After graduating in 1996 with a degree in statistics and actuarial science, Osborn was commissioned as an ensign in the United States Navy and entered flight training in Florida and Texas.

Subsequently designated as a naval aviator, he was eventually assigned to the Fleet Air Reconnaissance Squadron One (VQ-1) "World Watchers" at NAS Whidbey Island, Washington, flying the EP-3E Aries aircraft.

[2] In a September 2003 article in the Naval Aviation News, Osborn told Jim Turnbull that once he regained control of the plane he "called for the crew to prepare to bail out.

After an emergency landing at the Lingshui Air Base on Hainan Island, Osborn and his crew were taken to a Chinese military barracks where they were detained and interrogated for 12 days.

By his superb airmanship, proven ability to perform under pressure, and steadfast devotion to duty, Lieutenant Osborn reflected great credit upon himself and upheld the highest traditions of the United States Naval Service.

[7] In 2007, the Aspen Institute selected Osborn to be a part of their Aspen-Rodell Fellows Program in Public Leadership[8] and was also elected vice president of the National Association of Unclaimed Property Administrators.