Bezos had paid close attention to the rapid rise of the World Wide Web, noting in 1994 that it was growing at an annual rate of 2, 300 percent, and therein looked for a pure entrepreneurial outlet. He began his research by making a list of the top 20 mail-order companies, observing that there were no book mail-order companies because a comprhensive catalog would have needed to be thousands of pages long and thus expensive to mail. Bezos decided that an Internet-based company would have the capability to offer a substantially wider selection of printed matter to consumers. Thus, he made a thorough study of the book business, beginning by attending the American Booksellers' Association's annual convention.

When Bezos told Shaw, his former boss, that he was leaving to launch an online book business, Shaw advised him to take some time to reconsider his decision in a characteristically creative way.He told Time that he pictured himself at 80 years of age and was certain that he would not regret either missing out on a six-figure Christmas bonus nor having tried to build an online business and failing.