It is headquartered in Plantation, Florida, and has offices in New York; Chicago; Richardson, Texas; London; Sydney; and Costa Rica.

TradeStation was founded by Cuban-born brothers William (Bill) and Rafael (Ralph) Cruz, who sought to create a way to design, test, optimize, and automate their own custom trading strategies.

In 1987, they released System Writer, a software product that enabled users to develop and “back-test” their own trading ideas using historical market data.

In 1989, System Writer Plus was released with new and innovative charting features, which the publication Commodity Trader Consumer Reports likened to “the system trading software equivalent of putting a man on the moon.”[4] In 1991, Omega Research released TradeStation and, three years later, struck a licensing deal with Dow Jones Telerate to offer TradeStation as a premium service to Telerate's institutional clients worldwide.

The software's back-testing, order-generation and trade execution capabilities were fully integrated for both securities and futures markets in 2003.

An entire industry eventually grew up around TradeStation's software, including seminars, publications, and user networks.

Its main subsidiary, Monex Inc., one of Japan's largest online securities brokerages, provides financial services to its nearly one million individual investors.