Born in Paisley, Renfrewshire in 1962, but raised in High Wycombe, Buckinghamshire, Findlay began his love affair with greyhound racing at an early age. Indeed, he has been known since his youth by the not-altogether-flattering nickname 'Harry The Dog'. A regular visitor to now-defunct greyhound racing venues in London, including Hackney, Harringay and White City, as a teenager, he later recalled,'I was surviving, without thieving, up until I was 20.' However, at that stage, heavily indebted, he was convicted of credit card fraud and sentenced to twelve months' imprisonment, of which he served nine, in Her Majesty's Prison Brixton.
Down the years, Findlay has made it his policy to back short-priced favourites – the shorter the better – with colossal sums of money. Consequently, he has won, and lost, fortunes on a regular basis. In September, 2007, for example, he backed New Zealand to win the Rugby World Cup and, although he managed to lay off £600,000 of his original £2.5 million stake during their 20-18 quarter-final defeat by France at the Millenium Stadium, Cardiff, still lost £1.9 million. On the other hand, Findlay has been a multiple winner of the Tote Scoop6, which he once described as the 'best bet on the planet', regularly entering massive permutations worth tens of thousands of pounds at a time.
In 2010, eighteen months after his Cheltenham Gold Cup triumph, was 'warned off' for six months by the British Horseracing Authority (BHA) – although his punishment was later reduced to a fine of £4,500 on appeal – for a technical infraction involving laying one of his own horses, Gullible Gordon. Investigating betting patterns surrounding a novices' chase at Chepstow in October 2009, which Gullible Gordon won, the authorities also investigated a novices' hurdle at Exeter a year earlier, brought to their attention by Findlay himself, in which Gullible Gordon finished only sixth, despite starting long odds-on. On that occasion, Findlay bet £80,000 on his horse to win but, following a disagreement with trainer Paul Nicholls regarding tactics, also laid £18,000 on Gullible Gordon to lose. So, while there was never any suggestion of foul play, Findlay had technically, broken the rules. He was, however, dismissive of the decision, later saying, 'being warned off was the biggest load of bollocks of all time and a complete ****ing liberty.'
In 2013, Findlay suffered further disappointment when he tried, but ultimately failed, to establish Coventry Stadium as a centre for British greyhound racing. He invested £1.7 million in the venture, by which stage he had, in his own words, 'run out of money'; in the absence of an official Bookmakers' Afternoon Greyhound Service (BAGS) contract or, in his opinion, support from the Greyhound Racing Association (GRA), Findlay found it impossible to turn a profit and closed the venue the following year.