Repayments of business debt after business ceases.

EXECUTIVE SUMMARY
* Interest payments made after the cessation of business operations are deductible if the debt is
allocated to business expenditures.
* A guarantor who is unable to recover from the debtor or co-guarantor is entitled to a bad debt
deduction, for both principal and interest.
* Guarantors are generally denied an interest deduction under Sec. 163(a), except for interest paid
and accrued after a corporate debtor's discharge in bankruptcy.
**********
When a small business fails, the entity or the owners are often required to pay its debts long after
business operations cease. This article discusses the treatment of these payments and payments by
guarantors of the entity's debts.
Seventy-two percent of the 23 million small businesses in the U.S. are sole proprietorships,
according to the Small Business Administration's (SBA) Office of Advocacy. Approximately 83% of
small businesses use some form of credit. (1) Lenders often extend loans to these businesses based
on the principal owner's creditworthiness. The business owners may have to borrow the funds used
in the business, personally guarantee the business's debt or seek a guarantee from acquaintances or
family. According to the SBA, one-third of all small businesses fail after just two years; however, the
entity or its owners often continue to pay debts long after business operations cease. Is the interest
deductible?
Example 1: E decides to open an ice cream parlor as a sole proprietorship and borrows $100,000 to
purchase the assets of an existing ice cream business. Three years later, E closes his business, sells
the assets and pays a portion of the business debt. E continues to pay the remaining debt long after
business ceased. Can E deduct the interest?
This article discusses the circumstances under which (1) former business owners can deduct interest
on these payments and (2) guarantors can take a bad debt deduction when required to pay the
outstanding debt.
Interest Tracing Rules
The Tax Reform Act of 1986 enacted Sec. 163(h)(1), which eliminated the personal interest
deduction and limited the deductibility of other types of interest. This forced taxpayers to classify
interest to determine its proper tax treatment. The interest tracing rules under Temp. Regs. Sec.
1.163-8T(a)(3) classify interest expense based on the taxpayer's use of the debt proceeds. Thus,
taxpayers are required to maintain records of the link between expenditures and related debt. Under
Temp. Regs. Sec. 1.163-8T(a)(3), disbursements of debt proceeds are traced to specific expenditures
and the debt allocated accordingly. Interest on that debt is allocated in the same way. Moreover,
under Temp. Regs. Sec. 1.163-8T(c)(1), the allocation is not affected by the use of property to secure
the debt. For example, if a taxpayer borrows $50,000, secured by his or her personal art collection
and uses the proceeds to purchase business equipment, the interest is business interest.

Reallocation Rules
Temp. Regs. Sec. 1.163-8T(c)(2) states that interest expense on debt used for business purposes
remains business interest until the earlier of the date the debt is repaid or is reallocated to another
expenditure. Debt recurred to acquire a capital asset (e.g., equipment) is reallocated to another
expenditure when the asset's use changes or, if earlier, when proceeds from the asset disposition are
used for another purpose. The reallocated debt cannot exceed the proceeds from the asset
disposition. When the asset's use changes, the reallocated debt cannot exceed the asset's Fair
market value (FMV) at the time of the change.
Example 2: On Jan. 1, 2002, I took a five-year, $50,000 loan to purchase equipment for use in his
sole proprietorship. On May 31, 2004, I stopped operating his business, but continues to pay off the
equipment loan. He does not use the equipment in another activity. The interest on this loan is
business interest until I repays the loan.
Example 3: The facts are the same as in Example 2, except that I converts the equipment to personal
use on Oct. 1, 2004, when the loan's principal balance is $35,000 and the equipment's FMV is
$25,000. The interest on the loan is business interest from Jan. 1, 2002-Sept. 30, 2004. Beginning
Oct. 1, 2004, interest on $25,000 of the principal is no longer deductible business interest; interest
on the remaining $10,000 continues to be business interest.
Example 4: The facts are the same as in Example 2, except that I sold the equipment on Oct. 15,
2002 for $24,000 and used the proceeds to pay his spouse's medical expenses. The debt's principal
balance as of Oct. 15, 2002 was $30,000. The interest is business interest from Jan. 1, 2002-Oct. 14,
2002. Effective Oct. 15, 2002, 80% of the interest ($24,000/$30,000) is personal interest, while the
remaining 20% ($6,000/$30,000) is business interest.
Example 5: R, a limited liability company (LLC), obtained a $100,000 10-year note to acquire
business assets on Jan. 1, 2002. On June 1,2004, R sold these assets for $55,000 and invested the
proceeds. The original debt was $40,000 on June 1, 2004; R continues to pay interest and principal
until maturity. The interest expense passed through to the LLC's owners is business interest from
Jan. 1, 2002-May 31, 2004, then investment interest until maturity. Had R sold the assets for
$30,000 when the outstanding debt was $40,000, only the interest on the $30,000 would be
investment interest; the interest on the remaining $10,000 would be business interest.
Accrued Interest
Under Temp. Regs. Sec. 1.163-8T(c)(2), debt is allocated to an expenditure for the period beginning
on the date the debt proceeds are used to make the expenditure and ending on the earlier of the
date the debt is repaid or reallocated. Interest accruing on a debt for any period is allocated in the
same manner as the debt, regardless of when the interest is actually paid. Under Temp. Regs. Sec.
1.163-8T(c)(2)(ii)(B), accrued interest is treated as debt; interest accruing on unpaid interest is
allocated in the same way as the unpaid interest.
Example 6: On Jan. 1, 2002, S, a calendar-year taxpayer, borrowed $10,000 at 10%, compounded
semiannually. S immediately invested the proceeds in an investment security. On July 1, 2002, S sold
the investment for $10,000 and used the proceeds for business expenditures. On Dec. 31, 2002, S
paid $1,025 of accrued interest on the debt. Even though the debt was business debt at the rune the
interest was paid, $525 of the interest (($10,000 x .10 x 6/12) + ($500 x .10 x 6/12)) is investment
interest, because it accrued during the period in which the debt proceeds were associated with the
investment security.

