Confessions of a Day Trader

A financial thriller that chronicles the exuberance of quick stock market success and the devastation of greed.

In 1992, Jay Jackson needed a respite from the hustle and bustle of Silicon Valley, so he moved to Kauai, Hawaii, bought a bed-and-breakfast, and got a beautiful Hawaiian girlfriend. After eight years, he’s content with his decision, but he’s suffering some financial distress: his savings are depleted, and the slagging tourism industry is pinching his B&B profits. Stevy Stanford, an old friend known for his razor-sharp mind and dogged pursuit of financial windfalls, calls to let Jay in on his latest venture: a technology company, Galaxy, has concocted a way to revolutionize digital advertising and has acquired 14 patents to corner the market. Stevy has inside information that the company’s soon to go public, so he buys the rights to another investor’s future stock holdings, anticipating a massive score in the near future. Jay enthusiastically jumps onboard despite his lack of investment savvy, eager to ride Stevy’s wave to financial freedom. However, the market gets hit by a major correction, and then the tragedy of 9/11 brings it to a crashing halt. Galaxy’s initial public offering is continually postponed, and when it merges with another company, it significantly dilutes the value of Jay’s and Stevy’s holdings. Jay is so beleaguered that he starts playing craps at casinos to supplement his income, and Stevy seems poised for financial ruin. Debut author Free intelligently weaves a tale about the elusiveness of luck and the magnetic draw of greed. Jay, his narrator, frantically chases the ultimate win, sacrificing the contentment of his former, island-bound life: “I believed good fortune came in waves. I believed that there was an ever-present dialectic: winning, then losing, then flat lining.” The microscopic focus on the minutiae of financial deals will intimidate many readers; as a result, the book will primarily appeal to those with an interest in and some knowledge of investment. Also, the plot tends to digressively wander too far afield; for example, a subplot involving Jay’s tutelage of a 17-year-old girl seems out of place. However, the book offers a thoughtful take on the psychological stakes of gambling.

A technically challenging and narratively undisciplined novel but a philosophically astute look at the foibles of modern capitalism.