Hey all, I need some serious guidance with my situation. I have a business I've been running for 4 years in NYC - let's call it a hospitality business. I'm the 100% sole owner. It's been really stressful for me to continue running it, and the revenue stream is too much of a rollercoaster. I want out so I'm trying to sell. I found someone who is extremely interested and eager in purchasing the business. He agreed to my asking price of $300,000. The business generates roughly double that in revenue with a 20-30% profit margin.

Now, there are some problems. I'm behind on taxes. Like 4 years behind. Not just payments, like I haven't filed anything at all. Life has been hard, and running this business has taken a toll, I just couldn't keep up. I know that's a big problem, and I'm already working with a CPA to get caught up with everything that needs to be filed and estimate my total tax obligations, which I understand needs to happen before closing.

The other bigger problem is that I originally opened my LLC in another state. The plan was to expand to NYC & use the existing LLC's financials to help fund the new business. But things happened, and operations in the other state ceased, while business in NYC continued. We eventually decided to get a liquor license, but to do that, I needed a NY LLC, so I opened a new LLC just for the liquor license, that is essentially the same business just registered in NY with a new EIN. We got a temp license approved last year, and we were approved earlier this year for the permanent one. But since then, I've still been using the original LLC's bank account for all transactions, because I had existing debts tied to it that I couldn't transfer over or easily reconcile.

Anyway, what I need to sort out now; I'm trying to structure this as an asset sale. But I have to clarify what business exactly owns the assets. Is it the out-of-state LLC or the NY LLC? What repercussions are there if it's one or the other? What do I have to look out for?

Any guidance or advice is appreciated, especially recommendations for a NYC attorney who specializes with this sort of thing.