Planning Strategy
To maintain the business interest deduction, proprietors should be advised (1) not to change how
they use business assets after operations cease and (2) to avoid using the assets for personal
purposes. If a proprietor changes use, he or she should document the date that the use changes;
documentation should include the loan balance, as well as the asset's FMV. Establishing the asset's
value enables the taxpayer to continue to deduct business interest for any loan amount in excess of
the asset's value as of the date of change. He or she should also seek other sources of cash for
personal expenditures, rather than selling business assets.
The above examples illustrate how interest payments made after business operations cease can
continue to be deductible. However, under Sec. 163(a), a taxpayer can deduct such interest only if
he or she is liable for the debt. If a person pays another's obligation, neither gets an interest
deduction. In sole proprietorships, the person deducting the interest has to be directly liable for the
debt. In the case of a failed business entity, the entity liable for the debt should pay the interest to
preserve the deduction. However, what happens when the entity does not have any assets remaining
to pay the debt, which occurs in many cases. Often, the owner or another party--the guarantor--pays
the entity's obligation, which changes the tax consequences.
Guarantors
Small business owners often have to execute a guarantee or ask family or friends to execute such an
agreement for their business's debt. Additionally, employees often advance funds to straggling small
businesses. When the entity becomes insolvent, the guarantor (2) has to meet the obligation. The
resulting tax consequences to the guarantor can vary depending on whether the debt is business or
nonbusiness.
Bad Debts
Under Regs. Sec. 1.166-9(a), a loss sustained by a guarantor unable to recover from a debtor is a
bad debt loss. Because the guarantor acquires the debt by subrogation (i.e., the substitution of one
debt for another), he or she must prove that the debt is unrecoverable from the original debtor to
deduct the loss. Typically, the subrogation right is worthless when the guarantor pays the creditor.
The guarantor must also be unable to recover from any co guarantor to deduct that portion of the
debt. Kegs. Sec. 1.166-9(a) and (b) treat the guarantor's payment of both principal and interest as
bad debt. A business bad debt is an ordinary loss deduction; a nonbusiness bad debt is a short-term
capital loss. (3)
A guarantor's tax classification is critical in determining the tax treatment of payments required on a
guarantee. Regs. Sec. 1.166-9(d) states that, to deduct these payments, the guarantor must have
entered into the guarantee in the course of his trade or business or in a transaction entered into for
profit. Further, the guarantor must demonstrate that he or she received reasonable consideration for
entering into the agreement. Under Kegs. Sec. 1.166-9(e), such consideration has to be direct and in
the form of cash or property with respect to guarantees for related individuals. These requirements
are often a trap for the innocent taxpayer who has guaranteed a loan for a family member or friend
and is now repaying the bank without an offsetting tax deduction.
Example 7: E borrowed $100,000 from a bank to purchase the assets of an ice cream business.
Because E did not qualify for the loan on his own account, his father-in-law agreed to guarantee it. E
later closed the business and sold all the assets for $60,000. He used the proceeds to reduce his
bank loan to $40,000. However, E was unable to pay the balance of the loan and had no personal

