The virgin Flim Flam brothers: Run blatant scams. Use lies and sweet words to earn customers. Their rules do not apply to them. Attempt to monopolize on the market. Only good for defeating other con artists. Probably settled down with a business.
 
The Chad Iron Will: Always delivers as stated in the contract. Tries to reach agreements with customers following the contract. Respects the rules and makes sure to learn whenever they backfire on him. Satisfies the demand of other ponies. pays his goat employees. Entrepreneur seeking new profit opportunities.

A fantastic day for capitalism!

Who would win? A relatively large group of ponies, including royal family, or an AnCap Chad minotaur who knows ponies never read the contracts?

If it took more than one shot, you weren’t using a Jakobs.