Call Us

About Our Firm

The Rollover Company is an independent financial advisory firm serving clients throughout the country. Founded in 2001, we have developed our business by reaching out, nurturing and maintaining close, trusting relationships with each of our clients.

The Rollover Company

We’re committed to helping our clients build, protect and preserve their assets. We do this by providing guidance to help you develop an overall retirement income strategy, and offering a variety of insurance and investment products to help achieve the objectives of that strategy.

The team at the Rollover Company is here to help ensure that you receive all the assistance you need, not only in developing your retirement income strategy, but in maintaining it throughout your retirement.

Meet Charles Winfrey Senior Advisor

As the senior advisor at The Rollover Company, Charles Winfrey is focused on helping clients work toward their retirement dreams through a well-thought-out strategy for retirement income.

Charles got his start in the industry in 1995, working for First American Bank where he worked as a personal banker until he moved to John Hancock Financial Services in 1999. Then in 2001, after realizing there was a better way to assist those preparing for retirement, he started his own company. His business philosophy is simple: to help clients increase cash flow and net worth, while also minimizing the taxes they incur.

Charles holds life and health insurance licenses in Tennessee, Georgia, Mississippi, Alabama, Virginia, Texas and Maryland.  He has also received his Series 65 securities license. He has a Bachelor of Business Administration degree in finance from the University of Memphis.

He is a member of the National Association of Insurance and Financial Advisors (NAIFA) and has been recognized by the Nashville Business Journal’s Top 40 Under 40. He has used his financial acumen to assist the Lane College Board of Trustees and the local chapter of the Boy Scouts of America.

Charles was lucky to find love at an early age, as he married his sixth grade sweetheart, Nancy. Together, they have two children, Everett and Lauren. They reside in Nolensville, Tennessee.

In his free time, Charles enjoys travelling, writing, reading and spending quality time with his family.

Meet Nancy Winfrey President

Nancy A Winfrey is an accountant, wife, mother and president of The Rollover Company. She has served the Nashville community with her financial acumen for the past 16 years. Nancy is a native of Nashville and graduated with honors from Tennessee State University with a degree in accounting.

Nancy began her career as an accountant for Arthur Andersen, LLP in 1999, and later worked as an auditor for Ernst & Young, before serving as president and co-founder of the Rollover Company. Nancy has traveled throughout this country advising corporations and small businesses on how to effectively minimize their tax liability while maximizing their revenue. Nancy now uses that skill set in assisting pre-retirees and retirees in efficient tax management and income maximization.

Nancy is happily married to her groom, Charles, and they are the proud parents of their two gifted children, Charles III and Lauren Grace.


Please do not put off future planning

Retirement lifestyle is in your hands, but it will take planning to get you to where you want to be.
Hope is not a very reliable strategy, so if you want to own your future, you must begin to plan for retirement ... today.

We want to help. Please contact us by filling out the form below, or by calling us at 615-678-6603.

We can meet with zero obligation on your part. If you can invest one hour today for a Customer Care Needs Analysis discussion, we can place you on the path toward owning your tomorrows.

Request Customer Care Needs Analysis
Phone Number:

Investment advisory services offered through Brookstone Capital Management, LLC (BCM),a Registered Investment Advisor. The Rollover Company, Inc. and BCM are independent of each other.

The content of this website is provided for informational purposes only and is not a solicitation or recommendation of any investment strategy. Investments and/or investment strategies involve risk including the possible loss of principal. There is no assurance that any investment strategy will achieve its objectives.

Charles Winfrey and/or The Rollover Company are not affiliated with or endorsed by the Social Security Administration or any other government agency.

Any comments regarding protection and preservation of assets refer only to fixed insurance products. They do not refer, in any way to securities or investment advisory products. Fixed Insurance and Annuity product guarantees are subject to the claims-paying ability of the issuing company and are not offered by Brookstone Capital Management.