Those who know me understand that I love a good bet. The stakes rarely matter and I really don't even care whether I win or lose. I just like to challenge people and watch the psychology of winning and losing. You learn a lot about someone's character when you bet them a single dollar. Some people jump up-and-down in joy after winning $1. And others will make excuses and complain rather than fork over a $1 loss.
In November/December 2011, one of my co-workers started chirping about what a stud cyclist he used to be, how he had a sweet Colnago bike, and how he should ride to and from work with me (he lives in Fairfax, the neighboring town to San Anselmo). After a couple weeks of excuses - having to drive the kids to school, living on top of a big hill, the weather, etc. - I suggested the following bet. From January 1st, 2012 to June 30, 2012, I would pay him $5 for every commute he made to or from his house to work; and he would pay me $1 for every day that he did not commute either way. It was a simple bet, one that I would not have made if I had done the math in my head. But I thought it was a pretty safe bet given a) he had not ridden in years and b) I assumed that the rainy season would keep him off of the bike with any regularity. He whittled me down to me allowing him to ride from the Larkspur Ferry rather than making the whole trip (saving himself about a half hour and a big hill from Downtown Fairfax to his house) and we had a bet. We shook hands and he set up a spreadsheet to keep track of his rides and the money. The stakes were high. He could hypothetically win $25 per week from me. Now to dig out his Colnago from storage, lol.
January had me worried. No rain and he immediately fired up and rode on 1/4, 1/9, 1/12 and 1/13. The week of the 9th really got me scared with him riding three legs and me owing him $13 for that week alone. Thankfully, the pace quickly slowed to only three more rides to finish out the month. January tally - seven legs riding (-$35) fifteen days no riding (+$15). I lost $20.
February was a slow month of riding for him, 18 days of off (+$18) and only two commutes (-$10) for a $8 monthly winner for me. We had to negotiate the fact that Washington's Birthday was a holiday where the office was closed. He didn't work/ride that day, but I still wanted my dollar. I begrudgingly caved on that technicality. End of February, I am still down $12.
By March, I could feel that he was regretting our bet. Again, he only rode only twice ($-10) and slacked-off twenty days (+$20). More curiously, both of the days that he rode were days that I was not in the office. I certainly ribbed him about his choice of riding days. My peers in the office also got into the game of chastising him about his lack of motivation. All in all, at the end of March, I was down $2, but I was wildly entertained. This was the point of the whole bet in the first place.
As of today, April 3rd, I have ridden both days so far this month and he has not ridden either day. Tie game. No money owed as of this morning. But, sadly, upon getting to he office today, I learned that yesterday was his last day in the office. What do we do now?!? Does the bet survive even though he quit? I don't know where he is working (I will soon find out). It may be Marin or San Francisco or otherwise. There are 20+ work days in April/May/June that I could have profited from. Of course, if you ask him, he will say that he is riding to work every day, now. I'm sending him an invoice for $60.