“I don’t really know where we are going,” said Drake Olson on a recent joyride shortly after takeoff from the Haines airport in his 1979 Piper Super Cub. “It’s all just one big feel out.”
It’s a clear blue day with only a few clouds at the edge of the skyline, but Olson is intently focused on the instruments in front of him. He keeps a steady conversation going, but it’s clear his mind is on the task in front of him as he reacts to minute pressure and wind differences as the plane gains elevation.
The plane wobbles slightly. He comments on the cold air burbling off the Ferebee Glacier, and the shifting storm patterns that are transitioning from south to north during the morning, making the air “confused.”
“If you’re thinking straight, you’re always feeling, sensing, watching,” says the 68-year-old. “All of us — no matter what you’re doing — you’re trying to get in that state of flow where you’re focused and there’s no noise.”
Olson finds that flow state when he’s fulfilling a childhood dream of flying.
His passion has helped him carve out a unique niche in the Southeast Alaska flying community ferrying climbers, skiers and paddlers to remote sites in the vast and varied mountain ranges around the Chilkat Valley and beyond. Olson’s natural inclination — developed for years as a professional race car driver in his 20s — has kept him and his clients safe since 1997 when he started Fly Drake, his charter flying service that he continues to operate today.
One of his specialties is glacier landings, in which pilots must not only deal with wind and weather, but also the changing ice forms like crevasses on the surface.
“There’s not a lot of demand — it’s pretty niche,” said Doug Riemer, a longtime pilot who runs Nordic Air in Petersburg.
Olson’s service has allowed him to pioneer recreational access around the Chilkat Valley, where helicopter flying is restricted to narrow corridors in the Upper Valley. Olson has developed a reputation among hardcore adventurers for his skill, humor and folk philosophy.
“He knows the area so well and he’s at one with the land out there. You feel comfortable when you’re flying with him,” said Ryland Bell, a professional snowboarder who lives in the Chilkat Valley.
A childhood dream interrupted
Olson dreamed of following the footsteps of his father, a pilot who flew reconnaissance planes for the Navy.
“Ever since I had consciousness, it’s been airplanes. Airplanes were so cool as a kid,” said Olson.
But his dad, who was mostly emotionally distant, was focused on sports cars, horses and beer, discouraged the younger Olson, who had a heart murmur that would have excluded him from the service. The family kept horses and lived on a farm in Connecticut.
Despite his hope to fly, Olson got his first taste for engines as a race car driver. He started on an amateur circuit as a young man. He showed a natural ability to find efficient lines around a race track. Soon, he was traveling around the country in a tattered pickup truck he used as a camper to sleep in. The 1983 rig is still parked in his hangar at the Haines Airport, with 375,000 miles on the odometer.
“I lived like a dog,” he said.
With his talent, he soon had engine builders and dealers lined up to get him to drive their cars.
He had success in international racing, notching big wins even as a relatively unknown upstart.
But before long, the realities of the sport caught up to him. A GT prototype he was driving left the ground because of an air disturbance, and he got in a serious crash.
“I was lucky to survive,” he said. He continued to race for three more years after that, but felt rattled by the crash, and felt commodified by sponsors.
He started dabbling in flying and soon met Paul Swanstrom whom he flew with to Haines. (Swanstrom declined to comment on this story.) He flew around Alaska for the next two weeks. He had a vision of what ski planes could do in a country like Alaska.
“I said ‘This is it’,” said Olson.
He returned south and bought a Cessna 180, which he still flies. Within a few years, he had moved to Haines and started working as a pilot. In 1997, he decided to open what became known as Fly Drake.
Fly Drake takes off
From his hangar at the Haines Airport, Olson runs the business by himself, waking up early in the morning to do maintenance.
It hasn’t been easy. Olson is no fan of the paperwork and maintenance that is required of the job when he’d rather be flying. He lives a modest life, driving a 1987 VW sedan and chopping cords wood to heat his shop and home.
He’s learned some hard lessons through some close calls.
A change in lighting during the day can make a safe flight turn precarious. Winds can shift in minutes, and weather can appear out of nowhere.
“I always feel like I’m one little problem away from disaster,” he said.
For glacier landings, a relatively common occurrence is attempting a landing on snow that isn’t hard enough to support a plane landing. Olson has had trips where he and his crew have had to dig for hours to build a ramp out of a pit in the snow.
Through it all, he’s learned to trust himself, and to not get caught in the excitement.
“You learn to leave your ego in a drawer,” he said.
He pointed to a duo of internationally known snowboarders, Vincent De Le Rue and Sam Anthamatten, who visited a few years ago with a handful of spots mapped out. When he flew out there, there was mostly bare rock and ice, not the fluted snow spines that most riders seek. He realized that the famous snowboarders didn’t know the area well enough to pinpoint the right spots on a map. He ended up suggesting another area full of powder-covered spines that he’d seen earlier. (Anthematten and De Le Rue did not respond to messages to confirm the details of this story.)
“You realize the customer is not always right, in fact the customer is often wrong,” he said.
His reputation and the niche he’s carved out has earned him modest renown for his appearances in high profile ski films, including the 2014 Teton Gravity Research film “Deeper”. The film features Jeremy Jones, an internationally-known snowboarder, pioneering multi-day trips in remote areas of Southeast Alaska.
Olson said for the film, he and Jones were able to find what became known as the “spine institute” in the Fairweather Mountains, a magnificent array of snow spines coming down the mountain, that the athletes considered some of the best conditions they’d ever encountered for boarding. For the crew, it felt like a pioneering way of accessing the mountains using planes instead of helicopters.
“It was magic. It was magic for me. It was magic for them,” said Olson. Still, the conditions were fleeting. Olson said the conditions there haven’t been the same since.
Ryland Bell is featured in the film, and had been flying with Olson for years. He said he always feels safe flying with Olson, even while the latter appears relaxed, joking with the passengers and playing music through the headsets.
“So many other pilots are very serious and don’t want to shoot the shit too much,” said Bell. “To a certain extent the vibe I get from them is they’re nervous.”
Bell recalled one trip where his climbing partner had been dropped off by Olson a few days before, only to realize they didn’t have a second sleeping bag. A few days later during a short break in the weather, Olson was able to land and drop off more gear. The weather window was short, and the crew scrambled to get everything unloaded as a wall of dark storm clouds rolled towards them. Olson jumped into the cockpit and headed straight for the clouds.
“He just disappears into the wall — it’s full “Hidalgo” — a sandstorm over the desert,” said Bell referring to the 2004 film about a horseback adventure competition set in Arabia.
Olson, for his part, still has his doubts about whether the risks are worth it.
“You’ve got to really want it. Sometimes I wonder if I really want it that bad,” he said.
For now, the thrill of finding his flow state is too strong to resist.