Finances · built & verified July 13, 2026

The money map is live: one doc, one monthly sweep, zero guesswork

You asked whether we actually have processes that notice "this account hit its limit — time to move money." We didn't — the targets existed on paper, scattered and partly contradictory. Now we do: a single canonical rulebook, an automated first-of-the-month sweep, and a tested pipeline that hands you the exact transfers to make.

Where every dollar sits, and why

The full spec lives in docs/money-map.md in the finances repo — the single source of truth. Every other document now points there instead of restating numbers.

AccountRoleTargetOverflow goes to…
Business checkingChase PERFBUS S-corp operating float — ~2 months of payroll + overhead cap $40k Cash Plus, monthly, booked as an owner distribution
Personal checkingChase Paycheck landing pad, kept deliberately thin ~$4k Cash Plus, monthly
Cash PlusVanguard — the hub All card autopays pull from here. $115k liquidity floor (~5 months of burn) + $30k tax reserve $145k Brokerage — invested, not parked
BrokerageVanguard, core index Absorbs everything above the targets: 80% VTI / 20% VXUS, dividends reinvested no cap — (buy and hold)

Untouched by the sweep: the 529 (auto glide path), SEP IRA, BTC IRA, Caroline's brokerage, and the HSA. The ~$15k UI position rides along as the play bucket under the 5% rule. One open variable is flagged in the doc: if the Gusto withholding bump replaces quarterly estimates this fall, the $30k reserve shrinks and the Cash Plus target drops toward $115k.

The 1st-of-the-month sweep

01 · 7:23 AMCron firesA standing job on the always-on machine, first of every month.
02 · agentClaude computesPulls live balances from Tiller, runs the algorithm, runs health checks.
03 · todoistTask landsOne Finance task with the exact transfer lines and buy order.
04 · you~10 minutesYou execute the moves. No agent ever touches money — computes only.

The math, in order:

  1. Skim checking: anything above $4,000 moves to Cash Plus (skip under $1k).
  2. Skim the business: anything above the $40,000 cap moves to Cash Plus as an owner distribution (skip under $2k), with the FreshBooks entry booked after it posts.
  3. Invest the excess: whatever Cash Plus holds above $145,000 after those sweeps becomes a two-line buy order — 80% VTI / 20% VXUS (skip under $2k).

The same run also verifies every card's autopay actually executed, scans for anomalies and dead account feeds, logs a net-worth snapshot to a running ledger, and — on quarterly runs — nags about the manual balances that go stale (home value, BTC IRA) plus the upcoming estimated-tax date.

Tested tonight — and the test earned its keep

I ran the full pipeline end-to-end in dry-run mode before trusting it. It worked, and it caught a genuinely dangerous edge case:

⚠️ The in-flight trap

Tiller's feed hadn't yet absorbed yesterday's restructure — the $18.5k Cash Plus → brokerage transfer and the VTI/VXUS buys. The raw algorithm therefore said "invest another $20,100," which would have moved the same money twice.

The agent cross-checked recent activity, spotted the in-flight transfer, adjusted the balance, and correctly skipped the invest leg. That safeguard is now a codified rule in the sweep prompt — the in-flight guard — not a judgment call.

What the dry run would have told you to do this month

One move only: skim ~$1,599 from personal checking to Cash Plus. The business account is under its cap, and Cash Plus — after the restructure — sits almost exactly on its $145k target. The plan landed right on the number.

Documentation, de-noised

Your instinct was right that the rules were smeared across files with contradictions. Fixed:

What happens next