as a member of the creek nation, simmons received (convert|160|acre|) km when the tribe disbanded. in the 1920s, oil flowed on his hand. he became an oil broker and entrepreneur, buying and selling oil leases, and started a real estate business. during the great depression, he sold oklahoma farmland to african americans in east texas, who had made money in the oil boom. meanwhile, he expanded his oil lease-trading business into texas, louisiana, arkansas and kansas. he dealt with oil barons such as william skelly, founder of skelly oil, and frank phillips, founder of phillips petroleum.