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I would say it's useful, but before considering it, and the questions it poses, I would ask a different question. Is the race fixed?

There are two ways the race could be fixed:

1- It does seem like the bigger VC firms bias the outcome. Getting investment from Andreessen Horowitz or being a graduate of Y Combinator helps you get attention and money, and increases your odds. So perhaps you need to add a fourth question. Who else has bet on this jockey and this horse?

2- But there is another way in which it could be fixed. It could be that the system pays out more than it takes in. That if you were able to place a bet on every horse in every race that you would come out ahead. In this case while it's nice to assess jockey quality it may be more important to just place a lot of bets. I do think that VC's do some of this as well.

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