Leaving Houston, the team takes a brief hiatus from interviews with a 2-day drive to Chicago that allows them to reflect on the experience thus far. Once in the Windy City, they find themselves speaking with Zach Kaplan, the CEO and Co-founder of Inventables, a company that connects product developers with novel materials. Zach recounts the many rejections he's been dealt over the years, emphasizing perseverance in the face of challenge. Next, the team heads to Chicagoland Skydive to meet with skydiving instructor Ward Hessig. Once a policeman on track to becoming a lawyer, Ward discusses the fortuitous turn of events that led to his shift in paths. After their chat, the Roadtrippers nervously prepare for a skydive, but are ultimately able to let go of trepidation by following Ward's advice to "push through fear and embrace the reward."