As long as you keep all of the business assets and liaibilities seperate, you should be fine. There can be no comingling of any assets.
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Your companies cannot set up IRA's. That is an INDIVIDUAL Retirement Account, which you set up outside your businesses. Filing a bankruptcy for a business does not make sense unless you want someone to take over the liquidation. The business cannot get a discharge. Your ownership interest in the LLC's is an asset in your personal filing, so if the LLC's have any value, you may want to reconsider filing. You should consult with a local attorney.
You need to structure the LLCs correctly and keep them separate to protect each one from the other. The IRA (even a SEP and SIMPLE only) is your account and your money. Talk to a CPA about setting it up if you are using company funds to matching or even fund it. The money is held by a third-party on your behalf and the fund is not affected by your company.
Mr. Goldstein is a Virginia-licensed attorney only. The information is not, nor is it intended to be, legal advice. You should consult an attorney for individual advice regarding your own situation. Answering this question does not in any way constitute legal representation. Contacting Mitchell Goldstein or the Goldstein Law Group does not constitute legal representation, nor is any information you provide protected by attorney-client privilege until otherwise advised.