For some business owners, succession planning is a complex and delicate matter involving family members and a long, gradual transition out of the company. Others simply sell the business and move on. If you are leaning toward a business sale, here are eight ways to prepare:

1. Develop or renew your business plan. Identify the challenges and opportunities of your company and explain how and why it is ready for a sale. Address what distinguishes your business from the competition and include a viable strategy that speaks to sustainable growth.

2. Ensure you have a solid management team. You should have a management team in place who have the vision and know-how to keep the company moving forward without disruption during and after a sale.

3. Upgrade your technology. Buyers will look more favorably on a business with up-to-date, reliable and cost-effective IT systems. This may mean investing in upgrades that make your company a “plug and play” proposition for a new owner.

4. Estimate the true value of your business. Obtaining a realistic, carefully calculated business valuation will lessen the likelihood that you will leave money on the table. A professional valuator can calculate a defensible, marketable value estimate.

5. Optimize balance sheet structure. Value can be added by removing nonoperating assets that are not part of normal operations, minimizing inventory levels and evaluating the condition of capital equipment and debt-financing levels.

6. Minimize tax liability. Seek tax advice early in the sale process — before you make any major changes or investments. Recent tax law changes may significantly affect a business owner’s tax position.

7. Assemble all applicable paperwork. Gather and update all account statements and agreements such as contracts, leases, insurance policies, customer/supplier lists and tax filings. Prospective buyers will request these documents as part of their due diligence.

8. Selling in the future? Plan to use your time wisely. If you are considering selling in the short or long term, it is a good idea to have your trusted business adviser conduct a “check-up” on your company’s financial statements . From this, your adviser can help create an improvement plan designed to better position your company for sale down the road, within a time frame that meets your business needs.

Succession planning should play a role in every business owner’s long-term goals. Selling the business may be the simplest option, though there are many other ways to transition ownership.

Over the last several years, virtual currency has become increasingly popular. Bitcoin is the most widely recognized form of virtual currency, also commonly referred to as digital, electronic or crypto currency.

While most smaller businesses are not yet accepting bitcoin or other virtual currency payments from their customers, more and more larger businesses are. Businesses also can pay employees or independent contractors with virtual currency. But what are the tax consequences of these transactions?

Virtual Currency 101

Virtual currency has an equivalent value in real currency and can be digitally traded between users. It also can be purchased with real currencies or exchanged for real currencies and is most commonly obtained through virtual currency ATMs or online exchanges.

Goods or services can be paid for using “virtual currency wallet” software. When a purchase is made, the software digitally posts the transaction to a public ledger. This prevents the same unit of virtual currency from being used multiple times.

Tax impact

Questions about the tax impact of virtual currency abound and the IRS has yet to offer much guidance.

In 2014, the IRS ruled that bitcoin and other convertible virtual currency should be treated as property, not currency, for federal income tax purposes. This means that businesses accepting virtual currency payments for goods and services must report gross income based on the fair market value of the virtual currency when it was received, measured in equivalent U.S. dollars.

When a business uses virtual currency to pay wages, the wages are taxable to the employees to the extent any other wage payment would be. You must, for example, report such wages on your employees’ W-2 forms. They are subject to federal income tax withholding and payroll taxes, based on the fair market value of the virtual currency on the date received by the employee.

When a business uses virtual currency to pay independent contractors or other service providers, those payments are also taxable to the recipient. The self-employment tax rules generally apply, based on the fair market value of the virtual currency on the date received. Payers generally must issue 1099-MISC forms to recipients.

Finally, payments made with virtual currency are subject to information reporting to the same extent as any other payment made in property.

Deciding whether to go virtual

Accepting virtual currency can be beneficial because it may avoid transaction fees charged by credit card companies and online payment providers (such as PayPal or Venmo, in some cases) and attract customers who want to use virtual currency. It can also pose tax risks as guidance on the tax treatment or reporting requirements is limited.

It is important to research and contact your business adviser on the tax considerations when deciding whether your business should accept bitcoin or other virtual currencies.

Nonprofits typically work hard to make the world a better place and their success depends greatly on financial health and integrity. That is why many nonprofits need to employ a chief financial officer (CFO). Depending on your size and other factors, you may be one of them.

What are the CFO’s responsibilities?

Generally, the nonprofit CFO is a senior-level position charged with oversight of the organization’s accounting and finances. He or she works closely with the CEO/executive director, finance committee and treasurer and often serves as a business partner to your program heads. CFOs typically report to the CEO/executive and director or board of directors on the organization’s finances, analyze investments and capital, develop budgets and devise financial strategies.

