During the mid-1980s, he went back to Ireland and worked at Campbell Catering and then at Bewley’s Oriental Cafes. He became the Managing Director of Bewley’s Bakery, Bewley’s Franchising and Bewley’s Oriental Café and his responsibility included overseeing the development of the brand in overseas market such as in Japan, USA and UK. It was in 1999 when he opened PERK coffee shops in Dublin which was later sold to Insomnia. All the proceeds of the coffee shop sale were reinvested into Insomnia and Bobby became the CEO and shareholder of the company. From 2004, the business has expanded from 17 shops to 70 shops. The turnover has increased from 5 million euros to 21 million euros. In 2010, he stepped down from the position of CEO and became the chairman of Insomnia so he could concentrate of his portfolio of business.