Most families have a budget spreadsheet. A few have a financial advisor. Very few have a family office, the team of specialists that rich families hire to look at their money from every angle at once. A CIO for investments. A tax strategist. An estate attorney. A risk officer for insurance. Someone whose whole job is to say “have you considered the opposite?”

I am not rich enough for any of that. But I built one anyway. It runs on my home server, costs almost nothing, and has already paid for itself.

The plumbing

Three layers, all open and boring:

  • SimpleFIN pulls transactions from every bank, credit card, and brokerage into one place.
  • Actual Budget (self-hosted) is the ledger and the envelope budget.
  • Claude Code is the brain. A cron job runs it every morning. It categorizes new transactions, matches Venmo charges against email receipts, flags anything weird, and emails me a short report. On Sundays it writes a weekly review. On the first of the month it reconciles.

That layer alone is worth the afternoon it took to set up. But the interesting part is above it.

The roles

I wrote a handful of specialist “agents.” Each one is a prompt with a specific mandate, reading the same folder of documents about our finances:

  • Chief Investment Officer: asset allocation, concentration risk, fee drag, opportunity cost.
  • Risk / Insurance Officer: coverage adequacy, coordination between policies, what falls through the gaps.
  • Tax Strategist: federal and state efficiency, retirement account ordering, multi-year planning.
  • Estate Planner: wills, trusts, beneficiaries, guardianship for Margot, incapacity.
  • Contrarian: the case against whatever I am about to do.

Any meaningful decision (large, irreversible, or multi-year) gets routed through the relevant subset. The Contrarian always gets a vote. They disagree with each other constantly, which is the whole point. It stops me from getting one confident answer that happens to be wrong.

Where it paid off

I fed every policy we have into the repo: home, auto, health, disability (personal and work), short- and long-term, dental, vision, life (term, whole life, two VULs), horse, dogs, Steph’s business liability.

The findings were not subtle:

  • Our auto liability was at Colorado state minimum despite a net worth long past the point where that made sense. One bad intersection and we would have lost almost everything. Fixed.
  • The disability stack coordinates cleanly. The employer policy does not offset against our personal ones, which changed the math on a buy-up offer about to expire.
  • A pending disability buy-up option had a definition-inheritance question I would have missed. The specialists caught it on the first pass.

A human family office would have found all of this too. The difference is that this one is always running, never bills an hour, and can look at something before breakfast because I had a weird thought in the shower.

The point

This does not replace our CPA, estate attorney, or financial advisor. I still use all three. What it replaces is me showing up under-prepared, asking vague questions, accepting the first answer, forgetting to follow up. Now I walk in with the right questions and the documents already pulled. At least that’s how it works today…

The tooling is unglamorous. A cron job and a folder of Markdown. The real upgrade is the posture it creates, treating our own finances with the seriousness a founder gives their company.