The CFO’s role and responsibilities will vary significantly based on the organization’s size, as well as the complexity of its revenue sources. In smaller nonprofits with budgets of $1.5 million to $10 million, CFOs often have wide responsibilities — possibly for accounting, human resources, facilities, legal affairs, administration and IT. Midsize organizations, with budgets running up to $40 million and simple funding and programming, also may require their CFOs to cover such diverse areas.

In larger nonprofits, though, CFOs usually have a narrower focus. They train their attention on accounting and finance issues, including risk management, investments and financial reporting. CFOs of midsize organizations with diverse programs (for instance, several programs that generate revenue) or governmental funding may have a similar focus.

What are your requirements?

Nonprofits with small budgets and straightforward operations probably assign these responsibilities to the executive director or choose a more affordable option, such as hiring an outsourced CFO. As organizations grow and their financial matters become more complex, though, CFOs can help steer the ship.

Experts suggest weighing the following factors when determining whether to bring a CFO on board:

Static organizations are less likely to need a CFO than nonprofits with evolving programs and long-term plans that rely on investment growth, financing and major capital expenditures.

Who is right for you?

With CFOs playing such an essential role, your nonprofit should devote considerable time and effort to hire someone with the right qualifications. At a minimum, you want a person with in-depth knowledge of the finance and accounting rules particular to nonprofits. A CFO who has only worked in the for-profit sector may find the differences difficult to navigate. Nonprofit CFOs also need a familiarity with funding sources, grant management and, if your nonprofit expends $750,000 or more of federal assistance, single audit requirements.

What about educational and professional credentials? The ideal candidate should have a certified public accountant (CPA) designation and optimally an MBA.

In addition, the position requires strong communication skills, strategic thinking, financial reporting expertise and the creativity to deal with resource restraints. It also is useful if the CFO has had experience in an organization with a wide range of functions — for example, human resources and IT — so that he or she can identify when outside professional expertise vital to the success of your organization is needed.

Finally, it is beneficial to find a CFO who has a genuine passion for your mission is highly beneficial as it makes it easier for the CFO to understand that success for a nonprofit is not only about the bottom line.

Asset to your organization

CFOs bring many advantages to the table. Not only can they help maintain fiscal health and assist the organization in achieving its goals, but they also can boost your credibility with potential donors and watchdogs. If your budget is growing and financial matters are becoming more complicated, you may want to add a CFO, or outsourced CFO, to the mix.

Sidebar: The outsourcing alternative

Does your organization lack the size or complexity to warrant having a full-time chief financial officer (CFO) on staff, but desire the financial peace of mind the position may provide? Nonprofits often look to existing staff when filling the CFO position, but in-house accounting staff may not possess the requisite financial expertise. A popular option is to outsource CFO responsibilities to your CPA firm. With outsourcing, you gain cost-efficient access to top-notch expertise as well as other benefits at a far less cost. An outsourced CFO may also provide a strategic sounding board for the CEO/executive director and board of directors. To learn more, please contact SKR+CO’s Business Advisory team.

In a much-anticipated ruling that confounded the expectations of many court watchers, the U.S. Supreme Court has given state and local governments the green light to impose sales taxes on out-of-state online sales. The 5-4 decision in South Dakota v. Wayfair, Inc. was met by cheers from brick-and-mortar retailers, who have long believed that the high court’s previous rulings on the issue disadvantaged them, as well as state governments that are eager to replenish their coffers.

The previous rulings

The Supreme Court’s holding in Wayfair overruled two of its precedents. In its 1967 ruling in National Bellas Hess v. Dept. of Revenue, the Court tackled a challenge to an Illinois tax that required out-of-state retailers to collect and remit taxes on sales made to consumers who purchased goods for use within the state.

That case involved a mail-order company. The high court found that, since the company’s only connection with customers in Illinois was by “common carrier” or the U.S. mail, it lacked the requisite minimum contacts with the state required by the Due Process and Commerce Clauses of the U.S. Constitution to impose taxes. It held that the state could require a retailer to collect a local use tax only if the retailer maintained a physical presence, such as retail outlets, solicitors or property in the jurisdiction.

Twenty-five years later, in Quill Corp. v. North Dakota, the Supreme Court reconsidered the so-called physical presence rule in another case involving mail-order sales. Although it overruled its earlier due process holding, it upheld the Commerce Clause holding. The Court based its ruling on the Commerce Clause principle that prohibits state taxes unless they apply to an activity with a “substantial nexus” — or connection — with the state.

