AAR44 - Taxes Nobody Warns You About
About this episode
Evan and Andrew discuss hidden tax traps that can affect investors, including self-employment taxes and the wash-sale rule.
In this episode of At Any Rate, Evan and Andrew break down the hidden tax traps that can catch even the most responsible investors off guard. From the brutal reality of self-employment taxes on your side hustle to the surprise tax bill hiding in your High-Yield Savings Account, they discuss the rules you need to know to protect your wealth. They also cover the "wash-sale rule," how 401K withdrawals can bump your tax bracket, and the massive benefits of utilizing a Roth IRA. Topics Covered: The Side Hustle Surprise: Being self-employed means paying both sides of the employment tax (around 15.3%) and requires filing quarterly estimated taxes. HYSA Tax Trap: The interest earned in a High-Yield Savings Account is taxed as ordinary income and is not automatically withheld. The Wash-Sale Rule: You cannot sell a stock for a loss to claim a tax deduction and then immediately buy it (or a similar asset) right back within a 61-day window. 401K Withdrawals: Every dollar pulled from a traditional 401K is taxed as ordinary income, which can unexpectedly push you into a higher tax bracket in retirement. The Roth Advantage: Roth IRAs offer incredible flexibility because you can pull out your…
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