An Indian-origin London-based entrepreneur, Siddharth Shankar, who sold his business for $500 million last year, has opened up on the challenges he faced after selling his company, including confronting an existential crisis. He is known for founding Tails Trading, a firm that became one of the largest brand portfolio companies in the world. While he was leading the company, Tails Trading reached a major goal by selling its consumer brand division for $500 million in 2024. He recently appeared on the Trending Diary podcast and talked about his journey from humble beginnings to building a $500 million firm without debt or external investment. He reflected on how his early life, cultural transitions, and mindset shaped his path as an entrepreneur. Offering valuable insights on bootstrapping, resilience, and sustainable growth, he also spoke about his move to the UK, the challenges of starting a business from scratch, and how he overcame them. He also opened up about the emotional side of the exit, explaining how it didn’t quite align with what his family thought would bring happiness. He said that he found the transition after selling his company tough as it impacted his daily routine. After 15 years of constant hustle, he found it difficult to cope with the sudden lack of purpose—joking about how even PlayStation and golf have their limits. Letting go of his entrepreneurial mindset proved to be a real challenge. “How much PlayStation can one play? How much golf can I play? What more can I do? It’s not that easy to switch off,” he said. He explained how he was flooded with congratulatory messages after selling his company but also highlighted that he did not feel happy about it as he struggled an abrupt absence of meaning to his life. “I sold the business because I wanted the best for the business, not for myself,” Shankar said.