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Ollie the Trolley

An Omaha Classic Finds New Owners and New Life

You might say that Deb Skinner and George Davis are Omaha’s foremost facilitators of fun.

“Life is too short, too hard and too serious not to have fun,” Deb shares.

So when the pair started their search for a business to purchase, it was no surprise that the company they chose was one almost completely dedicated to good times.

Deb and George are the proud new owners of Ollie the Trolley, a name synonymous with Omaha and, you guessed it…fun. They have hit the ground running and have a bevy of fresh ideas for the classic trolley business that has been providing event transportation to Omahans since 1985.

“There are some lovely wineries and breweries around the metro area and we’re looking into partnering with them to offer winery and brewery tours. We’re also looking into offering a tour of tasting and cigar bars around Omaha, a shop ‘til you drop charter for senior citizens in and around the metro area and a holiday lights tour,” Deb says.

And if you are looking to experience the Old West, you might be in luck. Deb, who is involved in a Wild West re-enactment group, has an idea for a tour that will involve cowboys pretending to rob and highjack Old Ollie.


"We provide a niche service that is not only nostalgic, but more sophisticated. It's a niche market and it's dignified, traditional, and more upscale."
- George Davis


The Wild West re-enactments and new tours will be coupled with the more traditional trolley uses, such as high school reunions and wedding parties. Nearly half of Ollie the Trolley’s bookings come from brides and grooms celebrating their special day. Any way you look at it, when you see a group riding around town on these classic trolleys, they are always having a good time.

Deb and George appreciate not only the good time aspect of Ollie the Trolley, but also the nostalgic vibe that comes with riding on an open-air trolley fitted with wooden benches. The look and feel of the trollies are unique in comparison to charter and/or party buses, and Deb and George want to keep it that way.

“We provide a service that is not only nostalgic, but more sophisticated. It’s a niche market and it’s dignified, traditional, and more upscale,” George says.

Niche markets is something Deb knows a lot about. Her professional life has included stints in marketing, tourism and event-planning. George’s background is in the transportation industry, something that will come in handy in the years ahead. Both Deb and George are from Omaha and found each other after moving away for several years, then returning to Omaha, they are now engaged!

Ollie the Trolley offers 22, 32, or 47 passenger trolleys and has a total of eight trolleys operating throughout Omaha. 

Deb and George were pleased with their experience with The Firm.

“They are a good brokerage firm. They kept each side honest and did a good job gathering information and kept the process moving,” George says.


The Firm Deal Review

Buyer Training Period: 90 days, over 130 pre-booked trolley reservations

Law Firms: Gross & Welch, William Lindsay; Steier Law, David Steier

Reason for Sale: Retirement

Year Established: 1985

Financing: Equipment loan at Core Bank, Ron Baumert

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The Firm makes no warranties or representation in consideration to the information provided above. All communication regarding this business must occur directly with The Firm Advisors, LLC. The Firm is not a real estate brokerage and does not sell real estate. The Firm solely advises on exit strategy.