New York. Thirteen children were born of this union; seven of whom died in early childhood; two—Watson and Oliver—were killed at Harper's Ferry.

As a tanner, at Hudson, Brown was successful, but he gave up his business there and moved to Richmond, Pennsylvania, in May, 1825, where he established a tannery. He was appointed postmaster at Richmond in 1828, and held the office until he moved to Franklin Mills, Ohio, in 1835. He left Richmond "because of financial distress."[17] At Franklin Mills, he secured a contract for building the Ohio and Pennsylvania Canal from there to Akron. The next year, he undertook some speculations in real estate, and in company with a Mr. Thompson, borrowed $7,000 with which to buy a tract of one hundred acres, for an "addition to Franklin." During the same year, he, with others, organized the Franklin Land Company, and purchased the water power, mills, lands, etc., in both the "upper" and "lower" Franklin villages, combining the two water powers at a central town-site, which he and his associates laid out.[18] In these, and other schemes, Brown became so deeply involved that he failed during the bad times of 1837; lost nearly all his property by assignment to his creditors, and was then not able to pay all his debts, some of which were never liquidated. His father also lost heavily through him.[19]

His failure in business should not of itself count against him, but some of the methods which he employed to extricate himself from his financial embarrassment, were of a most fraudulent and criminal character. July 11, 1836, he applied to Heman Oviatt and others, to become security for him on a note for $6,000 to the Western Reserve Bank. The note was not paid, and the bank got judgment against the makers in May, 1837. August 2d, the judgment debtors gave a joint judgment bond for the amount of the judgment against them, payable in sixty days. The bond not being paid, the bank sued again, and Oviatt had to pay the bank in full. The nature of the wrong done to Mr. Oviatt by Brown is described by Mr. Villard on pages 37 and 38. He relates that at the time of this transaction, Brown had a "penal bond of conveyance," but not the title, for a piece of property known as "Westlands," which he assigned to Oviatt, as collateral for Oviatt's having endorsed the judgment bond to the bank. When the deed to the Westlands property was duly given to Brown, he recorded it, without notifying Oviatt of this action. Later, he mortgaged the property to two men, again without the knowledge of Heman Oviatt. Meanwhile, Daniel G. Gaylord had recovered a judgment against Brown in another transaction, and to satisfy it caused the sale of Westlands by the sheriff. By collusion with Brown, the property was bought in at the sale, by his friend, a former business associate, Amos P. Chamberlain. Oviatt "brought suit to have the sale of Westlands to Chamberlain set aside as fraudulent, but the Supreme Court of Ohio held that Chamberlain had a rightful title, and dismissed the suit. John Brown himself was not directly sued by Oviatt, being, to use a lawyer's term, 'legally safe' throughout the entire transaction.... Even after this lapse of years his action in secretly recording the transfer of the land, and then mortgaging it, bears an unpleasant aspect."[20] Meanwhile, the parties to the fraud upon Oviatt quarreled. Brown refused to give up occupation of the land to Chamberlain; assuming that Chamberlain had not treated him fairly in the matter; and held possession of the property, in "a shanty on the place, by force of arms, until compelled to desist by the sheriff...." Finally, the sheriff arrested Brown and two sons, John and Owen, who were thereupon placed in the Akron jail. Chamberlain, having destroyed the shanty which Brown had occupied, and obtained possession of the land, allowed the case to drop, and Brown and his sons were released.[21] Mr. Sanborn, on page 55, disposes of the matter in this way:

Brown was not so staid and prosaic in his daily walk and conversation as to be indifferent to the sports and amusements of life. He seems to have been simply an active man of the world, getting as much worldly enjoyment for himself out of his environment as possible. He was a horseman with a fancy for horse racing; and while at Franklin, indulged in the very interesting and sportsmanlike business, or diversion, of breeding "fast running horses for racing purposes." He bred from a well known horse of that time called "Count Piper"; and the name of another favorite sire was "John McDonald." He is said to have dismissed criticism of his conduct from a moral point of view, by the argument that "if he did not breed them some one else would."[22]

From 1837 to 1841 Brown lived alternately at Franklin, and at Hudson, Ohio. In 1838 he became a "drover," and drove cattle from Ohio to Connecticut. In this business he had trouble with his associates, Tertius Wadsworth and Joseph Wells, who furnished the capital; and was sued by them for an accounting.[23] In December, 1838, "he negotiated for the agency of a New York Steel Scythes house." And in January, 1839, he made his first venture in sheep, at West Hartford, Connecticut. He brought the sheep to Albany by boat, and drove them from there to Ohio. In June of that year he made his final drive to the east with cattle, and, while at New Hartford, committed a crime of unusual enormity. It appears that he proposed to the New England Woolen Company, of Rockville, Connecticut, to act as its agent in buying wool, and induced it to intrust to him $2,800 with which to begin purchasing the wool. The negotiations for this money were a deception throughout, in pursuance of theft. Brown did not intend to buy any wool with the money which he sought to have intrusted to his keeping for that purpose; but did intend to convert it to his own use—to make "a much brighter day" in his affairs. He also deceived his wife, whom he caused to believe that he was trying to secure a loan.