E20: Winston Justice Shares His Journey from NFL to Finance

Join Kris Benson and Alec Ogletree as they interview former NFL offensive tackle Winston Justice who opens up about his journey from an 8-year playing career to financial advising. 

Winston discusses lessons from his NFL days, entrepreneurial experiences starting a coffee shop, and feeling unprepared transitioning to finance. Winston also shares advice on relationships. Don’t miss his insights on serving clients as an advisor today on managing life after the game!

Here are some power takeaways from today’s conversation:

[02:53] The importance of being present - both in family and career

[10:29] Pursuing off-field opportunities through entrepreneurship

[12:37] Starting a coffee shop business with his brother-in-law while still playing

[14:07] Lessons learned from his experience in venture capital investing

[28:45] The sacred bond of trust in financial advising

[31:37] Facing imposter syndrome in finance

[34:51] Building community beyond the game

Episode Highlights:

[10:29] Pursuing Off-Field Opportunities Through Entrepreneurship

Winston became interested in pursuing opportunities off the field due to the uncertainty of an NFL career. He shares how starting a coffee shop business with his brother-in-law while still playing gave him enjoyment in working with family. It also provided a learning experience in entrepreneurship, such as figuring out operations without prior knowledge. Winston then discusses his experience partnering with former NBA player Jamal Mashburn in a venture capital fund focused on healthcare and education. He learned that to truly add value as an investor, he needed experience operating a business to understand management teams beyond initial pitches. This experience informed his decision to later pursue public market investing.

[28:45] The Sacred Bond of Trust in Financial Advising

Winston gets that advising people on their money is deep. While folks talk freely about other stuff, finances are sensitive. Doesn't matter how much money someone's got - they stay guarded about it. He knows gaining clients' trust to help plan their future means really listening without judgment. Winston sees being a part of people's lives through this financial advising bond.

[31:37] Facing Imposter Syndrome in Finance

Winston reflects on feeling unprepared when he began his career in finance at Wells Fargo despite his accomplishments in football. He emphasizes feeling like an "imposter" when walking into rooms of highly educated professionals. However, he persisted because he knew what he wanted to do. Winston also emphasizes the importance of building relationships with teammates while playing to maintain community after retiring, when it can be harder due to life changes like family and location. Now as a financial advisor, Winston focuses on understanding his clients' goals and risk tolerance to create tailored portfolios.

[34:51] Building Community Beyond the Game

Winston understands the power of community both during and after an athletic career. Winston recognizes it can be difficult to recreate that same sense of belonging once sports are over. The business world doesn't provide the same built-in community that sports did. However, maintaining connections with former teammates and intentionally joining new communities, such as through his children's activities, has helped Winston feel less isolated in his post-playing life. He sees the importance of having a strong support system, especially when facing new challenges.

Resources Mentioned:

https://www.bernstein.com/our-team/locations/nashville/winston-justice.html