📝 Commercial Promissory Note Default Demand Letters
Enforcing notes and loans between businesses and business partners
Sergei Tokmakov, Esq.
Sergei Tokmakov, Esq.
California Bar #279869 · Commercial Contracts & Business Disputes
⚖️ Understanding Promissory Notes

A promissory note is a written promise to pay a specific amount on demand or at a definite time. It's a negotiable instrument governed by UCC Article 3 and state contract law. This page covers notes and loans between businesses and business partners: a company lending to another company, a founder or member lending to the business, shareholder loans, and vendor financing.

Essential Elements of a Promissory Note
  • Unconditional promise to pay: "I promise to pay" (not "I will pay if...")
  • Fixed amount: Specified dollar amount (may include interest)
  • Payable to order or bearer: "Pay to the order of [Lender]" or "Pay to bearer"
  • Payable on demand or at definite time: Due date or "payable on demand"
  • Signed by maker: Borrower's signature
Types of Promissory Notes
TypePayment TermsExample
Demand NotePayable whenever lender demands"Payable on demand"
Term NoteDue on specific date"Due August 1, 2025"
Installment NoteMonthly/periodic payments"$500/month for 36 months"
Balloon NoteSmall periodic payments + large final payment"$200/month, $10,000 due on maturity"
Secured NoteBacked by collateral (security agreement)"Secured by a lien on Borrower's business equipment"
Unsecured NoteNo collateral"This is an unsecured obligation"
Key Note Provisions That Affect Collection
  • Interest rate: Fixed or variable; stated annual rate
  • Late charges: Penalty for late payment (often 5% of payment or $25, whichever is greater)
  • Default interest: Higher interest rate after default (e.g., prime + 5%)
  • Acceleration clause: Allows lender to declare entire balance due upon default
  • Attorney fees: Loser pays winner's legal fees
  • Confession of judgment: Borrower pre-authorizes entry of judgment (banned in some states)
  • Prepayment: Whether borrower can pay early without penalty
🔍 Identifying and Documenting Default
What Constitutes Default?

Read the note carefully. Default typically includes:

Type of DefaultDescription
Payment defaultMissed installment or failure to pay at maturity
Non-monetary defaultBreach of covenant (e.g., failure to maintain insurance on collateral)
Insecurity defaultLender deems itself insecure (rare; requires good faith belief of impairment)
Cross-defaultDefault on another obligation triggers default on this note
Bankruptcy filingBorrower files for bankruptcy (automatic stay complicates collection)
Cure Period Requirements

Many notes include a cure period:

"Borrower shall have 10 days after written notice of default to cure the default before Lender may accelerate the note."

If your note has a cure period:

  • Send written notice of default specifying the breach
  • Wait the full cure period before taking further action
  • If borrower cures within the period, default is waived
  • If borrower doesn't cure, you can then accelerate
Strict Compliance Required: Failure to provide the required notice and cure period may waive your right to accelerate or may give the borrower a defense in court. Follow the note's procedures exactly.
Calculating the Amount Due

Before demanding payment, calculate the exact amount owed:

  • Principal balance: Original amount minus payments made
  • Accrued interest: Calculate from last payment to demand date
  • Late charges: Per the note's late fee provision
  • Default interest: If note provides for higher post-default rate
  • Advances made: If you paid property taxes, insurance, or other costs on borrower's behalf
  • Attorney fees: If already incurred and note allows recovery
Pro Tip: Attach a detailed accounting to your demand letter showing how you calculated the balance. This demonstrates professionalism and reduces disputes about the amount.
✍️ Acceleration and Demand Strategy
What Is Acceleration?

Acceleration means declaring the entire unpaid balance immediately due, rather than waiting for future installments to become due.

Acceleration clause example:

"Upon default, Lender may declare the entire unpaid principal and accrued interest immediately due and payable."

Why accelerate?

  • Allows you to sue for full balance now (don't have to wait for each missed payment)
  • Starts statute of limitations running on entire debt
  • Creates urgency for borrower to settle
  • Required before foreclosing on secured notes in most states
Acceleration Process
  1. Verify default occurred and any cure period has expired
  2. Calculate total amount due (principal + interest + fees)
  3. Send written notice of acceleration to borrower
  4. State deadline for payment (typically 10-30 days)
  5. Describe consequences (lawsuit, foreclosure if secured)
Demand Letter vs. Acceleration Notice

These are often combined in one letter:

