Derek left school at 16 and worked for 2 years as a laboratory assistant at Pilkingtons in St Helens. After 2 uneventful years, he embarked on a journey to become a trainee manager at Woolworths. At the young age of 20, he ventured into entrepreneurship by establishing his own business, specializing in the sale of bread and flour confectionery.

He successfully expanded this enterprise to encompass four shops, catering to both large and small outside events. By the time he reached the age of 25, Derek had taken on the lease of a sizable pub in Rochdale, marking a significant milestone in his career.

Derek's pivotal moment arrived when he assumed the role of Retail Director at Mansfield Brewery in 1981. Over the next decade, he oversaw various aspects of the company that directly impacted its financial performance. However, his entrepreneurial spirit beckoned, as he yearned to break free from working for others who fell short of his expectations.

In 1991, after a decisive "discussion" with the aging Chairman of Mansfield Brewery, Derek made a life-changing decision. With the unwavering support of his wife and a survival instinct, he embarked on a new venture, founding his own pub chain named Tom Cobleigh. Securing private equity funding, Derek initiated this venture with a single pub. With a skilled management team assembled by his side, he meticulously grew the chain to a staggering total of 78 pubs in just three and a half years. The remarkable success of Tom Cobleigh led to an initial public offering (IPO) valued at £64 million. Eleven months after its debut on the stock exchange, Rank PLC acquired the chain, folding it into their leisure division.