Business & Real Estate Swaps: Are Real Estate Executives Missing Another Chance to Defer Taxes?

By James Brennan, Exchange Solutions Group:
Commercial real estate executives have adopted like-kind exchanges as a default mechanism included in purchases and sales. However, along with underlying real estate assets developers and investors often lose valuable opportunities to defer capital gains taxes.

Commercial real estate executives have adopted like-kind exchanges as a default mechanism included in purchases and sales. However, along with underlying real estate assets developers and investors often lose valuable opportunities to defer capital gains taxes. Gas station tanks, construction equipment, and business aircraft are just a few examples of exchange opportunities we have identified on client balance sheets over the years.

Take for example a hypothetical coal company in Kentucky trading as Cleaner Coal Technologies. Cleaner Coal Technologies has been in business for twenty years. The primary owner, Henry Duggett, wants to sell Cleaner Coal Technologies, move to the Powder River Basin and reinvest the sales proceeds in new equipment, a new brand, and a new physical plant. The company recently received an offer to purchase all outstanding shares and the ownership entity for twenty million dollars. If Henry had significant negotiating power, he might be able to simply sell his stock and pay long-term capital gains on the sale. If he had the right buyer, he might be able to negotiate a tax free reorganization and then use his new stock as collateral for a loan to finance his new company.

However, most buyers will either want to purchase the assets only or insist that the stock sale be classified as an asset sale. As such, the purchase price would be allocated among all of the company’s assets and Henry would have to pay taxes on the net capital gains taxes at the federal and state level. This gain would be exacerbated by depreciation recapture on any capital assets that were depreciated during the last twenty years. All-in-all, the sales price of twenty million dollars could be reduced as much as 35-40 percent.

If Henry considers an asset sale, then his tax advisor should be looking for other opportunities to save him money. In Henry’s case, he should be exploring the possibility of like-kind exchanges. If Henry were to map out his sale and repurchase and convert his ownership in equipment, intellectual property, and real estate into new equipment, intellectual property, and real estate, Henry could bury his cost basis into his new investment and successfully defer a majority of his capital gain.

Goodwill of one company is never going to be like-kind to the goodwill of another company. Nevertheless, the IRS clarifies that intellectual property “such as trademarks, trade names, mastheads, and customer-based intangibles can be separately described and valued apart from goodwill.” The IRS further points out that exchange clients must take heed of the like-kind definitions applicable to intellectual property and personal property and must make sure that their replacement property is like-kind in both nature and character. Furthermore, it provides that depreciable tangible personal properties are of a like class if they are either within the same general asset class or within the same product class.

Whether intangible personal property is of a like-kind to other intangible personal property generally depends on the nature or character of the rights involved (e.g., a patent or a copyright) and the nature or character of the underlying property to which the intangible personal property relates.

As corporate real estate executives, deeper levels of planning provide more areas for you to create value for your clients. The tax planning related to the sale of a business, in particular, gives an opportunity to create a competitive advantage over your peers.