On a tenebrous winter morning in Denver, Colorado, Leo Jenkins felt the weight of the world crushing him. Leo has a decision to make - maintain a comfortable position in a career he's no longer passionate about - or take a massive leap of faith. Giving up everything he's ever known, Jenkins sells his business, purges every possession that won't fit into a single backpack, and sets off into the world in pursuit of answers.

Along the way, Leo accepts a challenge from another former Army Ranger to see how far they can travel together in three weeks with nothing but a backpack and 100 dollars to raise awareness and funds for a veteran charity. By any means necessary, the two manage to traverse two continents and film an award-winning documentary along the way.

In true nomadic hobo fashion, the pair stow away on coal trains, talk their way onto a boat, hitch rides, and walk their way over 8,000 miles in 21 days, raising nearly 33,000 dollars for their fellow veterans.

Leo's personal journey continues through Eastern Europe, Thailand, Australia, New Zealand, and beyond. Upon arrival in Alaska, Jenkins allots himself 24 hours to find and buy a vehicle to drive south, continuing his exploration of not just the world, but of the mind.

Contains mature themes.