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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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.
Your Advisor's Credentials Just Became a Participation TrophyIndustry Insights
GPT-4 scored 85% on the CFP, passed all three CFA levels, and aced all four sections of the CPA. The three hardest credentials in finance — and no human holds all of them. Your advisor has maybe one or two. What are you paying 1% for?
Tax Gain Harvesting: The Flip Side Everyone IgnoresTax Strategy
Everyone knows about tax-loss harvesting. But deliberately selling winners to realize gains — when your tax rate is 0% — is equally powerful and almost nobody does it.
Introducing Alistair: AI-Powered Financial Coaching That Actually WorksProduct Updates
After months of building, we're launching Alistair — an AI assistant you talk to like a human advisor, without the 1% fees, referrals, or 20-minute annual check-ins.
Meet the FIRE Calculator Microtool: Know Exactly When You Can QuitMicrotools
The FIRE movement has millions of followers but most calculators give you a single number and bounce. Alistair's FIRE microtool walks you through every scenario — Coast FIRE, Barista FIRE, and the real math behind your number.
Bonds Aren't Boring — You Just Don't Understand ThemInvesting
Most investors treat bonds as the boring safe part of their portfolio. But bonds are more complex — and more interesting — than stocks. Here's what you're missing.
Meet the Rent vs. Buy Microtool: Stop Guessing About the Biggest Financial Decision of Your LifeMicrotools
Buying a home is the largest purchase most people ever make — and the advice you get is terrible. Alistair's Rent vs. Buy microtool does the actual math and helps you think through what no mortgage calculator will tell you.
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