Kai Kaapro, owner of Trolley Pub, first had the idea for a pedal powered party machine in 2010 after seeing a similar vehicle while traveling in Amsterdam. At the time, an eco-friendly, pub-crawling trolley was a novelty. After returning to the states, Kai contacted his old fraternity brother, and soon to be business partner with a great new idea. Fast-forward to 2015, Trolley Pub operates pedal powered booze cruises in five locations across the country. We sat down recently with Kai for our latest installment of Raleigh Hustles Hard to learn more about how Raleigh’s favorite mobile party came to be.
Kai, who was attending law school at the time, said he never had an entrepreneurial spirit. “This wasn’t planned. I never expected to be anything but an attorney. We really just wanted to build the first one out of curiosity. We thought it was a really cool idea and wanted to see what would happen.” After painstaking research, they finally found a manufacturer in Bend, Oregon willing and able to build the first Trolley Pub prototype.
In 2011, Kai and his business partner founded Trolley Pub, LLC and opened the first location in Tucson, AZ. “I tried to run it while I was still in law school in Pennsylvania. It didn’t work out very well, if you can imagine. Eventually, a large streetcar project caused the Tucson location to lose viability. “Luckily, I had a good friend in Jeff Murison, the president of the Hillsborough Street Association in Raleigh. I was discussing my situation with him at a conference and he immediately suggested Raleigh as a perfect location.” Trolley Pub Raleigh opened in the spring of 2012. “The environment in Raleigh is perfect. After visiting, I quit every obligation I had and moved out here. I met my wife the first week I was here, on the Trolley Pub! Raleigh has been so good to me.”
It was hard for us to categorize Trolley Pub. Is it a transportation service, a downtown Raleigh tour operator, a mobile bar? Technically, it’s all of the above, but Kai assures me it’s much simpler than that. “People are renting it out for a fun group experience, while getting to know the area better better. At the end of the day, Trolley Pub is just entertainment.”
While it’s all entertainment for the customers, owning Trolley Pub is not easy. There is a lot of moving parts and liability when it comes to operating a mobile BYOB bar for 14 people. However, Kai admits that the biggest challenges were the legal hurdles when launching. “Between both the city and state regulations, licenses for motor carriers, alcohol licenses and laws, the hardest part was being granted the right to legally operate.” He says he was a bit naïve in the beginning, which helped him to jump right in. “I had never been out of college in the real world so I was very over confident thinking this would be easy.” There have been numerous obstacles unique to each location, but Raleigh was an outlier in terms of the launch process. “In 2012, Raleigh basically just said OK. They wanted to work with us from the beginning and we’ve still never really had an issue with this city.” Unfortunately, that’s not been the case elsewhere for Trolley Pub. Opening in Arlington, VA was much more difficult given its proximity to Washington, DC. “We had to take our case up to the state level, and eventually try to have a bill passed for our business to operate.” Even with all the regulatory hurdles, Trolley Pub Arlington opened in 2013. In 2014, the Madison (WI) and Houston (TX) locations were born. Most recently, Trolley Pub opened a location in Charlotte and has plans to expand into the Virgin Islands in November. Kai has a vision for further expansion, focusing on emerging markets like Wilmington (NC) and Detroit.
On a more local level, Kai’s vision for Trolley Pub Raleigh is focused on transforming the warehouse at 323 W Davie Street, which is currently the trolley take-off point, into a hang out spot. “We’re still in the preliminary planning stage, but our ultimate goal is to build out a gift shop / bottle shop in the front of the store selling local merchandise and have a sandwich bar style restaurant in the back connecting to a rooftop bar.”
Even with all the positive forward motion, Trolley Pub has had its fair share of detractors. Some downtown Raleigh residents have called it loud and obnoxious, while others have had issue with the vehicles slowing down traffic. Kai tells me, even though he was a bit thin skinned at first, it was important to him to be attentive to feedback and open to criticism while maintaining his vision and goals for the customer experience. “It hurt my feelings at first because I’ve thrown everything into this but ultimately it’s more important to me to be a good neighbor to the folks who live and work downtown. If someone has an issue, we try our best to be extremely responsive. If someone doesn’t want us near his or her house, we’ll change the route. We’ve even changed hours of operation to be more accommodating, late night. We’ve also spent a lot of time training our staff to be responsive and enforce the rules strictly."
Although Kai had no plans to be a small business owner, he finds that this lifestyle suits him better than he expected. “Once I dipped my toes in, I enjoyed being a business owner so much that I stuck with it. My favorite part is finding ways to please the customer and making sure they are happy with the money they’ve spent. Selfishly, I love the time management, control, and creative freedom it allows me, but more importantly I love seeing people walk away happy.”
Learn more about Trolley Pub and some of Kai’s favorite small businesses in the area below:
Thanks for stopping by the porch,
Porch Fly Clothing