Charles Winfrey and Associates
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1900 Church Street
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Nashville, TN 37203

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His 15 Years Helping Pre-Retirees and Retirees Leads The Nashville Entrepreneur To Multi-Media Platforms As A Radio Host And Author Of "Seven Secrets of Financial Success"

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 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 “product pushing” 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.

“Many financial advisors want to be that one stop shop for everyone, but I didn’t feel that was the right path for me,” says Winfrey, who maintains his original office in Brentwood but whose main location is Nashville. “As I noticed my clients were getting older, our firm shifted our focus from general financial planning to retirement income and estate planning.” 

As founder and 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 found that they lower their 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.

As stated on the home page of The Rollover Company, Winfrey believes that the key to taking that first step for any client is not about making a choice of investment products, but discovering their true desires and needs. A plan should be built first, before choosing such products. The firm offers a simple, easy to understand 3 Step Review to help prospective clients get a handle on these needs and desires and to determine if their current strategies match well with their personal concerns and financial situation.

The page also lists five critical questions that Winfrey believes people should ask any financial advisor to help determine if they need further review of their plan. “One of the unique aspects of this business is helping people transition from what I call ‘emotional’ planning to ‘logical’ planning. When people invest based on emotions, they’re open to a lot of misconceptions that these critical questions are designed to break through. I want to help them filter these myths and misconceptions with the reality of their planning process.”

One key paragraph sums up how The Rollover Company is different from other financial firms: “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.”

Over the years, 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 as a weekly hour program with another advisor who worked out of his office. Winfrey later did the show solo and shortened its length to half an hour for its longtime slot of Tuesdays from 12:30 – 1 p.m. He is currently shopping for a new radio outlet.

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 that “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. The “Seven Secrets” are designed to give people the courage to undertake some important tasks that can change their life. These include changing your spending habits; overcoming the need to keep up with the Joneses; understanding the difference between wealth and income; resolve to be and remain debt free; accept financial responsibility; generate income from multiple streams; and of course, education!

He is currently writing a follow-up book, 52 Weeks to Financial Success, for release in early 2015.

“All of these endeavors are an outgrowth of the need that people had that inspired me to start The Rollover Company,” Winfrey says. “These people would get their 401(k) s and then didn’t know what to do with that money now that they were moving from the accumulation to the preservation stage of their lives. It all starts with helping them avoid the penalty by rolling it over. The next step is finding ways to have income in retirement. So we not only help them with moving money over and preserving it, we are also targeting more guaranteed or safe retirement plans. We teach them how to take their money out in the most tax efficient way and that will last them for their entire life. Our strategies are geared towards giving them lifetime income on an individualized basis.”

That said, Winfrey offers the following clarification: “We don’t offer cookie cutter solutions but there are similarities in the mix of products we recommend to our clients. But everyone receives an individual customized plan based on their goals and objectives. And this may go without saying but we only want to work with people we connect well with and who are open to the information and services we provide.”

The leap of faith Winfrey took in leaving John Hancock and exercising every last bit of credit he had to start The Rollover Company reminded him of a time several years earlier when he came to a similar career crossroads. When he graduated college and completed his internship, the bank offered him a paid position. Because he felt the offer was insultingly low, Winfrey was the first person in his position to ever turn it down. His parents thought he was crazy to give up a guaranteed salary with benefits for a commission based position, but ultimately his success at John Hancock paved the way for him to venture out on his own.    

“John Hancock provided an office, a desk, just about everything I needed to work with clients,” he says, “and here I was again starting from scratch, renting office space, buying equipment, printing business cards and letterhead. There are so many things involved in starting a firm that you take for granted.”

Although Winfrey had to agree to a “non-compete” clause as part of his leaving John Hancock, he could work in his fledgling firm with clients who left the company voluntary. Very comfortable working with educators, he aggressively began arranging meetings with teachers in local schools – but the biggest boon to establishing The Rollover Company was radio marketing and free workshops in the Nashville area.

Figuring he could only reach so many schools per day, and acknowledging that most teachers didn’t want to meet with him on weekends, he invested in on air commercials which advertised both his services and his seminars. To his happy surprise, 150 people registered for his first event in 2002 called “Women, Wisdom and Wealth” at the Renaissance Hotel in Downtown Nashville. When he heard a local mortgage broker doing his own radio show, Winfrey called him and said he needed a mortgage broker to refer business too. The broker invited Winfrey to appear on his show, and Winfrey started his own program two weeks later. 

Though there are many facets to the array of services he offers, the overall goal that Winfrey hopes to achieve for any client of The Rollover Company is to protect the money that his clients have already earned and create lifetime guaranteed income for them and their heirs. “Everyone wants to maintain the same lifestyle they had when they were working and when we implement a plan and they see that this is possible, they’re very happy,” he says. “It’s all about having a business of integrity that offers people true peace of mind during their retirement years.”

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