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Will Regan has a diverse work experience spanning several industries. Will began their career as an Interest Rate Swaps Trader at Manufacturers Hanover in 1983 and later transitioned to a similar role at NatWest from 1986 to 1989. In 1996, Will Regan co-founded Union Bar and served as a Founding Partner and Operator until 2008. Will also co-founded Lotus in 2001 and was involved in the company's operations until 2008. In 2003, they joined CMC:Berkshires as a Co-Founder and Managing Partner, as well as a Board Member. In 2006, they became a Founding Partner and Operator at The Double Seven, and in 2007, they took on a similar role at Los Dados. Lastly, from 2010 to 2014, they were a Founding Partner and Operator of The Lambs Club Restaurant at The Chatwal Hotel.

Will Regan attended Tufts University from 1979 to 1983, where they obtained a Bachelor of Arts degree in Economics.