In the early aughts, when Shardul Shah first met technology entrepreneur Joshua Motta as undergraduates at the University of Chicago, Motta seemed unusually reserved.

“I found it challenging to meet his intellect,” said Shah, a partner at venture capital firm Index Ventures. “As a consequence, [our discussions] were more about me than him. I really couldn’t get him loose.”

Once the young men came to know each other better, Motta opened up and Shah realized why it was so difficult to loosen him up. Unlike other students at the prestigious university, Motta worked as a CIA officer. He was effectively obliged to be reticent. “I realized much later how that eventually played to his advantage, being in the intelligence community,” Shah said.