Criticism of the physical presence rule

The rule, established in Bellas Hess and affirmed in Quill, has been the subject of extensive criticism. This has been particularly true in recent years as traditional stores have lost significant ground to online sellers. In 1992, the Court noted that mail-order sales in the United States totaled $180 billion, while in 2017 online retail sales were estimated at $453.5 billion. Online sales represented almost 9% of total U.S. retail sales last year.

It is estimated that states lose $8 billion to $33 billion in annual sales tax revenues because of the physical presence rule. States with no income tax, such as South Dakota, have been especially hard hit. South Dakota’s losses are estimated at $48 million to $58 million annually.

The sales tax at issue

In response to the rise in online sales and the corresponding effect on sales tax collections, South Dakota enacted a law requiring out-of-state retailers that made at least 200 sales or sales totaling at least $100,000 in the state to collect and remit a 4.5% sales tax. The 2016 law also included a clause declaring an emergency in light of the need “for the support of state government and its existing public institutions …”

South Dakota subsequently sued several online retailers with no employees or real estate in the state. It sought a declaration that the sales tax was valid and applicable to the retailers, along with an injunction requiring the retailers to register for licenses to collect and remit the tax. A trial court dismissed the case before trial, and the State Supreme Court affirmed, citing its obligation to follow U.S. Supreme Court precedent, however persuasive the state’s arguments against the physical presence rule might prove.

The Supreme Court’s reasoning

The majority opinion — penned by Justice Kennedy but joined by the unusual mix of Justices Thomas, Ginsburg, Alito and Gorsuch. It described the physical presence rule as “unsound and incorrect.” According to the Court, the rule becomes further removed from economic reality every year.

Quill, the opinion said, creates market distortions. It puts local businesses and many interstate businesses with a physical presence at a competitive disadvantage compared with remote sellers that need not charge customers for taxes. Kennedy wrote that the earlier ruling “has come to serve as a judicially created tax shelter for businesses that decide to limit their physical presence and still sell their goods and services to a State’s consumers — something that has become easier and more prevalent as technology has advanced.”

In addition, the Court found that Quill treats economically identical actors differently for arbitrary reasons. A business with a few items of inventory in a small warehouse in a state is subject to the tax on all of its sales in the state, while a seller with a pervasive online presence but no physical presence is not subject to the same tax for the sales of the same items.

Ultimately, the Supreme Court concluded that the South Dakota tax satisfies the substantial nexus requirement. Such a nexus is established when the taxpayer “avails itself of the substantial privilege of carrying on business” in the jurisdiction. The quantity of business the law required to trigger the tax could not occur unless a seller has availed itself of that substantial privilege.

Of course, as the Court acknowledged, the substantial nexus requirement is not the only principle in the Commerce Clause doctrine that can invalidate a state tax. The other principles were not argued in this case, but the high court observed that South Dakota’s tax system included several features that seem designed to prevent discrimination against or undue burdens on interstate commerce, such as a prohibition against retroactive application and a safe harbor for taxpayers who do only limited business in the state.

The impact

The significance of the Supreme Court’s ruling was felt almost immediately in the business world, with the share prices of major online retailers quickly dropping (even those that do collect and remit sales taxes). It is not just the behemoths that could be affected, though.

The Court recognized that the burdens of nationwide sales tax collection could pose “legitimate concerns in some instances, particularly for small businesses that make a small volume of sales to customers in many States.” But, it said, reasonably priced software eventually may make it easier for small businesses to cope. The ruling also pointed out that, in this case, the law “affords small merchants a reasonable degree of protection,” such as annual sales thresholds.

Further, the Court noted, South Dakota is one of more than 20 states that are members of the Streamlined Sales and Use Tax Agreement (SSUTA). These states have adopted conforming legislation that provides uniform tax administration and definitions of taxable goods and services, simplified tax rate structures and other uniform rules. Colorado does not participate.

Closer to Home

Colorado has an incredibly complex sales and use tax system, with over 300 jurisdictions that impose and administer tax, including home-rule cities, or cities who collect their own sales tax. Business owners can learn more by reviewing Colorado’s Sales and Use Tax General Information and Reference Guide; however, confirming your tax liability with your CPA is recommended.

What next?

In light of the Supreme Court’s decision, states may need to revise or enact legislation to meet the relevant constitutional tests — including, but not limited to, the substantial nexus requirement. If you have questions regarding sales tax collection requirements for your business, please contact your business adviser.

Starting early on your 2018 tax planning is especially critical this year, as tax reform has substantially changed the tax environment. Tax planning helps determine the total impact new laws may have on your particular scenario and identifies proactive tax strategies that make sense for you this year, such as the best way to time income and expenses. From this analysis, you may decide to deviate from tax approaches that worked for you in previous years and implement a new game plan.

