Launching a City Tour: Q & A with Winnipeg Trolley Company Founder Ben Gillies

Ben Guillies Head Shot

Ben Gillies – Founder, Winnipeg Trolley Company

This month we had the pleasure of sitting down with Ben Gillies, the founder of the Winnipeg Trolley Company – Winnipeg’s only city tour and charter service using a 1920’s trolley.

Founded in 2011 by Benjamin Gillies and business partner, the Winnipeg Trolley Company offers sightseeing tours and charters aboard Manitoba’s only trolley.

Ben and the Winnipeg Trolley Company are entering their second season of operations and are fresh off a win at the annual Tourism Winnipeg awards – taking home the 2012 Tourism Winnipeg Innovation of the Year Award! The tour provides tourists and Winnipeg a glimpse into the cities sights, sounds, history, architecture, monuments (Winnipeg has more then you think) and celebrities. The entire interview is below. Enjoy!

CPLT: Tell us the story behind how or why you started your business? What was your ‘ah-ha’ moment?

BEN: It appears Winnipeg is slowly becoming more of a tourist destination. With the human rights museum, an expanded convention centre, the return of the Jets, and other developments, there will be a growing number of visitors to Winnipeg over the next few years. One attraction our city is currently lacking is a general city tour. We wanted to provide that service, but we did not want to just use a regular bus. Rather a vehicle that will stand out, and is appropriate to Winnipeg’s story. What with the large collection of early-20th-century architecture in the downtown, we thought a trolley—designed to resemble an original 1920s Winnipeg streetcar—would be appropriate. Not only is it a unique and exciting vehicle for tourists, but trolleys in other cities have become popular vehicles for charter for weddings, reunions, and other events.

Winnipeg Trolley

The Winnipeg Trolley Company’s trolley waiting for guests at the Forks in Winnipeg.

CPLT: Describe the vision for your business now vs. when you first had

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the idea to start your business (share any learnings you feel other entrepreneurs should know about the evolution of ‘vision’)?

BEN: On the tours side, when we first started out, we were very focused on the downtown, and on a heritage-specific tour. Our original tour discussed mainly the story of Winnipeg from about 1870-1920, using the buildings that date to that period. Visitors seemed to really enjoy that tour, but were also interested in knowing about what makes Winnipeg interesting in 2013 as well. We decided it would be a good idea to explore Winnipeg throughout the ages. After all, there are definitely more modern sites and attractions (like the Manitoba Museum, MTS Centre, Manitoba Hydro Building) that visitors have found to be worth knowing about. As such, we have created more of an overall city tour that, while still

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having historical facts, now provides something for everyone—from history, to architecture, to sports, to gardens—and that Winnipeggers have said they find fascinating and enjoyable, as it shares stories and information most of them also don’t know. As one woman said, she has lived in Winnipeg for her entire life, but the day she took our tour was like visiting an entirely new city.

Guests enjoy a tour of Winnipeg

Guests enjoy a tour of Winnipeg!


A Wedding party having some fun with trolley.

CPLT: What were the very first things you did after your ‘ah-ha’ moment?

BEN: Manitoba has some very stringent regulations in the transportation sector, so we had to ensure we would actually be allowed to drive this new and unique vehicle in the city. This meant meeting with representatives from the Department of Transportation, as well as finding a mechanic who felt comfortable and qualified to look after our vehicle once it arrived in Winnipeg. Additionally, to operate in Manitoba, we are required to possess a Manitoba Taxicab Board license. We applied for this immediately, as failing to receive one would have ended the whole process of starting up our company. We prepared our business plan and application to the taxicab board; we also met with a number of organizations in the city including Tourism Winnipeg, the Downtown Winnipeg BIZ, and the Chamber of Commerce, which all lent support to our application. We then went through the hearing approval process—presenting to the board, responding to their questions, and then responding to the opposition made by other taxicab and limo companies to our application. The board unanimously approved our application, and from there we began the process of setting up our company.

CPLT: What is your view on the creation of a written business plan as the foundation of your start-up vs. rolling up your sleeves and start selling something? Which did you do?

BEN: In order to apply for a taxicab business license, we were required to prepare a business plan, so there was never debate as to whether or not it would be worthwhile. We did find it useful, as it forced us to analyze trends in the tourism and transportation industries, assess our competitors, and consider what some challenges might be, and how we could deal with those challenges should they arise. Still, nothing can really compare to actually going out and trying to market your product. Even if the general trend in an industry is growth, will customers be interested in what you have to sell? A business plan can suggest

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whether or not they might in broad terms, but it is not until you have actually created the product that you can know for certain. The business plan was a necessary process for us, but rolling up your sleeves and working on your actual product offers a far more satisfying feeling, for sure.

