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Gary Cloudman has a diverse work experience spanning several years. Gary currently holds the position of Managing Director - Head of Chicago Office and Fiduciary Services at Angeles Investments, where they oversee the private client affiliate of the company and manages a significant amount of advised assets. Prior to this, they served as the Senior Wealth Consulting Manager - Head of Family Office Practice at Metropolitan Capital Bank & Trust, where they provided comprehensive financial solutions for high-net worth individuals and families. Gary also worked at The Criterion Group as a Member, advising family businesses and start-ups on various matters such as generational succession, financing, and governance. Earlier in their career, they gained experience as a Law Clerk at Attorneys' Title Guaranty Fund, where they conducted research and analysis on legal topics, and as a Legal Intern at First National Bank of America, where they managed matters handled by outside counsel and ensured regulatory compliance.

Gary Cloudman received a Bachelor of Arts (B.A.) degree in Political Theory and Constitutional Democracy from Michigan State University, where they studied from 2002 to 2005. Gary then pursued higher education at the University of Illinois College of Law and obtained a Doctor of Law (JD) degree, completing the program from 2006 to 2009. In 2009, Gary furthered their legal education at the Northwestern University Pritzker School of Law, where they earned a specialized Master of Laws (LLM) degree with a focus on Taxation, finishing their studies in 2010.