Jon Whicker had a weight-loss problem. The finance manager and father of two from Utah, who at his heaviest weighed in at about 400 pounds, had joined a dieting competition with some family members. Several weeks in, things were going great until Whicker, 37, encountered an unusual dilemma: He had lost too much too quickly.

HealthyWage is a weight-loss initiative with an interesting twist — participants have bet their own money and stand to gain considerable payouts — but for health and safety reasons they place limits on shed poundage in a given timeframe, limits Whicker had broken. For the $10,000 prize Matchup competition, rules cap loss at 16.59% of starting weight over a 12-week period.

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