The Alistair Blog
Stories about the broken world of traditional financial advice, deep dives into our microtools, and updates on what we're building to fix it.
Tax Strategy
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Donor-Advised Funds: The Charitable Giving Loophole for Regular PeopleTax Strategy
DAFs were traditionally for the ultra-wealthy. Now you can open one with $5,000, front-load years of charitable giving into one high-income year, and slash your tax bill immediately.
State Income Tax Arbitrage: Should You Move to Save?Tax Strategy
The difference between California's 13.3% top rate and Florida's 0% can be hundreds of thousands of dollars over a career. But taxes aren't the only cost — here's the full equation.
Year-End Tax Moves That Actually Move the NeedleTax Strategy
Every December, financial sites publish the same generic list: 'max your 401(k).' Here are the strategies that actually save thousands — and the deadlines you can't afford to miss.
The 0% Capital Gains Bracket: The Best-Kept Secret in Tax PlanningTax Strategy
A married couple can realize over $130,000 in long-term capital gains and pay exactly $0 in federal tax. This isn't a loophole — it's a feature of the tax code that almost nobody uses correctly.
The Marriage Tax Penalty (and Bonus) ExplainedTax Strategy
Getting married changes your tax bill — sometimes by thousands. The IRS doesn't care about your wedding budget. Here's when tying the knot saves you money and when it costs you.
Tax Gain Harvesting: The Flip Side Everyone IgnoresTax Strategy
Everyone knows about tax-loss harvesting. But deliberately selling winners to realize gains — when your tax rate is 0% — is equally powerful and almost nobody does it.
The Backdoor Roth IRA Could Disappear — Here's What to Do NowTax Strategy
Congress has tried to close the backdoor Roth IRA loophole multiple times. With each new administration, the window narrows. Here's how it works, why it's at risk, and what to do before it's gone.