![\"Siddharth](\"https:\/\/www.europesays.com\/uk\/wp-content\/uploads\/2025\/05\/Siddharth_Shankar_1747212958156_1747212958477.jpg\" "\\"Siddharth")
Siddharth Shankar on the void he experienced after selling his company for $500 million(YouTube\/@trendingdiarypodcast) <\/p>\nSiddharth 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\u2019s largest brand portfolio companies, culminating in a $500 million exit for its consumer brand arm last year.<\/p>\n
Siddharth Shankar on the void he experienced after selling his company for $500 million(YouTube\/@trendingdiarypodcast) <\/p>\n
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<\/a>, the India-born founder described the emotional aftermath of the exit and how it was quite at odds with familial expectations of happiness.<\/p>\n After the $500M exit<\/p>\n For Shankar, the hardest part about the exit was losing his routine.<\/p>\n \u201cFor 15 years, I’ve got up in the morning and I’ve had something to do,” he explained. \u201cAnd then one fine day, you get up in the morning and you’re like, \u2018What do I do now?\u2019\u201d<\/p>\n \u201cHow much PlayStation<\/a> can one play? How much golf can I play?\u201d he wondered. \u201cWhat more can I do? It\u2019s not that easy to switch off,\u201d he explained.<\/p>\n \u00a0<\/p>\n<\/p>\n The Indian-origin businessman, who turned to entrepreneurship after a high-profile banking career in New Delhi<\/a>, 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.<\/p>\n \u201cThere was a feeling of happiness because I had messages, calls, emails pouring in… suddenly I had a lot more [supporters],\u201d 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.”<\/p>\n \u201cI sold the business because I wanted the best for the business, not for myself,\u201d Shankar said, adding that perhaps he should have been more selfish.<\/p>\n Shankar is not the only entrepreneur who has experienced feelings of emptiness and discontent after selling his business – Indian-origin Vinay Hiremath<\/a>, co-founder of Loom, had earlier spoken about this issue too.<\/p>\n