If you thought you were edgy by backpacking across Europe after college with little more than a Eurail train pass and a big beer budget then try heading out on a bicycle with only $2. In April 2001, Keiichi “Kei” Iwasaki of Japan found himself bored working for his dad and decided to set out for a big adventure across his homeland with only 160 yen (about $2) in his pocket. Iwasaki enjoyed his joyride so much that he kept going. He hopped on a ferry to South Korea and began biking west. And kept going for years.

Over the past 8 years, Kei has visited 37 countries and traveled 28,000 miles (which makes that spinning class look easy, right?), but his trip hasn’t been all sunshine and gumdrops—he has faced pirates, a rabid dog, arrest and marriage. He’s made his money by doing magic tricks for tourists on the street. Next, he plans to head to Africa. Dude is so hardcore.