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“Sleep’s incredibly overrated,” Gilbert said over the phone. “If I sleep past 5:30 in the morning, something’s gone wrong.” Agassi hugs Gilbert after defeating Pete Sampras at the Tennis Masters Series Final 18 March, 2001, in Indian Wells, California. MIKE NELSON/AFP/Getty ImagesGilbert won 20 singles titles as a player and was ranked as high as fourth in the world in 1990. He retired for good in 1995, but began a very successful career in coaching with Andre Agassi, who won six major championships while Gilbert was his coach.
Gilbert described the stock market like a tennis opponent he constantly battles every day. He started trading on his own without a broker five years ago, with GoDaddy and SalesForce two of his current holdings. Gilbert likened Twitter market forces like playing a difficult tennis opponent, like a tricky lefty. This aspect of a constant match against the market has enabled his love of stocks to grow over time. It's an extension of his passion for competing, how he roots for his stocks like the Bay Area sports teams he loves, the Raiders, Warriors and A's.