The origin of Jason Eastwood’s landscape career can be traced back to ripe age of 11, when a neighbor asked if he would mow his lawn. Jason noticed an old riding lawn mower trailer in the back corner of the neighbor’s yard and negotiated a lawn services trade for the trailer. After a few weekends restoring the little trailer with his father, Jason was riding his lawn mower with the trailer in tow down the road to offer his services to customers that were once out of reach. As Jason’s referrals grew to other areas of Central Florida, Jason's mother offered to drive him to mow lawns after school.

After graduating Lyman High School with honors, Jason attended the University of Central Florida and during his college years, Eastwood Lawn Service grew to a 2 truck operation that employed a couple of his close friends and his brother. In 1994, during Jason's senior year at UCF, he purchased Tuff Turf of Central Florida, Inc. and become president of Eastwood’s Tuff Turf, Inc. In the summer of 2002, Jason purchased a 10-acre nursery in Oviedo to operate Eastwood Tuff Turf of Central Florida, Inc.

As a core value of Eastwood Tuff Turf, Jason strongly believes in promoting from within. His employee base started with a couple of friends and his brother, who each currently manage a division at Eastwood Tuff Turf. While many lawn service and design firms claim to have a grass roots operation, Eastwood Tuff Turf has the history of one.