How making a bold comment to his boss helped this startup CEO land his first investment-banking job

When Rob Wiesenthal - the cofounder and CEO of on-demand-helicopter startup Blade - was a young college student, he didn't have quite the same suave, business-savvy attitude that he has today.

That said, he still had the same determination and drive that's constantly pushed him to take risks toward success. Wiesenthal recently told Business Insider one story that's a perfect example of that attitude.

As a summer intern in the IT department at First Boston, which would later become Credit Suisse, Wiesenthal was still figuring out his career path and debating if he wanted to go into investment banking.

One morning, legendary investment-banking mogul Bruce Wasserstein - who was also Wiesenthal's indirect boss - called Wiesenthal into his office because his printer was having issues.

The two got to talking, and Wasserstein asked him, "If you're interested in investment banking, why aren't you a summer analyst?" to which Wiesenthal responded, "Well my dad's not the CFO of Occidental Petroleum, and he's not the CEO of Proctor & Gamble, and you give all those jobs to the kids of clients."

While the bold statement surprised and slightly angered Wasserstein, it also made him take action. The next day he offered Wiesenthal a position as a summer analyst, the position that kick-started Wiesenthal's entire career.

He was hired full-time after college, then worked his way up the ranks to become the head of entertainment and digital media under Frank Quattrone in 1999. He would later move on to C-suite roles with Sony and Warner Music Group before leaving to found Blade.

"If I didn't go in and fix Bruce Wasserstein's printer that day, this whole career trajectory wouldn't have happened," he said. "It's so bizarre. That conversation could have gone a very different way."