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William Dearie has extensive work experience in the insurance industry. In 2004, they started working at Deans & Homer, where they held various roles including Chief Executive Officer, Executive Vice President, and Underwriter. William worked at Deans & Homer until 2019. In 2019, they co-founded Covie, a company in an unknown industry. Additionally, in 2014, they became the Chairman of the Board at DH Adjusting.

William Dearie attended Y Combinator in 2021 but did not obtain a degree or pursue any specific field of study. Prior to that, there is no available information about their education history, including any degree or field of study at Trinity College-Hartford, The Browning School, or St. David's School. Additionally, in 2014, William obtained a certification as an Insurance Agent from the California Department of Insurance.