After a semester at Lees-McRae College, Will took the money he earned washing dishes and selling grilled-cheese sandwiches at Grateful Dead concerts and moved out west.

After a while working for Taco Bell in Jackson Hole, Wyoming, he spent the next five winters snowboarding while living out of a van in Big Sky, Montana.

[2][3] At one point, he spent 30 days living in a snow cave near Valdez, Alaska without showering, and snowboarding the Chugach Mountains, before ending up with frostbite.

He returned to Greenville, North Carolina in 1999, making enough money selling Christmas trees to embark on a three-month surfing trip to Costa Rica.

MacKenzie observed his boyhood idol, Payne Stewart, winning the 1999 U.S. Open which rekindled his love affair with the game of golf.