Shackleford discovered his affinity for mathematics when he began to study algebra in school at approximately 11 years old. He described how math had become something new and interesting.
Before launching his websites, he was a government actuary in Baltimore. It took him approximately one year to convince his wife that going into business for himself within the gambling industry was the right thing to do. He then left his job as an actuary to work on his websites.[4]
Today Shackleford is best known for his websites, The Wizard of Odds and The Wizard of Vegas, which contain analyses and strategies for casino games. In 2002, after moving to Las Vegas, he published a paper with rankings of slot machine payout percentages that were previously considered unavailable.[5] The Time Out Las Vegas referred to the survey as groundbreaking.[6] This paper was referenced by Palms Casino Resort to advertise their competitive payouts.[1]
Shackleford sold his sites on September 19, 2014 for $2.35 million to LCB Network.[7][8]
Shackleford also analyzes new games for game developers and casinos. Clients include Hilton, Realtime Gaming, Playtech, and Shuffle Master. He is the author of Gambling 102: The Best Strategies for All Casino Games (Huntington Press, 2005). Previously, he was an adjunct professor of Casino Math at the University of Nevada, Las Vegas and a contributing editor to Casino Player magazine.
Shackleford is periodically consulted on gambling issues outside of Nevada. In 2010, Pittsburgh Live requested a consult on whether the gaming companies in Pennsylvania would tighten their blackjack rules.[9]
Every year, professional gambler, Max Rubin hosts the Blackjack Ball, an invitation-only event where a winner is given the title of “The Best Gambler in the World.” To win this title, participants are quizzed with gambling trivia and mathematical questions. They also face a second series of tests where their skills are put to the test (card counting, signaling, etc.). The 2011 winner was Michael Shackleford[10] where he beat Anthony Curtis to take the title.[1]
Before changing careers, Shackleford worked as a claims adjuster and later as an actuary for the United States Social Security Administration from 1992 until 2000.[11] His main responsibility there was estimating short-term costs and benefits of Social Security law changes. But he was best known for researching the most popular baby names for each year since 1880.[12][13] The results of this research have been published in many books, newspapers, and magazines, and the Social Security Administration now officially publishes a new list every year of the previous year's most popular names, along with all the previous years' names.[14][15]
Shackleford lives in Las Vegas, Nevada with his wife and three children.