In 1837 at the age of eighteen he moved to Green Bay in Wisconsin and began working for his elder brothers, Charles and Henry who became publishers of the newspaper ‘Wisconsin Democrat’.
After two years he relocated to Madison in Wisconsin and started working as editor of the ‘Wisconsin Enquirer’ when his brother Charles bought shares of the newspaper.
Thereafter he relocated to Southport (presently Kenosha) in Wisconsin and set up a weekly newspaper called ‘Southport Telegraph’ becoming its editor. Around 1845 while working with the newspaper he came to know about ‘Voree Record’, that is three small brass plates that were found by James J. Strang, a prospective successor of the founder of the Latter Day Saint movement, Joseph Smith.
Strang’s insistence of his being the real prophet of God linking the incident of unearthing the plates and invitation to people at large to view them drew Sholes to meet the man and see the plates. Sholes wrote an article in this regard. Although he felt Stang to be "honest and earnest", he was unable to accept either the plates or prophetic claims of Strang.
He embarked into politics and from 1848 to 1849 served ‘Wisconsin State Senate’ as member of ‘Democratic Party’, one of the two main contemporary political parties in the US. His brother Charles was also into politics and served ‘Wisconsin State Legislature’. Charles also remained mayor of Kenosha.
Sholes played an important role in the movement that sought abolition of death penalty in Wisconsin. In 1851, the report of trial of John McCaffary, who was convicted of murdering his wife and faced subsequent death penalty by the State of Wisconsin, was published in his newspaper, ‘The Kenosha Telegraph’.
He served ‘Wisconsin State Assembly’ as member of ‘Free Soil Party’ from 1852 to 1853.
Once again he served ‘Wisconsin State Senate’ for a year from 1856 to 1857 but this time as member of the other main contemporary party, the ‘Republican Party’. He worked with two Republican papers namely ‘Milwaukee Daily Sentinel and News’ and ‘Milwaukee Free Democrat’.
Throughout the American Civil War he backed the ‘Republican Party’ and President Abraham Lincoln. In 1863 he was inducted by the President as Collector of Customs at the port of Milwaukee.
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While serving as editor of a newspaper in Milwaukee, he unsuccessfully attempted to build a device for typesetting to overcome odds created due to strike called by compositors in his printing press.
During that time he used to visit C.F. Kleinsteuber's machine shop, a common place and workshop for amateur inventors. With the objective of building a machine that can impress numbers on book pages, tickets etc. he began working with another printer Samuel W. Soulé and succeeded in creating a numbering machine which they patented on November 13, 1866.
The duo showed their creation to another amateur inventor Carlos Glidden at Kleinsteuber who was working on a mechanical plow. Glidden pondered whether the machine could be developed into a letter printing one and referred Sholes to a short note that was published in ‘Scientific American’ in July 1867 giving an account of invention of a prototype typewriter called the ‘Pterotype, by John Pratt of London.
Sholes was intrigued by the idea and decided to devise a new machine less complex than Pterotype. This time Glidden joined Sholes and Soulé in the new project and also funded it. The trio created a keyboard with two rows of black and white keys with the first row made of ivory and the second of ebony. The number keys consisted of 2 to 9 and the alphabetical keys A to Z. O and I were considered to suffice the numerals 0 and 1 respectively. The resemblance of the keyboard with that of a piano made ‘Scientific American’ use the phrase ‘literary piano’ while writing an article about it.
On June 23, 1868, and subsequently on July 14, patents were granted to them for the invention.
Among the many potential investors the trio sent letters written on their new machine, James Densmore of Meadville, Pennsylvania could anticipate the revolutionary change that this device could bring in. Densmore bought 25% shares of the patent, even before he saw the machine for himself, by paying bills worth $600.
However when Densmore finally saw the machine he was disappointed with its current form and suggested to develop it further, which discouraged Glidden and Soulé who eventually left the project.
Sholes and Densmore went on to develop the machine further and in this process manufactured around fifty machines with an average cost of $250 each.
As the duo approached ‘E. Remington and Sons’ to examine the refined machine it proposed to buy their patents. In 1873 Sholes relinquished his patent rights to the company for $12,000. The company then fine tuned the machine and marketed it as the first commercially feasible typewriter in 1874 at $125 each. It was called the ‘Sholes-Glidden’.
Sholes continued his work of refining the typewriter all through 1870 and in this way invented the ‘QWERTY’ keyboard in 1873.