INVESTOR DILIGENCE GUIDE
What Your Next Lead Investor Will Ask About Your Financial Model
The 15 questions sophisticated investors ask in every first serious meeting and how to make sure your answers hold up
15
INVESTOR QUESTIONS
6
CRITICAL AREAS
$500M+
RAISED BY CLIENTS
100+
FOUNDERS ADVISED
WHAT’S INSIDE
Six sections. Every question that matters.
This guide is organized around how lead investor conversations actually unfold, not how founders wish they did.
SECTION 01
Revenue Model & Growth Assumptions
How investors probe whether your top line is built from first principles or just a growth rate.
Q1 - Q3
SECTION 02
Unit Economics & Margin Structure
LTV/CAC, gross margin methodology, and payback period — and why the calculation often matters more than the number.
Q4 - Q6
SECTION 03
Burn, Runway & Cash Discipline
What investors are really asking when they probe burn rate and the runway milestone question most founders answer wrong.
Q7 - Q9
SECTION 04
Use of Proceeds & Capital Deployment
Why 'sales and marketing: 40%' is not a use of proceeds and what investors actually want to see.
Q1 0 - Q11
SECTION 05
Financial Controls & Reporting
How your monthly reporting cadence signals execution quality before investors look at a single number.
Q1 2 - Q13
SECTION 06
Assumptions & Sensitivity
The scenario planning questions that separate founders who've stress-tested their model from those who haven't.
Q1 4 - Q15
INSIDE THE GUIDE
The preparation checklist that closes gaps before they cost you a term sheet.
Every item is rated HIGH or MED priority based on how frequently it surfaces in real investor meetings.
Revenue derivable from first-principles inputs
HIGH
Cohort-level retention data, consistently defined
HIGH
LTV/CAC methodology defensible under scrutiny
HIGH
HIGH
Gross margin clean - nothing misclassified
HIGH
Burn reconcilable to bank statements on the spot
HIGH
Quarter-by-quarter headcount and deployment plan
MED
Base / upside / downside with different assumptions
MED
MED
+ 8 more items in the full guide
WHAT YOU’LL LEARN
Preparation, not performance.
Investors don't ask hard questions to trip founders up. They ask them to determine whether you understand your business well enough to deploy their capital responsibly.
What investors are really asking
The surface question and the underlying concern are rarely the same thing. This guide surfaces both for every question.
Specific preparation steps for each question
Not 'know your numbers' but exactly what to prepare, which sensitivity analyses to run, and what follow-ups to anticipate.
A 15-item pre-meeting checklist
HIGH and MED priority ratings on every item, so you know exactly where to spend your preparation time.
The questions that most often derail raises
Written from the perspective of advisors who have sat on both sides of the table, as founders, as investors and as senior investment bankers.
Craig Irvine
Founder & Managing Director
Merrill Lynch · Citigroup · Macquarie
25+ years senior financial leadership
Startup founder & investment banker
US & Asian capital markets
Registered: Weild & Co., FINRA
ABOUT THREE VECTORS CAPITAL
Written by advisors who've sat on both sides of the table.
Three Vectors Capital is a Fractional CFO and Financial Advisory firm serving Seed through Series B growth-stage startups. We've supported 100+ founders across 30+ industries and helped clients raise over $500M in equity, debt, and project finance.
Craig Irvine founded Three Vectors after two decades as a senior investment banker at Merrill Lynch, Citigroup, Daiwa, and Macquarie — and after experiencing fundraising firsthand as a startup founder. This guide is written from that dual vantage point: what investors actually look for, and where founders most commonly leave themselves exposed.
Affiliate of Weild & Co. · FINRA/SIPC Member Broker-Dealer & Investment Bank
Serious growth requires serious financial leadership.
GET THE GUIDE
Download the guide and close the gaps before your next investor meeting.
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Affiliate of Weild & Co, a FINRA/SIPC member broker-dealer and investment bank