The trick is to have enough assets so that you don't have to sell them for money. You get a loan against your assets (which in today's climate very likely has a

The trick is to have enough assets so that you don't have to sell them for money. You get a loan against your assets (which in today's climate very likely has a smaller interest rate than you'll see in appreciation of your assets) to live off of, which is tax free. You pay that loan back over 10 years and each year you sell a small portion of assets to limit your tax and/or you take out other loans to help pay for previous ones. Imagine you have $2,000,000 in liquid assets that appreciate around 6% annually on average. You borrow $100k at 3.5% over 10 years. In year one you'll pay back ~$13,500. So you sell %13,500 in assets which won't even be taxed. In year 2 you borrow another 100k and sell some assets that lost value during this time using tax loss harvesting and/or you borrow even more money to help pay back interest and principal on older loans. You can continue this indefinitely as your compounding assets are returning much more than your loan interest. In essence, with enough in assets you can easily create a perpetual income machine that has no or little in terms of taxable income. With clever accounting, tax loss harvesting, and smart deductions/credits you can avoid paying taxes more or less through debt-as-income.