Lolly the Trolley
"We are Cleveland's best ambassador," says Sherrill Paul Witt of Lolly the Trolley, the business she co-founded in 1985 with Peter Paul. "We have been out there promoting this city for 27 years—and changing people's minds. There are people who have said to us, 'I moved here because of this tour.'"
Non-profit clients like the Cleveland Clinic and universities including Case Western Reserve use Lolly the Trolley as a recruiting tool. And today, about half of the business is devoted to weddings, reunions, student tours and other special events. The rest of Lolly's riders are area residents curious about their hometown, or visitors who want a proper introduction to the city when they arrive.
And that's exactly what they get: a 2-hour, 20-mile jaunt through the city where personable tour guide/drivers share more than 100 points of interest. "There is no one who knows more about Cleveland than we do," Witt says, relating how the original tour script she wrote in 1985 has evolved significantly. "Then, there was no North Coast Harbor and Tower City hadn't opened," she says. "Ohio City was just coming to life, and the Warehouse District was barely bubbling. The Flats was still the hot place to go."
Despite this, Cleveland had a rich story to tell and always has, Witt says. The manufacturing, the wealth on Millionaire's row, the philanthropists who shaped Cleveland's history—these stories continue to engage Lolly the Trolley’s riders. But what surprises out-of-towners the most is our hospitality. "We have a very big heart," Witt says. "The two things we hear the most are, 'What a friendly city,' and, 'Boy, is it a clean city.'"
This makes Witt proud as she reflects on the bootstrapping days of Lolly the Trolley, when she and now ex-husband, Peter Paul, started the business. They got the idea while traveling in Boston for a friend's wedding. They hopped aboard a trolley named Lolly and took a sightseeing tour of the city. "I said, 'Wouldn't it be cool to have this in Cleveland, Ohio?'" Witt recalls.
So the couple came home and began doing the groundwork. They called a trolley manufacturer, who balked at the idea of a Cleveland tour. "He never believed we'd get it off the ground," Witt says.
And they weren't so sure either when they began seeking funding for their first vehicles. Sherrill and Peter needed to raise about $50,000 and were turned down by 300 influential Clevelanders. "Thanks to COSE and the early entrepreneurship conference, I was able to find some investors and we got the company up and running," Witt says. Years later when the couple was going through a divorce, they took COSE's Strategic Planning course, and Witt says it "kept us sane and able to grow the business."
"That course helped us get through one of life’s most painful personal events because it helped us take some of the emotion out of running the business," Witt says.
At first, Lolly the Trolley was literally run out of a "shoe box" boarding point on Public Square. It grew in the 1980s and 1990s, weathered the post 9/11 blow to the tourism industry, and now the company is in a more comfortable place, with 15 tour guide/drivers and 8 trolleys.
What makes the tours a special experience for riders is the tour guides—they are the real assets of the company. Trolley Tours hires mature adults; all are between the ages of 45 and 76. And they're real characters who are passionate about learning and finding exciting nuggets to share on their tours. "We are a very personal business—we affect people's lives and give them special memories," Witt says.
Sherrill and Peter personally answer the phone and work to match clients with just the right tour guide. She’s the face of the business, and Peter is the backbone of the business, she says. He handles financials, operations and oversees hiring. “The vehicles are in beautiful shape thanks to his supervision,” Witt says.
Meanwhile, the company continues to evolve as the Cleveland landscape changes and grows. “Cleveland is a tremendous city, and we are so happy to be able to present Cleveland in its true form,” Witt says. “And that is as a vibrant, very real Midwest city with a rich history and resilient people.”