The son of a diamond merchant, Weiss failed his 11 plus exam on the day King George VI died. He subsequently worked for his father in Hatton Garden for 15 years. He admits to enjoying gambling too much, since it became legal to bet on the high street on 1 May 1961. He also acknowledges having been a long time Newcastle United FC supporter since the Wembley 1952 FA Cup Final. Later in life, he very nearly recruited their former striker, Jackie Milburn, to stand for his Captain Rainbow's Universal Party in 1985 in Tyne Bridge.