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 Marriage Tax Penalty (and Bonus) ExplainedTax Strategy
Getting married changes your tax bill — sometimes by thousands. The IRS doesn't care about your wedding budget. Here's when tying the knot saves you money and when it costs you.
The Latte Factor Is Real — But It's Not About CoffeeMoney Basics
David Bach was right that small expenses add up, but he picked the wrong target. The real latte factor in 2026 is subscriptions, convenience fees, and algorithmic pricing.
Alistair vs. Empower: The Dashboard or the Coach?Industry Insights
Empower gives you a free financial dashboard with net worth tracking and an investment checkup — then pitches 0.89% AUM wealth management. Alistair puts an AI assistant in your pocket for $4.99/month. Which one actually makes you better with money?
Alistair vs. Domain Money: The Human-AI Financial Advice ShowdownIndustry Insights
Domain Money pairs you with a dedicated CFP for a flat annual fee starting at $2,900. Alistair puts an AI assistant in your pocket for $4.99/month. Which path actually makes you wealthier?
Alistair vs. Range: Two Visions for the Future of Financial AdviceIndustry Insights
Range charges $3,950/year for a team of human advisors wrapped in software. Alistair puts the AI itself in the driver's seat — for $4.99/month. Which model actually delivers better financial guidance?
Loss Aversion: Why Selling Hurts Twice as Much as Buying Feels GoodMoney Psychology
Kahneman and Tversky won a Nobel Prize proving that losses hurt roughly twice as much as equivalent gains feel good. That one insight explains most investing mistakes — here's how to override your own brain.
Social Security Will Be There — Here's What You'll Actually GetRetirement
The trust fund depletion headlines are terrifying. But even in the worst-case scenario, Social Security will pay ~77% of promised benefits. Here's what that means for your retirement plan.
The HSA Is the Best Retirement Account Nobody UsesRetirement
Triple tax-advantaged: contributions are pre-tax, growth is tax-free, and withdrawals for medical expenses are tax-free. After 65, it functions like a Traditional IRA. Why isn't everyone maxing this?
The Case for Self-Managing Your MoneyIndustry Insights
The financial advice industry depends on you believing this is too complex to handle yourself. It's not. Here's why self-management is not only possible — it's the better choice for most investors.
Trump Accounts (530A) Explained: What Parents Need to Know About the New Children's Investment AccountsIndustry Insights
Trump Accounts launched July 4, 2026, giving millions of U.S. children a tax-advantaged investment account with a $1,000 federal seed deposit. Here's how they work, who qualifies, contribution limits, and how much they could be worth.
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