  • Notice of Default: "You failed to make the payment due on [date]"
  • Notice of Acceleration: "We hereby accelerate the note and declare the entire balance of $[X] immediately due"
  • Demand for Payment: "Pay $[X] by [date] or we will file suit"
Timing Considerations
  • Send demand promptly after default: Delays can waive your rights or suggest you don't take default seriously
  • Allow reasonable time to respond: 10-30 days is standard depending on amount
  • Consider borrower's situation: If borrower is insolvent or in bankruptcy, acceleration may be futile
  • Check statute of limitations: In some states, accelerating starts a new SOL clock
📄 Sample Demand Letters
Sample 1: Installment Note - Missed Payment with Cure Period
[Lender Company Name] [Address] [Date] [Borrower Company Name] Attn: [Officer or Manager Name] [Address] SENT VIA CERTIFIED MAIL Re: Notice of Default and Opportunity to Cure Promissory Note dated [Date] Original Principal: $[Amount] Dear [Officer or Manager Name]: This letter is formal notice that [Borrower Company Name] is in default under the Promissory Note dated [date]. DEFAULT: You failed to make the monthly payment of $[amount] due on [date]. As of today, you are [X] days past due. AMOUNT DUE TO CURE DEFAULT: To cure this default, you must pay the following by [date - 10 days from letter]: Missed payment (principal & interest): $[amount] Late charge (per Note Section [X]): $[amount] TOTAL DUE TO CURE: $[Amount] CONSEQUENCES OF FAILURE TO CURE: If you do not cure this default within 10 days as required by Section [X] of the Note, we will: 1. Accelerate the Note and declare the entire balance of $[total] immediately due 2. File a lawsuit to recover the full amount plus attorney fees and costs 3. [If secured: Initiate foreclosure proceedings on the collateral] PAYMENT INSTRUCTIONS: Send payment via [check/wire/ACH] to: [Payment address/instructions] We hope to resolve this without acceleration or litigation. Please contact us immediately if you need to discuss payment arrangements. Sincerely, [Signature] [Name] [Title]
Sample 2: Acceleration and Final Demand
[Lender Company Name] [Address] [Date] [Borrower Company Name] Attn: [Officer or Manager Name] [Address] SENT VIA CERTIFIED MAIL Re: Notice of Acceleration and Demand for Payment Promissory Note dated [Date] Dear [Officer or Manager Name]: NOTICE OF DEFAULT: [Borrower Company Name] is in default under the Promissory Note dated [date] for failure to pay [describe default: missed payments since X date / payment due at maturity on X date]. NOTICE OF ACCELERATION: Pursuant to Section [X] of the Note, we hereby ACCELERATE the Note and declare the entire unpaid balance immediately due and payable. TOTAL AMOUNT NOW DUE: Principal balance: $[amount] Accrued interest through [date]: $[amount] Late charges: $[amount] [Other fees/advances if applicable]: $[amount] TOTAL AMOUNT DUE: $[Amount] Interest continues to accrue at [X]% per [year/month] until paid in full. DEMAND FOR PAYMENT: We demand payment in full of $[amount] by [date - 15 days from letter date]. REMEDIES: If payment is not received by the deadline, we will immediately file suit and pursue all available remedies, including: • Judgment for the full amount plus continuing interest • Attorney fees and court costs as provided in Section [X] of the Note • Bank levy and other judgment enforcement remedies available against a business debtor • [If secured: Foreclosure on the collateral securing this Note] ATTORNEY FEES: Section [X] of the Note provides that the prevailing party in any dispute shall recover reasonable attorney fees. This letter serves as notice under that provision. If we retain counsel, you will be liable for our attorney fees in addition to the principal, interest, and costs. We prefer to resolve this without litigation. Contact us immediately to arrange payment or discuss settlement. Payment should be sent to: [Payment address/instructions] Sincerely, [Signature] [Name] [Title] Enclosure: Accounting Statement
🛡️ Secured Notes and Collateral Rights

If the note is secured by business collateral (commercial real estate, equipment, inventory, receivables), you have additional remedies and considerations.

Types of Security Interests
Collateral TypeSecurity DocumentEnforcement Remedy
Commercial real estateMortgage or Deed of TrustForeclosure (judicial or non-judicial depending on state)
Business vehiclesUCC-1 on title; security agreementRepossession
Equipment/inventoryUCC-1 financing statement; security agreementUCC Article 9 sale or repossession
Accounts receivableSecurity agreement; UCC-1Direct collection from account debtors
Demand Letter for Secured Note

Your demand letter should reference the security:

  • Identify the collateral specifically
  • State that you have a perfected security interest
  • Warn that foreclosure/repossession will occur if not paid
  • Reference the security agreement and any recorded documents
Foreclosure vs. Lawsuit Decision

Foreclosure (secured by commercial real estate):

