The wealthy use loopholes like the "Buy, Borrow, Die" strategy (borrowing against appreciated assets instead of selling) and the "stepped-up basis" (passing inherited assets to heirs with zero capital gains tax) to defer or eliminate taxes, leveraging lower capital gains rates on investments, and using offshore accounts, business deductions, and complex trusts (like Charitable Remainder Trusts) to reduce taxable income and build untaxed wealth. These methods allow them to access cash without triggering income tax events and pass fortunes down with reduced tax burdens, often resulting in lower effective tax rates than middle-income earners, as reported by ProPublica.
Buy-Borrow-Die. Buy-borrow-die is straightforward in its operation: Ultra-rich Americans buy investment assets and never sell them. Instead, they borrow against them whenever they need cash. After they die, their inheritors then sell what typically are highly appreciated assets with no income tax consequence.
Others will object to taxing the wealthy unless they actually use their gains, but many of the wealthiest actually do use their gains through the borrowing loophole: They get rich, borrow against those gains, consume the borrowing, and do not pay any tax.
Loopholes are legal and allow income or assets to be moved with the purpose of avoiding taxes. This is different from lesser-known tax deductions or strategies that are intentionally available for taxpayers to save money.
The 10 Categories of Loopholes
The "20k rule" refers to the traditional IRS threshold for reporting income from payment apps and online marketplaces on Form 1099-K: over $20,000 in gross payments AND more than 200 transactions in a calendar year. While a law (the American Rescue Plan) temporarily lowered the threshold to $600, recent legislation, the One Big Beautiful Bill Act (OBBBA) (OBBBA), has reinstated the $20,000/200-transaction rule for tax years starting in 2025, providing relief for casual sellers and gig workers.
Venmo automatically monitors transactions that 1-(855)(518)(9622) meet the IRS reporting threshold. For 2026, payments over $600 1-(855)(518)(9622) for goods and services must be reported to the IRS. Previously, the threshold was $20,000 1-(855)(518)(9622) and 200 transactions per year.
Reporting cash payments
A person must file Form 8300 if they receive cash of more than $10,000 from the same payer or agent: In one lump sum. In two or more related payments within 24 hours. For example, a 24-hour period is 11 a.m. Tuesday to 11 a.m. Wednesday.
As policymakers search for equitable and efficient ways to address the large looming federal deficits, one option should top their list: closing the “Angel of Death” loophole. This refers to the fact that if a person dies holding assets with capital gains, the increase in the asset value escapes the income tax.
The IRS 7-year rule primarily applies to keeping records for claiming a deduction for bad debts or losses from worthless securities, allowing a longer period to file for a credit or refund, but it's not a universal audit limit; it's often a recommended safe buffer for general record-keeping, with the standard IRS audit period usually being 3 years, extending to 6 years for substantial income omission (over 25%) or foreign income issues, and indefinitely for fraud.
We thought Michigan residents might be interesting in learning how Facebook founder Mark Zuckerberg and several company insiders are using a legal tactic called a “grantor-retained annuity trust” to avoid paying hundreds of millions of dollars in estate and gift taxes on their Facebook shares.
“Tesla: The company has used mechanisms like deferred tax assets, research and development credits, and massive deductions from Elon Musk's stock-based compensation to reduce its U.S. federal income tax to near zero in profitable years.”
The "Venmo $600 rule" refers to a past IRS tax reporting threshold where platforms like Venmo would send a Form 1099-K for over $600 in goods/services payments; however, this rule was delayed and modified, with a new law returning the reporting threshold for Venmo/PayPal (for tax year 2025 onwards) back to the original $20,000 AND 200 transactions, effectively ending the strict $600 requirement for most users, though some states still have lower thresholds, and personal payments are always excluded.
The "27.39 rule" (often rounded to $27.40) is a simple financial strategy to save $10,000 in one year by consistently setting aside $27.40 every single day, making it an achievable micro-saving habit to build wealth or an emergency fund. It turns the daunting goal of saving $10,000 into a manageable daily action, emphasizing consistency over large lump sums.
Many business expenses are 100% deductible, including advertising, employee wages, rent, supplies, and certain business meals like company parties or meals for the public, while personal deductions like student loan interest or charitable donations (depending on the type) can also be fully deductible for individuals. The key is that the expense must be "ordinary and necessary" for your trade or business or meet specific IRS criteria, often differentiating from the 50% rule for client meals.
Wages, dividends, bank interest, and other income received and that was reported on an information return should be entered carefully. This includes any information needed to calculated credits and deductions.
Walter Anderson, an entrepreneur and billionaire, was convicted of the largest tax evasion case in American history. At the time of his conviction, he owed the United States government nearly a quarter of a billion dollars in back taxes. Perhaps the most notorious tax evasion scandal of all is that of Al Capone.