His initial oil venture started with a young manhood friend,
E. W. Marland. In 1908 McCaskey became an investor and a director of the
101 Ranch Oil Company of
Ponca City founded by Marland to explore for Oklahoma oil. By 1910 however, the company was on the verge of failure having run out of money and only having found natural gas. A drilling lease was obtained on the Willie Cry Ponca Indian allotment and on June 11, 1911 the well "Willy-Cries-For-War" struck oil, bringing wealth to the company and its investors. The company's 1911 oil discovery in North Eastern Oklahoma opened up oil development in a great region from Eastern Oklahoma west to Mervine, Newkirk, Blackwell, Billings and Garber and led to the founding of the
Marland Oil Company, later renamed the Continental Oil Company, or
Conoco. McCaskey quickly moved on to other opportunities, organizing the Southwestern Oil Company with leases in Ranger, Texas and took into this new venture
Lewis Haines Wentz, a former sauerkraut salesman in his brokerage company and J. J. McGraw, a Ponca City Banker. In this capacity he promoted the Newkirk,
Blackwell, Billings, Graber and the
Tonkawa Three Sands Field, one of the best known oil fields of its day, producing income of over one million dollars per month in the 1920s. During this time he also formed and was president of a number of companies in the area including the
Kay County Gas Company, The Kiowa, and the Peoples Fuel and Supply Company. ==Ventures in Fort Worth==