  • Pro: Get the property; may cover debt if property has equity
  • Con: Expensive, slow (6-18 months in many states), may not cover full debt if underwater
  • Some states allow deficiency judgment after foreclosure; others don't

Repossession (business vehicles/equipment):

  • Pro: Fast; can often repossess without court order if no breach of peace
  • Con: Collateral may have depreciated; must follow UCC Article 9 sale procedures
  • Can sue for deficiency after UCC sale

Sue on the note (ignore collateral):

  • Pro: Faster judgment; can levy business accounts
  • Con: If borrower has no assets/income, judgment is worthless
Dual Track Strategy: You can pursue both foreclosure and a lawsuit on the note simultaneously in many states. This maximizes pressure on the borrowing business to settle.
🤝 Loans Between Businesses and Business Partners

Many commercial note disputes are between parties who know each other well: a company that lent to an affiliate or a supplier, a founder or LLC member who advanced money to the business, a shareholder loan, or vendor financing extended to a business customer. The relationship makes the documents informal, and the informality is what the borrower attacks first.

Outside my practice: personal, family or household loans between individuals. I take notes and loans made between businesses or for a business purpose.
The "It Was Equity, Not a Loan" Problem: When an owner or affiliate advances money to a business, the borrower (or its other owners) often argues the money was a capital contribution, not a loan. If the advance is treated as equity, there is no fixed repayment obligation to enforce, and the lender may also lose a business bad debt deduction.
Documenting That a Business Advance Was a Loan

Many business-partner loans lack a full loan package. Here's what I look for to show the advance was debt:

  • A signed note or loan agreement: Principal, interest, maturity, and repayment terms in writing
  • Board, manager, or member approval: Minutes, written consents, or an operating agreement provision authorizing the borrowing
  • Books and records: The advance booked as a loan payable on the borrower's balance sheet, not as paid-in capital
  • Payment history: Interest or principal payments show the borrower treated it as debt
  • Correspondence: Emails or messages acknowledging the balance and discussing repayment
Common Defenses Business Borrowers Raise
DefenseYour Rebuttal Strategy
"It was a capital contribution"Show the note, the approval, the loan-payable entry, and any interest or principal payments
"It was already repaid or offset"Demand proof of payment; reconcile the ledger and bank records
"The terms were different"Your written note controls; parol evidence rule limits oral modifications
"You agreed we could pay from future profits"Check whether the note is a demand note or has a fixed maturity; the written terms control
"The company can't afford it"Inability to pay is not a defense to the debt; negotiate a workout or payment schedule
Illustrative Scenario
Illustrative scenario (a hypothetical, not a description of a past matter): One LLC extends vendor financing to a business customer under a short written note with a 12-month repayment term. The maturity date passes with only partial payments. The next step is a formal acceleration and demand letter on attorney letterhead with a 15-day deadline, attaching the note and a payment ledger. A borrowing company that wants to keep operating often answers with a repayment proposal, and that proposal can become a written workout agreement. Every matter turns on its own documents, and no outcome is guaranteed.
How I Work a Commercial Note Default
  1. Document review: The note, any security agreement or guaranty, the approvals, and the payment history
  2. Demand on my letterhead: Notice of default and acceleration where the note allows it, with the balance calculation attached
  3. Workout negotiation: Often the best outcome, a written payment schedule or restructured note
  4. Draft complaint where warranted: Prepared as leverage and marked DRAFT - NOT FILED; filing or representation is a separate written engagement
  5. Tax documentation: If the business debt proves uncollectible, I document the collection effort for an IRC §166 business bad debt deduction (see Tax Write-Off tab)
Dual Strategy: Every demand I send on a commercial note serves two purposes: a genuine collection effort and documentation for a potential business bad debt deduction if the debt proves uncollectible. Your CPA will thank you.
📊 When You Can't Collect: IRC §166 Bad Debt Tax Deduction

If a business borrower truly cannot or will not pay, the promissory note may qualify for a bad debt deduction under Internal Revenue Code §166. This is where demand letters become tax documentation, and it's a strategy I coordinate with my business clients' CPAs.

