Small Business Spotlight: Ollie the Trolley, Experience the Nostalgia in Omaha

Apr 3, 2024 | Business, Core Bank, Customer Spotlight, Omaha, SBA

Climb aboard and follow the journey of Ollie the Trolley, a sophisticated transportation business owned and managed by Deb Skinner and George Davis since 2014. Ollie the Trolley’s mission is “all about fun” and began in 1985. It is iconic for weddings, group corporate transportation, and specialty tours. Deb and George are the fourth owners expanding the transportation and entertainment company with specialty and historic tours. Their specialty tours are either public or private to destination locations around Omaha.

George found his interest in the Ollie the Trolley business with his passion for transportation. He had been in the transportation industry for many years, including a stint as a Presidential appointee in the George H. Bush Administration at the Federal Department of Transportation. Additionally, George served as the Assistant Mayor of the City of Omaha. George also spent 7 years with the Union Pacific Railroad learning railroading and trucking, and 3 years with Federal Express.

Deb has been involved with tourism, marketing, fundraising and event planning at the national, state and local levels for over 25 years. She served as a Tourism Marketing Consultant for the State of Wisconsin for 13 years before returning to Omaha to work for the Convention & Visitors Bureau.

The Ollie the Trolley team includes a staff of 17, including drivers, maintenance, and garage personnel, and accounting to run the operation of the nine-trolley fleet. The team plans on adding a new mini bus to the fleet this spring. The Ollie the Trolley business uses Core Bank’s financial services with several accounts, including payroll.

Core Bank was recommended to Deb and George by their accountant and was the first bank and only one responsible to go into business with them. George and Deb have been loyal customers using the system where cash and reservations are processed with $514.000 going through.

George shared that they’ve developed a great partnership with Core Bank as it is a top lender for small businesses. “Core Bank helped us with our PPP and EIDL loan during COVID time to keep them us business. Core Bank saved us,” George exclaimed, “I would recommend anyone, especially anyone in small business to work with Core Bank.”

Ollie the Trolley is an Omaha icon and a family tradition which entertains and educates locals and visitors with private and public tours. Their vision is to be viewed by their customers and peers as a transportation service that is not only nostalgic, but sophisticated, dignified, traditional and upscale.

Deb and George created a number of public and private tours for entertaining and educating customers using their transportation company.

On Saturdays through May 25th you can take a Bloody Mary Tour where attendees get breakfast with their first Bloody Mary and then travel to two other bars to enjoy the best Bloody Marys in Omaha and Papillion and make new found friends.

The Taco Tequila Night on Wednesdays will begin May 22nd and  run through the summer.  Customers will be transported to the most authentic Mexican restaurants and learn new songs and learn about South Omaha culture by the tour guide, a singer in a Mariachi band..

A newest tour includes the history of Omaha’s Wild West and how it shaped the whole country in its westward movement. The trained historian shares the history of the Nitty Gritty City of Omaha. They make a stop at Jobbers Canyon Historic District, where settlers bought their wagons, supplies, tools, and food to continue their travels going west to find their gold.  The trolley is hijacked by outlaws stealing a chest full of gold.  They head to the Bellevue Berry Farm where guests are greeted by Cappers and 100% authentic wild west reenactors, as well as a professional card shark.  The card game ends in a shootout between the outlaws, Sheriff and deputies.Then customers mingle, take pictures and have lunch with the Cowboys.

They also host a haunted cemetery tour that is a history lesson about Omaha when it was a wicked little city, the hauntings, the criminals and how the city was run by gangsters and brothels. The trolley stops at famous Omaha area cemeteries like Prospect Hill. The tours are narrated by trained Historians dressed up as undertakers.

Another popular Ollie the Trolley tour is the cherished holiday lights tour in December riding through Omaha’s most spectacular neighborhoods to view Christmas light displays.

Ollie the Trolley transportation is also used during the Berkshire Hathaway annual shareholders meeting and during the College World Series.

For 39 years, Ollie the Trolley has maintained a veteran team of safe and courteous drivers. Customers can count on punctuality, familiarity with the route, and reliable, safe driving on all of their reservations. They all carry a commercial driver’s license and are fully insured.

Ollie the Trolley has continued to offer unique transportation services catering to people’s needs, creating memories and fun for metro Omaha and Council Bluffs clients. They may  transport 100 weddings parties and their guests in 2024. Many customers are repeat second, third generation clients. They promote their services on Facebook and its website as well as a subscriber email communication called Olliegram.

“We are making plans to celebrate owning the business for 10 years this August. Deb and I hope to manage and operate the company a few more years and then it might be time for the next generation to carry on the Ollie the Trolley legacy,” George shared.