Orlando was an editor and newspaper owner. He was born in Frankfort and educated at home by his mother Margaretta Brown and by private tutors. Like his father, John Brown, Orlando attended Princeton. He graduated in 1820. He read medicine with his Uncle Dr. Preston Brown but soon gave it up. He then attended Transylvania University, receiving his law degree in 1823. For five years, Brown practiced law in Alabama.
After much searching for a profession, Orlando became an editor. Orlando founded the Commonwealth, a Frankfort newspaper, with A.G. Hodges in 1833. He served as its editor for ten years. The paper was supportive of the Whig Party. In 1840, he edited The Campaign, a short-lived newspaper that was a platform for the Whig Party. Orlando was an ardent supporter of the Union and the Constitution. It is not surprising that in 1862, during the U.S. Civil War, Orlando resumed as editor of The Frankfort Commonwealth for seven months. The paper favored the preservation of the Union.
Like his brother Mason, Orlando served as Kentucky's Secretary of State. He held the post in 1848 during Governor John J. Crittenden's administration. Soon after, in 1849, Orlando became the Commissioner of Indian Affairs in President Zachary Taylor's administration. However, he was unhappy in the position and resigned in 1850.