Pushing Forward: Couple’s Paths Lead to Ollie the TrolleyApr 28, 2022 05:15PM ● By Kara Schweiss
Photo by Bill Sitzmann
In 2014, George L. Davis Jr. was working as a retail store manager following a unique career path that had branches in transportation and politics. His now-wife, Deb Skinner, was a development director for a health care foundation and had a background in marketing and tourism.
Davis was ready for a career change.
“I was dissatisfied. I didn’t see any opportunities for advancement and growth, and because I was already mature, I had graduate and postgraduate degrees,” he said. “I said, ‘I don’t have to stay here. I can do something different with my life that would give me satisfaction’…so we were talking and Deb said, ‘Why don’t we look at buying a business, and you tell the rest of the story?’”
The rest of the story began with their purchase (as Davis Entertainment) of Ollie the Trolley, which the couple have now co-owned for nearly eight years. They settled easily into their respective roles of Davis as general manager and Skinner as marketing director. “It was a natural fit,” Skinner said. “Our backgrounds just came together with this.”
Margaret Dunn founded Ollie the Trolley in the mid-1980s as a single trolley, and, under a series of owners, the business grew over the years to multiple trolleys, which look like traditional streetcars and are outfitted with nostalgic details like wooden benches, but do not run on tracks or use a pole to draw power from an overhead wire. Davis and Skinner manage a fleet of nine trolleys today with names like Ollie (of course), and the rhyming Polly and Guacamollie—but also Porkchop, Buttercup, and Trolley Brown. Drivers must have a commercial driver’s license to operate the trolleys, which carry a maximum of 32 to 47 passengers, depending on the specific vehicle. The business consists of a variety of private charters and public tours and peaks in the summer with a staff of around 20, but runs on a varying scale year-round.
“We have heated trolleys, and in the summertime, we have four trolleys that are open-air and the others are all air-conditioned,” Davis said.
The trolleys are especially popular for wedding parties, with as many as 600 bookings a year, and for other private bookings like corporate events and personal celebrations for 15 or more participants.
Ollie the Trolley public tours include Haunted Cemetery tours, led by trained historians (including Davis, who dresses up like an undertaker) that feature local cemeteries and infamous locales from Omaha’s “Wicked City” period. Taco Tequila Tuesday tours highlight South Omaha and a tour guide with a mariachi background teaches participants a few new songs during the ride. Other public tours include River City History tours in partnership with The Durham Museum, Bloody Mary Brunch and Tours on Saturdays, and seasonal College World Series and Holiday Lights tours. The company’s newest offerings—introduced this spring—are Beer, Barbeque & Bourbon tours that include visits to Nebraska Brewing Co. and Soldier Valley Spirits, along with stops for food and activities like indoor golf.
Davis and Skinner have been together for a decade and married in 2019. They both grew up in Omaha but spent years away from the community for work. Skinner was in Wisconsin for 20 years, as owner of Skinner's Riverside Marina in Marinette for seven years and as a tourism marketing consultant for the state for 13 years. She returned to Omaha in 2003 to work for the Convention & Visitors Bureau followed by later positions in marketing and development. Davis served as a presidential appointee in the George H. Bush Administration at the Federal Department of Transportation. “I’ve walked with presidents and I’ve helped the homeless,” he said. Davis remained in Washington, D.C., for another decade before returning to Omaha in the mid-1990s.
“When I came back from the Bush administration, I went into banking for a short period of time. Then I became assistant mayor in Omaha for Hal Daub, as well as his civil rights director,” Davis said. “Then, when I left his administration, for a short while I managed the small business network. I taught business classes and political science classes at Metro [Community College] and I enjoyed teaching for 11 years.”
Davis’ resume also includes seven years with Union Pacific and three with Federal Express, and the stint in retail management before he and Skinner bought Ollie the Trolley.
“Two people with no money had no business buying a business,” Skinner said, with Davis laughing heartily in response. “But we had great resumes, so we were able to get a loan and buy the business.”
Ollie the Trolley’s tagline is “all about fun,” but the journey has had some detours, like when the business had to move twice when buildings it leased space in were sold. “Trying to find a building for eight or nine trolleys is not easy,” Davis said, adding that the fleet is now comfortably ensconced at 1716 Cuming St., just north of downtown. When the COVID-19 pandemic hit, the successful business had to abruptly put on the brakes. Fortunately, grants and loans kept things moving.
“We had to hang on,” Davis said. “We were able to survive it and keep going.”
Now they’re rolling along again nicely.
“We’re an Omaha icon and the business has been around 37 years now,” Skinner said. “We think this is going to be our biggest year ever.”
Visit olliethetrolley.com for more information.
This article originally appeared in the May 2022 issue of Omaha Magazine. To receive the magazine, click here to subscribe.