Two men rock climbing in Bend, Oregon. Jordan Siemens | Iconica | Getty Images

While most people jump in their cars or walk to public transportation to get to work, Darren Pleasance starts up his plane. Pleasance's family decided to make Bend, Oregon, their permanent home in 2010 even though it meant flying back and forth to the Bay Area for him. When he was tapped by Google to lead its global customer acquisitions team a couple of years later, he explained he would be out of the country most of the time. "I had done 15 years on the road consulting, so I could say, 'Look I'm not going to be an absentee manager,'" Pleasance said. "'I'll be in Mountain View or anywhere else in the world.' And they could believe me." Allowing him to remain a 10-hour drive — or a 70-minute commercial flight — away from Mountain View, California, wouldn't be that big of a deal, he contended. Plus, the licensed pilot promised he would check in often, whether it was virtually or flying himself in. Google agreed – and the situation has worked ever since. "Everything we do is via video conference so I have an office set up at home," he said. "It doesn't matter where I am."

Darren Pleasance's plane in his Sunriver, Oregon house, about 10 miles outside of Bend, Oregon. Darren Pleasance

Bend to Bay

While Bend isn't even in the same state as San Francisco or Seattle, it's becoming an option for the tech community, especially those with families who are finding themselves outpriced by exorbitant housing prices. Zumper reports that the highest one-bedroom median rent price in the U.S. this past January was in San Francisco at $3,400. Third place was place San Jose, California, coming in at $2,460. Oakland, California, is at $2,160, making it seventh. An 848-square-foot house in Sunnyvale, California, recently went for an all-cash offer of $2 million in two days. Meanwhile in Bend, a one-bedroom will set you back about $1,100, according to Zumper. An American Community Survey released last year found more than 9 percent of Bend-Redmond employees work from home, making it the most popular remote employee area in the state. And according to the handful of Silicon Valley and tech industry folks who've moved up there, it's the ideal balance between having an actual life outside of work and being in the same time zone as the main tech hubs — despite the long commute. Dino Vendetti, managing partner of Bend-based early stage venture capital fund Seven Peaks Ventures, said he gets a call or an email every week from Silicon Valley about someone moving or wanting to move to Bend and connect with the tech community there. "Our social life is five to 10 times better than it is in the Bay Area," Vendetti said. "People aren't spending one to two hours commuting each day. They don't get the burnout you experience when you are in that kind of grind." Ten years ago moving away from Silicon Valley might have been career suicide, but companies are willing to be more flexible to retain talent, Vendetti said. He moved to Bend in 2012 after living in the Bay Area for 12 years, and said he will never go back. "You're not out in Hickville," he said. "The community here is very intellectual."

Bend benefits

Cloud-based network technology Kollective was based in Sunnyvale, California, 2½ years ago, when CEO Dan Vetras found out his rent was going up three times because Apple had moved into its office building. So he floated the idea of starting an office in Bend. He had lived in Seattle for almost 20 years, and knew the Californians would not move to a rainy city. Because of Bend's location near the Deschutes River sheltered by the Cascade Mountains, it doesn't get that much rain. The city claims the average yearly precipitation is less than 12 inches, and it gets 158 clear days a year with 105 more that are mostly sunny, the remainder with "substantial sunshine." "Honestly it was an easy sell to get people to go somewhere where the weather is nice nine or 10 months of year," Vetras said.

Kollective team building event walking the Deschutes Trail in Bend, Oregon. Courtesy of Kollective

He began his campaign to convince his employees to relocate, starting with the promise they could buy property. About one-third of the company – 13 employees – made the move at the time. Today Kollective maintains a small presence in the Bay Area. The Bend office has tripled and the majority of the new hires are there. "Over half my employees were renters, not homeowners (when we were in Silicon Valley), which seems pretty ludicrous considering we work in the tech industry and we're one of the highest-paying industries, if not the highest-paying industry in the world," Vetras said. If you have to go into the main Silicon Valley, it's a "beautiful drive," said Seven Peaks Ventures general partner Matt Abrams. He was working at Hyperion when it was acquired by Oracle in 2007, eventually becoming vice president of engineering for the company. He had moved to Bend in the early 2000s, so he found himself doing the commute to Redwood City, California, weekly. And because of Bay Area traffic, he often was the first person in office. He'd catch the 5 a.m. flight from Bend and be at Oracle by 7 a.m. – while everyone else was still stuck on the road. Eventually he left Oracle in 2015 to work at Seven Peaks Ventures, but still commutes to the Bay Area once every three to four months and to Seattle every other week. "I'm an outdoor person," Abrams said. "If I wasn't in the mountains, I'd be a much angrier person."

Matt Abrams enjoys the great outdoors in Bend, Oregon. Matt Abrams