Unable to adapt to the culture of a big corporation, Osborne moved into technical writing, for which he proved to have a great flair.In 1975, Osborne wrote An Introduction to Microcomputers. The book was self-published and hit the market just as the personal computer revolution was taking off It eventually sold over 300,000 copies. He turned his success into a major publishing operation, which produced 40 personal-computing titles – of which he wrote 12 himself. During this period Osborne also became a columnist in the top-selling InfoWorld computer magazine and was a sought-after computer pundit, celebrated for his iconoclasm.

In 1979 his publishing company was bought by McGraw-Hill, where it still thrives as McGraw-Hill/Osborne Media.Osborne formed the Osborne Computer Corporation in 1981 The first product was the Osborne I portable computer. Weighing 23 pounds and the size of a small suitcase, the machine was often described as “luggable” rather than portable. A unique selling point of the computer was that it came with a software bundle consisting of a word-processor program, a spreadsheet and other popular application programs; in this way users could have the computer up and running without the need to buy additional software. It was said that the retail value of the software was more than the computer’s $1,795 selling price.More than 100,000 Osborne I computers were eventually sold across the United States and in Europe.

However, competition soon arrived in the form of portable computers from Compaq and Kaypro. In addition, the IBM-compatible computer was becoming the industry standard, making other designs obsolete. This competition, made worse by some strategic marketing errors, led to a huge inventory of unsold machines resulting in bankruptcy in September 1983. The extraordinary story of the Osborne Computer Corporation – boom to bust in three years – was told at length in Osborne’s book Hypergrowth, published in 1984.Undaunted by the failure of his company, Osborne began a new venture, Paperback Software International, in 1984. His idea was to sell software at low prices, through ordinary bookshops instead of software retailers. His most successful product was a $99 spreadsheet VP-Planner, a clone of the popular Lotus 1-2-3 spreadsheet that sold for $495.