Roelof was born in Claremont in Cape Town in 1965. He completed his schooling at Groote Schuur High in Cape Town, before attending the University of Cape Town, earning his B-Com degree. Roelof qualified as a Chartered Accountant in 1992 after completing his articles at Price Waterhouse Coopers. He obtained a Post Graduate Diploma in Tax Law at the University of Cape Town. Roelof is a sports enthusiast and loves a round of golf, being a handicap of 11. He attends most rugby games at Newlands Stadium, and is actively involved at the Hamiltons Rugby Club in Green Point. Roelof has been involved in the tourism and hospitality industry since 1995.