Leo's Misadventures is about Leo McGregor, a twenty-year-old surfer dude from Kitty Hawk, North Carolina, who won a $156 million lottery. He decided to get out of town for a while to get away from the locals who badgered him for a handout. He hitchhiked across America to Santa Monica, California, via Route 66. After a thirty-nine-day journey across the country, Leo ended up at the Santa Monica Pier with a journal full of stories and a girlfriend named Abby Walker. When he left Kitty Hawk, he had no idea what he would do when he arrived at his destination. Would he turn around and head back east or stick around on the West Coast for a while? Leo and Abby rented a beach house on the Pacific Ocean near the famous pier to give them time to figure things out. On his journey, Leo had given a lot of thought about the best way to use the money he had won. After much thought and discussion with Abby, he decided to start a charitable foundation. He and Abby found a nice office space near the pier and leased it for one year. Leo needed an attorney and found one in Santa Monica named Jess who helped him set up the foundation. With his charitable foundation up and running, Leo needed someone to run the day-to-day operations. He found Freddy, who lived in Malibu with his adopted parents, to fill this critical position. Leo, Abby, Jess, and Freddy became good friends and enjoyed themselves on the coast when they weren't working. Eventually, Leo bought an apartment building on the beach and converted it into a surf shop. He hired Brody, a local surf builder, to run the shop and use locals to help create the boards. Any profits would be donated to charity. With everything running smoothly, Leo began to ponder the need for similar charities in other parts of the country--or internationally.