A native of Boston, Jackson graduated from Harvard College in 1761 and then moved to Newburyport, where he pursued a successful career as an import-export merchant in addition to other business ventures.

[1][2] He graduated from Harvard College in 1761 and then moved to Newburyport to start a mercantile career by joining the business of merchant Patrick Tracy.

[3] Jackson's business also involved considerable risk; his partners and he sometimes traded in banned products including guns and gunpowder, and one of their ships was seized off the coast of Portugal by the British Navy.

[3] In June 1776, he freed Pomp and in the manumission document cited his belief that slavery was improper, particularly as the Patriots were arguing for individual liberties that every man ought to possess.

[4] During the war, he was investigated for overcharging for goods he provided to the army, and accusations that he had marked-up some supplies by as much as two thousand percent, which he denied, proved to be a source of irritation for him.

[5] In conjunction with Samuel Adams and Stephen Higginson, Jackson authored a public condemnation of the rebellion and he also organized a counter-demonstration in Boston.

[5] He approved of the new United States Constitution, but questioned whether it was strong enough to insulate political leaders from the temporary ebbs and flows of popular opinion.

[5] He also believed the Constitution's checks and balances were insufficient for preventing demagoguery, which the events of the 1780s convinced him was a major concern.

[6] After George Washington became president, Jackson visited him at the temporary capital in New York City, intending to request appointment as Collector of Customs for the Port of Boston.

[4][6] In 1791, Jackson was appointed Inspector of Internal Revenue for the Second District of Massachusetts, with responsibility for enforcing federal tax laws in the same area where Shays’ Rebellion had earlier taken place.

[7] Jackson continued to serve in the supervisor's position until July 1802, when the first Democratic-Republican president, Thomas Jefferson, succeeded at abolishing federal taxes.

[7] Among Jackson's other ventures was an entity, "Proprietors of Locks and Canals on the Merrimack River", formed to advocate the use of water power to promote business growth in New England.

[3] They were the parents of 10 children: Edward, Robert, Henry, Charles, Hannah, James, Sarah, Patrick, Harriet, and Mary.