In 1876, he began making common-sense buckets in a small shop on Kinzie Street in Chicago.

It doubled and then redoubled in size, and in 1889 Webster moved to a new plant on Western Avenue and Fifteenth Street.

[3] In the early 1890s a group of investors, one of whom was Mark Twain, gave Webster Manufacturing the contract to make the Paige Compositor.

Webster built a new five-story building at the Western Avenue plant to deliver 3000 compositors under the contract.

Unfortunately, the compositor was expensive to manufacture and when it broke down only the inventor's chief engineer, Charles Davis, could fix it.

What had seemed like a profitable business venture, cost Mark Twain a fortune and almost bankrupt Webster Manufacturing.

In 1897, having returned to his core business, Webster built a two-million-bushel grain elevator on the newly opened Manchester Ship Canal in England.

After refining the device into what he thought to be a workable ignition system, Webster signed a contract with the Cadillac Automobile company which intended to make it standard on their cars.

After Webster's death, the company struggled until the 1930s, when it introduced a popular intercom called the Teletalk.

In a speech on open versus closed shops, he argued “I think the union stands as a great middle wall between the small manufacturer and the great overwhelming power of organized capital.”[11] His straightforward solution to labor unions was to “grant a fair day’s work for a fair day’s pay.”[11] As a result of his position, Webster enjoyed a level of trust with both management and labor.

[12] In 1907, when the contract between the Chicago newspaper publishers and the Typographical Union expired, they were unable to come to terms.

Strong noted, "His decision at so critical a stage in the development of relations between capital and labor and in union practice attracted the attention of many industries in addition to newspapers.

His declared intention was to create a place “to alienate the affections of his grandchildren from their parents.”[4] In 1917, he commissioned Maurice, who had just been licensed to practice architecture in Illinois, to build a large wood frame summer house.

His grandchild, Stokely Webster, would later describe it as a "magical place"[1] that would shape his approach to art.