Randy Cashmore

The heart and soul of our firm, Randy, is a natural coach. After spending 25 years coaching high school and college football, Randy now spends his time coaching people through their investment and retirement challenges.

He enjoys offering people the real-world solutions and tools they need to prepare for a confident, comfortable retirement.

“We focus on financial advice for the Average Joe and Jane,” Randy says. “Our guiding principle is simple: No suits, no ties, just nice guys — ready to talk with you about your financial options for retirement.”

After studying history and economics at Murray State University, Randy founded Big Fun Entertainment, a production company that allowed Randy to pursue his passion for public speaking and coach football at Warren High School and Harper College for over 25 years.

In 2000, a year after becoming a father, Randy went to work for a large, international financial firm for four years. He eventually decided to open his own independent financial firm and, today runs Cashmore Financial Group in a way that puts clients’ needs and goals front and center.

Randy and his wife, Kristin, have three children: Zachary, Nathan, and Abigail. Away from the office, Randy enjoys history, music, and sports. He’s also a self-described “transportation buff” who loves old cars and model trains.

Makayla is a lifelong resident of the Grayslake area and a 2019 graduate of Grayslake Central High School. She spent a year at Franciscan University and taught kindergarten for a semester. Makayla is a parishioner at St. Gilberts Catholic Church and is heavily involved with their youth ministry program.

As with many of us, Makayla’s life path has been altered a bit by the specter of Covid-19. She is currently pursuing an undergraduate degree in early childhood education with a full course schedule at the College of Lake County. Makayla spends her days working with us at Cashmore Financial Group and we are grateful for her performance and work ethic.



Zack is a lifelong resident of Grayslake and attended Grayslake Central High School. He is competitive, principled, and loyal to those who count on him. Unafraid to take the road less traveled. In 2017 Zack toured Ireland with a group of high school all-American football players for a playing tour of the country. Upon returning from Ireland and despite dozens of football scholarship offers, Zack decided not to play football in college and went on to attend Illinois State University. Ironically it was at Illinois State where he realized his desire to become a journalist would be a career choice riddled with political overtones and unethical behavior. Thus Zack’s journey led him to partner up with Cashmore Financial Group. His knowledge, work ethic, and commitment to doing what right makes him an invaluable asset to our firm.

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