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Debt Management

Debt management strategies and payoff planning

The Yellowstone Capital Settlement: What $534 Million in Canceled MCA Debt Teaches Small Businesses

New York's $1.065 billion settlement with Yellowstone Capital canceled $534 million in small-business MCA debt for over 18,000 merchants — but canceled debt is generally taxable income unless you can claim an exclusion like insolvency, so here's how to spot an illegal MCA and get your books ready.

The Rule of 72: The Mental-Math Shortcut Every Business Owner Should Use Before Investing Retained Earnings

Divide 72 by an annual rate and you get the approximate years for money to double: $50,000 at 9% doubles in 8 years, while a 24% credit card balance doubles what you owe in 3. How business owners can use the Rule of 72 to compare investments, price debt, and gauge inflation's drag on idle cash.

Loan Covenants for Small Business Borrowers: How DSCR, FCCR, and Tangible Net Worth Decide When a Performing Loan Can Be Called

Loan covenants—DSCR, fixed charge coverage, tangible net worth, and leverage limits—can put a small business borrower in default while every payment is current. A practical breakdown of affirmative, negative, and financial covenants, cure periods, waiver requests, and what to negotiate before signing a credit agreement.

Got a 1099-C? Why You Might Owe Nothing (and the Mistake That Costs People Thousands)

A 1099-C does not automatically mean a tax bill. This guide covers when canceled debt is taxable, the five Form 982 exclusions (bankruptcy, insolvency, qualified farm, real property business, principal residence), the 2026 expiration of the student loan and mortgage forgiveness exclusions, and the recordkeeping that proves insolvency to the IRS.

IRS Tax Relief Programs: A Practical Guide to Resolving Tax Debt Without Falling for Scams

A walkthrough of the IRS's four core tax debt relief programs — installment agreements, Offer in Compromise, Currently Not Collectible status, and penalty abatement — including the 2026 shift to automatic first-time abatement, the 21% OIC acceptance rate from the 2024 IRS Data Book, and how to spot Offer in Compromise mills flagged on the IRS Dirty Dozen list.

IRS Form 433-D Explained: How to Set Up a Direct Debit Installment Agreement and Stop the Late Notices

Form 433-D authorizes a Direct Debit Installment Agreement (DDIA) with the IRS — $31 setup online with direct debit versus $130 without, automatic monthly payments, and a reduced 0.25% failure-to-pay penalty. A walkthrough of who needs the form, how to complete each section, and how it differs from Forms 9465, 433-A, and 433-F.