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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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.
Zero-Based Budgeting: Why Every Dollar Needs a JobMoney Basics
Most budgets fail because they're aspirational, not intentional. Zero-based budgeting forces a hard question no other method asks: what is this dollar actually doing for me?
The Car Loan Is a Wealth Destruction MachineDebt & Credit
Financing a depreciating asset at 7% while it loses 20% of its value the moment you drive it off the lot isn't just bad math — it's the single biggest wealth-building mistake middle-class Americans make.
The Scarcity Mindset: How Growing Up Broke Shapes Every Money DecisionMoney Psychology
Growing up without money doesn't just affect your bank account — it literally rewires how your brain processes financial decisions, even decades after your circumstances change. Here's the science and how to break the pattern.
Credit Card Rewards: Are You Gaming the System or Is It Gaming You?Debt & Credit
The points-and-miles community treats credit cards like a game to be won. But the data shows that rewards cards make you spend more — enough to erase any cash back. Who's really winning?
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