Top News

Siddharth Shankar, a London-based entrepreneur of Indian descent who sold his firm for $500 million last year, has spoken about the difficulties he encountered, such as dealing with an existential crisis.

He is credited with starting Tails Trading, which grew to become one of the biggest brand portfolio businesses globally.

In 2024, Tails Trading achieved a significant milestone under his leadership when it sold its consumer brand segment for $500 million.

He recently discussed his path from modest beginnings to developing a $500 million company without debt or outside financing on the Trending Diary podcast.

He considered how his upbringing, societal shifts, and mentality influenced his career as an entrepreneur. He spoke about his journey to the UK, the difficulties of establishing a firm from scratch, and how he overcame them, while also providing insightful advice on resilience, sustainable growth, and bootstrapping.

He also spoke candidly about the emotional aspects of the departure, describing how it didn’t exactly fit with his family’s expectations of happiness.

He said that since it affected his daily schedule, the adjustment after the sale of his business was difficult for him.

Joking that even golf and PlayStation have their limitations, he found it hard to handle the abrupt lack of purpose after 15 years of relentless hustling. It was rather difficult to let go of his business attitude.

“How much can a person play on a PlayStation? How much golf am I allowed to play? What more am I able to do? Turning off isn’t that simple,” he said.

He described how he received a ton of congratulations after selling his business, but he also made it clear that he was unhappy about it since he was struggling with an unexpected lack of purpose in life.

Shankar said, “I sold the company because I wanted the best for the company, not for myself.”