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This is not a game where you get rich quick. The best way to make money in this game is by showing, but it takes time to build a good show string. The way showing works to earn money is every horse in a class except the one that places last earns some number of points (how many depends on the level of the show and the horse's placing). You will earn a daily showing bonus that is about 11% of the number of points of all your horses (75% of your points weekly, split into daily installments). You should be sure to train all your horses every week (except foals who don't train) and show them twice a week to earn as many points as you can. Don't worry about negative profit numbers, since those only calculate winnings minus entry fees, if your horse is earning points, that will eventually pay far more than the horse looses. It will take time for young horses to train up to higher classes and to build a decent number of points, but a good show string is the way to get rich in this game.

You should check out the Available to Adopt program to get a couple of show horses with lots of points to jump start your show herd. http://hj2.huntandjump.com/forum/discussion/18046/available-to-adopt-free-show-horses-for-new-players#Item_8