With a cameo in the 2010 TGR flick Deeper and a profile on National Geographic Television, Olsen is becoming a legend in the bush-pilot world. A former race-car driver, he spent his 20s living out of his pickup like a ski bum but hanging around racetracks. He worked as a mechanic and did whatever it took to get behind the wheel of a car. When he says, “It turns out I was a good driver, and I was fast,” it’s classic Olsen understatement. In fact, he raced the legendary 24 Hours of Le Mans and won the 1985 Porsche Cup. After a few nasty wrecks, though, he “began to wonder if it was really worth it all” and quit the sport at age 35 for the “safety” of flying single-engine planes in Alaska—a notoriously deadly profession.
But he’s survived 16 years of what he calls “mountain work,” so when at the bottom of our second lap of carveable spring corn he barks at us to pile into the plane, the three of us move fast. He has no interest in getting stuck up here for the next week, and as soon as we stow skis and packs and buckle our seat belts, Olsen guns the engine, speeds across the snow, and darts us through the narrow slot and swirling clouds to safety.