You want to avoid entering horses in shows that they aren't ready for because that will result in the horse having negative profits. Watch to see if they leveled up recently because that will tell you to wait about a month before entering them again.

Another thing you might want to change is to go to the bottom of the Barn Manager page and make sure they are showing only Competitive horses. Right now, your horses are showing in every show regardless of whether they are ready, which will also lose you money.

Cloud Peak Stables said:

It looks like you entered your horse in every Fed and Special show available, but his scores indicate he wasn't ready. For example, a %0.00 score in dressage means he just leveled up and has no experience in that new level. So as a result, he placed 12th in that class and any placing under 7th will lose you money.

You want to avoid entering horses in shows that they aren't ready for because that will result in the horse having negative profits. Watch to see if they leveled up recently because that will tell you to wait about a month before entering them again.

Another thing you might want to change is to go to the bottom of the Barn Manager page and make sure they are showing only Competitive horses. Right now, your horses are showing in every show regardless of whether they are ready, which will also lose you money.