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 Accuracy Problem in AI Financial AdviceProduct Updates
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.
The Trinity Study: The Paper That Taught America How to RetireRetirement
Three professors, one spreadsheet. How a 1998 academic paper from a small San Antonio university became the foundation of the FIRE movement and changed how millions think about retirement.
The 0% Balance Transfer Game: When It Works and When It BackfiresDebt & Credit
A 0% APR balance transfer sounds like free money. But the 3-5% transfer fee, the credit score impact, and the ticking clock can turn a smart move into an expensive trap. Here's how to play it right.
Good Debt vs. Bad Debt Is Too SimplisticDebt & Credit
The personal finance world loves to call mortgages 'good debt' and credit cards 'bad debt.' But a 28% APR credit card and a 7% mortgage are both bad math. Here's a better framework.
How to Use Alistair to Self-Manage Your FinancesMoney Basics
A practical walkthrough of how to use Alistair for budgeting, net worth tracking, retirement planning, tax strategy, debt management, insurance, home buying, and portfolio analysis — with real examples.
When You Should NOT Pay Off Low-Interest DebtDebt & Credit
Conventional wisdom says all debt is bad. But prepaying a 3% mortgage while carrying a 7% expected stock return is mathematically destructive. Here's when keeping debt is the smarter play.
Student Loan Repayment in 2026: A Strategy for Every SituationDebt & Credit
Between SAVE, IBR, PAYE, PSLF, and refinancing, student loan repayment has become a maze. Here's a decision tree for every scenario — whether you're pursuing forgiveness or paying them off.
Sinking Funds Are the Budgeting Hack Nobody Talks AboutMoney Basics
Why do 'unexpected' expenses keep wrecking your budget? Because they're not unexpected — you just didn't plan for them. Sinking funds fix this permanently.
Monthly Subscriptions Are the New Credit Card DebtMoney Basics
The average American spends $219/month on subscriptions they've forgotten about. Auto-renewal has become the most profitable business model in history — and you're the product.
How to Budget When You Don't Know What You'll Make Next MonthMoney Basics
Freelancers, commission-based workers, and gig earners face a budgeting problem most advice ignores. Here's a system that works when your income doesn't.
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