So I got an email from an upscale provider with the subject line, "Losers make it happen, winners make it happen."

… was that this provider doesn’t think there’s any difference between losers and winners.  🤓

your post assumes that SHE reached out to you, which to me means you had either seen her in the past or she was randomly messaging......... and my question then is,  how did she have your address to even reach you ?  
Her statement obviously worked cuz you are spreading the word of her message and she obviously got your attention. For the rest of us though if we do not have any more info then she will look at you as the loser cuz the message stopped with you since the rest of us have nothing to go on. Those kind of messages are  intriguing to me at least to send back a quick response and see where it goes .....but maybe I just have more time on my hands

If I'm not mistaken, HB might still be the best...

Doesnt know your thought process because golf daddy is functionally illiterate.  

I agree that the HB looks excellent on you. Certain brands look better on some women and other brands on others. But what do I know? It all comes off eventually. lol

Purely from a marketing perspective and avoiding other judgements, if you get feedback from a potential client about the ambiguity or other confusion about your marketing materials, it would make sense to adjust that in the future.  Feedback is valuable. Worse is to put out clunkers that no one even bothers to reply to.