'Money doesn’t fill void': UK entrepreneur who sold his business for Rs 4,656 crore plans to return to work

Tom Grogan’s struggle to adjust after achieving financial independence echoed similar sentiments expressed by other high-profile entrepreneurs.

Tom Grogan, 35, who helped bring the US fast-food chain Wingstop to the United Kingdom, said that life after selling a majority stake in the business for GBP 400 million (around Rs 4,656 crore) had not been as fulfilling as expected. The entrepreneur, who built the brand in the UK over nearly a decade, acknowledged that despite financial security, he struggled to find purpose after the sale and was now preparing to re-enter work life.

As reported by Fortune, Grogan began developing Wingstop UK from scratch, initially contacting the company’s American headquarters through a cold email. After facing over 50 rejections from potential investors, he eventually managed to establish 57 restaurants nationwide.

Reflecting on his experience, he said the years spent building the business had completely occupied his mind. “For seven years, your whole mind is occupied on making a success of this business. It’s all you think about. And then when you get there, it’s just a bit surreal. It’s like, okay, it’s done now. Now what? And money doesn’t necessarily fill that void either,” Grogan said.

Grogan, who once worked as a construction labourer earning GBP 5 per hour, added that he had no firm plans for his next project, though it was unlikely to involve food or hospitality. “You have to now change your head from we’re not business building anymore. We’ve gone from being an entrepreneur to managing money — and they’re two different skill sets. So we have to discover the world of financial instruments, stocks, bonds — all of that stuff that’s all new to us, but we’re being strategically careful,” he explained.

Although he became a multimillionaire through the sale, Grogan said he had avoided unnecessary spending and continued to rent his home. He noted that he and his co-founders, Herman Sahota and Saul Lewin, were taking their time deciding what to pursue next. “It’s boring. I can’t live life sat on a beach. I think we need something to occupy our minds, to challenge ourselves. You need a purpose every day to wake up for, which we don’t have right now,” he said.

Grogan’s struggle to adjust after achieving financial independence echoed similar sentiments expressed by other high-profile entrepreneurs.

Brian Chesky, co-founder and CEO of Airbnb, once admitted that becoming a billionaire after his company’s initial public offering did not bring the happiness he had imagined. “At the bottom of the mountain, you have hope. But the problem is when you get to the top of the mountain oftentimes you are at the top by yourself, disconnected,” Chesky said. He described the period following Airbnb’s IPO as “one of the saddest” of his life, explaining that he had expected success to “fix everything” but instead found it isolating.

Indian-origin businessman Siddharth Shankar, who sold his company for $500 million, also reflected on the mental and emotional aftermath of an exit. He said that although the sale brought financial comfort, it disrupted his routine and left him struggling to fill the void left by years of continuous work. After 15 years of constant involvement in his company, he said he found it difficult to switch off the habits of entrepreneurship.

He remarked that despite external validation, the absence of structure and purpose made the transition difficult, adding that even leisure activities such as golf or gaming could not replace the sense of drive that came with building a business.