Oosterhouse's career as a carpenter began at the age of 12, when he began learning carpentry as an apprentice to his neighbor, a carpenter. He continued to work in carpentry and construction throughout school following in the footsteps of his older brothers, Todd and Tyler, who are also carpenters. For his formal education, he attended the Grand Traverse Area Catholic Schools. Oosterhouse has a B.A. in nutrition and communication from Central Michigan University.
After college, Oosterhouse relocated to Los Angeles to pursue a career in film and television. In LA, he worked behind-the-scenes for the Project Greenlight as a production assistant and tape coordinator.
When auditioning for a new show on TLC, Oosterhouse landed a part on the show Trading Spaces, and joined the cast in their fourth season.

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