Goodyear gave up the practice of law in 1887 to form a lumber company with his brother, Frank H. Goodyear, under the firm name F. H. & C. W. Goodyear.
They invested in timberlands, lumber mills, coal, and railroads in remote areas of Pennsylvania and New York.
They bought up large tracts of timberland that were considered inaccessible for harvest, because the lands were isolated and away from the streams that were typically used to transport logs.
 To access the timber, they built railroad spurs for transport, and local sawmills to process the trees into lumber.
In many areas, they built company towns for workers in the isolated sawmills.
They achieved great financial success with these strategies.

The Goodyears were the world's largest manufacturers of hemlock lumber, with an annual output around 200,000,000 board feet of hemlock, and nearly as much in hardwood.
In the late 1890s as the lumber business expanded, Goodyear joined his brother's Buffalo and Susquehanna Railroad, which Frank had created in 1893 by the merger and consolidation of several smaller logging railroads.
When Goodyear joined, Frank stepped down as president of the railroad and assumed the positions of first vice president and chairman of the board.
Charles Goodyear became second vice president and general manager of the railroad, while Marlin Olmsted became president.

 
Between 1901 and 1905, the brothers moved South, purchasing 300,000 acres of virgin yellow pine timberland in southeastern Louisiana and southwestern Mississippi, near the southern end of the Pearl River.
In 1902, the brothers chartered the Great Southern Lumber Company in Pennsylvania, establishing their offices in the Ellicott Square Building in downtown Buffalo.

The brothers began construction of the Great Southern Lumber Company sawmill, which was the largest sawmill in the world, in southeast Louisiana, and developed the company town of Bogalusa, where workers and their supervisors and families would live.
It was designed and built from the ground up, to include hotels, classes of housing, churches, schools, YMCA and YWCA, and similar services.
To bring harvested trees to the sawmill and transport processed lumber to markets, the Goodyears established the New Orleans Great Northern Railroad, which connected Bogalusa to the national railroad network and to New Orleans.

In 1906, the brothers extended the Buffalo and Susquehanna Railroad from Wellsville to Buffalo, nearly 90 miles.
Frank Goodyear did not live to see the Bogalusa sawmill completed, dying in 1907 of Bright's disease, shortly before the Panic of 1907.
The Great Southern Lumber Company sawmill began operation in 1908.
Goodyear took over for Frank at the Buffalo and Susquehanna Railroad, among other companies they owned.
He appointed William H. Sullivan as the general manager of the Great Southern Lumber Company and town boss of Bogalusa.
After the city was incorporated, Sullivan served as mayor until his death in 1929.

At various points in his career, Goodyear was president of: Goodyear Lumber Co., Buffalo & Susquehanna Coal and Coke Co., Buffalo and Susquehanna Railroad, Great Southern Lumber Company, and the New Orleans Great Northern Railroad Company; and director of the Marine National Bank, and General Railway Signal.
Goodyear gave up the practice of law in 1887 to form a lumber company with his brother, Frank H. Goodyear, under the firm name F. H. & C. W. Goodyear. They invested in timberlands, lumber mills, coal, and railroads in remote areas of Pennsylvania and New York. They bought up large tracts of timberland that were considered inaccessible for harvest, because the lands were isolated and away from the streams that were typically used to transport logs.  To access the timber, they built railroad spurs for transport, and local sawmills to process the trees into lumber. In many areas, they built company towns for workers in the isolated sawmills. They achieved great financial success with these strategies.
The Goodyears were the world's largest manufacturers of hemlock lumber, with an annual output around 200,000,000 board feet of hemlock, and nearly as much in hardwood. In the late 1890s as the lumber business expanded, Goodyear joined his brother's Buffalo and Susquehanna Railroad, which Frank had created in 1893 by the merger and consolidation of several smaller logging railroads. When Goodyear joined, Frank stepped down as president of the railroad and assumed the positions of first vice president and chairman of the board. Charles Goodyear became second vice president and general manager of the railroad, while Marlin Olmsted became president.
 
Between 1901 and 1905, the brothers moved South, purchasing 300,000 acres of virgin yellow pine timberland in southeastern Louisiana and southwestern Mississippi, near the southern end of the Pearl River. In 1902, the brothers chartered the Great Southern Lumber Company in Pennsylvania, establishing their offices in the Ellicott Square Building in downtown Buffalo.
The brothers began construction of the Great Southern Lumber Company sawmill, which was the largest sawmill in the world, in southeast Louisiana, and developed the company town of Bogalusa, where workers and their supervisors and families would live. It was designed and built from the ground up, to include hotels, classes of housing, churches, schools, YMCA and YWCA, and similar services. To bring harvested trees to the sawmill and transport processed lumber to markets, the Goodyears established the New Orleans Great Northern Railroad, which connected Bogalusa to the national railroad network and to New Orleans.
In 1906, the brothers extended the Buffalo and Susquehanna Railroad from Wellsville to Buffalo, nearly 90 miles. Frank Goodyear did not live to see the Bogalusa sawmill completed, dying in 1907 of Bright's disease, shortly before the Panic of 1907. The Great Southern Lumber Company sawmill began operation in 1908. Goodyear took over for Frank at the Buffalo and Susquehanna Railroad, among other companies they owned. He appointed William H. Sullivan as the general manager of the Great Southern Lumber Company and town boss of Bogalusa. After the city was incorporated, Sullivan served as mayor until his death in 1929.
At various points in his career, Goodyear was president of: Goodyear Lumber Co., Buffalo & Susquehanna Coal and Coke Co., Buffalo and Susquehanna Railroad, Great Southern Lumber Company, and the New Orleans Great Northern Railroad Company; and director of the Marine National Bank, and General Railway Signal.
Charles W. Goodyear