Timothy Dexter was an incredibly eccentric person and businessman. He was also incredibly lucky.
Born in Massachusetts on January 22, 1747, Dexter had neither schooling nor money. He began life as a farm laborer alongside his father before becoming an apprentice to a Boston leather dresser at 16.
Five years later, Dexter completed his apprenticeship and moved to Newburyport, where he had his first stroke of luck. There, he met and married a wealthy young widow and purchased a large mansion using her money.
Dexter quickly became unpopular amongst his neighbors, who saw him as an ill-educated and unrefined man that married into money. Undeterred, he set out to increase his fortune by purchasing a number of large ships and launching an international trade business. When his neighbors heard the news, they purposely gave him bad business advice in the hopes that he would lose his fortune and move away.