Please read our bios to learn more about us.


At Ray Olson Family Financial Planning our experienced professionals have helped many people just like you with similar issues and concerns. We specialize in creating an approach that is designed to address
your individual situation.

Please read our bios to learn more about us.


Ray Olson, Jr.

President and Owner

What’s the best advice you’ve ever received? In business, concentrate on doing one thing extremely well and master it. Don’t get sidetracked by other businesses unrelated to yours.

What is your favorite quote and why?
“Investor Returns = Investment Returns - Investor Behavior.”
— Warren Buffet

This is probably the best and simplest summary of investing. We like to say that “We’ve solved the investment problem, but not the Investor problem.”

When you are not at the office, you can often be found doing what? JMU football, being active outdoors, especially Wintergreen skiing & hiking, golfing and tennis. Indoors, I enjoy playing the guitar and binge watching some new show.

What is your most treasured memory? Meeting my wife Cammie on the beach at the Outer Banks!

For what in life do you feel most grateful? How fortunate I am to live the life I have while others in this world are not so lucky. And for my family — Cammie, Stephanie, and Julia.

If you could spend the day with anyone, who would it be and what would you like to learn? John F. Kennedy. I always looked up to him since I was a boy during the Civil Rights Era. I’d want to know what advice he could impart on leadership as well as working and caring for others who are different from you.

Why do you do what you do? I love helping people achieve their different dreams. With my background I get so excited putting those skills to work to help them map out an individualized plan. While, I have always loved investing, I have learned that it requires much more than building portfolios. I have a deep level of caring and enjoy problem solving, I actually prefer listening to talking, and find great satisfaction in helping others succeed in life.

Review Ray's Education and Work Experience on LinkedIn »

Ray has been featured on the Admired Advisor Podcast and quoted in the Wall Street Journal.

Cooper Casillas

Wealth Advisor
Director of Next Generation Planning

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, demeaner 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.

Kathryn Winfree

Senior Client Service Associate
Kathryn Winfree

What do you enjoy most about being a team member of Ray Olson, LLC I really appreciate the family atmosphere of the company. I immediately felt welcomed and part of the team right away and love the way we work together to help clients.

How are your personal qualities reflected at work? I am very task driven and like to check things off a list. I bring that into my work so that I don’t forget to do things and make sure it’s done right the first time. I am also very organized and like things neat and kept that way. I bring that into work by having a place for everything and not keeping unnecessary things.

When you are not at the office, you can often be found doing what? Spending time with my husband and daughter. I also enjoying running and run several races a year.

What is your favorite quote and why?
"And in the end the love you take is equal to the love you make."
— The Beatles

Because it helps me value each day as you may not know if it’s your last; life is short so live and love fully every day.

For what in life do you feel most grateful? I am most grateful for my husband and daughter. Family and making great memories are very important to me.

Kathryn joined our group in 2016, she spent the prior ten years working at Wells Fargo supporting three financial advisors. Kathryn has received an Associate of Applied Sciences degree in Computer Networking.

Cammie Olson

Director of Marketing and Co-Owner

What is your favorite quote?
"When you change the way you look at things, the things you look at change.”
— Wayne Dyer

What is your most treasured memory? When Ray proposed to me. We met at the beach so he recreated the beach on his back deck... sand, a CD playing ocean sounds, a baby pool filled with water. My engagement ring was on a flipper in the pool.

What professional achievement are you most proud of and why? Earning the Series 7! It is an incredibly intensive exam requiring months and months of preparation and I was working full time and pregnant with our second daughter when I became licensed.

If you could spend the day with anyone, who would it be and what would you like to learn? My father, John Geoghegan, who died in Vietnam when I was six months old. I want to know simple things - how he walked, how he talked, what kinds of food and music he enjoyed. Did he like dogs? Have I made him proud?

For what in life do you feel most grateful? Being a wife and mother.

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Robin O’Sullivan

Marketing/Events & Client Service Coordinator

What do you enjoy most about being a team member of Ray Olson, LLCI love how everyone has their own strengths and talents. This team is so welcoming and supportive as I have been learning the ropes. Everyone brings something different. We also have great clients. The relationships created are so different from most corporations of today. Ray has a big heart, and you can see his desire to help others in everything he does.

What’s the best advice you’ve ever received? It’s ok to not be ok. I think we get wrapped up in trying to be ok so we don’t offend others, or make them uncomfortable. But there are times when we aren’t ok, and that is perfectly ok. Sometimes you don’t need to be fixed, you just want someone to sit with you in your brokenness until you are ready to move forward in whichever way you choose.

