Investing and Allocating Capital Questions and Answers
100 questions on investing and allocating capital answered by Richard C. Wilson. How family offices set policy, allocate capital and invest across funds, direct deals, real estate and private markets.

All 100 Questions
- How should a family office set target returns for each part of its portfolio?
- How should an investment plan change when a family's spending needs change?
- How can a family balance long-term growth with current income?
- How should a family invest when its wealth is concentrated in one business?
- When should a family sell shares in a company it founded?
- How can a family reduce the risk of holding too much wealth in one asset?
- How should a family set limits on exposure to one company, sector, or country?
- How can an investment portfolio protect purchasing power over time?
- How should a family account for inflation when planning returns?
- How can a family set a return target that matches its real needs?
- How should a family compare expected returns with the risk of permanent loss?
- What is a practical way to estimate how much investment risk a family can bear?
- How should a family decide how much debt its investment portfolio can support?
- When does borrowing make an investment portfolio too fragile?
- How should a family plan for capital calls during a market downturn?
- How much cash should be reserved for taxes, spending, and commitments?
- How can a family avoid being forced to sell investments at the wrong time?
- How should a family plan liquidity across different investment horizons?
- What should a family do when private investments delay returning capital?
- How can a family manage currency exposure across its global assets?
- How should a family decide whether to hedge foreign currency risk?
- How should a family invest money held in multiple trusts and entities?
- How can an investment plan account for assets the family cannot easily sell?
- How should a family set a benchmark for a portfolio with unusual assets?
- How can a family tell whether an investment strategy is working?
- Which investment results should a family review each quarter?
- How should a family separate market returns from the effect of investment decisions?
- How can a family measure performance after fees, taxes, and inflation?
- How should a family compare investments with different risk levels and time horizons?
- When should a family change an investment manager or strategy?
- How can a family avoid changing course because of short-term market moves?
- What decisions should an investment committee make, and what should it delegate?
- How often should an investment committee meet to review the portfolio?
- What information should investment staff prepare before a committee meeting?
- How should a family handle disagreements about a proposed investment?
- Who should have authority to approve investments of different sizes?
- How can a family document why it made an investment decision?
- What should happen when an investment falls outside the family's agreed limits?
- How can a family make investment decisions quickly without skipping review?
- When should a family bring in an independent investment adviser?
- How should a family compare the cost of an adviser with the value received?
- How can a family spot conflicts of interest in investment recommendations?
- What questions should an investor ask about how an adviser is paid?
- How should a family evaluate an investment opportunity from a close contact?
- What safeguards help when a family member brings a deal to the committee?
- How can a family assess whether an investment sponsor has enough experience?
- What evidence helps verify an investment manager's track record?
- How should a family judge performance when a manager has a short history?
- What does a family need to learn about a manager's past losses?
- How can investors tell whether a manager's strategy is repeatable?
- What should a family check about an investment firm's ownership and finances?
- How should a family assess whether a manager can handle a larger pool of capital?
- What signs suggest an investment fund is taking more risk than its returns show?
- How should investors compare fund fees, expenses, and carried interest?
- What fund terms matter most when a family commits capital?
- How can a family negotiate clearer reporting and investor rights in a fund?
- What should investors understand about lockups, gates, and withdrawal limits?
- How should a family decide whether to invest in a new fund or an established one?
- How can a fund manager make a clear case for a family office investment?
- What should a fund pitch say about how investor capital will be used?
- How can a manager show that a fund's interests align with its investors?
- What portfolio details do family investors expect in regular updates?
- How should a manager respond when an investment is underperforming?
- What makes a capital call notice clear and useful to investors?
- How should a family choose between a pooled fund and a separate account?
- When does a separately managed account make sense for a family?
- How should a family assess the tradeoff between liquidity and potential return?
- How can a family compare private investments with publicly traded alternatives?
- What should a family consider before investing in private credit?
- How should a family assess the risk of borrowers in a private lending deal?
- What protections should an investor look for in a private credit agreement?
- How can a family evaluate the quality of collateral behind a loan?
- What should investors examine in the terms of a secondaries transaction?
- How can a family assess whether a private market valuation is realistic?
- What does a family need to understand about valuation methods for private assets?
- How should a family plan for assets that may take years to sell?
- When does investing in infrastructure fit a family's goals?
- How can a family evaluate an investment in natural resources?
- What should a family consider before buying farmland as an investment?
- How should a family compare owning property directly with investing through a fund?
- What costs should an investor include when estimating a property's net return?
- How can a family decide whether an investment property is worth renovating?
- What should a family assess before investing alongside an operating business?
- How can a family protect its position as a minority investor in a private company?
- What rights should investors seek when they do not control a company?
- How should a family assess a company's cash flow before investing?
- What financial measures help compare businesses in different industries?
- How can a family tell whether a company's growth depends on too much debt?
- What should investors examine in a company's plans for using new capital?
- How can a family assess a startup's path to sustainable revenue?
- What milestones should investors set before releasing additional startup capital?
- How should a family decide whether to join a later funding round?
- What rights should an investor understand before buying shares in a private company?
- How can an investor judge whether a company's valuation leaves room for growth?
- What should a family consider before making an investment through a special purpose vehicle?
- How should a family assess the tax impact of an investment before committing?
- When should a family use an investment holding company?
- How can a family coordinate investment decisions across trusts and generations?
- What records should a family keep for each investment and capital commitment?
- How should a family plan its investments around upcoming tax payments?
