February 23, 2026

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Hi Everyone,

If an investor sat across from you tomorrow and started asking hard questions about your business, how many could you answer on the spot?

These 10 questions typically appear during investor due diligence, but they're just as useful if you're bootstrapped and never plan to raise – they test whether you know your business well enough to make good calls with your money.

Your story

1. If your leadership team each wrote two sentences describing what the business does and why it wins, would they all say the same thing?

If they wouldn’t, your pitch will go in different directions depending on who's in the room. Worth testing before an investor does it for you.

2. Can you describe your market with bottom-up numbers (who buys, what they pay, and how you reach them)?

Broad market size estimates don't hold up under questioning. Investors want to see that you can name the segment you're winning, how many buyers are in it, and why your sales approach can reach them.

3. Does your growth story match your spending?

If you're telling a growth story, your spending should show efficient growth.

If you're telling a discipline story, your costs should back that up. Investors will compare the two.

Your numbers

4. If someone asked how you calculate a key metric, would finance, sales, and product give the same answer?

If different teams define retention, acquisition cost, or revenue differently, that's a serious measurement and credibility problem (and it's probably already causing confusion internally).

5. Do you know how much of your revenue comes from existing customers vs new ones, and what it costs you to keep each group?

Tracking the combined number can make things look healthy while the underlying retention (how much revenue stays without counting upsells or new deals) is weak.

Breaking it apart shows you where growth is actually coming from.

6. Have you measured what it costs to grow revenue from existing customers, or are you assuming it's cheaper than winning new ones?

Selling more to existing customers is often cheaper than finding new ones, but not always. When companies shift budgets toward upselling without tracking the actual cost, they sometimes end up spending more overall without realizing it.

Measure it the same way you'd measure the cost of acquiring a new customer, and then decide where to put your money.

7. Can you produce a one-page view of your unit economics by customer type?

This means being able to show, for each customer segment, how much it costs to acquire them, how long until you make that money back, and what margin you earn.

The precise numbers matter less than whether you can produce them at all and explain how you got there.

Your cash

8. Do you know how much you're spending to generate each new dollar of revenue?

Burn multiple is a simple ratio: divide your net cash burn by the new revenue you generated in the same period.

If you burned $270,000 and added $100,000 in new revenue, your burn multiple is 2.7.

That number should come down as the business grows. At early stages, a burn multiple around 2-3 is common. At $20-50M in revenue, it's closer to 1. If yours is going the wrong direction, that's worth understanding before someone else asks you about it.

9. Can you explain what your spending looks like under the growth plan, and what you'll have achieved before the money runs out?

"We have 18 months of runway" isn't a plan. A solid answer covers what your burn is today, what it becomes as you hire and grow, and what concrete milestones you'll hit before you need more money or reach breakeven.

10. If revenue comes in 30% below forecast, do you already know what you'd cut?

If you have to figure it out in the moment, you'll make worse decisions under pressure. Writing down those triggers now, while things are calm, means the decision is already half made when you need it.

How to use this

Go through the ten questions and answer honestly.

You don't need to do it in a meeting – just write your answers down.

Any question where the answer is "I don't know" or "it would take us a while to pull that together" is a gap worth working on.

That's true whether you're actively raising, planning to eventually, or bootstrapped and want to run a tighter business. "The questions test whether you know your numbers well enough to make good decisions.

If you want to go further, FundersClub's Series A checklist walks through the full preparation process, from financials to legal to investor targeting.

Go deeper

👉 Andreessen Horowitz: The Insider's Guide to Data Rooms – what investors want to see in a data room, what to leave out, and common red flags

👉 First Round Review: The Fundraising Wisdom That Helped Our Founders Raise $18B – tactical advice on preparation, timing, and running a tight process

👉 Airtree Ventures: The Burn Multiple – how to calculate it, what good looks like, and benchmarks for SaaS and non-SaaS models

👉 NFX: The Fundraising Checklist — 13 Proof Points for Series A – this is a broader readiness checklist covering traction, unit economics, team, and narrative

Coming up tomorrow

Tomorrow, we'll cover how to bring real problems to your board without losing their confidence.

Have a great week!

P.S. How many of the 10 questions could you answer confidently right now? Let us know – we're curious how ready you are to raise investment.