie is the number of people looking for a slice. In its 2010 annual report, the Northwest Multiple Listing Service said there are at least 289 sales associates from 39 companies in Island County.

But competition and a sluggish real estate market aren’t the only trials for a new brokerage. The building Oliver rented, formerly the law offices of Skinner and Saar, is on SE Pioneer Way, a street expected to undergo at least eight months of construction in 2011.

Several businesses in the past year have relocated to other parts of town in order to avoid the upcoming disruption.

But if anyone can pull this off, it’s Oliver, according to Oak Harbor Chamber of Commerce director Jill Johnson. She described the man as having out-of-the-box marketing techniques and an upbeat sales style that sets him apart.

“He’s got a completely different vibe that a lot of realtors and it will be interesting to see how he does,” Johnson said.

Oliver’s “style” is likely the result of his sales experience, which is as broad as it is extensive. In his early 20s, he enjoyed success promoting rock-n-roll concerts and managing punk bands in Seattle. After that, he spent time in the perfume industry, even owning his own business in San Jose, Calif.

He also spent time working for Upchurch Scientific, now Idex Health and Science, Harbor Tower Village as an activities coordinator, and as manager for Cramer’s Home Center in Oak Harbor.

But Oliver learned the most from the time he spent on the showroom floor of his parents’ furniture store.

“That’s where I honed my sales skills,” he said.

Oliver is more than confident about his chances for success. While some merchants may view the upcoming construction as a bank-breaking disturbance, he sees it as an $8.35 million investment in his new business.

Downtown will be forever changed for the better and those willing to stick out a few months of inconvenience will reap the benefits, he said.

As for the real estate market, Oliver said he may be a “different cat” who is willing to throw up the cards now and again, but all his risks are calculated. He’s done his homework and believes there is enough business on Whidbey Island to support GO Realty.

But even if there isn’t, Oliver is confident his skills and experience will pave the way to success. After all, there are more than a few businessmen out there that have proven that a booming housing market isn’t everything.

“Donald Trump didn’t earn his money in a good market,” Oliver said.