At Uptown Motors, you’ll find plenty of beautiful vehicles, but the real story isn’t sitting on the showroom floor. It’s in the relationships built over the years, the customers who return generation after generation, and the longevity of employees who understand that a successful dealership is about far more than putting someone behind the wheel.
“We take care of individual needs,” says John Pentler, president of the Wauwatosa dealership, now in its 80th year of business. “I can’t tell you how many calls I get from people asking, ‘Can you help me?’ Many of our best customers over the decades started their relationship with us because of an issue. That's how you earn customer loyalty.”
Pentler is a third-generation owner who has been at the Mayfair Road store for 22 years, carrying on a family business with deep roots in Wauwatosa and a history of growth. Here are some of the significant milestones along the way:
• 1946: Uptown Motors began when brothers Irv and Ray Pentler opened a used-car lot on Center Street. Irv sold a Mercury convertible he had put away when he was in World War II and bought three used cars to start the business. The business took its name from the surrounding Uptown neighborhood.
• 1965: The dealership moved to its current Mayfair Road location.
• 1991: The family opened a dealership in Slinger, where John’s brother, Mark, serves as president. The operation offers Chevrolet, Chrysler, and Jeep models.
• 1996: The Mayfair Road store underwent a full renovation.
• 2023: The family expanded its Ford operations with the addition of Uptown Lincoln at 2001 N. Mayfair Rd., along with a truck service center farther down the street. The Lincoln dealership is highly visible from the freeway.
The truck service center is just one example of how Uptown responds to the needs of the market. Companies such as Amazon and FedEx rely on the dedicated service space in the 14-bay building to keep their fleets running efficiently.
Across both campuses, Uptown employs 200 people, both full- and part-time. “We invest heavily in our people,” Pentler says. “Management leads by example. The result is longevity. Our service manager has been here for 46 years. Our controller has been here for 50 years.”
Pentler remembers a time when car salesmen were often viewed as fast-talking and pushy. He never liked that stigma. Instead, Uptown has embraced a laid-back, comfortable approach to customer service.
“Our business is a people business,” he explains. “It’s amazing how you can catch up on life during a customer’s oil change.”
While the dealership is consistently busy, business typically peaks in the summer and again in December, when year-end deals attract buyers. For Pentler, though, there’s another special part of the season.
“I love the surprise part of it when it’s a gift,” he says.
For some customers, it’s their first car. For others, it’s another vehicle from a favorite brand. Pentler says those cars often become part of a family’s history. Children remember road trips, family vacations, and everyday moments spent in the family car, creating associations that can last for generations.
While the basics of car sales remain much the same, today’s consumers are more informed. Buyers arrive with more knowledge about vehicles, pricing and options, leaving less room for negotiation and putting an even greater emphasis on trust and relationships.
Giving Back
Uptown is also known as a supportive community partner, sponsoring sports teams and local events, including the recent Oktoberfest in Elm Grove.
“We are part of a small community. People come to us for help, so it’s nice to give back,” Pentler says.
That spirit of gratitude has been passed down through the generations.
“My biggest blessing was being able to work with my dad,” Pentler says, reflecting on his father and mentor, Glenn, the dealership’s previous president, who passed away in 2024. “Not many people get to spend time with their dad like I did. He was genuine. He would help the most powerful people in the community, as well as those who were struggling, all with the same level of respect. Plus, he would be as close with the car wash guy here as with the general manager.”
That same appreciation for customers, employees and the community has become part of the culture at Uptown, as the dealership celebrates its 80th anniversary with gratitude and pride.
"Our business is a people business. It’s amazing how you can catch up during an oil change."