On December 19, 1871, the U.S. Patent Office granted Twain his first patent (#121,992) for an adjustable strap that could be used to tighten shirts at the waist – he intended to eliminate suspenders, which he thought were uncomfortable. Twain also received patents for a self-pasting scrapbook, which sold more than 25,000 copies, and a history trivia game. (If you have either of these items, contact "The Antiques Road Show"... you'll be very happy that you did.) The process of entrepreneurship excited him so much that it slipped into his work. In A Connecticut Yankee in King Arthur's Court, for example, one of his characters said that "a country without a patent office and good patent laws was just a crab, and couldn't travel any way but sideways or backways."
Twain's adjustable straps didn't catch on, the biggest reason being that he approached the problem all wrong. Mohammed Islam, an engineering professor at the University of Michigan, has specialized in the development of patents. He teaches "Patent Fundamentals for Engineers," a class in which he points out that entrepreneurs have to ask themselves, 'What's the pain? Does the problem hurt people enough so that they're willing to pay for the solution? Will the product have a sustainable advantage that's different from other solutions? There has to be a competitive advantage to get beyond the first sale." Twain didn't look beyond his own pain. He needed a broader audience.
Doug Neal, managing director for the Center for Entrepreneurship at the University of Michigan, agreed, saying that it's "extremely important for entrepreneurs to honestly determine who they're providing what specific value. You have to put yourself in your target customers' shoes and find out if they really see the value your idea brings. Many false starts can be traced to a failure to do this successfully."
Despite his disappointments as an entrepreneur, new technology remained a passion for Twain. The early typewriter, a clumsy configuration of rollers and spindly arms at its inception, consumed him -- he couldn’t keep his hands off it -- and he became the first person to submit a typed manuscript to a publisher. The telephone fascinated and frustrated him -- he spent hours on the line. But service was particularly bad around his Connecticut home, so he spent a lot of time grumbling about the phone company and writing satirical letters of complaint. (Things haven't changed all that much.)
Unfortunately, his love of technology overcame his better judgment when he met James W. Paige, who was developing a machine that would become the Paige Typesetter. Between 1880 and 1894, Twain invested a fortune in it -- including his royalties from The Adventures of Huckleberry Finn. The hapless Paige filed for a patent, only to see it sit as a pending document for eight years -- the first Patent Office examiner died before the process was complete; a second examiner went insane; and the patent attorney who originally prepared the case also went crazy and died in an insane asylum. Meanwhile, mechanical problems forced Paige to redesign the machine.
By 1894, Twain was nearly bankrupt. He closed his Hartford home and headed for Europe, in part because his unprofitable investment had taken a toll on his resources and his imagination. Without realizing it, Twain experienced what true entrepreneurs know is the key to eventual success: failure. Fortunately, he had a job he could fall back on… and he was pretty good at it.