Family Offices & Foundations

The mandate and what it permits. The allocation or the manager under review. The commitment and its horizon. The council, the board, or the trustees who have to live with it.

• ·IRS — private foundation rules, excise tax and qualifying distributions
• ·SEC — adviser and exempt-reporting obligations, plus issuer filings
• ·OECD — cross-border tax standards and reporting frameworks
• ·IMF · World Bank — macro and country risk across a multi-decade horizon
• ·EUR-Lex — EU rules where the structure crosses jurisdictions

Every claim carries a provenance tag. [SOURCED] means traced to a verified reference. [INFERRED] means analytical inference — flagged automatically. Claims that cannot be traced are labelled as inference, never presented as fact.

• The Architect maps the structure — mandate, allocation, entity and where each holding actually sits.
• The Strategist reads the horizon the commitment has to survive: the cycle, the mission, the next generation.
• The Engineer works the numbers — the manager's record, the fee load, the sensitivity of the base case.
• The Counsel surfaces fiduciary duty, cross-border exposure and what governance would question.
• The Contrarian sole mandate: argue this commitment is a mistake, and name the obligation to the next generation this breaks.

Five complete analyses. Five distinct angles. Not five versions of the same answer. Then they challenge each other, anonymously. Then they converge — and when one perspective refuses to, that dissent is preserved rather than averaged away.

Output:GO / PIVOT / NO GO / INSUFFICIENT BASIS · Confidence score · Decision matrix · Minority Report · Testable predictions.

Questions Pilot5.ai helps with

• Does this allocation still serve the mandate, or has the mandate quietly drifted to fit it?
• What would the family council ask about this commitment that we have not answered yet?
• Is this new manager genuinely additive, or are we paying twice for exposure we already hold?
• Would this program still be defensible in ten years with the foundation's name on it?
• What is the strongest argument against committing, and can we answer it on the record?

Common questions

Is family and portfolio data confidential?

Family and portfolio content is never used to train any AI model. A pseudonymization layer replaces personal and entity identifiers with reversible tokens before anything reaches a model, and restores them only in your result — automated detection reduces what reaches a provider, though it cannot guarantee elimination. Each deliberation leaves a timestamped record you can retrieve by ID. Retention periods and Zero Data Retention mode are set out in our Privacy Policy.

Does it replace our advisors or the investment committee?

No. Advisors bring a recommendation; this brings the argument against it, kept on the record rather than raised once and lost. Pilot5.ai does not provide investment, tax or legal advice, and the family's decision remains the family's.

What does it cost per question?

The estimate is shown before the deliberation runs, reserved at launch, settled on completion, with any excess refunded, so the cost is known before the question is asked. Current rates are on the pricing page.