Many variables

A tremendous number of variables affect your overall tax liability for the year. For example, the timing of income and deductible expenses can affect both the rate you pay and when you pay. By reviewing your year-to-date income, expenses and potential tax, you may be able to time income and expenses in a way that reduces, or at least defers, your tax liability.

Act now

Under the TCJA tax reform legislation, most of the provisions affecting individuals are in effect for 2018–2025 and additional major tax law changes are not expected in 2018.

Starting sooner will help prevent you from making costly assumptions under the new tax regime. It will also allow you to take full advantage of new tax-saving opportunities.

A large number of variables affect your overall tax liability for the year. It is especially critical this year because tax reform has substantially changed the tax environment. Planning early in the year can give you more opportunities to reduce your 2018 tax bill.

If you own a business, this is particularly important for the new qualified business income (QBI). New strategies are available to help you time income and expenses to minimize tax liability.

Now and throughout the year, seek your business adviser to help you determine how tax reform affects you and what strategies you should implement to minimize your tax liability.

Tax reform has led to confusion over some of the changes to longstanding deductions, including the deduction for interest on home equity loans.

The IRS has since clarified that the interest on home equity loans, home equity lines of credit and second mortgages will, in many cases, remain deductible under the new laws, regardless of how the loan is labeled.

Previous provisions

Under prior tax law, taxpayers could deduct “qualified residence interest” on a loan of up to $1 million secured by a qualified residence, plus interest on a home equity loan (other than debt used to acquire a home) up to $100,000. The home equity debt could not exceed the fair market value (FMV) of the home reduced by the debt used to acquire the home.

For tax purposes, a qualified residence is the taxpayer’s principal residence and a second residence, (e.g. house, condominium, cooperative, mobile home, house trailer or boat). The principal residence is where the taxpayer resides most of the time; the second residence is any other residence the taxpayer owns and treats as a second home. Taxpayers are not required to use the second home during the year to claim the deduction. If the second home is rented to others, though, the taxpayer also must use it as a home during the year for the greater of 14 days or 10% of the number of days it is rented.

In the past, interest on qualifying home equity debt was deductible regardless of how the loan proceeds were used. A taxpayer could, for example, use the proceeds to pay for medical bills, tuition, vacations, vehicles and other personal expenses and still claim the itemized interest deduction.

The new tax rules

The new rule under tax reform limits the amount of the mortgage interest deduction for taxpayers who itemize through 2025. Beginning in 2018, a taxpayer can deduct interest only on mortgage debt of $750,000. The congressional conference report on the law stated that it also suspends the deduction for interest on home equity debt. And the actual bill includes the section caption “DISALLOWANCE OF HOME EQUITY INDEBTEDNESS INTEREST.” As a result, many people believed tax reform eliminates the home equity loan interest deduction.

On February 21, the IRS issued a release explaining that the law suspends the deduction only for interest on home equity loans and lines of credit that are not used to buy, build or substantially improve the taxpayer’s home that secures the loan. In other words, the interest is not deductible if the loan proceeds are used for certain personal expenses, but it is if the proceeds go toward, for example, a new roof on the home that secures the loan. The IRS further stated that the deduction limits apply to the combined amount of mortgage and home equity acquisition loans — home equity debt is no longer capped at $100,000 for purposes of the deduction.

Some examples from the IRS help show how the new rules work:

Stay tuned

The new IRS announcement highlights the fact that the nuances of tax reform  will take some time to flesh out completely. We will keep you updated on the most significant new rules and guidance as they emerge.

The sweeping changes of recent tax reform may impact the choice of how business taxpayers maintain their financials, specifically regarding the cash vs accrual methods of accounting. In tax years beginning after December 31, 2017, taxpayers may select their accounting method according to the new limits and conditions, as applicable:

Tax reform permits taxpayers in certain circumstances to recognize income for tax purposes no later than the year in which it is recognized for financial reporting purposes:

Tax law changes may impact on a businesses’ accounting method choice, and warrant a company to review and, possibly, revise those choices.

In a like-kind exchange, a taxpayer doesn’t recognize gain or loss on an exchange of like-kind properties if both the relinquished property and the replacement property are held for productive use in a trade or business or for investment purposes. For exchanges completed after Dec. 31, 2017, the TCJA limits tax-free exchanges to exchanges of real property that is not held primarily for sale (real property limitation). Thus, exchanges of personal property and intangible property can’t qualify as tax-free like-kind exchanges.

