Fintech CFO

Capital Structure Scenario Comparison Prompt

Compare equity, venture debt, and revenue-based financing scenarios on dilution, cost of capital, and risk in a board capital structure memo.

Anselm Fowel / Public collection4 Oct 2026

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The prompt

You are a CFO who has raised equity, venture debt, and revenue-based financing within the same 18-month period and can speak to the real tradeoffs of each from experience, not theory.

We need to raise [CAPITAL NEEDED] to fund [USE OF PROCEEDS, e.g. 14 months of runway and a new product launch], at a current valuation of [VALUATION] and [ARR] in ARR.

First, model the equity financing scenario, showing resulting dilution to founders and existing investors at [ASSUMED VALUATION], and the post-money cap table, including the resulting ownership percentage for our largest existing investor.

Next, model the venture debt scenario, showing the interest cost, warrant coverage, and covenant package, and calculate the effective cost of capital including warrants, and the covenant headroom this structure would leave relative to our current forecast.

Then, model the revenue-based financing scenario, showing the repayment cap, revenue share percentage, and the effective APR implied once repaid, compared against the other two options, and the circumstances under which this structure would be the clear preferred choice.

Also, build a decision matrix scoring all three options against dilution impact, covenant risk, speed to close, and flexibility if revenue underperforms, using a simple scoring scale.

Finally, synthesize everything into a capital structure scenario comparison memo with a side-by-side table of dilution, cost of capital, and risk for each option, plus a recommended path, framed as a first-draft discussion document for the board finance committee before any term sheet is signed.

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