Ben rolling up his sleeves and narrating the tour to his guests

Ben rolling up his sleeves and narrating the tour to his guests

CPLT: How much seed money did you start with? Where did it come from? What is your view on self financing vs. getting financing from external sources (friends, family, fools, angels, VC’s, crowd-funding, etc.) to get your business off the ground?

BEN: We applied for two loans through the federal and provincial governments designed to support the start-up of new companies. Additionally, each partner supplied $7,000. If I were to do it again, I would seek out ways of finding alternative funding. It has been suggested organizations like the Downtown BIZ, Tourism Winnipeg, and others might have considered providing financial support—perhaps for an ad in a brochure with our tour route, for example. Had we been able to find 10 organizations willing to put in $1,000 each in this manner, it could have provided a nice cushion of funding for us starting up. On the other hand, the student loan we took out did provide me with access to some very valuable resources, including workshops and a mentorship with an experienced business consultant—so it has been very worthwhile!

CPLT: What has been your largest success to date? What has been your largest failure to date? What has been your most important learning (personally and professionally)?

BEN: Formally, our largest success was winning the 2012 Tourism Winnipeg Innovation of the Year Award. It was phenomenal to be recognized by our peers in the tourism industry for the work we have done over the past year. More broadly, we received some very positive feedback from our customers over the past year, and a number of wedding planners commended us on our services and the professionalism of our drivers. Considering they are familiar with the level of service provided in the transportation industry, it felt good to know we ranked among the best in providing our customers with a positive experience.

Our biggest failure has to do with certification. We had been hoping to provide a wheelchair accessible vehicle, and so we purchased a trolley with a wheelchair lift. Manitoba regulations require all wheelchair vehicles to be D-409 certified, which ours was not (it is an American vehicle, conforming to American standards). Prior to purchasing the vehicle, we had spoken with the Society for Manitobans with Disabilities, and they said they would lend support to our appeal to have the Department of Transportation recognize the American standard in lieu of D-409. We also attempted to speak with a representative from the DoT, but they were not willing to provide any information until they had seen the vehicle. As such, we purchased the vehicle, made our case, but DoT refused us. We would have had to pay an estimated $30,000 to make the trolley D-409 compliant. This was an impossibility, and so we had to pay to remove the wheelchair lift.

CPLT: Are there useful tools or resources (ie. apps, websites) that you would like to share with the Catapult entrepreneurial community?

BEN: When we first started out, I made good use of the Canada-Manitoba Business Service Centre. As someone with zero background in business, it was a good starting point to get information about what steps would be necessary to eventually establish a company in Manitoba. They provided information themselves, and also recommended other places I could go. I imagine many members of the Catapult community will already have a background in business, but for anyone like me who could use some help learning the basics, I appreciated the resources available at the centre.

CPLT: What three pieces of advice would you like to impart on the Catapult entrepreneurial community?


  1. Know the government regulations of the industry you are in before you start purchasing capital equipment, and recognize these are not up for discussion. If we could do it again, we would not have bought a wheelchair-accessible trolley. We thought we were doing a good thing by trying to make our services available to customers in wheelchairs, but DoT did not see it that way, and proved unwilling to make any exception for us.
  2. Become familiar with, and make use of, social media. This is still something I am definitely learning, but what with all the social media sites out there, it is essential to have a strong online presence. Knowing what each site does, and how you can use its unique features to your advantage, is very useful. We are still building our own online presence, but already, we have had brides tell us they decided to use our services thanks to the photos of the trolley they saw on Pinterest—which is not a site I would have ever explored were it not for its usefulness as a marketing tool.
  3. Network, network, network. Everyone told me this would be key, and I now understand why. You need to get your name out there, and it seems to me people like knowing who they might be dealing with at a company. It is one thing to know a company exists, but far better to know that it is Ben who you will be dealing with should you ever choose their services. Also, as a young entrepreneur, I have found most people are eager to provide advice and suggestions—many of which I have sought to incorporate into my company.

CPLT: This last question is your opportunity to share a view about entrepreneurship and/or ask the community something that you would like to know. What is your rant and/or question?

BEN: Because marketing is so key, and is something I am still very much exploring, I am curious to know what strategies other small companies have used to get the most bang for their marketing buck (share your thoughts with the entire community using the comments areas below)? Perhaps especially businesses that are not ‘essential services’ but are more boutique or luxury items.

CPLT: Very lastly, would you like to make a special offer to our audience? If so, what is the offer?

BEN: Definitely! If any members of your community are interested in using our charter services, we can provide an hour free for any four-hour rental. If anyone is interested in taking our public tour, we can offer a 10% discount. Just mention this blog post so that I know you’ve read this. Both offers are valid through December 2013.

CPLT: Thanks Ben.

BEN: Thanks Jason

Facebook: /WinnipegTrolleyCompany
Twitter: @WinnipegTrolley

What did you think of Ben’s story? Do you share his views on entrepreneurship? Share your thoughts with us below.