Sherrill Paul
Cleveland Rocks & Sherrill Rolls

Sherrill Paul was born in April, 1948 in Montreal, Canada. She came to Ohio, the Akron area, as a very small child.

She grew up in Brecksville and graduated from Brecksville High School and then got a degree in Journalism from Ohio Wesleyan College. "I always say a Journalism Degree prepares you for everything and nothing."

After graduation Sherrill "bounced around". She describes herself as a classic entrepreneur "I don't play well with others." So she tried her hand at many different types of work from retail to temporary help placement to telecommunications engineer to customer service to sales.

"I got fired a lot because, as I say, I don't play well with others - no true entrepreneur does."

Entrepreneur Sherrill Paul at work

One woman she met owned a tour company and asked her if she wanted to be a tour guide. At the time Sherrill said 'no' ("How could I leave that wonderful job at the phone company - you know the one I hated?!")

It wasn't too much after that that the woman went out of business and Sherrill had the opportunity to buy her company, Bestconventions. Sherrill and her best friend decided to go into business together even though "we were both as dumb as a box of rocks and had no idea what we were doing."

The very next day all of the employees quit. Even her friend, it turned out, was not suited for the business and she left too.

Bestconventions ran walking tours and Step-on-Guide Service. Walking tours are exactly what they sound like. Step-on-Guided Services use an existing vehicle (like a city bus) and a tour guide points out highlights along the way.

Sherrill was married to Peter Paul at the time and in 1983 they traveled to Boston to attend a friends wedding. It was in Boston that they saw the first Lolly the Trolley and they both fell in love with the concept.

Sherrill just knew it could be done in Cleveland. She knew that there were a lot more people interested in Cleveland and all it had to offer but didn't want to take a walking tour. This could be just the thing they were looking for.

Lolly the Trolley Conductor Hat

She talked to the company owner in Boston who was shocked that she was even considering it. "Who would want to visit Cleveland, never mind tour it? That's the initial response I got."

But Sherrill knew better. She knew what the city had to offer and the wonderful future it held and she wanted to be part of it. She put together a business plan and went looking for investors. She contacted over 300 people (she documented the number because it was so amazing to her) and it took over two years, but finally she found five people willing to invest.

Lolly the Trolley and


Gus the Bus in action

Her husband still had a job, but quickly had to leave that to come work full time for the business. The business plan only called for one full time salary though, so Peter's time was not compensated.

The first Trolley arrived in April, 1985 one hour before the parade for the Cleveland Indians Opening Day and Lolly joined the parade. Sherrill spent the next day in an empty parking lot learning how to drive the trolley. "Driving it really isn't that difficult once you learn the basics."

Sherrill Paul with Lolly the Trolley

"I was preaching the benefits of Cleveland before there was anything to preach about." In 1987 the Galleria was built. 1990 brought Tower City and 1995 gave us the Rock n Roll Hall of Fame.

Lolly's first day came and no one showed up. Sherrill did the tour anyway, having her talking points recorded to be used as a training video. The second day two elderly ladies came and were thrilled to have a tour all to themselves.

They were to become great advertisements for the Trolley because they had such a good time. They toured downtown Cleveland, the Flats, Ohio City and many of the same places Lolly tours to this day.

Sherrill has a lot of faith in the city of Cleveland. "I think the "We Believe in Cleveland" program is true. The quality of life here is fabulous. It's almost like a little Chicago. We have wonderful restaurants, ethnic groups, and the river. So many things.

Cleveland just has to start believing in itself again. People from outside the city love it and can't wait to come back. But the people who live here don't seem to believe it."

Sherrill says people are always impressed with the tours and the city. They comment on the same three things all the time. "They always say how kind the people are, how friendly the people are and how clean the city is."

Although Sherrill had her moments of doubt starting up the business, they were fleeting moments at best. Once she got going and committed herself she knew it was the right thing to do.

Sherrill Paul with her "helper" Shadow

"When I was younger I wasn't necessarily the most positive person. Now that I am so deeply rooted in customer service I see how important a positive attitude is. After awhile it changes your chemistry and it's not spin anymore, it's real - you become a positive person."

There are now nine trolleys and five full time employees at this time and around twenty part time seasonal employees. It is Sherrill's practice, whenever possible, to hire mature adults who are retired. "They must love people and Cleveland and be willing to show it."

Sherrill Paul

She always warns about the misconception of owning your own business. Although people think it means you make your own hours and decide on a huge salary, the reality is "you have to give up so much when you have your own business. You have less free time then ever before. You don't go home at the end of the day and forget about things. When you finally go home, everything comes with you."

In the winter months Sherrill usually takes Sundays off and will go to Florida for a few weeks. "You have to be here to be able to give good service."

Peter Paul and Sherrill Paul

She feels an essential tool to success is self promotion, especially in the beginning. "You must know how to communicate both the spoken word and the written word and not all young people are trained in that today."

She is also very proud that having been in business over 20 years now, the 3rd graders she took on school tours are now teachers taking their classes, or brides using Lolly for their weddings. "We have imprinted an entire generation with good news about Cleveland."

In some ways her business is still recovering from September 11th and loss of business headquarters leaving Cleveland. "In some small way our finances are tied to the city. If they do well, we do well."

They have tours of everything from Lakeview Cemetery to an Ethnic Market tour to a general tour of the city - and most everything in between. They are even planning a Les Roberts Tour in April, taking you to all of the places Robert's character Milan Jacovich frequents. Click for upcoming tours and more information.

When Sherrill travels she always takes in a tour or two - and she says "I'm merciless. I am very critical because I know how important a good tour is. And I have enormous respect for someone who gives a good tour because it is very hard work."

Sherrill Paul and Lolly the Trolley
- integral parts of Cleveland

"We are in the business of making people happy. I will always go out of my way to make sure people know what a wonderful city Cleveland is and how much it has to offer."

Sherrill saw the good in Cleveland when so many people were afraid to look. She took a chance and it paid off - for her and for the city. She is not afraid of long hours and hard work and we have all benefited for her efforts.

Sherrill envisioned Cleveland with Lolly the Trolley and made it happen. Today, a Cleveland without Lolly the Trolley is unthinkable.