Breaking Ground for African American Financial Advisors, Charles Winfrey Finds His Niche with ‘The Rollover Company”

by LP Green, II

Proud to be among a small but growing number of African-American financial advisors throughout the U.S., Charles Winfrey boldly launched his firm The Rollover Company in Brentwood, Tennessee at a unique time in the country’s financial history.

When most people think of 2001, images of 9/11 come to mind, but even before the Towers fell, the stock market was going through a time of major correction. The dotcom boom of the late 90s created a euphoria where millions of people thought they could retire comfortably. But with the tech/dotcom bust, the economy soon shifted downward. In 2000, the market dropped nine percent and in 2001 another 14 percent. As companies trimmed their payrolls, the employees that received early retirement packages were clueless about what they could do with their money.

Winfrey, a graduate in Finance from the University of Memphis, had interned throughout college as a personal banker with First American Bank in Nashville and Memphis, established himself as a financial advisor at John Hancock Financial Services from 1999-2001.

Increasingly frustrated by his inability to offer objective advice and customized plans to clients – a scenario he termed “commoditization over customization” – he saw a powerful opportunity to help pre-retirees and retirees build, protect and preserve their assets via a concept called “rollover.” Winfrey learned early on that those who were most successful in the financial world were specialist rather than generalist and considering his young age, he felt that having a singular expertise would be to his advantage.

A rollover is the process of moving one’s retirement savings from a retirement plan at work (401(k), profit-sharing plan, etc.) into an Individual Retirement Account (IRA). Rolling over to an IRA within 60 days allows investors to keep their savings tax-deferred and typically gives them a broader choice of investments.

As Founder/CEO of The Rollover Company, Winfrey has done estate, income and investment planning to help clients accomplish four things: preserve their capital, increase their income, avoid estate taxes and protect their estate values. Both of his parents were lifelong educators, so working with soon-to-retire and retired teachers was a logical foundation for him to build a clientele on. But he has also advised physicians and business owners approaching retirement, as well as retired employees of AT&T, NES, General Motors, Nissan, HCA, Vanderbilt, Ford, Bridgestone and many others.

Those who have worked with Winfrey have achieved lower tax bills, eliminate taxes on their social security income, increase their fixed monthly income and obtain better protection for their financial future. Working with a clientele of predominantly (but not limited to) African-Americans in his home state of Tennessee as well as North Carolina, Georgia, Texas, Virginia, Alabama,Colorado, New Hampshire, Pennsylvania and Maryland, he has counseled hundreds of people on how to avoid the common investment mistakes made by most retirees.

The Rollover Company’s website includes the following declaration: “Some financial advisors focus only on helping you accumulate assets. Your accountant looks back as of December 31st to help you pay your correct tax bill. Our job is to help you look forward and cut future tax bills, and help you avoid financial problems in your retirement years and your estate plan.”

Winfrey has shared his vast financial knowledge in a variety of media platforms. Starting in 2005, he began hosting “The Charles Winfrey Show” on Nashville’s 760 AM (WENO), The Gospel. Nationwide, Winfrey is best known as the author of the 2013 book Seven Secrets To Financial Success. In the book, he offers encouragement to those who may feel that their life circumstances have left them in a hopeless financial rut. He busts the popular myth that tells people of a certain age that they have to earn six figures to retire wealthy, adding, “what your CPA, attorney and financial advisor may have missed can cost you thousands of dollars per year.”

As on his radio show, Winfrey’s book covers key topics like retirement, personal, business and estate planning, budgeting, emergency savings, life insurance and investing for college tuition. He is currently writing a follow-up book, 52 Weeks to Financial Success, for release in early 2015.

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