One of his biggest holdings is GoDaddy. Gilbert said he became interested in GoDaddy stock because he liked how the service worked on his personal website. He also liked what he heard a couple years ago from CEO Blake Irving in a TV interview. (Irving, chief executive since 2012, announced in August that he’s retiring at the end of the year.)
Since its 2015 initial public offering, GoDaddy stock has gained nearly 70 percent.
Gilbert said his biggest investing regret was not buying Apple shares decades ago when his wife told him to buy them. He said he owns the tech giant’s stock now, but not at the low entry point he could have had. “My wife had Apple computers before I even knew what a computer was,” he joked.
In Friday trading, Apple shares hit all-time highs back to their December 1980 IPO.
As a fierce competitor and an enthusiastic investor, Gilbert said he works to keep his emotions in check. At the same time, he said he tries to concentrate on the fundamentals of companies, while tuning out on the day-to-day developments out of Washington concerning President Donald Trump and Congress.
“I hate politics,” Gilbert said. “Same circus, different clowns.”
Like many investors, Gilbert worries that a black swan event, or a “crusher” as he calls it, could undo all his hard work. “You could have done everything right and get hit by the unforeseen.”
Nevertheless, Gilbert remains bullish on the Dow. “At some point this year, I think we’re going to hit 24,500,” he predicted.
The Dow Jones industrial average closed on Thursday just below 22,000; another 2,500 points would represent an 11.3 percent advance from current levels. From the beginning of 2017, the Dow has already gained about that same amount.