I have a successful company for many years but bought another company a couple years ago. The company I purchased has been hit hard and has never been profitable. Long story short, it is not in my interest to invest anymore money into the business to continue keeping it operational. Rather than doing that, I was planning on closing the business down and using the loss to help offset gains from my other business. Assuming I can do that?!
Here's the question that I'm hoping I can get help with - an existing employee has asked to sell the business to them. Since the business is unprofitable and without any assets, they are wanting a sale of essentially $1 as opposed to me closing the doors. I assume they would then take on all the obligations (payables, leases, etc.). I know I will discuss specific details around that with a tax advisor but I wanted to know if I can assume the same loss on a sale as I could closing the business down.
Short summary - I purchased the business for $150k and have never made a dollar. If I close it down I can assume a capital loss of $150k, correct? If I sold it for basically nothing to the employee, can I take the same loss?
