Investing Basics for Entrepreneurs

Chosen theme: Investing Basics for Entrepreneurs. Build a confident, founder-friendly investing foundation that respects your runway, amplifies your focus, and grows wealth alongside your company. Expect clear frameworks, hard-won stories, and practical prompts you can act on today.

Risk, Return, and the Founder’s Edge

Shift from chasing headline returns to evaluating risk-adjusted outcomes. Consider drawdowns, liquidity, and how an investment behaves in stress scenarios. Comment with your go-to metric—do you track maximum drawdown, volatility, or simple cash flow resilience?

Risk, Return, and the Founder’s Edge

Startups and angel portfolios often follow power laws—few winners, many zeros. Diversify accordingly. Balance concentrated conviction in your company with broader holdings. Tell us: what’s your current mix between your startup, cash, and diversified assets?

From Cash Flow to Capital Allocation

Hold an emergency buffer for both life and business. Many founders target six to twelve months of personal expenses and three to six months of operating costs. What’s your current runway target—does it truly match your sales cycle risk?

From Cash Flow to Capital Allocation

Debt can accelerate growth if cash flows are predictable; equity avoids fixed payments but dilutes. Compare APRs to expected ROI, and stress-test both. Share a time when financing structure made or broke a key decision for you.

Diversification Without Dilution

Core–Satellite Portfolio for Busy Builders

Let a broad, low-cost core do most of the heavy lifting. Add small satellites for learning or edge—like a sector ETF or a vetted angel check. Keep satellites tiny so curiosity never becomes catastrophic.

Assets That Complement Startup Risk

If your company is high-growth and cyclical, consider ballast: government bonds, cash-like instruments, or defensive sectors. Diversification works best when assets respond differently to stress. What’s your personal ballast when revenue gets lumpy?

Rebalancing Rituals You’ll Actually Do

Pick dates, not moods. Quarterly or semiannual rebalancing nudges you to sell a bit of what ran and add to what lagged. Put it on your calendar and share your ritual to keep yourself accountable.

Time Horizons, Compounding, and Optionality

Think of compounding like product retention: small, persistent gains stack meaningfully. Fees and taxes are churn. Lower them. Reinvest dividends. Even modest, consistent returns can meaningfully offset the volatility of entrepreneurial income.

Time Horizons, Compounding, and Optionality

Short-term needs in cash and ultra-short bonds; medium-term in balanced funds; long-term in growth assets. Label each bucket with its purpose so you don’t panic-sell. Which bucket needs attention in your plan today?

Public vs. Private: Where to Learn First

With transparent data, low fees, and daily pricing, public markets help you test hypotheses quickly. Practice journaling each trade or fund buy with a clear thesis and exit rule. Revisit monthly to refine thinking.

Overconfidence and Single-Company Exposure

Believing your insight in one domain transfers everywhere is dangerous. Cap position sizes, especially when your salary already depends on one company. What rule would future-you thank present-you for enforcing without exception?

Action Bias and the Dopamine Loop

Markets reward patience more than constant tinkering. Replace impulse trades with scheduled reviews. If you feel FOMO, write a 60-second memo before clicking buy. What’s your quick pause ritual?

Premortems, Checklists, and Cooling-Off

Run a premortem: assume the investment failed—why? Use a checklist for valuation, risk, and liquidity. Insert a 24-hour cooling-off period for any big move. Share your checklist to inspire another founder.

Your Personal Investment Policy Statement

State your why, return target, and maximum acceptable drawdown. Note tax considerations, liquidity needs, and ethical screens. Constraints make decisions easier and faster when emotions surge during market storms.

Your Personal Investment Policy Statement

Automate contributions, predefine allocation ranges, and restrict trading to calendar dates. If a rule requires lots of time, it will break. What two rules will you adopt this month?