At 17 I was the lunchtime bookie runner for a few Italians I worked with, they wrote their own slips and I never even looked at them, wasn't interested and the bets they talked about were Yankees, which meant nothing to me at the time. I never got to know if they won big or not as they would go themselves now and again, now I realise that was if they were collecting anything decent.
Being fairly weak willed in certain quarters it's a good thing I never took any notice of the process.
In recent years I've enjoyed chucking 20 notes at bet365 and had an afternoons enjoyment, mainly 50p bets as that's the amount required to watch the races and I'm not interested if I can't have the thrill of being involved in a close finish, it's quite exhilarating and worth 50p win or lose.
Anyway, biggest win, £145, an Aintree 50p double on Guitar Pete and Brown Pete(?), I was actually at the course on a chaps day out when they came in, I'd done my online bets before leaving home in the morning and only had small stakes singles at the course, either way it was a decent day.
Followed that up 2 days later with Pineau de Re in the sweepstake at work £80, my 2nd biggest ever win.
Played the lottery from day 1 until about 12mths ago and nothing more than the odd 80 quid or so and a few tenners, so sacked it off and now have a few premium bonds as a substitute, feel much better about that, only had £25 back so far but you never know...