59. Make $1,000+ per month – For business owners – deplete corporate assets/accounts over time to supplement retirement nearly tax-free
If money is held in a corporation, instead of selling the company, or closing the company and get hit by a 50% personal income tax on the closing corporate assets, transfer and slowly deplete the accounts of the corporation, (almost tax free) over a 10-30-year period, such as by paying yourself a low wage (with minimum tax cost) to supplement your pension or retirement needs, the interest on the corporate account also yields money.
Otherwise, you lose an immediate half of your corporate assets with a personal income tax hit when you sell or close the company.
For example, such as $100,000 in a corporate account, deplete account by $1,000 per month over 10 years while paying yourself a low wage, gives you a near tax-free transfer of corporate money into your personal account and supplements your retirement by $1,000 per month over 10 years.
You can invoice your previous employer while pensioned: you can incorporate a company and work as an independent contractor (thus also as a business owner) for your current employer instead as employee and thereby being able to earn almost double (you invoice 50-100% more), and use corporate invoices (including home-office tax deduction) to reduce your corporate taxable income (max is 38% corporate tax rate bracket, for over $50,000 of annual corporate income)
You give yourself a low wage and use this approach to transfer corporate balances to personal account nearly tax-free to supplement your retirement income.
You can transfer corporate money into your personal name tax-free, if you have your own company, have an audit confirm the value of your shares. Then, one year later, have the company buy back a percentage of your shares with its own cash. Same way, no profit has been achieved for you as a person thus no taxable event for long-term capital gains taxes. This is much more interesting if you want to cash in tax-free the money of your company. You could for instance, close personal debt, like credit card debt, close mortgage, etc or provide supplemental retirement income toward yourself tax-free. Talk with a tax attorney.
You can also have your company loan you money personally, like you company loans out 90% of its money to you, however you have to follow many rules to do it properly or the IRS will see this as a taxable event. Talk with a tax attorney.
You can also use an ESOP to transfer your wealth from your company into your personal name or to your relatives name (your children) (nearly) tax-free.