About our Firm

Here’s our story. We look forward to hearing yours.

Meet the Sherpa Financial Guides, Inc. Team

At Sherpa Financial Guides, Inc., we work with you to pursue your retirement goals. Our job is to be on the lookout for the best solutions that we can bring to you, search for the best available pricing and services and offer a holistic approach to your investment and retirement planning.


David J. Cunningham, ChFC President and CEO

David Cunningham has over 35 years of experience helping clients work toward their retirement dreams through a well-thought-out strategy for retirement income.

David got his start in the industry as a stockbroker and licensed insurance professional. He also served in the tax department at a financial services firm and as a senior loan officer for Cardinal Mortgage, Inc. David truly enjoys helping clients design financial strategies for wealth accumulation, risk management, and cash flow and budgeting.

David has passed the Series 63 and 66 securities exams and holds insurance licenses in Virginia and Hawaii. He earned his Chartered Financial Consultant® (ChFC®) designation in 1990. David has a Bachelor of Arts in psychology from Lafayette College in Easton, Pennsylvania, and completed postgraduate studies in wealth creation and planning from American College.

An active member of his community, David has served in leadership roles at his church and for the Haddon Heights Business & Professional Association in New Jersey. He also has had leadership positions with the Virginia Rockfish Valley Ruritan Club, the Nelson County Community Development Foundation and the Rockfish Valley Community Center, of which he is a founding member.

In his free time, David enjoys spending time with his wife and business partner, Mary, and two grown children, Benjamin and Sami. He also enjoys tennis, ping pong and golfing, as well as farming and playing the piano.

David and Mary live and work in Afton, Virginia, in a unique eco-home they designed and built in 2000. The couple’s 7,000-square-foot home’s exterior walls are entirely built out of straw bales to make the most of the walls’ thermal insulation qualities. The home captures the free resources that the Earth provides, including a geothermal constant 55-degree Earth temperature and passive heat from the sun — which has slashed their utility bills by more than half. The other half is photovoltaic roof panels delivering all electric power needed to the home and office.

Financial efficiencies are the hallmark of Sherpa Financial Guides, Inc. Through careful portfolio, tax budgeting and life goal planning, the best future is imagined and implemented, now, when we have the most planning flexibility.

"Of all the issues, money is the one that changes the fastest from any degree of increased clarity."


Mary S. Cunningham, MSDirector of Client Services

As the Director of Client Services of Sherpa Financial Guides, Inc., Mary Cunningham is focused on helping clients navigate and make connections to new information provided through financial planning.

Mary works directly with families to support college planning and help families prepare college funding strategies. She provides outreach to all our clients to stay in touch and plan annual review meetings for follow-up with updates that address questions and concerns.

Mary has spent more than 25 years in a variety of fields, including financial services; health care; pharmaceutical development; and adult education, training and development. She has a Bachelor of Science in business from the Wharton School of the University of Pennsylvania and a Master of Science in adult education training and development from St. Joseph's University in Philadelphia, Pennsylvania.

Mary was elected to the Nelson County School Board from 2010 to 2014. In 2012, she served on the Virginia School Board Association Board of Directors and represented Virginia's Central Region as chairman. Currently, she serves on the Board of Directors for the nonprofit Rockfish Valley Community Center.

Mary and her husband, David, have two grown children, who, thanks to planning and preparing family finances, gained maximum scholarship opportunities providing for their college education.


Tom GrinnellChief Investment Officer

Tom Grinnell has over 15 years of experience assisting clients with all aspects of their financial needs. As the Chief Investment Officer of Sherpa Financial Guides Inc., Tom brings his investment philosophy of using proven money managers and continually monitoring those managers, so the client always has best- in-class management. Tom believes in using both active and passive money management in the pursuit of a client’s long-term risk adjusted return, while employing true diversification with little to no overlap between those managers.

Tom started his career as an Advisor with AXA Financial in North Carolina where he helped clients construct a plan for their financial needs, then monitored and adjusted those plans so they stayed on track to fulfill their retirement dreams. Over the last 14 years, Tom was with BBT Investments Services in Charlottesville where he expanded his knowledge in all aspects of financial planning and money management. Tom enjoys helping clients understand their complete financial picture, understanding the risk inherit to that financial picture, then implementing a plan to minimize those risk in order to achieve their goals.

In his free time, Tom enjoys family time with his wife, Betsy, son Owen and daughter Maggie. Tom is an avid outdoors man, enjoying any activity that takes him out into the tranquil beauty of nature. If he is unable to get outdoors, he enjoys wood working, and loves amateur woodturning.

Tom and Betsy currently live in Crozet, where they have lived for the past 15 years. Both Betsy and Tom grew up in the Charlottesville area and were very excited to return to the area after living in Raleigh North Carolina for about 12 years, while Tom was attending NC State University and Betsy was teaching.

Tom is very excited about being a part of Sherpa Financial Guides, Inc because of the holistic team approach that the firm takes regarding their clients. Helping the client build a solid retirement vision, then guiding them along the way, while always providing the perfect client experience, is the vision of Sherpa Financial Guides Inc. team of professionals.

Schedule a Meeting

To schedule a time to discuss your financial future and the possible role of investments and insurance in your financial strategy, contact us at Tom@SherpaFinancialGuides.com or call us at (434) 987-1198 today!

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