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Cooper J. Casillas, CFP ®

Wealth Advisor
Director of Next Generation Planning

Cooper is a proud graduate of James Madison University, earning his bachelor’s degree in financial economics and a minor in writing, rhetoric, and technical communication. Combining his education, CERTIFIED FINANCIAL PLANNER™ designation, and passion for serving others, Cooper consistently delivers in his mission to educate and empower the next generation. 

Cooper resides in Bon Air and often frequents his hometown and large extended family in Northern Virginia. He is an avid outdoorsman and semi-professional angler; always on the prowl for his next adventure. To stay active, Cooper enjoys playing basketball with friends daily and is a lifelong Boston Celtics fan. 

What do you enjoy most about being a team member of Ray Olson, LLC? From the day I walked in the door I felt welcomed and part of the team. It may be cliché to say, but we truly are a big family here to support one another and those we serve.

What’s the best advice you’ve ever received? It’s okay to ask for help sometimes. Leveraging resources and personal connections demonstrates maturity, not weakness.

What is your favorite quote and why? “The best way to measure your investing success is not by whether you’re beating the market but by whether you’ve put in place a financial plan and a behavioral discipline that are likely to get you where you want to go.” – Benjamin Graham

Reading Benjamin Graham’s renowned text, “The Intelligent Investor” at an early age laid the foundation for my investment philosophy and passion for helping others achieve their goals; in lieu of idolizing flashy numbers.

When you are not at the office, you can often be found doing what? Exploring a new body of water in my boat, catching a few fish, and enjoying the subtleties nature presents.

For what in life do you feel most grateful? There is nothing I value more than my family. I am extremely blessed to be a member of the Casillas family and all the joy, laughter, and goodness each member (of 58) presents.

What is your favorite place in the world and why? Eagle Lake, a hidden gem in the mountains of Northern California, will always be a sacred place to me and my large extended family. I will always cherish the memories and adventures that helped ingrain values into my younger self and shape me into the man I am today.

If you could spend the day with anyone, who would it be and what would you like to learn? Bill Russell. As a diehard Boston Celtics fan, I’m in awe of his accomplishments on the basketball court and 11 championship rings, but I’m even more impressed with his character, demeanor and perseverance. He broke down racial barriers, served his community, and remained true to himself his entire life. A day with him would surely be full of epic stories, life lessons, subtle humor, a fountain of basketball knowledge, and result in an immense amount of gratitude on my end.

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