When you are not at the office, you can often be found doing what? At the moment we are in the busy season with our kids. They participate in many activities but still need to be driven around, soccer, pole vaulting, and scouts to name a few. However, when I get a free moment, I enjoy spending time with my friends, trying out new restaurants, participating in a bible study, or just going for a walk. I love adventures, from backpacking in the Appalachian Mountains to renting an RV for the weekend and going to the lake. During the colder months, I prefer going to the movies with the family or sitting on the couch crocheting by the fire.

What is your most treasured memory? When I was in high school, my mom and her sister took us out of school for the week of Thanksgiving to go to Disney World. We didn’t have much, so this was a splurge for our mom. It was also the last vacation we went on as a family before my sister went off to college. My mom hated roller coasters but for some reason went on Space Mountain with us. She sat behind me and held the back of my head the whole time to keep it from getting shaken around too much. We had lots of laughs on that trip, and everything just felt magical.

What is your favorite quote and why?
“But they that wait upon the LORD shall renew their strength; they shall mount up with wings as eagles; they shall run, and not be weary; and they shall walk, and not faint.”
—Isaiah 40:31 King James Bible.

In my youth I attended a church camp in the mountains, and there was a camp song based on this verse. It always reminded me that I’m not alone, and I don’t have to try and do everything myself. When I’m at my weakest, I can give it all to Him and He will carry me. I also like the idea of flying with wings of an Eagle.

For what in life do you feel most grateful? My husband. I should explain first that he is an introvert and realist, and I’m an extrovert and dreamer. He goes along with most of my shenanigans and isn’t afraid of whatever next big adventure that I plan for us. He keeps me grounded but encourages me in my hobbies and interests. He works hard so we can have a good life. The kids and I wouldn’t be the best versions of ourselves without his patience and leadership.

What is your favorite place in the world and why? The beach. I love listening to the ocean, smelling the salty sea air, and feeling the sun on your skin. Being outside is key for me. Things just feel calmer when you are in nature.

Why do you do what you do? When I read the expectations for this position, I felt like it was made for me. I love people and I love a good event. We have great clients, getting out of the office at an event gives me the opportunity to get to know each a little bit more. I also enjoy seeing connections being made between clients and hearing about shared interests.

What professional achievement are you most proud of and why? I know being a mother isn’t a profession, but I do feel very proud to raise two stubborn, smart, and independent children. But I also loved when I worked at Benedictine during their 100-year celebration. We held a birthday party at the school, full of military artillery, music, and educational displays. I learned so much about our graduates who came back to participate. I loved hearing their stories of going off to war right after high school. It really humbled me listening to what they had to go through at such a young age. We even had old news articles celebrating some of their achievements. Everyone seemed to have a great time.

If you could spend the day with anyone, who would it be and what would you like to learn? My mom died suddenly in 2019. She was typically a quiet person, and I had always done all of the talking when we were together. After spending time with her after a surgery she had, I asked her questions about herself and tried to listen more. I didn’t realize I only had a few more days with her at that point. If I could spend more time with her, I’d just sit and listen. I’d want to know what life was like for her growing up, raising us kids on her own, and her favorite memories.

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Working Together

With the many demands on your time and the complexities of the financial decisions you face, the comprehensive wealth advisory approach we provide can help make a real difference, both for your family and your business.

Team of Experts

We understand that your investment portfolio is only one aspect of your whole financial picture, which is why we work with a team of experts, including your CPA and Estate Attorney, to determine the most beneficial course of action and strategy for all of your wealth needs. And if you don’t have a CPA or Estate Attorney, we can help you find the right one, based on your specific goals.

We also work with Third-Party Administrators, Custodians, Record Keepers and other professionals in order to help meet all of your retirement plan needs.

It is our goal that by having a team of experts working closely together, we maximize the effectiveness of your plan to help ensure that it stays in synch, with every item properly addressed.

Comprehensive Approach

In order to help you maximize your potential for success in all areas of your financial life, we focus on these important areas:

Wealth Enhancement

This process can be key to creating and maintaining your financial comfort. It can include:

  • Managing resources and your portfolio
  • Tax planning and tax efficiency issues
  • Personal savings
  • Simplifying your financial life
  • Education funding

Wealth Transfer

Proper estate planning is the most effective way to help ensure that you are able to provide for the financial health and well-being of your family. It also can reduce or prevent much of the stress that so often occurs when heirs attempt to sort out a family member’s estate.

Charitable Giving

We help you fulfill any philanthropic goals you might have and maximize the effectiveness of your charitable legacy.

Wealth and Income Protection

We work to ensure that your wealth is protected against catastrophic losses, an extended illness or disability and identity fraud. Business owners might also want to consider strategies to protect their wealth and the value of their businesses.

Retirement Plans

We also offer a comprehensive range of retirement plan solutions, from 401(k) plans to profit sharing plans, defined benefit plans and many other qualified plan types, we provide the options you need and the guidance you deserve. This means we can help you plan for — and enjoy — a more secure retirement, both personally and professionally.