On February 10, 1818, Jackson, Daniel Pinckney Parker and other members of the Boston Associates, were granted the charter of the Suffolk Bank by the Massachusetts General Court.

In 1822 he appointed himself as agent of Proprietors of Locks and Canals, gaining the ability to determine "who could start what mill and where in Lowell, and for how much".

On May 27, 1835, it made its maiden trip to Boston, with Jackson, George Washington Whistler, and James Baldwin aboard.

[5] Although Jackson had hoped to retire after the railroad began operating in 1835, but his poor business decisions did not make that possible.

For example, In the late 1830s, he liquidated nearly all of his interest in the Lowell Mills to invest it into real estate, which turned into a disaster.