India, May 14 -- Siddharth Shankar has the kind of money that most people can only dream of - but that has not made him immune to feelings of emptiness. The Indian-origin entrepreneur, based in London, built and led Tails Trading to become one of the world's largest brand portfolio companies, culminating in a $500 million exit for its consumer brand arm last year.

In a recent podcast, Siddharth Shankar opened up about the existential crisis he experienced after selling the business. During his appearance on the Trending Diary podcast, the India-born founder described the emotional aftermath of the exit and how it was quite at odds with familial expectations of happiness.

For Shankar, the hardest part about the exit was losing his routin...