Can today's AI tools calculate a cap table for a new equity round? Here's what I tested:
can you calculate the price per share for a new financing, given this cap table, and tell me the main things to look out for? please identify any questions you have before you can make the calculations.
Please round the shares to full shares and round the share prices to 4 significant digits. Please output a spreadsheet with the details.
existing common shares: 10 million
existing preferred shares: 2 million, bought at $1 per share
unconverted premoney SAFE, $500k with a 20% discount and $8mm cap
unconverted postmoney SAFE, $750k with a 20% discount and $10mm cap
new equity round (SAFEs will convert) of $1.5mm at a $12.5 mm premoney valuation. premoney SAFE will convert using investor friendly method ( investor friendly refers to converting the premoney safe so that new investors do not bear the dilution associated with converting that safe)
no existing option pool, no changes in the pool.
A pretty simple example, much simpler than a typical scenario where a company may convert 10+ SAFEs in a round. Unfortunately, while the logic sounded reasonable, the math was wrong. Why? Basic structural errors in calculating the correct share counts to use for the share prices led to a series of miscalculated share prices and share counts.
While the errors aren't huge, the impact is meaningful: wrong share prices, wrong share counts, and if implemented, it would have left founders confused, investors unhappy, and credibility lost. Watch the video above for the details from ChatGPT and Claude, compared to the default Cap Table and Exit Waterfall Tool.
AI tools are better than your average blog post at explaining how investment structures work. But it can’t (yet) teach you to ask the right questions for your specific situation. Experienced human judgment still matters.