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Olson hopes to sell the contraptions to health clubs (to be installed on the ceiling), ski resorts (as a mode of transportation between the lift and the lodge), and amusement parks. To cater to the latter, he's currently working on an electric prototype that would allow for greater speeds.
Still, Olson has yet to find a buyer. He says a company in Korea recently purchased a prototype to be used in marketing the Skyride as transportation, but he's still looking for U.S. buyers who will use it in some tangible way.
Though all of his friends and family who were interviewed think the Skyride is thrilling and the idea is innovative, some of them cautiously question Olson's motivation for taking on such a massive project that has cost so much money and lasted so many years.
"It's gone beyond my understanding," says Chris Middlebrook. "I look at it and say, 'How can you sell this?' But I think he's been striving to do something on the scale of Rollerblades again. He's over 50 now and it might be that push, like 'I need to do this now.'"
Even Mark Lipson, who used to take those long rollerblading trips with Olson and who taught him how to hop freight trains when they were teenagers, hedges a little bit.
"I think it's awesome," Lipson says. "But you know, it's a hard sell because it's expensive. He's ambitious there."
His friend Mike Milo, who worked for Rollerblade in its infancy, has faith that Olson is absolutely onto something.
"I learned a long time ago with Scott that just because I can't envision something with my limitations doesn't mean it can't work," Milo says. "For a long time, people laughed at Rollerblades, and look at what happened with that."
Milo does hesitate on one point, however: "His biggest success with Rollerblades was when he was selling it to individuals," Milo says. "But now he's going to have to deal with the big business guys again."
It's late October, and Olson is getting ready to hawk the Skyride at the International Association of Amusement Parks and Attractions trade show in Orlando, Florida, in a couple of weeks.
He's positive and upbeat, even when queried about his competition.
At an adventure park in New Zealand, there's a contraption called the Shweeb that's nearly identical to Olson's Skyride except that the pedal-powered capsules are clear tubes rather than cars and the track is several feet lower to the ground. Google invested $1 million in it in 2010, stating it believed the Shweeb could someday transform the way we navigate cities.
"Oh, yeah, the Shweeb," Olson says. "Their concept is very similar to mine, but there's nothing wrong with that. I think there's room for both of us."
Olson mentions another "ride" that's his biggest competition at ski resorts: the Wiegand, an alpine coaster that's similar to a slide.
"I've talked to ski resorts about buying the Skyride and they'll say, 'We were actually thinking about buying a Wiegand,'" Olson says. "My product, even though I designed it to be more fitness, it can be a ride, too."
Despite Olson's enthusiasm, he sounds a little bit tired. He confesses that he would sell the whole Skyride company in a heartbeat so that he can move onto the next idea, which would involve creating fitness products for people with disabilities. He'd also like to just go off and travel the world for a little while.
"I keep hoping maybe this one will be easier than the others," he says. "I keep praying to the entrepreneurial gods."