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.
Read the postCategories
All Posts
Showing 81–90 of 95 posts
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.
Meet the 401(k) / IRA Optimizer: The $100K Question You've Been AvoidingMicrotools
Traditional or Roth? The answer depends on your tax bracket today versus retirement — but most people just guess. Alistair's optimizer runs the math so you actually know.
2 Hours a Year: The Ugly Truth About Advisor AvailabilityHorror Stories
The average client gets about 2 hours of actual advisor attention per year. The rest of the time, you're talking to an assistant, a junior associate, or nobody at all.
Meet the RSU Tax & Selling Optimizer: Stop Leaving Six Figures on the TableMicrotools
RSUs and ISOs can be life-changing wealth — or a tax disaster. Alistair's RSU microtool models every sell strategy, AMT exposure, and state tax hit so you don't guess your way through equity compensation.
Why Most People Should Own Exactly One FundInvesting
The financial industry thrives on complexity. You need this tilt, that factor, this alternative. But the data says you'd probably beat 90% of professionals with a single target-date fund.
Ready to fire your advisor?
Alistair gives you everything a traditional advisor does — plus tax strategy, estate planning, and 24/7 access — for a flat subscription.
Try Alistair Free7-day free trial · No credit card required