In the beginning, Jenna Boller is challenged to go on a road trip. Mrs. Gladstone offers Jenna a chance to take her to all of Gladstone’s Shoe Stores across the country.
At the start of the road trip, Jenna come to find out that another Shoe Company and Mrs. Gladstone’s own son, Elden, wishes to take over Gladstones and change the entire company.
Mrs. Gladstone and Jenna travel to Texas for their last stop to the main branch of Gladstone’s Shoe Stores where they meet Harry Bender. Harry Bender, Jenna, and Mrs. Gladstone work hard to save the company.
Harry Bender leaves to go find more help with the upcoming stockholders meeting, on his way he is hit head on by a drunk driver and killed on impact leaving Jenna and Mrs. Gladstone to fend for the company themselves.
When Jenna and Mrs. Gladstone arrive at the stockholders meeting, Elden has Jenna escorted to a Taxi and sends her on the way to the airport back to chicago informing her she is being fired.
Jenna tells her taxi driver to go back, once she gets to the meeting and if finally inside she puts her stocks to Mrs. Gladstone staying with the company and puts them against Elden. In the end she wins and Gladstone’s is saved.