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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"I'll Refer You to Someone for That": The Narrow Expertise ProblemHorror Stories
Your financial advisor manages investments. But what about taxes? Estate planning? Insurance? Each referral is another fee, another relationship, and another gap in your financial plan.
Meet the Monte Carlo Retirement Simulator: Because Straight-Line Projections Lie to YouMicrotools
Most retirement calculators draw a straight line and tell you you're fine. Real markets don't work that way. Alistair's Monte Carlo simulator runs 1,000 scenarios to show your actual probability of success.
Dollar-Cost Averaging vs. Lump Sum: The Math Has a Clear WinnerInvesting
Every study says investing a windfall all at once beats spreading it out. So why does everyone still recommend dollar-cost averaging? The answer is psychology, not math.
Meet the Debt Payoff Strategist: The Math Behind Snowball vs. Avalanche — and Why Both WorkMicrotools
Snowball or avalanche? One saves more interest, the other builds momentum. Alistair's debt payoff microtool shows you the exact paydown path — debt-free date, interest saved, and which strategy wins with your numbers.
Emergency Funds in 2026: 3 Months, 6 Months, or 12?Money Basics
The old rule was 3-6 months of expenses. But in a world of rising costs, gig-economy income, and longer job searches, the math has changed. Here are the real numbers.
Meet the Social Security Claiming Optimizer: The $100K Decision You Only Get One Shot AtMicrotools
Claim at 62, 67, or 70? The difference can be $100,000+ in lifetime benefits. Alistair's microtool calculates breakeven ages and shows which claiming strategy maximizes your total lifetime payout.
Meet the 529 College Savings Planner: The Number That Changes Every Year You WaitMicrotools
College costs are rising at 5-6% per year — faster than general inflation. Alistair's 529 planner models the real future cost of college and shows your monthly gap so you're not scrambling in senior year.
Meet the Retirement Withdrawal Safety Microtool: The 4% Rule Is a Starting Point, Not a PlanMicrotools
The 4% rule works — until it doesn't. Alistair's withdrawal safety microtool stress-tests your portfolio against market crashes, inflation, and your actual spending to find your sustainable withdrawal rate.
Roth vs. Traditional: The Complete Decision FrameworkRetirement
It's the most common retirement question — and the most commonly answered wrong. The decision has nothing to do with age and everything to do with marginal tax rates.
Meet the Mortgage Payoff vs. Invest Microtool: The Debate That Math Actually SettlesMicrotools
Pay off the mortgage early or invest the extra cash? It's the most debated question in personal finance — and the answer is math, not feelings. Alistair's microtool runs both scenarios side by side.
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