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.
After the $500M exit
For Shankar, the hardest part about the exit was losing his routine.
“For 15 years, I’ve got up in the morning and I’ve had something to do,” he explained. “And then one fine day, you get up in the morning and you’re like, ‘What do I do now?’”
“How much PlayStation can one play? How much golf can I play?” he wondered. “What more can I do? It’s not that easy to switch off,” he explained.
The Indian-origin businessman, who turned to entrepreneurship after a high-profile banking career in New Delhi, said that he was flooded with congratulatory messages from relatives and friends after the exit. Yet his happiness was tinged with a feeling of discontent.
“There was a feeling of happiness because I had messages, calls, emails pouring in… suddenly I had a lot more [supporters],” he admitted. “Your cheeks are hurting because you’ve been smiling for too long, and then you keep your phone down and that content is not there.”
“I sold the business because I wanted the best for the business, not for myself,” Shankar said, adding that perhaps he should have been more selfish.
Shankar is not the only entrepreneur who has experienced feelings of emptiness and discontent after selling his business – Indian-origin Vinay Hiremath, co-founder of Loom, had earlier spoken about this issue too.
(Also read: Indian-origin co-founder who sold his startup for nearly $1 billion says he has no income, is looking for internships)
