Make It

Playing stocks is like tennis — 'it's a great rush,' says ESPN analyst Brad Gilbert

Listening to Brad Gilbert cover tennis matches at the U.S. Open — which heats up this weekend at Flushing Meadows in New York — there's no doubt about his passion for the sport he played professionally, and coached at the highest levels.

But Andre Agassi's former coach told CNBC recently he's also really passionate about trading stocks. Wall Street is "like a tennis match," said Gilbert, currently an ESPN analyst. "It's a great rush. Every day starts new. That's what I love about the market."

Since he was 18, the now 50-something California native Gilbert said he's "always been fascinated" about stocks. (He also loves to give the pro players nicknames.)

Drawing further parallels to tennis, Gilbert said he likes being the one in control. "Whether I'm right or wrong, I have no one to complain to." He said he manages his portfolio through an online brokerage account, and trades about two times per week.

"I get up early in the morning. Get my coffee. See what the market is doing," he said on "Squawk Box" last week,. He added in an off-camera interview he likes to buy stocks and options. "I don't ever play the dark side. I never short. I go into cash if I'm worried."

"It's a great rush. Every day starts new. That's what I love about the market." -Brad Gilbert, ESPN Tennis Analyst

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.

Brad Gilbert
Nick Wass | AP
Brad Gilbert

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.