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Matthew Wheeler started their work experience as a Caddy at The Misquamicut Club in 1995, where they worked until 2004. Matthew then joined Guy Carpenter as a Senior Risk Analyst in 2005, responsible for brokering deals between insurance companies and reinsurance companies. In 2008, Matthew co-founded SportsRecruits, an organization that empowers student-athletes to pursue their dreams through platforms like LacrosseRecruits.com and VolleyballRecruits.com.

Matthew Wheeler attended Wesleyan University from 2001 to 2005, where they earned a Bachelor of Arts (B.A.) degree in Economics.