In an attempt to complete the challenge without doing any actual work, Ryan hires a staff of squeegee veterans to do his dirty work for him. He approaches car owners, pedestrians, and small businesses in an attempt to secure contracts to squeegee windows with his new company 'SqueegeeCO'.
In an attempt to complete the gnarliest stunt of all time, Ryan decides to jump out of a plane with no parachute. Realizing that he will die in the process, he makes peace with God, gives his possessions away to charity, and plans his own funeral before heading to the Toronto Airport to jump to his death.
Ryan decides he wants his friend for life to be a huge celebrity and sets his sights on 90's fitness star Hal Johnson. Through the help of a private investigator, Ryan tracks down Hal Johnson only to find that he wants no part in Ryan's lifelong friendship. The rejection sends Ryan into a tailspin and he struggles to find a new 'friend for life' while dealing with the heartbreak Hal Johnson has caused him.
Ryan decides that Daytime TV is the new Late Night TV and sets out to create a Late Night Talk Show modeled after 'The Ellen Degeneres Show'. He films a pilot Episode and brings a test audience of middle aged women in to choose whether they liked Ryan's new Late Night TV Show better then The Ellen Degeneres Show
Ryan decides that he will get the notoriously chauvinist book "I hope they serve beer in Hell" by Tucker Max banned from bookstores. He interacts with bookstore owners, customers and feminist authors in an attempt to have the book banned while at the same time struggling with the ramifications of having to retire his own chauvinist stories.
Ryan realizes that women have thousands of fashion products designed to enhance their appearance and in response decides to create 'Python Pants', the world's first pair of pants designed to enhance a man's package. Ryan pitches the pants to fashion designers, clothing retailers, and stores before setting up shop at 'Tryst Lingerie' to sell 'Python Pants' to unsuspecting customers.