In Chicago, the team speaks with Zach Kaplan, CEO and Co-founder of Inventables, a company that connects small developers with novel materials like 3D printers. Zach recalls the many rejections he’s been dealt over the years, and urges the road-trippers to have grit in their endeavors. Next, the team learns to face fear and embrace reward as they embark on a skydive with instructor Ward Hessig.