Work Out How Much to Raise and What It Buys You

    You are a startup CFO. Size this round properly.

The business: {{what_you_do}}
Current revenue and growth rate: {{numbers}}
Current burn and cash: {{monthly_burn_and_balance}}
Team: {{headcount_and_planned_hires}}
What I think I need: {{your_instinct}}
Stage and last round: {{history}}

Round sizing is a milestone question, not a number question. The correct amount is whatever it takes to reach the next set of proof points, with a real margin, and the wrong amount is a round-number figure chosen because it sounds like the stage you are at.

Part 1 — Define the milestone.
What must be demonstrably true for the next investor to fund this at a meaningfully higher valuation? State it as evidence, not activity: a revenue level, a retention curve, a repeatable acquisition motion, a technical result, a regulatory clearance. Then tell me honestly whether the bar for that next round is where I think it is — the requirements have moved substantially since 2021 and many plans are still built on the old numbers.

Part 2 — Cost the path there, bottom-up:
- Hires: role, start month, fully loaded cost including on-costs and recruiting, not salary
- The lag between hiring someone and them producing anything, which is a real cost founders always omit
- Non-people spend tied to the plan
- Existing burn, and how it grows as the team does
- Sum to the cash needed to reach the milestone

Part 3 — Add the margin, which is the part people cut and then regret:
- Time buffer: everything takes longer than the plan. Add a meaningful multiple to the timeline, not 10%.
- Fundraising itself takes months of a founder's attention, during which growth usually slows. Budget the runway to start the next raise well before the money runs out, not to end when it does — raising with three months of cash is negotiating from the worst possible position and every investor can see it.
- The plan where revenue comes in at half the forecast: does the round still reach the milestone?

Part 4 — Sanity-check the number against dilution. At a plausible valuation, what percentage does this round cost, and what does the cap table look like after it plus the option pool? If the answer is uncomfortable, the options are a smaller round with a tighter milestone, or a better story before raising — not a bigger valuation you cannot justify.

Give me: the number, the milestone it buys, the months it lasts, the dilution it costs, and the one assumption most likely to be wrong.