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Linebacker-Turned-Advisor Reggie Wilkes 'Taking Deep, Happy Breaths of Satisfaction'

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How do pro football players pass the offseason? Huddling with their honeys? Kicking back with a book? Jumping on a paddleboard? Working at a wirehouse studying for their Series 7 exam?

That last one would be a surprise — but it’s exactly what Reginald “Reggie” Wilkes, former 10-year NFL linebacker with the Philadelphia Eagles and Atlanta Falcons, chose to do. In an interview with ThinkAdvisor, he tells his unusual story.

Today, at 64, Wilkes is a 32-year veteran financial advisor and senior vice president helming The Wilkes Sports Group at Janney Montgomery Scott. Assets under management: more than $200 million.

The most recent addition to the Bryn Mawr, Pennsylvania-based team is Marques Colston, a former 10-year NFL wide receiver and New Orleans Saints Hall of Famer.

The Wilkes Group’s clients are top NBA and NFL players and their families, as well as team coaches and physicians, attorneys and business owners.

As a pre-med student playing football at Georgia Tech, Wilkes was committed to becoming a physician. Playing professional football was “the last thing on my mind,” he recalls in the interview. 

But his plans for a career in medicine were shelved during senior year, when he was drafted by the Eagles.

In the offseasons, he worked at Merrill Lynch. That’s when he decided that financial advisor would be his post-retirement profession; in 1988, he indeed kicked off that second career. At Merrill, he was soon running The Wilkes Group. After a decade with the firm, he left to launch a venture capital fund, Safeguard Scientific.

In 2008, he returned to Merrill for a second decade at the wirehouse, which he found entirely different from the first. He describes how in the interview. In 2017, he joined Janney.

Part of the conversation was devoted to what Wilkes says are similarities between working the gridiron and managing money. He also talks about the pivotal role that former NBA champion Rasheed Wallace played in his career.

Wilkes, a native of Pine Bluff, Arkansas, who was raised in the South, is a minister’s son; his grandfather was a bishop of the African Baptist Church. When he was growing up, his mother worked at a university as its director of financial aid.

ThinkAdvisor recently interviewed Wilkes by phone. Speaking from the Philadelphia area, he offered his recommendation for what firms can do to expand advisor diversity. Though he personally has suffered no racial discrimination in the industry, he revealed his long-ago discomfort as the only Black person in the room at FA incentive-trip cocktail parties.

Here are highlights of our conversation:

THINKADVISOR: Was it your dream to play professional football?

REGGIE WILKES: That was the last thing on my mind when I was a pre-med student at Georgia Tech. But I liked football and played it in college. In my fourth year, scouts started coming around; I was drafted by the [Philadelphia] Eagles as their first pick. I felt that football was a means to an end because I didn’t want to be a financial burden on my parents.  

While you were playing pro football, offseason you worked at Merrill Lynch. What prompted you, later on, to make financial advisory your second career?

Over time, I saw that a lot of my former teammates had squandered the money they made in successful second careers. I heard such horror stories about players getting taken advantage of by organizations that didn’t have a separation of services, such as agents who were financial advisors. I decided to go into finance, and Merrill Lynch helped me with that journey. They gave me a pathway.

Do your athlete clients seek your services at the start of their career or, regrettably, after they’ve lost much of their money?

Both. I have recent draft choices in football and basketball, and clients who want a fresh start and come based on word-of-mouth. Their experiences with other advisors may not have been mutually beneficial. I’m being careful with my words here!

What do most of your athlete clients need help with the most?

Basic, fundamental planning. I advise them to think about the end at the beginning and to prepare. The same strategy works for doctors, lawyers and other professionals that we serve: We talk about the plan at the very beginning — what their goals and objectives are and asset allocation. They’ve got to tell us what they want in life.

What do you especially make clear to players?

A lot of athletes don’t understand fundamental things about proper asset allocation and diversification of investments — having different buckets for stocks, bonds, cash, real estate, alternatives, venture capital.

You stress that pro athletes, and others, need a financial plan. Please elaborate.

