Siddharth Shankar, an Indian-origin entrepreneur who sold his business for $500 million, recently shared his remarkable journey and the personal challenges that followed. In a candid episode of the Trending Diary podcast, Mr. Shankar opened up about his path from humble beginnings to building a $500 million empire without external investment or debt.
Mr. Shankar discussed how his formative years, cultural shifts, and mindset shaped him into the entrepreneur he is today. He offered insights on bootstrapping, resilience, and sustainable growth while also talking about the experience of moving to the UK, building a business from scratch, and overcoming challenges.
Most importantly, he highlighted the emotional aftermath of the exit and how it conflicted with his family’s expectations of happiness. Mr. Shankar revealed that he found the transition tough after selling his company, mainly because he missed having a daily routine. “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 explained.
life after business exit
Despite the external validation, Mr. Shankar struggled with the sudden lack of purpose and meaning in his life after the sale.
“I sold the business because I wanted the best for the business, not for myself,” he said. Siddharth Shankar launched his first business while studying computer science engineering. In 2016, he pursued an MBA at the University of Strathclyde in Glasgow, gaining a global perspective under mentors like Phillip Taylor.
In 2017, he co-founded Tails Trading to connect British brands with Asian markets, focusing on empowering small businesses. After his co-founder left in 2019, Mr. Shankar took full ownership, scaling Tails into the 14th largest brand portfolio company worldwide.
During COVID-19, he pivoted to local UK markets, partnering with supermarkets to ensure resilience and fuel future expansion. In 2024, he made a bold decision and sold Tails Trading’s consumer brand arm for over $500 million, a strategic move to leverage specialised expertise for the company’s next phase. Mr.
Shankar’s candid reflections offer a glimpse into the often unspoken emotional challenges that can accompany financial success and underscore the complexity of life after a major business exit.