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In fact, he jokes, ''it's quite simple, really''.
Mr Glassford (73), of Milton, was the biggest winner on Saturday after the launch of the TAB's new bet type, the Triple Trio, where punters have to select the trifecta - or first three horses across the line - in each of the last three races at a meeting.
Mr Glassford is not a regular punter on the horses, but the promotion of the new bet type caught his attention, and he had two bets on the Trentham meeting - one on his own selections and a $10 Easybet of random selections chosen by computer.
''I just saw it advertised in the paper a couple of days before and I thought that would be worth a go at,'' he said.
''I didn't think I would be successful.''
Successful is an understatement.
Mr Glassford's $10 Easybet managed to include some rank outsiders including Jaggard, which paid $19.10 for a place, knocking out many punters. Mr Glassford's six-figure return is a far cry from his previous best day on the punt.
''I might go to a race meeting and win $50, or I might come home sometimes with $100 and think you've had a good day, but you've bet on every race,'' he said.
Mr Glassford and wife Loraine were having a family day at their Milton home with their five children, including their daughter and her family who were visiting from Perth. It was the first time in more than five years the family had all been together.
Two of Mr Glassford's children were watching the last race and son Martin checked his father's TAB phone account shortly after the last race. The money was in his account within 10 minutes, but news of the win took a lot longer to sink in.
''It took us an hour to work it out on Saturday night all the same,'' he said.
''I couldn't comprehend it.''
Mr Glassford was in line to win $100,000 but due to a firm track at Trentham, one of his horses in the final leg was scratched, and two more 10% shares transferred on to the winning substitutes, netting a total windfall of $300,000.
Mr Glassford, who had a variety of jobs before retirement,
was quick to rule out the idea of becoming a professional punter.
''I had a mail run in Milton, and I've farmed and had a dairy - I've tried everything.''
Mr Glassford has no plans for the money, although he would like to share it with his family.
Four other winners around the country won a combined total of $400,000.
The next Triple Trio will be held on Wellington Cup day at Trentham but Otago punters might have the inside word on February 1 when the Triple Trio is held on the feature meeting at Wingatui.
But be warned - Mr Glassford plans to be there.