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Jim is a partner in Taft’s Tax practice and practices principally in the areas of federal tax law; tax credit financing; individual, partnership and corporate tax planning; M&A; tax-exempt organizations and general commercial and corporate law.

Jim has been actively practicing in the area of the New Markets Tax Credits (NMTC) program since its inception in 2001. He has organized community development entities (CDEs) and represented CDEs, borrowers and other parties in structuring and closing numerous NMTC transactions. Jim also advises clients regarding Qualified Opportunity Zone matters.

Jim advises LLCs, partnerships, corporations and individuals in connection with the formation of new companies, mergers and acquisitions, formation of joint ventures, like-kind exchanges, ownership succession planning, and general business operations. These clients are involved in a variety of industries, including banking, venture capital, real estate, construction, consulting and investing.

Jim also advises charitable and non-charitable tax-exempt organizations, including health care entities, schools, religious and civic organizations. In addition to advising management of these organizations with respect to matters pertaining to general operation and maintenance of tax-exempt status, Jim has assisted clients in forming, restructuring and dissolving tax-exempt organizations, as well as forming donor- advised funds.

Prior to joining the firm, Jim worked at the law firm of Lewis Rice and Fingersh in St. Louis, Missouri, where he concentrated his practice in federal and state taxation. He also clerked for the Hon. Robert P. Ruwe of the U.S. Tax Court in Washington, D.C.

The sale of a C corporation business that is structured as an asset sale is subject to two levels of tax. There is a tax on the corporation (21% federal) and a tax on the shareholders when the sales proceeds are distributed (20% federal). By comparison, on a sale of stock, a shareholder is only subject to a tax of 20% (federal).

In some cases (admittedly not common), the goodwill of a business may be more appropriately treated as owned

Continue Reading Did You Know that you may be able to reduce your tax on a sale of a corporate business by allocating part of the sales price to personal goodwill?

Content by Dimitrios Lalos (Minneapolis) and Nathan Hagerman (Indianapolis)

Effective July 1st, Minnesota instituted new Retail Delivery Fee obligations for sellers of product delivered into Minnesota to raise revenue for infrastructure and road improvements. Sellers with $1 million or more in retail sales must collect and remit to the Minnesota Department of Revenue, or pay themselves, a new Retail Delivery Fee of fifty cents per transaction that equals or exceeds $100 (before application of sales and use taxes) of taxable

Continue Reading Did you know Sellers Must Collect a Retail Delivery Fee for Products Delivered to Minnesota Customers?

When a company sees its stock value drop, this can result in employees holding options that are “underwater“ or “out of the money“. This can significantly undermine the intended incentive effect desired by the employer in issuing the option.  For these reasons, employers might consider whether to reduce the exercise price on outstanding awards to equal the current market value of the stock, a.k.a. option repricing.

While there are various business impacts of repricing that will need to be considered

Continue Reading Did you know that you can reprice underwater employee options without triggering tax to the employee?

Oftentimes when a partnership plans to sell real estate, some partners want to cash out while other want to roll over into other real estate tax-free.  The challenge is that if the partnership receives cash in part to pay to the partners cashing out, then all the partners would be taxed on their percentage of that cash. 

As discussed in a prior “Did You Know,” one way to do address this is through a “drop and swap.”  Another alternative is

Continue Reading Did you know that you can cash out a partner in like kind exchange using an installment note?

When an S corp seeks to wind up its affairs by selling assets in an installment sale and then liquidating, the distribution of the note along with other property (e.g., cash retained or downpayment) can trigger unintentional acceleration of tax on the deferred gain.

The Internal Revenue Code provides that an S corp may distribute an installment note to its shareholders in liquidation without triggering tax on the deferred gain from the note. However, for those seeking to take advantage

Continue Reading Did you know a liquidating distribution of an installment note by an S corp can trigger gain?

Generally, buyers of businesses want to buy assets so they can take a step up on a tax basis. Sellers prefer to sell stock, so their gain will be taxable at favorable capital gains rates. Some gain is usually taxable at higher ordinary income tax rates in an asset sale. Accordingly, S corporation owners who have been asked to sell assets typically request, and buyers typically agree to, an increase in the purchase price to account for the additional tax

Continue Reading Did you know that state tax PTE election may offset the additional tax on an S corporation asset sale vs. a stock sale?

Beginning in 2022, businesses are now required to capitalize specified research and experimental expenditures  (“SRE expenditures“) and amortize (deduct) them over time.  Expenditures attributable to domestic research are amortized over five years and expenditures attributable to foreign research are amortized over 15 years.   SRE expenditures are generally research and development costs in an experimental or laboratory sense for product development or improvement and include software development costs.

If the property with respect to which the SRE expenditures are being amortized

Continue Reading Did you know you could lose the benefit of R&D deductions in the sale of your business?

As you probably know, in a like-kind exchange, any sale proceeds that you do not apply to purchasing a new investment property will be taxable (up to the total gain on the property). The challenge with making a like-kind exchange of property in a seller-financed sale is that the seller doesn’t receive any (or very little) cash at closing.  As a result, even if the seller rolls that cash over into a new property, subsequent payments received on the note

Continue Reading Did you know you may be able to make a 1031 exchange of property that you sell on an installment note?

A common structure in the acquisition of the assets of a business is for the seller to receive equity from the acquirer in addition to cash. Receipt of a partnership or LLC interest in exchange for property is generally non-taxable. A seller can obtain substantial tax savings by deferring gain on the low-basis assets by specifying in the agreement that specific high-basis assets will be sold for cash and that certain low-basis assets will be exchanged for partnership interests. 

To

Continue Reading Did you know in a sale of assets to a partnership for cash and partnership interests you can reduce tax by specifying which assets are sold and which are exchanged for partnership interests?

In the recent case of ES NPA Holding LLC v. Commissioner, the IRS argued that a profits interest can only be received tax-free by a service provider when the service is rendered directly to or for the benefit of the entity issuing the interest. The facts of the case are complicated, but in short, in the ES NPA case, the person that received the profits interest had rendered services to a corporation which was a member in the LLC (taxed

Continue Reading Did you know you can receive profits interest tax-free even when the services are not rendered directly to the partnership?