In 1861, he pooled his $600 savings with a friend, and set out for western Pennsylvania to the newly discovered oil fields, where he found and developed his fortune, eventually becoming one of the most important men in John Rockefeller's Standard Oil Trust.
He was married to his childhood sweetheart for over 30 years until her death and had four children. Rogers was an energetic man, and amassed a great fortune, estimated at over $100,000,000. He invested heavily in various industries, including copper, steel, mining, and railways.
His final life's achievement was the building of the Virginian Railway (VGN) from the coal fields of southern West Virginia to port near Norfolk at Sewall's Point, Virginia in the harbor of Hampton Roads. Financed almost entirely from his own resources, his Virginian Railway competed with the Chesapeake and Ohio and Norfolk and Western railroads for coal traffic. Built following his policy of investing in the best route and equipment on initial selection and purchase to save operating expenses, the VGN enjoyed a more modern pathway built to the highest standards, and provided major competition to its larger neighboring railroads, each of whom tried several times unsuccessfully to acquire it.
Although Rogers died in 1909 just as his railroad was completed, the 600 mile Virginian Railway followed the Rogers philosophy throughout its profitable history. The Virginian operated some of the largest and most powerful steam, electric, and diesel locomotives throughout its 50 year history, resulting in a following of railway enthusiasts which continues to the present day. The Virginian Railway was merged into the Norfolk and Western in 1959 where much of the former VGN trackage is still in use in 2004 as the preferred route for eastbound coal for Norfolk Southern Corporation.
The diverse Rogers, who was at times known as a fierce businessman nicknamed "hellhound Rogers," was also a modest but generous philanthropist who apparently never forgot his roots. He gave generously of time and money to his his hometown of Fairhaven, MA and his friends Mark Twain, Helen Keller, and Dr. Booker T. Washington. It was later revealed in Dr. Washington's papers that Rogers had funded over 100 institutions in the South for the betterment and education of negroes.