Why the Depth Layer Was Never Going to Be a Prompt.
Standard AI drafts the email. Reading a plan — formulas, fact patterns, what's missing — is a different problem class. Why depth had to be built, not prompted.
26 Jun 202616 min
Post-BBB planning, plan-review methodology, and the category in motion.
The portability election is free, the deadline is real, and the unfiled 706 is the most common — and most expensive — omission a reviewer finds in surviving-spouse files. What DSUE actually preserves, and the cases where skipping the filing cost seven figures.
Standard AI drafts the email. Reading a plan — formulas, fact patterns, what's missing — is a different problem class. Why depth had to be built, not prompted.
What advisors actually pay for in a plan review — and why a beautiful report with no defensible finding is worth exactly nothing.
After Connelly, redemption-style buy-sells funded with corporate-owned life insurance inflate the estate they were meant to protect. The review checklist.
The six qualification elements in plain English, with examples of which companies qualify and which don't — does a food manufacturer? Yes.
The exclusion is per taxpayer. How founders multiply it before a sale, the Roblox example, and the spousal question — addressed both ways with footnotes.
Every element the IRS tests on a §1202 claim, in the order an examiner runs it. Interactive, saves your progress, prints to PDF.
A free educational issue-spotter that reads your facts into a lane — and surfaces the gimmes and gotchas specific to your situation.
The §643(f) gate, the adjacent attack vectors, the six structural mitigants, and the residual risk no honest analysis pretends away.
The science says the strategy works; the art is the client's tolerance for a contestable position. Where appetite for risk meets the work required to support it.
A new brief publishes every Friday, starting 19 June 2026.
Benchmark runs against synthetic client files. The same four deliverables an advisor would see in the portal — with the prospect data invented and the disclaimers real.
Retired physician, $8.4M estate, revocable trust from 2014 with a pre-ATRA formula clause. Portability never elected on first spouse.
Second-generation family business, $38M gross, ILIT funded through a family LLC. Valuation discounts never applied; buy-sell out of date.
Blended family, $3.2M estate, plain-vanilla documents. The kind of file that looks fine on the surface — and has one finding you want to catch.