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The idea I am about to propose may seem a bit farfetched, but I knew a fellow who did it, and did pay his way through life for a few years as an unknown bicycle racer. To make it work, he did have to race almost every weekend all summer long within a hundred or two-hundred mile radius. He did almost as much driving as he did training.
We all know that the big bicycle racing stars get paid directly for winning races, and are paid by their sponsors to wear patches on their jerseys, ride certain brands of bikes and so on.
What you may not know is that it is possible to work professionally on a smaller scale as a racer. Do not expect big dollars from this business, but you can make a living at it.
First, you have to be a good enough racer to win some major local races.
These races usually pay in physical prizes instead of cash for two reasons. One is so that serious racers can maintain their 'amateur' status in case they can qualify for the Olympics. The other is that many regional races are sponsored by manufacturers and merchants who want a bit of product publicity. For the owner of a ski resort to pay cash to a winner does not make as much sense as giving that racer a season ski pass.
So, the trick is to win all the trinkets you can, and then sell them. You'll get all sorts of stuff such as warm-up suits, bicycle helmets, and restaurant dinners. Some are worth quite a bit. Some are silly. I know a fellow who won a Campagnolo 57-tooth chainring for third place in a time trial.
Going a step further, you could be a 'fence' for other racers. Whenever they win something, they could bring it to you to get it sold. You'd keep a percentage, perhaps ten to twenty-five percent of the proceeds. You might establish connections in bike stores and second-hand dealers. In a short time they would get to know you, and realize that the items you bring are all legitimate merchandise.
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