Siddharth Shankar, an Indian-origin entrepreneur who sold his business for $500 million, recently appeared on a podcast and shared his remarkable journey. The entrepreneur, based in London, is known for founding and leading Tails Trading, a company that grew into one of the world's largest brand portfolio companies. Under his leadership, Tails Trading achieved a significant milestone with a $500 million exit for its consumer brand arm in 2024. Mr Shankar garnered attention not only for his business success but also for his candid discussions about the personal challenges that followed, including an existential crisis after the sale.
In a candid episode of the Trending Diary podcast, Mr Shankar first opened up about his journey from humble beginnings to building a $500 million empire without external investment or debt. He discussed how his formative years, cultural shifts, and mindset shaped him into the entrepreneur he is today, offering insights on bootstrapping, resilience, and sustainable growth. He also talked about the experience of moving to the UK, building a business from scratch and overcoming challenges.
Most importantly, he also talked about the emotional aftermath of the exit, highlighting how it conflicted with his family's expectations of happiness.
Watch the video here:
Mr Shankar revealed that he found the transition tough after selling his company, mainly because he missed having a daily routine. After 15 years of being constantly engaged, he struggled with the sudden lack of purpose, joking about the limits of leisure activities like PlayStation and golf. He found it hard to switch off from his entrepreneurial mindset.
"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.
Following the sale of his company, Mr Shankar received a flood of congratulatory messages, but beneath the surface-level happiness, he felt a sense of discontent. Despite the external validation, he struggled with the sudden lack of purpose and meaning in his life.
"I sold the business because I wanted the best for the business, not for myself," Mr Shankar said.
About Siddharth Shankar
Siddharth Shankar, an Indian-origin entrepreneur, 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, managing 285+ consumer brands and serving 150,000+ customers across retail, HORECA, wholesale, and convenience stores.
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.
