By Anne Field

Winston Justice, 40, spent nine years as an offensive tackle, playing for the Philadelphia Eagles, Indianapolis Colts, and the Denver Broncos. But he always knew he would need a second career. While still playing football, he got an M.B.A. in finance and ended up leaving the field to become a financial advisor.

Justice is now CEO of SageSpring Private Wealth, a part of SageSpring Wealth Partners, in Nashville, Tenn. Justice spoke with Barron's Advisor about his football career, how he decided to make finance his second act, and the lessons from the field that he applies to the business of financial advice and planning.

When did you start thinking about switching from football to finance? I was drafted by the Eagles in 2006. But I saw a lot of people getting cut and realized I needed to prepare for a life after football. I didn't want football to be the best time in my life. I wanted to keep growing.

When I started thinking about what I'd want to do, finance and investing seemed interesting. But I wanted to be able to hit the ground running. So I went back to school to get an M.B.A. with a major in finance at The George Washington University.

While I was still with the Eagles and in business school, I reached out to successful athletes who I knew were successful after they stopped playing. I ended up starting a small venture-capital firm that focused on healthcare and education with one of the people I connected with. We ran that firm from 2010 to 2016.

After playing for the Eagles, I was traded to the Colts for one year and then to the Broncos for two years. Then, there weren't more opportunities for me on other teams. That's when I decided I really needed to make my transition.

What was your first role in finance? My early jobs weren't client-facing. First, in 2014, I was at Wells Fargo where I worked with an advisory team, preparing for client meetings, creating decks for portfolio managers, and analyzing different strategies. It was a really good learning opportunity. After that, I had the chance to do something different, joining a hedge fund of funds at a company called Pacific Income Advisers. They invested in multiple strategies for institutions, foundations, endowments, large family offices, focusing on low-beta strategies to bring down the volatility of the portfolio.

My next move was client-facing. That was at AllianceBernstein, where I helped lead a team that managed assets for small institutions and foundations, like a local YMCA or a private family foundation. Plus we worked with family offices with leaner staffs that outsourced a lot of functions to outside firms. We interacted a lot with the families, and that grew into working with high-net worth people who were exiting a business. We helped them before the sale to get the most out of the sale and then on transferring knowledge and values to the next generation. There are a lot of dynamics wrapped into a family business.

What were some of those dynamics? The biggest thing I learned was we were in a sacred position. We could really help a family achieve their financial goals and achieve goals they might not have even thought of. Like, how do you want your wealth to express your family values? It was more of a holistic relationship than just portfolio management. Those lessons were a foundation I brought with me to Sage, where I am now.

What specific family experiences stick in your mind? We had a family with a really large business started by the father. There were three kids, two were involved in business and the third wasn't. There was always a tension between the siblings who were part of the business and the one who wasn't. We held many sessions with the family on the best way for family members to communicate with each other.

When they ended up selling the company, we worked with the family to structure the business in a way that allowed them to get the most out of the sale in terms of taxes. Then we worked with each family member because they had an influx of capital. The father needed to find a purpose after running the business for so many years. I could relate to that personally. He guest lectured at his alma mater and created a scholarship that allowed the family to be active participants in the giving. He also started a private family foundation that allowed the family to get together and work on a common mission.

What have you done at Sage? In 2024 I moved to SageSpring Private Wealth. We developed a platform for family offices serving ultra-high-net-worth clients. We also developed an investment platform for our advisors to create portfolios for their clients. Most of the advisors on our platforms have grown and gained new business organically. But we recently acquired one firm in Orlando and we're working on more acquisitions this year.

Have you drawn on your football experience in your financial work? As an athlete, you have to be able to be flexible, work under immense pressure, and work with different types of people. In the wealth profession, you also need to be flexible in terms of how you serve your clients and how you work with people who might have different backgrounds from your own.

Another big lesson is working through failure. It's going to come up with any high-pressure job. In sports, if you lose a game, you can always look at the film and try to do better. You can do the same thing in business. If, say, we lose an employee, we can think about what we can do better in the future. If we don't meet a certain goal in a quarter, we need to see how we can improve. And if we beat our numbers for the quarter, we focus on using that experience to continually get better.

What was toughest about transitioning from football to a very different profession? Any transition is going to be hard. But just because it's hard doesn't mean it's bad. A lot of growth happens. And when you grow in a field you also grow as a person.

It's hard not to find your identity in what you do. But you need to make every effort not to have your identity be tied to your work. The hardest part of changing a career is losing a part of yourself. But you learn it's OK not to have all the answers. It's OK to be uncomfortable. That's hard to do if you're a high performer. You can't have the same success at first.

Thanks, Winston.

This content was created by Barron's, which is operated by Dow Jones & Co. Barron's is published independently from Dow Jones Newswires and The Wall Street Journal.

(END) Dow Jones Newswires

August 26, 2025 16:36 ET (20:36 GMT)

Copyright (c) 2025 Dow Jones & Company, Inc.