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I've read a variety of strategies on timing on settlement discussions with credit cards. The common one seems to be to try after first late payment, and then try again after the next.

I have not had time to start the settlement discussion yet. Some of my cc bills are only 2 statements behind, though some are now 3+. To be honest, initially, I just tried paying off the smaller ones I could afford and then realized that I was hitting 0 and somehow contracts just were not coming in.

[For the most part, I have been trying my best to pay off ~6 digits worth of credit card debt incurred from trying to build my startup (foolishly, on personal credit cards). I've spent weeks in grueling full day interviews, only to find that the full time offers aren't worth what I can earn just doing contract work.]

When is the best time to begin the settlement discussion with credit cards (to avoid bankruptcy)? And how does timing affect the discussion?

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Usually after 90 days they close and charge off your credit and sell it to a debt collector.

I would do it immediately after my first month late because they end up adding on late fees and before you know it you will owe 3 times the amount then what you really owe.

To start you need to have at least the first months late payment that is due available to pay them. Once you do, call up the company and state my account is over due but I can pay the first months over due amount and I would like to ask for a one time curtesy credit for the late fee.

Then ask them what is your new balance after your payment and the late fee credit.

How much of that is over due? How much of that I'd other late fees?

Then ask them if they can help you with a payment plan and have it start on next bill due date

You will most likely have to tell them you can pay 25% of what you owe including the new bill amount on the next bill due date.

They should allow you to do this 4 times and you will be caught up.

Make sure you ask them during your payment plan not to charge you another late fee.

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First contact the Consumer Credit Counseling Service. The organization offers free credit counseling and a debt management service for a small monthly fee depending on the state. Visit NFCC.org to find a CCCS office near you.

Then based on their advice I would move forward.

Per. Clark Howard Podcast/TV show.

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    If you're going to answer a different question than the one asked, you have to also explain why you think it is an X-Y problem. – Ben Voigt Apr 20 at 17:10

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