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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Meet the Estate Tax & Gifting Planner: The $15M Question Nobody Talks AboutMicrotools
Estate tax planning isn't just for billionaires. With a $15 million federal exemption — and 17 states taxing far smaller estates — more families than you'd think face estate taxes. Alistair's microtool shows your exposure and what gifting can do about it.
Meet the Tax Bracket Visualizer: Because Your Marginal Rate Isn't What You Think It IsMicrotools
Most people can name their tax bracket and have no idea what their effective rate actually is. Alistair's visualizer shows where each dollar of your income is taxed and why your '24% bracket' might really be 16%.
Meet the Home Affordability Calculator: What the Bank Says You Can Borrow vs. What You ShouldMicrotools
Banks will approve you for far more house than you should buy. Alistair's affordability calculator uses the 28/36 rule to show what's actually comfortable — so your mortgage doesn't own you.
The Backdoor Roth IRA Could Disappear — Here's What to Do NowTax Strategy
Congress has tried to close the backdoor Roth IRA loophole multiple times. With each new administration, the window narrows. Here's how it works, why it's at risk, and what to do before it's gone.
Meet the Life Insurance Needs Calculator: The DIME Method That Cuts Through the Sales PitchMicrotools
Insurance agents want to sell you a bigger policy. Your employer's 1x salary coverage isn't enough either. Alistair's DIME method calculator shows your actual coverage need — no commission attached.
Meet the Roth Conversion Ladder: Turning a Tax Time Bomb into Tax-Free WealthMicrotools
A large Traditional IRA is a deferred tax liability. Roth conversions can defuse it — but the timing and amounts matter enormously. Alistair's microtool models year-by-year conversions to find your optimal ladder.
"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.
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