About CSSports

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About CSsports

As a sports professional, you have very unique needs with expectations of great rewards. Your financial outlook is multi-faceted with a complex earning profile and variable career span. Unfortunately, and too often, the pressing demands of athletes and coaches lead to little time and resources for money management and financial planning. To be successful, you need a wealth advisor who knows how to manage and optimize your current cash flow while helping to protect your financial future.

That’s where we excel.

For over 20 years, the CrossleyShear and CSsports team has been driven by a singular passion – to be there for our clients at every step of their financial journey. Working in partnership with your management team, we’ll highlight the difficult and complex issues that accompany being a sports professional and create a pathway to your financial vision of tomorrow. Our success is driven by a promise to deliver personalized care and customized solutions for all your life’s needs – before, during and after your sports career – ranging from everyday spending advice and retirement planning to managing your investments, insurance, college savings and business planning. It’s a care commitment we live by every day. It’s about empowering our clients to help achieve their financial goals and provide financial confidence to those that matter most. All the while working by your side to plan for life’s uncertainties and celebrate life’s joys, on and off the field, court, rink or diamond.

Evan Shear, CFP® | CERTIFIED FINANCIAL PLANNER™


What skills help make you a successful financial planner?
In addition to holding a B.S. from the University of Florida, I earned my CERTIFIED FINANCIAL PLANNER™ certification, which is a rigorous certification process that includes demanding education, examination, experience and ethical requirements. I am analytical and attentive. During my past 20 years of practice, my goal has always been to provide clients with a high level of confidence in knowing that their financial goals are achievable. I always want my clients to feel like nothing in their financial life goes unattended.

What attracted you to financial planning and wealth management?
I am passionate about combining my analytical side with the enjoyment I find helping people. I emotionally tie myself to the well-being of all my clients and deeply care about their financial success. I work hard to understand both their fears and dreams and make them my own. I am willing to think outside the box to find creative ways to help my clients reach their goals.

What causes are meaningful to you?
I am actively involved with several national and local charitable organizations, but causes involving kids, Alzheimer’s disease, epilepsy and diabetes are personal to me. I serve on the Board of the Epilepsy Association of Central Florida’s Scholarship Foundation, a group dedicated to providing financial assistance to students affected with epilepsy and seizure disorders, as well as organizations dedicated to its research and care.

Finish this sentence. On Sunday afternoons, you can usually find me...
spending time with my family at sporting events including lacrosse, baseball or golf.

Outside of work, what’s been your biggest achievement?
My three kids. They definitely make me proud!

Who’s your biggest inspiration?
My father, who passed away at age 60, was very bright with a kind and gentle soul. He was always was there to listen and help everyone he could.

What traits in others matter to you most?
Honesty, integrity, humor, philanthropy and humility are all very important to me.

Dale Crossley, JD | Financial Planner

What skills help make you a successful financial planner?
My formal education includes a J.D. from Barry University School of Law, a M.S in business management and a B.A. in psychology, which all provide me with the ability to manage a wide range of wealth management variables, behavioral finance and emotions, as well as some helpful knowledge about issues with legal and estate planning. I really enjoy the leadership aspects of guiding a team for the common goal and the benefit of our clients.

What attracted you to financial planning and wealth management?
My entrepreneurial spirit combined with my strong desire to help others attracted me to wealth management.

What causes are meaningful to you?
I feel a strong connection to our local community and get behind various causes related to education, homelessness and hunger, as well as our rivers, lagoons and ocean. I am passionate about causes related to kids, particularly related to chronic illnesses and special needs and because of my son, I have a special interest in genetic syndromes. I also feel strongly about any causes related to aging and the elderly. I participate in the Shema Ministry Board and Scholarship Committee and serve on the Epilepsy Association of Central Florida’s Board and Preeclampsia Foundation Finance Committee.

Finish this sentence. On Sunday afternoons, you can usually find me...
involved in family activities, going to church, enjoying the beach, playing golf and yes, watching NFL.

Outside of work, what’s been your biggest achievement?
My 4 amazing children – Courtney, Lauren, Carrie and Dale

Who’s your biggest inspiration?
My 10-year-old son, Walter Dale Crossley III is such an inspiration to me. Born with a rare neurodegenerative genetic syndrome, Walter was not expected to survive or ever communicate or relate to others. Fortunately, he has proven the medical profession wrong with his unique personality, love, determination, patience, and fight. He is always the happiest and most genuine person in every room.

What traits in others matter to you most?
I value honesty, loyalty, compassion, unselfishness, and being respectful.

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