Ostrander graduated from Menlo-Atherton High School in Atherton, California, where he led the team to a Central Coast Section Division II championship in his senior year.
He chose Stanford, and after redshirting in his freshman year of 2003, Ostrander started the last two games of the 2004 season after starter Trent Edwards went out with injuries.
On September 30, 2007, Ostrander suffered a seizure while watching Edwards make his first professional start for the Buffalo Bills.
[2] His backup, Tavita Pritchard, led Stanford to an upset 24–23 victory and was named the starter for the next game against TCU.
Ostrander went undrafted in the 2008 NFL draft, but was signed as a free agent by the New Orleans Saints soon afterward.