AISense investor David Cheriton wrote Google its first check

With a net worth of $1.3 billion, Cheriton is likely the wealthiest full-time academic in the world. But yachts are not his thing. The Stanford computer science professor calls himself “spoiled” for taking the occasional windsurfing vacation to Maui. When pressed to recall his latest splurge, the best he can come up with is a 2012 Honda Odyssey (“for the kids”). His act of thinking is often punctuated by the clicks of three different-colored ballpoint pens that he rotates through his fingers.

The one expensive passion he does pursue? “Startup companies,” he says, as he continues to shuffle his pens. Blue. Click. Red. Click. Black. Click.

When Cheriton uses one of those pens to write a check to a startup, he usually ends up more in the black than in the red. Far more in the black. The first two companies he founded were sold to Cisco Systems and Sun Microsystems, respectively, for hundreds of millions. In all he’s spent more than $50 million out of his own pocket, investing in 17 different firms, which range from VMware to his latest, Arista Networks. But the topper was a $100,000 check he wrote in 1998 to a pair of Stanford Ph.D. students named Larry and Sergey. That check alone is now worth more than $1 billion in Google shares. “I feel like I’ve been very fortunate in investing, but I still have the brain of a scrounger in terms of spending money,” he says.

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