[1] He is the son of Diana and Richard S. Strickler Jr. His father served as managing director for mergers and acquisitions of financial companies at Morgan Stanley in New York until his retirement in 1989.

He made 7 cuts in 10 tournaments on the Canadian Tour in 2010, with his best finish a fourth-place tie at the Desert Dunes Classic in November.

[5] Strickler entered the 6th and final round tied for 4th, but struggled, finishing with a last-hole bogey to make the cut on the number.

Strickler returned to the renamed PGA Tour Canada in 2013, making six of nine cuts with his best finish coming at The Great Waterway Classic (T-4) where he shot -18.

[9] To wrap up the 2013 season, Strickler successfully advanced through qualifying school to earn conditional status on the Web.com Tour for 2014.

In 2014, Strickler returned to the PGA Tour at the Farmers Insurance Open after earning a spot in the Monday qualifier where he shot 6 under par with one eagle and six birdies.

On May 13, 2014, Strickler earned medalist honors at the HP Byron Nelson Championship qualifier after posting a 4-under-par 68, which included six birdies and an eagle on the par-5 18th hole at The Lakes at Castle Hills in Lewisville.