Bobby is a registered non-practicing Attorney with the Law Society of the Northern Provinces. He initially started his career as a Public Prosecutor, and in 1970 was admitted as an Attorney, Notary Public and Conveyancer. He practiced as an Attorney for 35 years, three of which were in Durban and the balance in Klerksdorp. He moved to Johannesburg in September 2005 to join Rand Leases Properties (Pty) Ltd as Head of Legal Services and was responsible for a number of commercial matters on behalf of the company, until his formal retirement in September 2010. Since then, he acted on a part-time basis as legal/commercial consultant to William Tell Holdings Ltd and South Ridge Properties (Pty) Ltd.

Bobby joined Christodoulou & Mavrikis Inc. in 2017 as a Consultant and is actively involved in planning the strategic direction of the firm, mentoring and encouraging the broader legal education of the professional staff and advising on legal matters from time to time.

Whilst in Klerksdorp, Bobby was a founding partner of the legal practice known as Waks & Brady Inc., consisting of seven directors and several lawyers. Specialist fields covered by Bobby during this time included Business Law, Estate Planning, Dispute Resolution, Property Law, Local Government Law, Notarial Services, and Mining & Minerals.

Bobby has been involved in numerous philanthropic activities during his time in Klerksdorp and since relocating to Johannesburg he has become an integral member of the local community by becoming involved with the Body Corporate in his residence; developing pre-school facilities in township (ASHA); Food Gardening; and a member of the Parish Pastoral Council of the Rosebank Catholic Church;

At the age of 71 Bobby is a regular squash and tennis player. He is married to Margaret and they have four children and six grandchildren.