assets. The bank looked to E's father-in-law to pay off the debt.
Based on the facts in Example 7, E's father-in-law cannot deduct the payments on his guarantee. To
qualify for the deduction, E's father-in-law would have to show a profit motive in guaranteeing the
loan.
Whether a bad debt is business or nonbusiness is a question of fact. According to Regs. Sec. 1.1665(b)(1), to qualify as a business bad debt, the debt must have been acquired in the course of the
taxpayer's trade or business or proximately related to that trade or business at the time of
worthlessness. Generally, payments made by a guarantor of a corporate obligation are deductible as
a nonbusiness bad debt. (4) The courts have long recognized that a shareholder's business normally
is not the same as the corporation's business, even if he or she is a controlling shareholder.
However, payments made by partners on behalf of their partnerships were business bad debts when
the partners' payments were in furtherance of the partnership's business. (5)
Taxpayers may qualify for a business bad debt deduction under other circumstances. In Rev. Rul. 71561, an employee was allowed a business bad debt deduction, under Regs. Sec. 1.166-9(a), on the
repayment of a guarantee granted to his supervisor, an officer of the employee's corporation.
According to the Service, the employee was motivated to guarantee the supervisor's debt to protect
his employment and his future potential with the company. This motivation was proximately related
to the taxpayer's trade or business as an employee. Further, in Rosati, (6) the court found that a
corporate officer was entitled to a business bad debt deduction on a guarantee when his action as a
guarantor was motivated by a desire to protect his employment.
Under Regs. Sec. 1.166-5(b), a guarantor may qualify for a business bad debt deduction by
establishing that he or she is in the trade or business of guaranteeing loans, a question of fact.
Further, the courts have found in favor of a taxpayer who had limited guarantor activities. For
example, in Alfred S. V. Carpenter, (7) the taxpayer had guaranteed loans to businesses he thought
would succeed. Over seven years, he guaranteed loans to seven corporations. The court allowed a
business bad debt deduction, concluding that, even though the bulk of the taxpayer's income came
from investments, he was in the business of guaranteeing loans. According to the court, a taxpayer
may have more than one trade or business activity. (8) Additionally, in Ruppel, (9) a taxpayer
prevailed in establishing his lending activities as a trade or business. Thus, the question arises as to
when a guarantee will qualify as a trade or business. Unfortunately, there is no bright-line test that
will ensure a business bad debt deduction. However, if a taxpayer enters into a transaction with a
profit motive, keeps separate books and records and reports a guarantee fee separately on his or her
return, the taxpayer may be able to establish an activity as a trade or business.
Tax Planning
According to the cases favoring taxpayers and Field Service Advice (FSA) 199911003, (10) a
taxpayer can establish his or her lending and/or guarantor activities as a trade or business based on
the following:
* Quantity of loans or guarantees over the year.
* Maintenance of detailed books and records.
* Holding out to the public of being in the lending or guarantee business.
* Advertisement of services and community reputation.

* Activity motivated by profit from interest and fees.

* Return disclosure of lending or guarantee activities.
* Relationship between debtor and taxpayer.
For related-party loans, guarantors should receive reasonable consideration for their service, to
preserve a deduction in the event that they must pay a debt.
Interest Deduction
Guarantors generally are denied an interest deduction under Sec. 163(a) for interest payments on
the primary debtor's default. Rather, they are often relegated to the less-favorable nonbusiness bad
debt deduction and the related capital loss limits. Interest payments are deductible only if the debt is
the taxpayer's direct obligation. The Service and the courts have reasoned that a guarantor is only
secondarily liable. Sec. 163 allows a taxpayer to deduct interest only on an obligation for which he or
she was primarily liable from the inception of the debt.
In Putnam, (11) for example, the Supreme Court stated that, under the theory of subrogation,
payments made by a guarantor did not create a new debt, but instead preserved the old debt, with
the guarantor substituted for the creditor. The debt is not discharged by the guarantor's payment,
but preserved against the primary debtor. Following Putnam, courts have applied this reasoning to
conclude that a guarantor remained secondarily liable to a primary debtor. The cases disallowing an
interest deduction hold that, if the debt when originally incurred was that of the primary debtor, it
will remain such, even if the guarantor later becomes directly liable to the creditor. (12) "The courts
reached this conclusion on the inapposite theory that the guarantor has a theoretical right of
recovery from the primary debtor." (13)
Bankruptcy
In Stratmore, (14) the Third Circuit, in reversing the Tax Court and other circuit precedent, held
that interest accrued and paid after a corporate debtor's discharge in bankruptcy is deductible by
the guarantor under Sec. 163. In that case, the taxpayers were officers and stockholders in a
manufacturing corporation and trod guaranteed certain of the company's debt. The company filed
for a Chapter 11 reorganization. As part of the reorganization plan, the company paid its creditors
25 cents on the dollar. The taxpayers agreed to honor their obligations of the remaining 75 cents
and also stipulated they would forgo their claims against the company. Any creditor whose debts are
discharged in bankruptcy is enjoined from instituting an action to collect such debt. Thus, if a
guarantor wishes to make a claim against a principal debtor, he or she has to do so before a
bankruptcy discharge.
Because the taxpayers (guarantors) had no legal action for reimbursement, the Third Circuit
concluded that the obligation for the debt became solely theirs. According to the court, to be
deductible, the interest has to be for the taxpayer's benefit. Interest is a payment for the use of
principal over time. Thus, the interest accumulated for the guarantor's benefit and should be
deductible by them. This decision should provide authority for a guarantor's interest deduction when
reimbursement is legally precluded by bankruptcy.
Insolvency
The Third Circuit, in Stratmore, did not address whether a primary debtor's insolvency has the same

