Sales & Conversion· 3 min read· By The SpideyChat Team

The Questions Investors and Lenders Ask Early

Being unable to answer a routine question is what loses the funding. A checklist for the early conversation.


A founder meets a lender with a plan, a forecast and considerable enthusiasm. The first three questions go well.

The fourth is what does it cost you to acquire a customer. She does not know. The fifth is what proportion of customers buy again, and she does not know that either.

The application does not proceed. Nothing about the business was wrong. What the meeting established was that the founder does not have the information anybody would need to assess it.

1. Know what the money is for, specifically

Not growth. A named use, with a figure and an expected effect. Vague purposes are the fastest way to end a funding conversation.

2. Know how it will be repaid or returned

From what, over what period, under what assumptions. This is the question behind every other question a lender asks.

3. Know your own numbers without looking

Revenue, gross margin, customer count, average order value, acquisition cost and repeat rate. A founder who has to check is a founder who is not using them.

4. Know what a customer costs to acquire

The single most revealing number in a first year business, and the one most founders have never calculated.

5. Know what a customer is worth

Over a realistic period, with the repeat behaviour you have actually observed rather than what you hope for.

6. Know where customers actually came from

By source, with numbers. This tells a funder whether the growth is repeatable or whether it was four favours from former colleagues.

7. Have a forecast you can defend line by line

Every assumption traceable to something observed. A forecast with an unexplained growth curve is read as a wish rather than a plan.

8. Know what happens if it goes badly

The downside case, what you would cut and how long the money lasts. Being able to discuss this calmly improves credibility considerably.

9. Have the paperwork ready

Accounts, management figures, bank statements, forecasts and anything about the structure. Delays in producing these read as disorganisation.

10. Understand what security is being asked for

Personal guarantees, charges and what they actually mean. Founders agree to these without understanding them and should not.

11. Know your competition honestly

Naming none is worse than naming three. A founder who says there are no competitors has not looked or is not credible.

12. Know your pricing rationale

Why this price, based on what. This is where a first year business is most easily exposed, because a price set by looking at competitors cannot be defended when somebody asks what it is based on.

13. Be ready for the diligence questions

Data handling, contracts, insurance and compliance, which is the same scrutiny set out in ai chatbot security questions to ask a vendor.

14. Capture the data from the first enquiry onwards

An assistant that records where every enquiry came from, what was asked and what happened next gives a founder the numbers a lender will ask for, built up from month one rather than reconstructed the week before a meeting. That capture discipline is set out in handling your first enquiries properly and the wider choices in deciding what to automate in year one. The same funding conversation for families appears in care fees and funding questions families ask. See features, start at try, and the sector view sits under startups.

Frequently asked questions

What do lenders ask a first year business?
What the money is for, how it will be repaid, what the trading position is, what security or guarantees exist, and what happens if the plan does not work.
What do early investors ask?
Broadly the same, plus who the customers are, how they were acquired, what it costs to acquire one, what they are worth and why this business rather than another.
What is the most common early mistake?
Not knowing your own numbers, because a founder who cannot answer what a customer costs to acquire signals that the business is not being run on evidence.

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