Use a Charitable Remainder Trust: You can defer capital gains by moving appreciated assets into a Charitable Remainder Trust (CRT) before you sell. A CRT is a type of trust that is for the benefit of both an individual (like you) and a charity. The individual receives distributions each year for a specified term.
In an asset sale, the seller faces double taxation: the company pays taxes on the sale of assets, and shareholders are taxed on the distribution of proceeds. Buyers may benefit from tax deductions on depreciated assets. In a share sale, the seller typically incurs capital gains tax on the sale of shares.
In a share deal, the buyer acquires a separate legal entity, while under an asset deal the assets and liabilities acquired can be transferred directly into the purchasing legal entity. However, it is often useful to establish a separate legal entity that takes over the business that was acquired via the asset deal.
In an asset sale, the ownership of these acquired assets would change hands, with the buyer negotiating separately for each asset. In a stock sale, ownership of such assets does not change hands in the same way. The target still retains its ownership typically, even if the target has a new owner.
In an asset sale, the ownership of these acquired assets would change hands, with the buyer negotiating separately for each asset. In a stock sale, ownership of such assets does not change hands in the same way. The target still retains its ownership typically, even if the target has a new owner.
Stocks are considered a capital asset, however personal property are also considered capital assets.
The short answer is that a stock sale is better for you, the seller, while the buyer benefits from an asset sale. But, since we're talking about the IRS, there are infinite variations and complications. As such, you will want to get professional tax and legal advice before proceeding.
The benefit of an asset sale, from the buyer's perspective, is that it can select which assets and liabilities to acquire in the deal, compared to a stock sale or merger, where the buyer acquires all the assets and liabilities of the target.