Although the real property limitation applies to exchanges completed after Dec. 31, 2017, transition rules provide relief for certain exchanges. Specifically, the real property limitation doesn’t apply to an exchange if the relinquished property is disposed before Jan. 1, 2018, or the replacement property is received by the taxpayer before Jan. 1, 2018. If the transition rules apply and all other requirements for a tax-free exchange are satisfied, an exchange of personal property or intangible property that is completed after Dec. 31, 2017 can qualify as a tax-free like-kind exchange.

The Tax Cuts and Jobs Act (TCJA) imposes a limit on deductions for business interest for taxable years beginning in 2018. The limit, like other aspects of the law, has raised some questions for taxpayers. In response, the IRS has issued temporary guidance that taxpayers can rely on until it releases regulations. While the guidance provides some valuable information, it also leaves some questions unanswered.

The prior-law limit rules

Prior to the TCJA, corporations could not deduct “disqualified interest” expense if the borrower’s debt equaled more than one and a half times its equity and net interest expense exceeded 50% of its adjusted taxable income. Disqualified interest included interest paid or accrued to:

Previously, taxpayers could carry forward excess interest indefinitely. And any excess limit could be carried forward three years.

These rules were for the so-called “earnings stripping” rules. They were intended to prevent corporations from wiping out their taxable income by deducting interest payments on debt owed to certain parties.

The new-law limit

For tax years beginning after 2017, the deduction for business interest incurred by both corporate and noncorporate taxpayers is limited to the sum of:

The limit applies to all taxpayers, except those with average annual gross receipts of $25 million or less, real estate or farming businesses that elect to exempt themselves and certain regulated utilities.

The amended rules allow for the indefinite carryforward of any business interest not deducted because of the limit. Excess limit, however, cannot be carried forward.

C-corporation business interest income and expense

The IRS announced it will issue regulations clarifying that, for purposes of Section 163(j) only, all interest paid or accrued on a C corporation’s debt is business interest. All interest on debt held by a C corporation and includable in its gross income is business interest income.

In addition, the regulations will address the proper treatment of interest paid, accrued or includable in gross income by a noncorporate entity (e.g., a partnership) in which the C corporation holds an interest. And the regulations will clarify that the disallowance and carryforward of a deduction for a C corporation’s business interest expense will not affect whether and when such an expense reduces the corporation’s earnings and profits.

Treatment of consolidated groups

For groups of affiliated corporations that file a consolidated tax return, forthcoming regulations will clarify that the business interest deduction limit applies at the group level. For example, a consolidated group’s taxable income for purposes of calculating its adjusted taxable income will be its consolidated taxable income. Intercompany obligations (e.g. debt between affiliated corporations) will not count when determining the amount of the limitation.

The regulations also will address several other issues related to the application of the limit to consolidated groups. These include the allocation of the limit among group members, the treatment of disallowed interest deduction carryforwards when a member leaves the group and the treatment of a new group member’s carryforwards. The regulations are not expected to treat an affiliated group that doesn’t file a consolidated tax return as a single taxpayer for purposes of the interest expense deduction limit.

Electing to be exempt from the interest expense deduction limit

Real estate and farm businesses can elect to exempt themselves from the Section 163(j) interest expense deduction limit. At first glance, making the election may seem like a no-brainer — but the election, which is irrevocable, can backfire.

Businesses that make the election must use the alternative depreciation system (ADS) for certain property (generally, real or farm property with a recovery period of 10 years or more) used in the business, regardless of when the property was placed in service. ADS depreciation is over longer periods, so an electing taxpayer’s annual depreciation deductions are reduced if the election is made. Electing businesses also can’t claim first-year bonus depreciation. Businesses should weigh the advantage of avoiding the interest expense deduction limit by making the election against the detriment of slower depreciation deductions if the election is made.

Treatment of pre-2018 interest carryforwards

According to the temporary guidance, the IRS will issue regulations clarifying that taxpayers with interest carryforwards from the last taxable year beginning before 2018 can carry them forward as business interest to their first taxable year beginning after 2017. The regulations will clarify that this business interest that is carried forward will be subject to potential disallowance under amended Section 163(j) in the same manner as any other business interest otherwise paid or accrued in a tax year beginning after 2017.

The regulations also will address the treatment of pre-2018 business interest under the TCJA-created IRC Section 59A, the base erosion and anti-abuse tax. The base erosion tax applies only to businesses with average annual gross receipts of at least $500 million.

Next steps

The IRS has requested comments on the rules outlined in its interim guidance. It also expects to issue regulations providing additional guidance on issues not yet covered and requested comments on which issues those regulations should address. Comments are due by May 31, 2018.