By 1800, Whitney had accumulated enough capital to go into business as a grocer and an importer of wine and spirits on his own, at first in partnership with a Scotsman named John Currie.

He was able to export some of that cotton during the war through Amelia Island in northern Florida, at the time still part of neutral Spain.

He is also reported to have purchased all the cotton bales used to build fortifications by Andrew Jackson's army during the Battle of New Orleans.

He invested in shipping, including the China trade and the Robert Kermit Red Star Line of packets.

The New York Stock and Exchange Board moved their operations from the Tontine Coffee House to the new building, adopting it as their first permanent home.

[12] In 1825, Whitney had a townhouse built at Number 7 Bowling Green, at the corner of State Street and Broadway—the current site of the old Custom House that is now home to the Heye Indian Museum.

The seven houses in the block, which faced across Bowling Green and straight up Broadway, were among the most fashionable in the city when they were built.

However, as the city quickly evolved, wealthy residents began to move "uptown" to Washington Square and Fifth Avenue.

Stephen Whitney, who was famous for refusing to bend to fashion, was still living at 7 Bowling Green when he died, even though the neighborhood had become somewhat run down and all of his peers had moved away.

[7] The contents of the Whitney living room at 7 Bowling Green have been on permanent display at the Museum of the City of New York since 1936.