I find myself using chatgpt to address such silly rebuttals:
Using Stock Equity and Debt Leverage to Defer Taxes ("Buy, Borrow, Die")
One common tax deferral strategy among the ultra-wealthy involves using appreciated stock as collateral to borrow rather than sell, avoiding capital gains realization:
1. Borrow Against Stock Instead of Selling
Rather than selling appreciated assets and triggering tax, investors use securities-backed loans (e.g., margin loans, SBLOCs) to access liquidity. Loans aren't taxable income, and the asset stays invested.
2. "Buy, Borrow, Die" Strategy
Buy: Acquire assets (e.g., tech stocks) and hold long-term.
Borrow: Use assets as collateral to finance consumption or reinvestment.
Die: Upon death, assets get a step-up in basis—heirs owe no capital gains tax on appreciation during the original holder’s lifetime.
Result: Capital gains tax is effectively erased.
3. Leverage to Offset Other Taxes
Debt proceeds can be used in ways that generate deductions (e.g., real estate, operating businesses, renewable energy). Interest may also be deductible if used for investment purposes.
Example:
Hold $10M in stock with $2M basis.
Sell: Trigger ~$1.9M in tax.
Borrow $5M at 4%: No tax triggered, $200K/year interest (possibly deductible), and maintain upside exposure.
Risks/Caveats:
Market volatility → margin calls.
Interest must be serviced.
Laws can change (e.g., step-up in basis under political scrutiny).
Aggressive strategies can attract IRS attention.
Also relevant: monetized installment sales, GRATs, private placement life insurance, deferred sales trusts. This is about deferral, not avoidance. Legal gray zones are everywhere.