Winslow received a B.A. from Cornell College in Mount Vernon, Iowa, in 1961, and was a member of the United States Army Reserve from 1962 to 1968. His father, Philip E. Winslow, founded the family’s original Volkswagen store in Colorado Springs in 1961.
“Two days after graduating from Cornell College, I went to work at Phil Winslow Motors and have been there ever since,” Winslow said. “When my father died suddenly in 1964, I succeeded him as president of the dealership at age 24, the youngest VW dealer in the United States at the time.”
Winslow worked with his mother as his business partner until her death in 1988, at which time his wife, Ann, joined him in the family enterprise. In 1983, the company added BMW and later sold the Volkswagen franchise in 2003.
Focusing solely on the luxury brand, Winslow relocated the business and built a brand- new facility, which opened in 2015. He also brought in fresh leadership by hiring Gregg Randolph, an experienced BMW dealer, as his managing partner.
“We knew that the upgraded dealership needed innovative, aggressive leadership,” he said. “Its convenient location has provided high visibility and easy accessibility from all parts of the city, and a sense of renewed energy at the store has helped position Winslow BMW for the future.”
As an automotive industry leader, Winslow has been active in local, state and national associations, serving twice as president of the Colorado Springs Automobile Dealers Association, chair of the Colorado Automobile Dealers Association and vice chair of the Volkswagen Dealer Advisory Council.
“Participating in the legislative process at the capital in Denver and testifying before various committees, I was able to advocate for issues affecting our industry,” he said. “We worked diligently to safeguard franchise agreements to protect dealers’ investments and to retain Sunday closing laws, which are favored by a vast majority of new-car dealers in our state.”
Winslow has also made volunteerism a priority in his life and has served on numerous boards on the state and local level, including the Colorado Springs and state of Colorado Jaycees; Penrose Hospital in Colorado Springs (community relations committee); Boys Scouts of America Pikes Peak Council; City of Colorado Springs Parks and Recreation Advisory Board and many others.
Currently, Winslow is a benefactor of the Children’s Literacy Center, headquartered in Colorado Springs, that offers tutoring throughout Colorado to underperforming students reading below their grade level.
He also supports the Unstoppable Woman initiative at the University of Colorado Colorado Springs (UCCS), which provides financial assistance for nontraditional students who are starting or returning to college after having overcome significant personal adversity.
For their good works at UCCS and beyond, Winslow and his wife, Ann, were proud to receive the 2021 UCCS College of Business Lifetime Entrepreneurship Award. They were honored for their important contributions to the retail automotive industry in Colorado Springs and for continuing to influence and impact the local community, both personally and professionally.
Winslow was nominated for the TIME Dealer of the Year award by Tim Jackson, president and CEO of the Colorado Automobile Dealers Association. He and his wife, Ann, have three children.