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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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.
The Single Fund Strategy: A Step-by-Step Guide to Investing With One FundInvesting
The single fund strategy is the simplest way to invest for long-term wealth: own one low-cost fund, automate contributions, and leave it alone. Here's exactly how to set it up.
Matrix Budgeting: The Finance Method That Scores Every Dollar Before You Spend ItMoney Basics
Matrix budgeting turns your spending into a simple two-by-two grid — scoring every category on value and priority so you cut what's dead weight and protect what actually matters.
Meet the Healthcare Cost Calculator: The Early-Retirement Expense Everyone UnderestimatesMicrotools
Healthcare is the line item that blows up early-retirement plans. ACA premiums are age-rated, subsidized by income, and reset completely at Medicare. Alistair's calculator shows your real pre-Medicare cost — and the bridge to 65.
Authorized Users and Credit Piggybacking: Does It Actually Work?Debt & Credit
Adding someone as an authorized user on your card can jump-start their credit history. It's also a known loophole exploited by strangers for profit. Here's how it really works — and whether it's worth it.
The 0.01% Checking Account Is Quietly Costing You ThousandsMoney Basics
The average American keeps over $10,000 in a checking account earning essentially nothing. It's the most expensive 'free' product you own — and fixing it takes fifteen minutes.
Credit Freeze vs. Fraud Alert vs. Monitoring: What You Actually NeedDebt & Credit
Three tools, three different jobs — and most people are paying for the one that protects them the least. Here's what each actually does and which one you should be using.
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