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.
Debt & Credit
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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.
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.
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.
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.
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.
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.
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?
Avalanche vs. Snowball: The Math vs. The PsychologyDebt & Credit
The debt avalanche (highest interest first) mathematically wins every time. But the debt snowball (smallest balance first) has a higher success rate. Here's why psychology beats math when it comes to debt.