Penny was educated at St Stithians College (1964–65) and Hyde Park High School (1966–68) in Johannesburg.

Penny was privately educated "in house" at Penny Brothers between 1970 and 1973 where Town Planner Professor EWN Mallows, Quantity Surveyor and Civil Engineer ACM Tyrrell, Company/Property Lawyer PJP Neall and Company/Tax Account AE Hirsowitz were put at his disposal for his tertiary education.

Penny is the owner of Chartwell Castle in north western Johannesburg, where he laid out the largest permanent hedgerow Maze in the Southern Hemisphere.

1 Landowners Association, assisted in the creation of The Greater Chartwell Local Area Committee, in what was then the outlying regions of northern Johannesburg.

The merger of the surrounding areas resulted in a rate based income being viable to afford the region with tarred roads along arterial routes and the provision of municipal water supply.