In the past, I have run several weight loss contests at work, and they usually work very well. To be inclusive to skinny people, we usually split the contest in half. Half the money goes to the person with the highest weight loss, and the other half goes to the highest percentage.
If you weigh 175 and lose 10lbs, that's 5.7%. I you weigh 250 and lose 10lbs, its 4%. Had a few women participate in the past also. And in general they are more sensitive to their weight, what I have done is just publish their delta and their percentage, not their actual weight, if requested to do so.
To keep people motivate over the year, not just planing to make a binge near the end, we also usually split each prize over the 4 quarters, so there is incentive to lose weight over a period of time rather than all at once. Much healthier.
As for the buy-in, you don't have to pay to play, but you can't win if you don't! Normally the buy-in is some multiple of $20 so it splits evenly. One year we did $40, one year $120. And cash up front so I don't have to be chasing people every quarter to pay up.
So who wants to do a weight loss contest?
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