As the world transitioned from horses and steam ships to motor cars and flying machines, one man was ready to steer America through the transformation: Augustus Post, a legendary transportation pioneer of the early 20th century. Born into affluence in Brooklyn in 1873, Post purchased the first motor car in New York City, was the 13th man to fly an airplane in the U.S., and once held the world distance record in a balloon. More than a visionary and adventurer, Post was a leader among a gang of early thrill-seekers who brought forth a vision of the world where anyone could be an explorer. Told through family members, historians who view Post as a key link in the modernization of transportation, animation, and an imagined radio announcer from the mythic 1950s, this hybrid documentary reveals Post's wide-ranging achievements and interests. But it also explores a complex individual whose widely scrutinized marriage and divorce was a source of great pain until his later years when a new relationship brought him comfort and solace. Uncovered for the first time, the story of Augustus Post is an unforgettable tale of imagination, spectacle, and discovery.