You shouldn’t invest money unless you’re having a discussion about your plan or completing one. If you do it right, it’s a beautiful thing. An athlete’s first goal may be to get to $10 million and then take time to enjoy life. Or, depending on the player, it could be $20 million or $50 million. They’ll accumulate money to invest properly to reach their goals, which may be to purchase their first home or help their parents or use it for their children’s education.

Are there any similarities between playing football and being an FA?

Many. Especially in the preparation, training and discipline of what you have to do to be successful. Both take a lot of study and analysis and making mistakes and overcoming mistakes. And, you have to work with a team.

What are the main things you keep in mind when investing clients’ money?

The discipline of maintaining liquidity, diversification and quality in the investment portfolio by staying up to date on the markets and trends and trying to look into the future without a crystal ball. 

Have you ever encountered discrimination or racism in the industry because you’re African American?

I honestly don’t think I have. I say that selfishly: People know me as a former athlete. So that’s helped. But there’s racial and sexual discrimination in the industry, and that’s unfortunate.

How should financial firms address racism?

You have to acknowledge that it exists. The first thing is to try to increase representation and retention of a diverse group of advisors and other employees. You’ve got to build an affirmative environment by building partnerships, for example. There are now many very successful women and a lot of people of color in the industry. You have to train people to understand that you can’t go up to someone and say the wrong thing.

What are some of the best places for firms to recruit Black advisors?

If you want to get good-quality candidates, it’s no secret that there’s a nationwide group called HBCUs — historically black colleges and universities. People are studying there who want to get into the industry. But once you get them in, you’ve got to figure out how to keep them in: Build an affirmative environment.

Where does that begin?

Put yourself in the shoes of others: Imagine being in a room where you’re the only African American. I’ve been on financial advisor elite trips, where you go to a cocktail reception and you’re the only [African American] there. People stare — you just want to hide. It’s not a good feeling until you get to know one another; and then it feels like, wow, we’ve been friends for 20 years! But someone has to cross that bridge, or you meet in the middle.

You had two 10-year stints working at Merrill Lynch. Why did you leave the first time?

To start my own venture fund, Safeguard Scientific. I started working with athletes. The first major one, besides former teammates and colleagues, was [former NBA champion] Rasheed Wallace. He was a lottery ticket in my fifth year! Rasheed and referrals from him led, over the years, to where I am today.

How did you like running your own firm?

The first couple of years, I was afraid to invest. I was scared to lose money for clients. It took me a while to realize that I was the one who was the educated advisor.

How was the experience of returning to Merrill in 2008 and staying till 2017?

No disrespect, but I longed for the Merrill Lynch I knew during my first 10 years there. It’s different now: Merrill is owned by a bank. Bank of America is a great company; but when I was at Merrill before, the advisors had a real big say-so in how the organization was run. Whatever you needed for the client, it felt like you didn’t have to ask. You knew they would accommodate you. The organizations now that are run by banks have a different mentality. There’s different oversight.

Why did you resign from Merrill to join Janney Montgomery Scott?

I knew the people here — they were [pursuing] me for a couple of years. At the end of 2017, I decided to bring my team here. Maybe I just thought it was time, and maybe it was the newness of doing something different with a different organization. I wanted that change. And I’ve been taking deep, happy breaths of satisfaction ever since. 

Do you market your practice?

I get referrals from existing clients: They say, call this player, call this parent. And I have a collaborative strategy with other professionals in the financial, legal and tax-planning businesses. I’ve been around for a while!

What do you like to do for diversion?

I love reading. I recently finished “The Great Influenza,” by John M. Barry. The 1918 pandemic was before they really understood viruses and how they work. And I’m a third of the way through “The Slave Trade,” by Hugh Thomas. I grew up in the South. It’s a [900]-page book, and I’m enjoying every chapter!

Where will you be enjoying the Super Bowl?

I’ll be with my family, watching it, probably, at our house. We usually have food. My son-in-law is a big football fan; so we’ll watch it all together — on a big screen, absolutely!

— More by Jane Wollman Rusoff on ThinkAdvisor: