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.
The Accuracy Problem in AI Financial Advice
Most AI tools answer financial questions by hoping the model's training data is recent enough. That's a recipe for disaster. Here's what we built instead.
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Required Minimum Distributions Are Coming for Your 401(k)Retirement
The IRS has been waiting patiently for decades. Once you hit 73, they start forcing withdrawals from your pre-tax accounts — and the tax bill can be staggering if you haven't planned for it.
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.
Fat FIRE vs. Lean FIRE vs. Barista FIRE: Which One Are You Actually On Track For?Retirement
The FIRE movement has splintered into subcultures with wildly different lifestyles and required nest eggs. Run the real numbers — not the fantasy — and see which tier you're actually heading toward.
The One-Page Retirement PlanRetirement
If your retirement plan doesn't fit on a single sheet of paper, it's too complicated. Here's a one-page framework that covers the only five decisions that actually matter.
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.
Mortgage Points: Buy Down the Rate or Invest the Cash?Debt & Credit
Paying mortgage points to lower your rate is essentially prepaying interest. The break-even is usually 5-7 years. But if you invest the money instead, the math looks very different.
Financial Infidelity Is More Common Than You ThinkMoney Psychology
Forty percent of adults admit to hiding financial information from their partner — secret accounts, hidden debt, undisclosed spending. The money isn't the real problem. The secrecy is.
Warren Buffett's 90/10 Portfolio: The Two-Fund Strategy He Left His WifeInvesting
90% S&P 500 index fund, 10% short-term government bonds. Buffett's instructions for his wife's trust are famous for their simplicity — but the strategy isn't right for everyone.
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