The questions every investor asks
Across a raise you will answer the same ten questions thirty times. The founders who do it well are not more eloquent. They have simply decided on the answer in advance.
Fundraising conversations converge. Different partners, different firms, near-identical questions. That repetition is an advantage: it means every answer can be prepared, pressure-tested, and reused.
Below is the structure of a strong answer to each. These are frameworks, not scripts. The bracketed parts are where your specific evidence goes, and the evidence is the entire point. An answer without a number in it is an opinion, and investors discount opinions heavily.
The questions
Why now?
Three forces converged in the last 18 months that make this the right time: 1. [Macro shift] 2. [Tech enabler] 3. [Customer behavior change] Before this, the same idea would have hit [specific blocker]. Now the constraint is gone.
How big is the market?
Bottom-up: [X target customers] × [Y annual contract value] = [$Z TAM]. We've validated [W%] willingness to pay at our current price point through [N pilots/contracts]. We're not betting on the broader [adjacent market] — just our wedge.
What's your CAC?
Blended CAC: $[X]. Payback: [Y months]. LTV/CAC: [Z]x. Our CAC has [improved / held steady] over the last [N] months because [reason — inbound %, channel mix, etc].
How is this defensible?
Three layers: 1. [Data moat / network effect / regulatory] — compounds with use 2. [Distribution moat] — hard to replicate 3. [Team / IP / specific advantage] Every competitor we're watching has [observable weakness]. We'll know we lost defensibility when [specific signal].
Who else is investing?
Lead status: - [Lead, if any] - [Co-leads / committed funds] - [Other named investors / soft circles] We're targeting close on [date] with [$X remaining]. Happy to share the cap table breakdown under NDA.
What are the risks?
Three honest risks: 1. [Real risk] — mitigation: [what we're doing about it] 2. [Real risk] — mitigation: [what we're doing] 3. [Real risk] — mitigation: [what we're doing] The biggest is [#1] because [reason]. If that breaks, the company breaks. We watch [specific metric] weekly.
How are you different from [competitor]?
[Competitor] solves [their wedge] for [their ICP]. We solve [our wedge] for [our ICP]. Overlap is real but the workflow is different enough that customers using both isn't unusual. Where they win: [their strength]. Where we win: [our strength]. We've [won / lost] head-to-head [N] times in the last [period].
Tell me about your team
[Founder 1]: [background, why this problem]. Previously [credibility marker]. [Founder 2]: [background, complementary skill]. Previously [credibility marker]. Early hires: [N] [domain experts]. Worked together at [shared context if any]. We've been heads-down on this for [duration].
Why this round size?
{{round_size}} gets us to [specific milestone] in [N months], which is what's needed for a [next round] at a [valuation logic]. Breakdown: - [N%] [hire / spend bucket] - [N%] [bucket] - [N%] [bucket / runway buffer] We could raise more, but it'd dilute without a clear path to using it.
Use of funds
Specific allocation: - [N%] Engineering hires — [what gets built] - [N%] GTM — [what motion] - [N%] Infrastructure / [specific bucket] - [~15-20%] runway buffer Key hires already in pipeline: [roles]. Expected start: [timeline].
The two answers that decide the meeting
"What are the risks?" is a test of self-awareness. Founders who claim there are no real risks are telling an experienced investor that they either cannot see their own business clearly or are willing to shade the truth. Name the genuine risk, then say precisely what you are doing about it and which metric tells you whether it is working.
"Who else is investing?" is a test of honesty, and it is the one most often fumbled. Investors talk to each other constantly. Inflating your round status is the single fastest way to lose a deal, because it is trivially checkable and it is checked.
Prepare once, reuse everywhere
Write these answers down before your first meeting, not after your fifth. Keep them somewhere you can reach mid-call. When an answer improves because a partner asked a sharper version of the question, update the saved answer rather than relying on memory.
Run your raise on this
Save your best answers once in VCTerminal and pull them up in a click during any call or diligence request.
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