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Mid Oct to November is not a huge difference. Just ask the new company to keep the November start date, as that’s what you originally planned for. I’m sure they would be fine with it.
Definitely do what you can to advocate for yourself. Paying back $15,000 is ridiculous and there has to be a way around it. Let them know you need to wait, especially considering you made plans with that start date in mind and changing them would be hugely costly for you.
Agree with asking to honor the original start date. Two weeks shouldn't make any real difference to them, but it makes a world of difference to you. If they're adamant about it, explain to them that you'd be forfeiting $15k and would need them to make that up for you to be able to justify accepting.
I think you should just explain the situation to them. They should completely understand. If they don't budge or give you consideration it should tell you lots about your new employer. Might be good to know their abilities to show mercy and conseration too. In my opinion there is absolutely nothing unreasonable about your inquiry. Go all in with full confidence and granting them an easy road of denial with a no harm, no foul mentality. They should understand the situation and not expect anybody to loose money from a sheduling need. This kind of sacrifice would be unreasonable in any financial climate but especially this one.
That’s silly they can’t wait two weeks. I’m sure they’d rather keep the $15K than have to pay you. Just tell them you have to stick to November due to prior commitments.
It’s a reasonable ask. You accepted the offer under one set of assumptions, and they changed the plan. I’d phrase it less like a demand and more like a request for support because of the shift. Or ask them to wait until November, like originally planned.
Mentor
I feel like flexing a few weeks is reasonable - feels like you could just ask eh new company to keep the same start date and hope they are reasonable and amenable to sticking with what they originally agreed upon