Osborn is a 1992 graduate of Kenyon College, in Gambier, Ohio, where he pursued a double major in English and political science and was a member of the swim team, on which he earned three NCAA championships and ten All-American honors.
He went on to earn his master's degree in comparative literature from Columbia University and initially planned to be a college professor.
He left the network in February 2004 and joined Entertainment Tonight in June 2004 as a correspondent, where he covered the Democratic National Convention.
He currently serves as Managing Editor of Warrior Maven, a military-specific news site focused on weapons, emerging technology and military history.
He also is a fan of the heavy-metal rock bands Metallica and Judas Priest as well as the English romantic poet William Wordsworth.