Financial success is often seen as the ultimate goal for entrepreneurs, but for some, it brings unexpected emotional challenges. Siddharth Shankar, the Indian-origin founder of Tails Trading, found himself facing just that after selling his company’s consumer brand arm in a $500 (Rs 427.19 crores) million deal. Despite the massive valuation and public praise, Shankar revealed that the aftermath of the sale left him grappling with a deep sense of emptiness and disconnection. His story sheds light on the lesser-known struggles that can come after achieving professional milestones.
A Celebrated Exit That Brought Unexpected Emptiness
Siddharth Shankar, who built Tails Trading into one of the world’s leading brand portfolio companies, recently discussed his emotional experience following the deal. Speaking on the Trending Diary podcast, he described how the public celebration did not translate into personal satisfaction. “There was a feeling of happiness because I had messages, calls, emails pouring in... suddenly I had a lot more [supporters],” he recalled. “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.”
Shankar explained that one of the most difficult adjustments was the sudden loss of structure in his daily routine. For over 15 years, his schedule revolved around building and running the business. “For 15 years, I've got up in the morning and I've had something to do,” he said. “And then one fine day, you get up in the morning and you're like, ‘What do I do now?’”
Attempting to fill the gap with leisure did little to help. “How much PlayStation can one play? How much golf can I play?” he asked, admitting the struggle to adapt. “What more can I do? It’s not that easy to switch off.”
According to Shankar, his motivation for selling the business was rooted in what he believed was best for the company’s future. “I sold the business because I wanted the best for the business, not for myself,” he said. However, he now questions whether being more self-focused might have helped him emotionally in the long run.
Who is Siddharth Shankar?
According to his LinkedIn, Siddharth Shankar’s entrepreneurial journey began in India, where he started his career in banking in New Delhi before shifting to entrepreneurship. He founded and led Tails Trading, a company that grew to manage over 285 consumer brands across multiple categories and became one of the world’s largest brand portfolio companies. Under his leadership, the company established a global distribution network serving more than 150,000 customers worldwide.
Shankar’s strategies included managing a £2 billion trade finance fund and navigating pandemic-related challenges by adapting the business model. In 2024, he successfully orchestrated a $500 million exit of the company’s consumer brand arm, marking a significant milestone in his entrepreneurial career.
A Celebrated Exit That Brought Unexpected Emptiness
Siddharth Shankar, who built Tails Trading into one of the world’s leading brand portfolio companies, recently discussed his emotional experience following the deal. Speaking on the Trending Diary podcast, he described how the public celebration did not translate into personal satisfaction. “There was a feeling of happiness because I had messages, calls, emails pouring in... suddenly I had a lot more [supporters],” he recalled. “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.”
Shankar explained that one of the most difficult adjustments was the sudden loss of structure in his daily routine. For over 15 years, his schedule revolved around building and running the business. “For 15 years, I've got up in the morning and I've had something to do,” he said. “And then one fine day, you get up in the morning and you're like, ‘What do I do now?’”
Attempting to fill the gap with leisure did little to help. “How much PlayStation can one play? How much golf can I play?” he asked, admitting the struggle to adapt. “What more can I do? It’s not that easy to switch off.”
According to Shankar, his motivation for selling the business was rooted in what he believed was best for the company’s future. “I sold the business because I wanted the best for the business, not for myself,” he said. However, he now questions whether being more self-focused might have helped him emotionally in the long run.
Who is Siddharth Shankar?
According to his LinkedIn, Siddharth Shankar’s entrepreneurial journey began in India, where he started his career in banking in New Delhi before shifting to entrepreneurship. He founded and led Tails Trading, a company that grew to manage over 285 consumer brands across multiple categories and became one of the world’s largest brand portfolio companies. Under his leadership, the company established a global distribution network serving more than 150,000 customers worldwide.
Shankar’s strategies included managing a £2 billion trade finance fund and navigating pandemic-related challenges by adapting the business model. In 2024, he successfully orchestrated a $500 million exit of the company’s consumer brand arm, marking a significant milestone in his entrepreneurial career.
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