By 1832, at age 26, Taylor had sufficient wealth to marry, leave the Howland company, and start his own business as a sugar broker.

As such he dealt with Cuban sugar growers, found buyers for their product, exchanged currency, and advised and assisted them with their investments.

[1] Taylor never visited Cuba, but his friendship with Henry Augustus Coit, a prominent trader who was fluent in Spanish, enabled him to trade with the Cuban growers.

When the Panic of 1837 allowed Astor to take over what was then City Bank of New York (today known as Citibank), he named Taylor as director.

[2] In the 1850s Taylor invested in iron and coal, and began purchasing interest in the Delaware, Lackawanna & Western railroad.

[3] Taylor held an interest in the New York, Newfoundland, and London Telegraph Company that Cyrus West Field had founded in 1854.

Taylor sat in 1871 on a committee made up of New York's most influential and successful businessmen and signed his name to a report that commended Tweed's controller for his honesty and integrity.