Why This Matters: A properly documented bad debt deduction can recover 20-37% of the lost amount through tax savings, depending on your tax bracket. On a $50,000 uncollectible note, that's $10,000-$18,500 back in your pocket.
IRC §166 Requirements
RequirementWhat the IRS Wants to See
Bona fide debtA genuine debtor-creditor relationship (not a gift disguised as a loan)
Debt became worthlessEvidence that borrower can't pay and further collection is futile
Collection effortsDemand letters, phone records, payment negotiations, proof you tried to collect
Debtor's financial conditionInsolvency evidence, bankruptcy filing, no attachable assets
Proper classificationBusiness debt (ordinary loss) vs. nonbusiness debt (short-term capital loss)
Business vs. Nonbusiness Bad Debt
Business Bad Debt (Better):
  • Loan was made in connection with your trade or business
  • Deductible as ordinary loss (no $3,000 limitation)
  • Partial deduction allowed
  • Example: Loan to a vendor, customer, or business partner
Nonbusiness Bad Debt (More Restrictive):
  • Personal loans that are not made in a trade or business
  • Treated as short-term capital loss
  • Must be TOTALLY worthless (no partial deduction)
  • Subject to $3,000/year limitation against ordinary income
  • Excess carries forward to future years

I document business bad debts only. I do not send collection demands on personal, family or household loans.

How Demand Letters Create IRS Documentation

The IRS specifically looks for evidence of collection efforts. For a business debt, the documentation record typically includes:

  • Formal demand letter with certified mail receipt: Proves you attempted collection on a specific date
  • Follow-up demand (if no response): Shows persistence and escalation
  • Final notice with litigation threat: Demonstrates you exhausted reasonable collection options
  • Debtor's financial assessment: Documentation of insolvency or inability to pay
  • Collection effort timeline: Chronological summary for CPA to attach to tax return
CPA Coordination Workflow

I work directly with your CPA or tax preparer to ensure the documentation meets IRS requirements:

  1. Intake: Determine debt structure: promissory note, loan agreement, trade receivable, or equity investment
  2. Document Collection: Gather the note, communications, payment records, and borrower financial info
  3. Demand on my letterhead: Establish a clear collection effort record against the business debtor
  4. Worthlessness Assessment: Document why further collection is futile
  5. CPA Package: Deliver a complete IRC §166 documentation package to your tax preparer including:
    • Description of the debt (amount, date, terms)
    • Debtor identification and relationship
    • Chronological collection effort summary
    • Evidence of worthlessness
    • Classification recommendation (business vs. nonbusiness)
  6. Tax Year Timing: Coordinate with CPA on which tax year to claim the deduction
Critical Timing Issue: The deduction must be claimed in the year the debt becomes worthless. If you wait too long, you may lose the deduction entirely. The IRS allows an extended 7-year period (instead of the normal 3 years) for filing amended returns for bad debt deductions, but don't rely on this, act promptly.

Fees for this work follow the attorney demand engagement described in the Attorney Services tab, starting at $2,500, with the final scope confirmed in writing before any work begins.

Referred by a CPA? I work with accounting professionals throughout California on business bad debts. If your CPA or bookkeeper referred you, mention it, and I'll coordinate directly with them on documentation requirements and tax year timing.
💼 How I Help with Commercial Note Defaults
Sergei Tokmakov, Esq.
Sergei Tokmakov, Esq.
California Bar #279869 · Commercial Contracts & Business Disputes

I handle commercial note defaults between businesses and business partners: the demand, the workout negotiation, and a draft complaint where warranted. My practice focuses on business disputes that fall between "too small for a big firm" and "too complex for small claims", typically $10,000 to $250,000 in dispute.

My Typical Client: A business holding a defaulted note from another business, often referred by its CPA. I send the demand on my letterhead, negotiate a workout where one is realistic, and if the business debt proves uncollectible, I prepare the IRC §166 business bad debt documentation so the loss at least generates a tax deduction.
Services:
  • Review commercial notes, security agreements, and guaranties for enforceability
  • Draft notice of default, acceleration, and demand letters to business borrowers
  • Negotiate settlements and workout agreements
  • IRC §166 business bad debt documentation for your CPA
  • Prepare a draft complaint where warranted (filing is a separate written engagement)
  • Advise on remedies against business collateral (UCC Article 9)
When to Involve an Attorney:
  • Note amount exceeds $25,000
  • Borrowing business disputes validity of note or default
  • Secured note involves business collateral
  • Multiple parties or guarantors involved
  • Borrower has filed bankruptcy
  • Note is past statute of limitations or close to it
Scope of my practiceI do not take creditor-side consumer-debt collection matters or personal, family or household loan collections. Business-to-business invoices, commercial contracts and payment-platform disputes are what I handle. Regulated consumer collection matters belong with licensed collection counsel, and I can refer you.
Enforce a Defaulted Commercial Note

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I take a dispute like the one on this page and write the demand myself, on my letterhead, then handle delivery and read the response you get back.

Request the attorney demand engagement, starting at $2,500

After a conflict check, I draft the demand on my letterhead, prepare the supporting chronology and damages figure, send it by certified mail and email, and review the first substantive response. Sergei Tokmakov, California Bar #279869.

Whether secured or unsecured, I can help your business enforce a note against another business and recover what it is owed.
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