"[Swinging] for the fences" literally means to swing a baseball bat as hard as you can at where you think a baseball will be thrown[1]. You're far less likely to connect with the ball, but you will propel the ball much farther if you do manage to.

Swinging for the fences is more apt for companies like Magic Leap, Groupon, Gilt, Pebble, etc.

I'd characterize this guy's approach as being more like "Moneyball." [2]

[1] https://en.wiktionary.org/wiki/swing_for_the_fences

[2] https://en.wikipedia.org/wiki/Moneyball

"Swing for the fences" is basically the same as "go big or go home." You are going to either strike out or hit a home run.

I'm not sure "Moneyball" fits here, the premise of Moneyball was using advanced analytics to take advantage of market inefficiencies.

I would say the baseball idiom that fits here is "cover (one's) bases"

https://idioms.thefreedictionary.com/cover+(one%27s)+bases

>cover (one's) bases To ensure one's safety or success by dealing with every potentially problematic aspect of a situation or activity. A reference to baseball, in which the defensive players must make sure all bases (and baserunners who may occupy them) are accounted for.

(I am fascinated about how many English (American?) idioms are derived from baseball and how I never really thought about it until a couple years ago)