Though barely educated or literate, Dexter considered himself "the greatest philosopher in the known world", and authored a book, A Pickle for the Knowing Ones, which espouses his views on various topics and became notorious for its unusual misspellings and grammatical errors.

[5] Dexter set up shop in the basement, selling moosehide trousers, gloves, hides, and whale blubber.

[3] At the end of the American Revolutionary War, he purchased large amounts of depreciated Continental currency that were worthless at the time.

[citation needed] To elevate his social status, Dexter began to write petitions supporting that he be considered for public office.

[7][8] On another occasion, practical jokers told him he could make money by shipping gloves to the South Sea Islands.

[2] While subject to ridicule, Dexter's boasting makes it clear that he understood the value of cornering the market on goods that others did not see as valuable and the utility of "acting the fool".

[2][5] He decorated this house with minarets, a golden eagle on the top of the cupola, a mausoleum for himself, and a garden of 40 wooden statues of famous men, including George Washington, William Pitt, Napoleon Bonaparte, Thomas Jefferson, and himself.

One section begins:[9] 'Ime the first Lord in the younited States of A mercary Now of Newburyport it is the voise of the peopel and I can't Help it and so Let it goue'The first edition was self-published in Salem, Massachusetts, in 1802.

The Massachusetts Probate Office valued his estate at $35,027.39 (roughly equivalent to $782,961 in 2023) at the time of Dexter's death in 1806.

[14] After his death, Dexter's Newburyport house had its household furniture, gilt balls, and much of the garden statuary auctioned off on 12 May 1807.

The Great September Gale of 1815 toppled most of the remaining statues, and the survivors were sold at another auction; some ended up being burned for firewood.

[15] Ultimately, fewer than six of the original 40 statues survived to the present day, being rediscovered during the Great Depression as a result of a Works Progress Administration survey; the most prominent one being that of William Pitt, restored by the Smithsonian Institution and currently on loan to the local Museum of Old Newbury.