Meet The Team

Richard "Skip" Fleming is the founder of Lodestar Financial Planning, a financial planning practice providing hourly, as-needed financial planning and advice in Colorado.

Skip provides financial advice and coaching to individuals and their families from all walks of life. He does not set minimum income or net worth requirements to engage in his financial planning, investment consultation, or portfolio review services.

A graduate of Virginia Commonwealth University with a Bachelor of Science degree, Skip is a CERTIFIED FINANCIAL PLANNER™ professional. He has been in the financial services industry since 2002, following a 24-year career in the United States Marine Corps.

As an Advisor, Skip is committed to guiding his clients in pursuit of their financial goals by bringing sound financial knowledge and trustworthy advice to the individuals and families he serves. His areas of focus include:

  • Broad-based financial planning
  • Financial foundation planning and coaching
  • Insurance planning
  • Retirement income planning
  • College planning
  • Investment allocation and advice
  • Military and Federal Employee Benefits
  • Special needs planning

The father of a special need’s young adult, Skip volunteers as a ski instructor with the National Sports Center for the Disabled and as a ski coach with the Special Olympics of Colorado. Understanding the concerns of families with special needs and the importance of coaching, he applies that understanding by guiding his clients toward productive, lifelong financial habits.

Skip is a former board memebr for Early Connections Learning Centers and the Financial Planning Association of Southern Colorado. He is a member of the Marine Corps League, and the Military Officers Association of America. Skip is also a member of the Professional Ski Instructors Association of America.

Married for over 39 years with two children and twin grandsons, Skip enjoys spending time with his family in the beautiful mountains of Colorado; skiing, biking, hiking, and fishing.

Skip offers a free, no-obligation initial phone call where you can discover for yourself if his services are right for you.

As the son of a bush pilot, David spent a unique and exciting childhood overseas in Africa and Haiti. After returning to the United States, he decided to pursue a career of adventure and service and earned an appointment to the United States Military Academy at West Point.

Upon graduation, he was assigned as an officer in the United States Army where he served a successful and rewarding career as an Armor Officer, commanding Soldiers at all levels from Platoon to Battalion, including four combat tours in Iraq and Afghanistan. During his military career he also served at the Department of State in Washington D.C. and the North American Aerospace Defense Command (NORAD) in Colorado Springs, giving him a broad and unique insight into the Department of Defense and Federal Service.

In 2014, at only 4 months old, David’s youngest son was diagnosed with a severe and catastrophic form of epilepsy called Dravet Syndrome. Through the struggles of caring for a medically fragile child, he was forced to learn how to navigate the complexities of coordinating insurance, government benefits, and the many financial pressures facing parents of children with disabilities. His passion for solving these tough problems eventually led to his pursuit of a financial planning career where he could continue serving others while capitalizing on his many experiences.

David has earned a Bachelor of Science degree from the United States Military Academy at West Point and a Master of Arts in Economics from Vanderbilt University. He is a proud veteran and special needs parent and lives in Colorado Springs, Colorado with his wife Whitney and sons Avery, Bennett, and Hugh.


  • BS, United States Military Academy at West Point
  • MA, Economics, Vanderbilt University


  • Series 65, Uniform Investment Advisor Law

Competent, Trustworthy, and Affordable advice
for the rest of us.

Let's Get Acquainted

We offer a complimentary "Get Acquainted" meeting to describe our services, and to see if our services are right for you.


  • Phone:
    (719) 685-0600
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1880 Office Club Pointe, Suite 1800
Colorado Springs, CO 80920

Investment advisor representative of and investment advisory services offered through Garrett Investment Advisors, LLC, a fee-only SEC registered investment advisor.
Tel: (910) FEE-ONLY. Lodestar Financial Planning may offer investment advisory services in the State of Colorado and in other jurisdictions where exempted.

Certified Financial Planner Board of Standards Inc. owns the certification marks CFP®, CERTIFIED FINANCIAL PLANNER™, CFP® (with plaque design) and CFP® (with flame design) in the U.S., which it awards to individuals who successfully complete CFP Board's initial and ongoing certification requirements..
Most of the great photographs used on this site were taken by professional photographer and neighbor Rowedean Doss, and are gratefully used with her permission.
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