Mary Olson did quite well in the telecommunications business. But when she purchased the Airlie winery in 1997, she was hardly your typical dot-com gazillionaire. Turns out that being loaded with Upper Midwest values was more than sufficient.

"I did a lot of the tractor work myself," said Olson, a native of Osceola, Wis., and, from her time at her uncle's dairy farm, "I knew that farming is up and down. That really comes in handy in Oregon [which has much more year-to-year climate variation than does California]."

And then there's that work ethic and the whole frugality ...