New Delhi, Dec. 4 -- When Navneet Gupta left his employer in 2020, he walked out with more than experience-a life-changing Esop payout. As an early employee, his stock options grew in tandem with the company's rapid rise, driven by a global mobility boom and a series of acquisitions in the cab-hailing segment.

But this was Gupta's third Esop liquidity event. The first two barely moved the needle. In the third case, the timing aligned. "I would say I got lucky. During that period, the large cab-hailing companies were acquiring smaller companies, and my company was one of them," he recalled. "The payout helped me buy my first house in Hyderabad without a loan and start my venture, ServiceGTD."

It also taught Gupta a lesson many discover t...