Interview with Shawn Wooden

Shawn Wooden turned to finance after a successful 9-year NFL career (1996-2004). The Notre Dame graduate and former captain has over 20 years of experience in the financial services industry.  

In his interview with Modern American Advisor, Shawn explained his journey from athlete to financial advisor and player advocate. He is passionate about helping players and goes the extra mile to represent each athlete’s best interests. 

Entering the NFL

Shawn’s best friend and college teammate referred him to an agent, but he did not have a financial advisor when he entered the NFL. “I didn’t do much due diligence to find an advisor, because I didn’t know what questions to ask.” 

Making the Dolphins roster was a challenge. “I had two surgeries during college, and the Dolphins drafted two other defensive backs before me.”  

Shawn graduated with a bachelor’s degree in computer science and had a job offer from Hewlett-Packard after graduation. “I kept in contact with the HP recruiter, in case I didn’t make the roster in Miami.” 

When Shawn entered the league in ’96, there were no guaranteed contracts in the NFL. A player could be released at the end of the season and not earn any more NFL money. Financial planning was important because a player’s NFL income could end quickly. 

After joining the Dolphins, Shawn asked other players who they used as a trusted financial advisor. “Some advisors only talked about investment returns, not about cash flow planning and risk management.” 

Shawn was fortunate to play with Dan Marino for four years. “He was an amazing teammate. I learned a lot from Dan Marino, Bernie Kosar, and Bernie Parmalee.”

Advocate for Players

Shawn’s coach at Notre Dame, Lou Holtz, told his teams that “great teammates are there for life.” He has been a vocal advocate for both active and retired NFL players. 

Wooden is the Vice President of NFLPA Former Players South Florida Chapter, President of the Miami Dolphins Alumni Advisory Board, and works regularly with the NFLPA as well as NIL clients. He has frequently spoken to Dolphin rookies when they enter the league. 

Shawn was also a plaintiff in the NFL players’ case against the league regarding thousands of concussion-related claims. He was the class representative for asymptomatic players. The settlement requires the league to pay all valid claims of retired NFL football players in full for 65 years. 

Associated Financial

Shawn is now the CEO and partner at Associated Financial.  

The business focuses on developing comprehensive, tailored plans for its clients with a family-driven approach. In addition to wealth management, the firm has become a major player in the design, administration, and implementation of investment strategies as well as employer-sponsored retirement plans and employee benefit and insurance plans. 

Advising Athletes

Name, Image and Likeness (NIL) rules allow student-athletes to receive compensation at the college level, with some college athletes receiving payments while still in high school.  

Wooden creates financial literacy content for athletes at the high school level. “It’s a different world for college athletes now. They need financial literacy to create the right team and ask the right questions.” 

Taxes are a key issue for NIL players. College athletes are issued 1099 forms and not W-2s. In most cases, no taxes are withheld from NIL payments. The result? Some players spend all their NIL money and cannot pay taxes on the income. 

When he meets with an athlete, he starts the conversation by asking: “What does money mean to you? Is it a way out? Do you want to create a legacy?” Players need a team that includes an agent, a financial advisor, and a CPA.   

Shawn emphasizes that income does not equal wealth, and that all athletes need a plan to manage cash flow. “I use the phrase cash flow rather than a budget. When some players hear the word ‘budget’, they feel limited and that they won’t have money to spend.” 

During his NFL career, Shawn noticed players who seemed to be spending everything they earned, or more.

“Don’t try to live like Dan Marino if you’re not Dan Marino.” 

Shawn Wooden

Players are often pitched business ideas by family and friends, and athletes may be pressured into investing in poorly planned businesses. 

“Investors need to understand the business before they invest. Entrepreneurs must provide a business plan if they apply for a bank loan. Is there a written business plan? What does success mean, and what does the business have to do to achieve success?” 

Professional athletes also have less time, particularly during the season. A trusted financial advisor can help them evaluate potential investments.  

Shawn believes that players need to build a brand and an identity during their athletic careers. He explains that: “Sports is what you do, not who you are.” He helps players deal with the transition out of professional sports, which can cause anxiety and other health issues. “I want to oversee the whole package in my role as a financial advisor.” 

Lifetime Learner

“I’m always climbing the mountain, always trying to learn,” Shawn explains.  

He holds his FINRA Series 6, 7, 63, 65, 24 and 51 securities registrations and completed an executive program for retirement planning at the Wharton School of Business. He also seeks out best practices from other advisors.

A Unique Skill Set

Shawn Wooden’s experience as an NFL player, player advocate, and trusted advisor helps players navigate the complicated world of sports and wealth management. 

About Shawn Wooden

Shawn Wooden is a former NFL player and financial advisor with more than 20 years of experience in the financial services industry. A Notre Dame graduate and former captain, Wooden played nine seasons in the NFL before moving into financial services. He is CEO and partner at Associated Financial and remains actively involved in supporting current and former athletes through his work with the NFLPA and Miami Dolphins Alumni Advisory Board.

Continue Reading

This interview appears in The Sports Issue: The New Money Game from Modern American Advisor.

Explore the full issue for more on the changing relationship between sports, wealth and financial advice, including perspectives from athletes, advisors and industry leaders.

Read The Sports Issue

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