Personal Investment Portfolio Review
Personal Finance for Entrepreneurs
Quick Answer
Enter your current investment holdings with amounts. Paste into Claude or ChatGPT. Get allocation assessment, fee drag analysis, and rebalancing recommendations appropriate for a founder with concentrated startup exposure.
What You Get
A personal investment portfolio review covering current allocation assessment, diversification analysis, fee drag calculation, concentration risk given existing business equity, rebalancing recommendations, and guidance on how to think about personal investing when your startup equity is already a concentrated bet.
Who Is This For
Founders who want to review their personal investment portfolio, entrepreneurs building personal wealth alongside their business, and business owners approaching a liquidity event who want to prepare their investment strategy.
About This Template
Most founders have the bulk of their wealth in their company and neglect their personal investment portfolio. When they do have a portfolio, it is often poorly allocated, expensive, or not aligned to their risk tolerance and time horizon. This template guides founders through entering their current portfolio holdings, then uses AI to assess the allocation, identify concentration risks and fee drag, and produce specific rebalancing recommendations appropriate for a founder who already has significant concentrated startup equity exposure.
Fill In Your Details
Your first name
e.g. 34
e.g. 10+ years, investing for retirement, or 5 years until anticipated liquidity event
e.g. S&P 500 index fund (VTSAX) $85,000
e.g. International index fund $20,000
e.g. Apple stock $35,000
e.g. Bond fund $15,000
List any other holdings with values
e.g. $9,000,000 implied equity in company (illiquid)
Gather these details then use them to fill in the prompt below.
AI Prompts
Generate investment portfolio review
Paste this prompt into Claude or ChatGPT with your portfolio data filled in.
You are a financial advisor reviewing the personal investment portfolio of a startup founder. Using the data below, produce a comprehensive portfolio review that accounts for the founder's concentrated startup equity exposure. Investor: [investor_name] Age: [age] Risk tolerance: [risk_tolerance] Timeline: [investment_timeline] Holding 1: [holding_1] Holding 2: [holding_2] Holding 3: [holding_3] Holding 4: [holding_4] Other holdings: [holding_5] Startup equity (illiquid): [startup_equity_value] Produce: 1. Current Allocation — breakdown by asset class including the illiquid startup equity 2. Liquid Portfolio Allocation — allocation excluding startup equity 3. Concentration Risk Assessment — given the illiquid startup equity, how much additional risk is being taken 4. Fee Drag Analysis — estimated annual fees for each holding and total annual drag 5. Rebalancing Recommendations — specific changes to the liquid portfolio given total financial picture 6. Founder-Specific Guidance — how to think about personal investing when you already have a concentrated startup bet 7. Liquidity Event Planning — how the portfolio strategy should change as a liquidity event approaches Note: this is educational guidance. Consult a registered investment advisor for personalized investment advice. Past performance does not guarantee future results.
Sample Output
This is an example of what AI produces when you use this template.
Concentration Risk Assessment
Total net worth including startup equity: approximately $9,155,000. Startup equity represents 98.3 percent of total net worth ($9,000,000 out of $9,155,000). Liquid investment portfolio: $155,000 representing 1.7 percent of total net worth. This is an extreme concentration by any financial planning standard — essentially all financial wealth is in a single early-stage company. This is not necessarily wrong for a founder — it is the nature of the bet. But it means your liquid portfolio should be managed as defensively as possible. The startup is your aggressive growth allocation. The liquid portfolio should provide stability, not more risk.
Founder-Specific Guidance
Three principles for investing as a founder with concentrated startup equity: 1. Your liquid portfolio is your financial safety net, not your wealth builder. The startup will make you wealthy if it succeeds. Your liquid portfolio should protect your ability to survive if it does not. Prioritize capital preservation and diversification over returns. 2. Avoid correlated risks. Do not own individual tech stocks — if the sector that your startup operates in has a downturn, your startup will suffer at the same time your public tech holdings decline. Own broad index funds that zig when tech zags. 3. As a liquidity event approaches, start thinking about the tax-efficient deployment of proceeds. Single-stock concentration from a company exit is a well-studied problem. Begin educating yourself on 10b5-1 plans, charitable remainder trusts, and qualified opportunity zones 12-18 months before any anticipated liquidity.