We scan new podcasts and send you the top 5 insights daily.
The ultra-wealthy avoid income and capital gains taxes by taking no salary and instead borrowing against their massive, unrealized stock holdings. This provides them with liquid cash for spending and investment while never triggering a taxable event, effectively hacking the tax code.
Billionaires like Mark Zuckerberg legally pay near-zero income tax by taking a $1 salary. Their wealth comes from stock appreciation. They access cash not by selling stock (a taxable event), but by borrowing against it. The core strategy is avoiding taxable income altogether.
The super-rich avoid capital gains taxes by borrowing against their appreciating assets instead of selling them. This allows them to fund their lifestyle tax-free. Since assets are only taxed upon sale, this deferral becomes permanent if they hold the assets until death, when the cost basis resets for heirs.
The wealthy build wealth by buying assets, borrowing against them tax-free for living expenses, and then passing the assets to heirs with a "stepped-up basis" upon death. This maneuver effectively eliminates capital gains taxes for the next generation.
The wealthiest individuals don't have traditional paychecks. Instead, they hold appreciating assets like stock and take out loans against that wealth to fund their lifestyles. This avoids triggering capital gains or income taxes, a key reason proponents are pushing for a direct wealth tax in California to address this loophole.
The wealthy pay less tax not because they earn less, but because they focus on reducing *taxable income*. Investments like real estate provide legal deductions such as depreciation, which significantly lowers the income they actually pay taxes on, a concept unavailable to most W-2 earners.
Instead of selling assets and triggering capital gains, the wealthy buy and hold assets like stocks. They then borrow against that portfolio tax-free for living expenses. When they die, a life insurance policy pays off the loan, allowing the original assets to pass to heirs tax-free.
Collectors buy art, have it appraised at a much higher value, and then borrow against that new value. Since loans are not considered income, this provides them with millions in tax-free cash for other investments, all without selling the underlying asset.
Instead of taxing unrealized gains, which forces asset sales and creates economic distortions, a more sensible approach is to tax the cash that wealthy individuals borrow against their assets. This targets actual liquidity and avoids punishing the long-term investment that builds the economy.
A major flaw in the unrealized gains tax is that it punishes all investors for the actions of a few. A more targeted and less destructive approach would be to tax the loans that wealthy individuals take out against their stock portfolios, targeting the actual cash they use without harming the underlying assets.
To counter the "Buy, Borrow, Die" strategy, the act of borrowing against assets should be a taxable event. This proposal suggests taxing the unrealized gain on an asset at the moment it's pledged as collateral for a loan. This forces the wealthy to pay taxes on their gains without having to sell, raising significant revenue.