Siddharth Shankar, a London-based Indian-origin entrepreneur, recently shared his experience of feeling empty and lost after selling his business for $500 million. Shankar built Tails Trading into one of the world’s largest brand portfolio companies, with its consumer brand division being sold last year. Despite the financial success, Shankar revealed that the emotional aftermath was difficult and did not match the expected joy from family and friends.
Loss of Daily Purpose After Exit
The biggest challenge for Shankar was losing his daily routine. For 15 years, he had a purpose every morning, but after the sale, he found himself asking, “What do I do now?” He spoke about struggling with filling his time, joking about how much golf or PlayStation one could play. The shift from constant work to free time was not easy to handle.
Mixed Feelings Despite Support
Though Shankar received an outpouring of congratulatory messages from friends and relatives, the happiness he felt was mixed with emptiness. He explained how smiling for long periods after receiving so much attention contrasted with moments of solitude when that sense of fulfillment disappeared.
Reflecting on His Motivations
Shankar admitted he sold the business for its benefit, not for personal gain, and wondered if being more selfish might have made a difference. His honesty highlights that even huge financial success does not guarantee personal satisfaction.
Similar Experiences Among Entrepreneurs
Siddharth Shankar’s feelings echo those of other entrepreneurs, such as Indian-origin Vinay Hiremath, co-founder of Loom, who has also spoken about the emotional challenges following a business sale.