effect as bankruptcy on a guarantor's liability for the underlying debt and, thus, entitlement to an
interest deduction. An earlier Tax Court decision, Tolzman, (15) found that the guarantor of a
corporation's debt became directly and primarily liable following the company's insolvency.
Creditors demanded payment, the corporation was unable to pay and the guarantor's obligation
became fixed, direct and noncontingent. Thus, the amounts paid for interest accruing sub sequent to
the insolvency were paid on the guarantor's own debt. The court stated,"[t]he mere fact that
petitioners at one time were guarantors of a corporate note is not controlling. Instead, we must
determine whether the interest accrued at a time when petitioners' liability was no longer secondary
and indirect."
Taxpayers who pay interest under an obligation as guarantor may be entitled to an interest
deduction if interest accrued after they became primarily liable for the debt. Guarantors may
become primarily liable for debt when a creditor demands payment after the original debtor
becomes insolvent or because the original debt was discharged in bankruptcy.
Conclusion
When the U.S. economy is sluggish, many small businesses fail and their owners are forced to pay
off related loans and interest. The resulting tax treatment of these payments can vary widely, based
on the taxpayer's ability to establish and document his or her relationship to the debt repayment and
the debtor. This article provided guidance on how to treat such payments, so that taxpayers may
receive the most beneficial tax treatment if they have to personally repay business debt.
(1) "Small Business by the Numbers--Answers to Frequently Asked Questions," SBA Office of
Advocacy (May 2003), available at www.sbaonline. sba.gov/advo/stats/sbfaq.html.
(2) For convenience, endorsers, indemnitors and others secondarily liable on a debt obligation are
referred to in this article as "guarantors."
(3) See Regs. Sec. 1.166-1(a) and -5(a)(2).
(4) See Regs. Sec. 1.166-8(b); Joint Committee on Taxation, General Explanation of the Tax Reform
Act of 1976, p. 158.
(5) See George A. Butler, 36 TC 1097 (1961), Mantell Davis, 11 TC 538 (1948) and A.L. Stanchfield,
TC Memo 1965-305.
(6) Ida Rosati, TC Memo 1970-343.
(7) Alfred S.V. Carpenter; 255 FSupp 613 (D OR 1966).
(8) See, e.g., C.W. Oliver, 138 F2d 910 (4th (Cir. 1943).
(9) Georqe Ruppel, TC Memo 1987-248.
(10) FSA 199911003 (3/19/99).
(11) Max Putman, 352 US 82 (1956).

(12) See Jacob Abdalla, 647 F2d 487 (5th Cir. 1981); J.
Nat Hamrick, TC Memo 1980-149; Mozell Rushing, 58
TC 996 (1972); John D. Byram, 705 F2d 1418 (5th Cir.
1983); and Loyd Gloder, 604 F2d 34 (9th Cir. 1979).
(13) See Benjamin Stratmore, 785 F2d 419 (3d Cir. 1986).
(14) Id.
(15) Alfred Tolzman, TC Memo 1981-689.

For more information about this article,

contact Dr. Kelley at
kelleycl@appstate.edu or Mr. Norman
at jnorman@gwllp.com.
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