How do I make vertical Letters stick to a round path

Hello everyone. I am in a stump really bad. trying to make little medals for the little girls i coach. I uploaded a video hoping I can better explain what is it that I am trying to do. in the video you can see that I pretty much converted the text to be vertical. my issue is for some reason after converting it i cannot get the vertical to still be vertical on the left side of the circle. its frustrating. any advice is greatly appreciated. TIA

I cannot view the video without creating a login. Can you post it on another media platform?

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