He is a former Liverpool season ticket holder, but Rob Lloyd has promised he will be backing the Blues when he attends tonight's match at Anfield.
His approach for Pompey marks his first professional interest in football.
The 44-year-old, born in Cheshire, made a career in the property market, starting as a commercial assistant in the early 1980s.
By the age of 26 he had already made his first fortune, but lost it all in the crash of the mid-1990s.
And it was whilst living in a caravan in North Wales in 1998 that he founded property firm Eatonfield, which he floated on the stock market in 2006. But only last week he had to raise a 900,000 funding deal with joint venture partner, Jenard Properties, after bank funding was withdrawn, plunging the group into trouble.
In 2007 he set up Rob Lloyd Racing and has spent more than 4m on training horses. In April 2009 he appeared on Channel 4's Secret Millionaire and gave away 40,000.
Watch Rob Lloyd in Channel 4's A Secret Millionaire
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