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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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.
Meet the FI Planner: The Complete Roadmap to Financial IndependenceMicrotools
Most FI calculators stop at your FIRE date. Real life has pensions, Social Security, time-bound expenses, and what-if scenarios. Alistair's FI Planner models them all so your plan holds up against reality.
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.
Meet the Value Matrix: Stop Cutting Costs Blindly — Start Spending on What MattersMicrotools
Most budgeting advice tells you to cut spending. The Value Matrix tells you where to cut and where to spend more — by scoring each category on joy, utility, and alignment with your goals.
Meet the Tax-Loss Harvesting Microtool: Your Portfolio's Hidden Tax RefundMicrotools
Tax-loss harvesting can save investors thousands per year in taxes. Most advisors do it once in December if you're lucky. Alistair's microtool walks you through it anytime — here's how it works.
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