Failing in his effort to establish himself in Virginia, he engaged in the sheep raising industry, in the spring of 1841, in company with Captain Oviatt, at Richfield, Ohio. He was successful and "gradually became known as a winner of prizes for sheep, and cattle at the annual fairs, in Summit County." By 1844 he had gained the reputation of a successful wool grower, and in that year formed "a partner-ship with Simon Perkins, Jr. of Akron, Ohio, with a view to carry on the sheep business extensively."[32] He moved to Akron April 10th of that year. Concerning his home at Akron, Mr. Villard says:

They occupied a cottage on what is still known as Perkins Hill, near Simon Perkins own home, with an extensive and charming view over hill and dale—an ideal sheep country, and a location which must have attracted any one save a predisposed wanderer.

Two years later it was decided to establish a headquarters at Springfield, Massachusetts. There Brown went "to reside as one of the firm of Perkins and Brown, agents of the sheep-farmers and wool merchants in northern Ohio, Pennsylvania, New York and Virginia, whose interests then required an agency to stand between them and the wool manufacturers of New England, to whom they sold their fleeces."[33]

Of this arrangement Mr. Villard says on page 35: "John Brown was within bounds in thus exulting; even though the Perkins partner-ship resulted eventually in severe losses and dissolution. At least it was a connection with a high minded and prosperous man, and it lasted ten years. When it was over, the partners were still friends, but Mr. Perkins did not retain a high opinion of John Brown's ability or sagacity as a business man." Mr. Sanborn states on page 57, that when Mr. Perkins was questioned by him, in 1878, about Brown's wool growing and wool dealing, he replied: "The less you can say about them the better."

As to the business, there seems to have been trouble from the commencement of it. Mr. Villard says on page 60: "Moreover some customers had just grievances, for the letter book contains far too many apologies for failure to acknowledge letters and shipments, and to make out accurate accounts, for so young a firm."

In August, 1849, Brown made his historic trip to London to superintend, personally, the sale of wool, which he had shipped to that market, because he could not obtain prices that were satisfactory to him from the manufacturers of woolens in his home market. The amount of wool so consigned was about two hundred thousand pounds. The Northampton Woolen Mills Company of Northampton, Massachusetts, had bid sixty cents a pound for this wool at Springfield. In London, September 17th, a lot of one hundred and fifty bales of it was sold for twenty-six to twenty-nine cents per pound. The buyer was the "Northampton Woolen Mills Co., of Mass., U. S. A."[34] Brown returned home in October "bringing back with him the portion of the wool which he had been unable to sell. The loss on this venture was probably as high as $40,000."[35] The firm of Perkins and Brown then began proceedings in liquidation, which had been under consideration for some time before Brown made the trip to Europe. The losses sustained by the company were upon a large scale. Suits against them were brought for more than one hundred thousand dollars.[36]

In 1850 Brown contemplated engaging in the manufacture of wine upon a large scale; and on December 4th, wrote to his sons to send him some samples of the wines they had made. He said: "I want Jason to obtain from Mr. Perkins, or anywhere he can get them, two good Junk bottles, have them thoroughly cleaned, and filled with cherry wine, being very careful not to roil it up before filling the bottles,—providing good corks, and filling them perfectly full. These I want him to pack safely in a very small strong box, which he can make, direct them to Perkins & Brown, Springfield, Mass., and send them by express. We can affect something to purpose by producing unadulterated domestic wines. They will command great prices."[37]

In 1846, Gerrit Smith, a wealthy philanthropist of Peterboro, New York, set aside one hundred and twenty thousand acres of his large estate in northern New York, to be divided up into farms, and given, without charge, to worthy colored people who would settle upon them and improve them for their permanent homes. Brown heard of this proposition in course of time, and made a proposal to Mr. Smith to settle among the negroes on these lands, and aid them by precept and example in their efforts at home building. In consideration of this, it is probable that Brown secured title to some land on equal terms with the negroes, and possibly secured options on other tracts, at satisfactory prices and terms of payment. His experience with the Oberlin College people in relation to the Virginia lands, heretofore referred to, was probably of service to him in this transaction with Smith. The tracts which he selected were at Timbuctoo, or North Elba, and in the spring of 1849 he located his family upon the land; but in March, 1851, moved back to Akron. Brown himself did not go to North Elba to live. His time was taken up in liquidating the tangled affairs of Perkins and Brown, and with the extensive litigation involved in the settlement of them.

Litigation seems to have been a constant and conspicuous feature of Brown's commercial life. Mr. Villard says[38] that "on the records of the Portage County Court of Common Pleas are no less than twenty-one lawsuits in which John Brown figured as defendant during the years 1820 to 1845. Of these, thirteen were actions brought to recover money loaned on promissory notes either to Brown singly or in company with others. The remaining suits were mostly claims for wages, or payments due, or for nonfulfillment of contracts.... In ten other cases he was successfully sued and judgments were obtained against him individually or jointly with others. In three cases those who sued him were non-suited as being without real cause for action, and two other cases were settled out of court. Four cases Brown won, among them being a suit for damages for false arrest and assault and battery, brought by an alleged horse thief, because Brown, and other citizens, had aided a constable in arresting him. A number of these suits grew out of Brown's failure in his real estate speculations. A serious litigation was an action brought by the Bank of Wooster to recover on a Bill of Exchange, drawn by Brown and others, on the Leather Manufacturers Bank of New York, and repudiated by that institution on the ground that Brown and his associates had no money in the bank. During the suit the amount claimed was rapidly reduced, and when the judgment was rendered against him it was for $917.65.... In 1845 Daniel C. Gaylord, who several times had sued Brown, succeeded in compelling him and his associates to convey to him certain Franklin lands, which they had contracted to sell, but the title for which they refused to convey. The court upheld Gaylord's claim. The only case in which Brown figured as plaintiff was settled out of court." This is consistently a bad record.