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Money Market vs Savings vs T-Bills: Your State Tax Decides
Investing9 min

Money Market vs Savings vs T-Bills: Your State Tax Decides

Three places to park cash that all quote roughly the same yield. The thing that actually separates them is your state income tax rate, and almost no comparison article puts a number on it.

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The Backdoor Roth Is Simple. The Pro-Rata Rule Measures a Date You Weren't Watching.
Investing9 min

The Backdoor Roth Is Simple. The Pro-Rata Rule Measures a Date You Weren't Watching.

Contribute to a traditional IRA, convert to Roth, done. That works cleanly only if your other traditional IRA balances are empty, and the balance that decides it is measured on December 31, not on the day you convert. Which means a rollover in November can retroactively tax a conversion you made in March.

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A Wash Sale Usually Just Delays Your Loss. Buying It Back Inside an IRA Destroys It.
Investing9 min

A Wash Sale Usually Just Delays Your Loss. Buying It Back Inside an IRA Destroys It.

Trip the wash sale rule in a taxable account and the loss is deferred, not lost: it moves into the cost basis of the replacement shares. Repurchase inside an IRA or HSA instead and there is no basis to move it to, so the deduction is gone permanently. Your broker will not flag it.

tax loss harvestingwash saletaxes
How Dividends Are Taxed, and Why a Dividend Is Not Free Money
Investing9 min

How Dividends Are Taxed, and Why a Dividend Is Not Free Money

On the ex-dividend date the share price drops by roughly the dividend. The cash did not appear from nowhere, it moved out of the share and into your account, and in a taxable account it moved through a tax on the way. Which is also why dividend capture fails twice over.

dividendstaxesinvesting basics
Your Company Withholds 22% on RSUs. Your Real Rate Is Probably 32%.
Investing10 min

Your Company Withholds 22% on RSUs. Your Real Rate Is Probably 32%.

RSUs are taxed as ordinary income the day they vest, but your employer withholds at a flat supplemental rate that has nothing to do with your actual bracket. That gap is why so many people in tech get an April bill they did not budget for. There is a second, worse error hiding on the 1099-B.

rsuequity compensationtaxes
Roth vs Traditional IRA: Which One Actually Wins
Investing10 min

Roth vs Traditional IRA: Which One Actually Wins

The whole Roth vs Traditional debate reduces to one question: is your tax rate higher now or in retirement? The math is symmetric. The decision is a bet on future tax rates. For most people under 40 who aren't high earners, Roth is the default that ages well.

retirementroth-iratraditional-ira
Roth 401(k) vs Traditional 401(k): How to Choose
Investing8 min

Roth 401(k) vs Traditional 401(k): How to Choose

A traditional 401(k) skips tax now and pays it in retirement. A Roth 401(k) pays tax now and skips it later. The whole decision is a bet on your future tax rate, and for a lot of people the answer is clearer than it looks.

401krothretirement
Where Your Property Taxes Actually Go
Investing6 min

Where Your Property Taxes Actually Go

Property tax is the most local form of taxation in the US, and the bill that finances most of public-school education, local police, fire, and roads. Here’s how to actually trace where the money lands.

property taxreal estatelocal government