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L. Scott Webster has a diverse work experience spanning various industries. In 1993, they served as a Legislative Intern in the US Congress. In 1997, they became the Business Owner of Webster Orchards, overseeing the operation of 1,000 acres of orchards and agricultural properties. In 1999, they became the CEO of The Fruit Company, a prominent online retailer of fresh fruit and gourmet gifts. Additionally, in 2021, they became a Business Owner of the Mount Hood Railroad, a historic tourist and commercial railroad located in the Columbia River Gorge National Scenic Area.

L. Scott Webster completed their Bachelor of Science degree in Business Finance from Brigham Young University, between 1991 and 1995. L. Scott later pursued a Masters of Business Administration (MBA) in Business at Duke University from 2005 to 2007.