Bill Carstanjen, COO of Churchill Downs, Inc., the corporation famously known for its Kentucky Derby, goes undercover at his own racetracks where he faces his fear of horses head-on, and is unable to hold back tears after working for one employee.

Joel Manby, President and CEO of Herschend Family Entertainment, a national theme park and amusement corporation, goes undercover in his own company where he meets a young man aspiring for his job, and finds that it might be easier to run a boardroom than to captain a boat full of kids.