There’s a moment at the end of almost every pitch where the investor leans back and asks:
“Do you have any questions for me?”
And nine times out of ten, the founder says something like:
“No, I think you’ve covered everything.”
I have sat on both sides of that table for over two decades now — writing cheques as an angel, and sitting with founders as an advisor before they walk into the room. And every time I hear a founder say “no questions,” something in me winces a little.
You haven’t covered everything.
You are about to take someone’s money. Possibly their advice. Possibly a board seat. Possibly their influence over the next five, seven, ten years of your company’s life.
You should have questions. In fact, you should be interviewing the investor just as hard as they’re interviewing you.
I’ve written before about the questions founders should be asking themselves before they go into the market. This is the other half — the questions for the person sitting across the table.
1. Why are you interested in my company?
Not “do you like the business.” Ask why.
What actually caught their attention — the market, the founder, the technology, the traction, the return math? You want to know what they’re really betting on. Sometimes an investor is backing your company for a completely different reason than the one you’re building it for, and you won’t find that out until month eight.
2. How do you make your money?
Founders almost never ask this one. You should.
Everybody in that room is in business. The investor too. So understand the model behind the cheque. Is this their own money, or capital they manage for other people? Do they have LPs to answer to? Are they a family office, a fund, a syndicate, a corporate investor, or an angel writing personally? What’s their time horizon? What happens when your company needs a second cheque later?
The economics of the investor shape the behaviour of the investor. A fund with a defined life and LPs to report to thinks very differently from someone deploying their own money on their own timeline. Neither is wrong. But you should know exactly who you’d be getting in bed with.
Before you get on my cap table, perhaps I should understand yours first. Not every money is good money. Money laundering is actually not a myth. People are in jail for money they had no business with.
3. What does your ideal investment look like?
Thesis. Stage. Cheque size. Sector. Geography. Ownership expectations. Follow-on appetite.
You don’t want to find out six months after closing that your investor’s model and your company’s trajectory were never built to travel the same road.
4. What happens after you invest?
One of my favourite questions to watch an investor answer, because the honest ones hesitate.
Some investors are genuinely helpful. Some are helpful when you ask. Some are helpful only on WhatsApp, and only when it suits them. Some genuinely believe the cheque was the beginning and the end of their job.
Ask plainly: “What should I expect from you after the money clears?” Listen closely to the answer. It will tell you more than the term sheet does.
5. How do you make decisions when things don’t go according to plan?
Because they won’t. They never do.
Revenue misses. Products fail. Founders make mistakes. Markets shift under your feet. Runway shortens faster than the model promised. This one would give you plenty answers. Watch for body language. Are they shocked when you ask this? Surprised or pissed? Each reaction means something. E get why.
The investor who looks wonderful on the way up can be a very different person on the way down. Ask how they handle bad news, specifically. You’re not looking for someone who promises nothing will go wrong — that person is either lying or inexperienced. You’re looking for someone who can tell you, honestly, what happens when it does.
6. Tell me about an investment that went badly.
Double click on question 5. Don’t just ask for the win. Ask for the loss.
What happened. What did they do. Did they blame the founder and disappear? Did they stay and help restructure? Did they write a hard, uncomfortable follow-on cheque when the easier thing would have been to walk away?
An investor’s failures will tell you more about their character than their wins ever will.
7. What do you expect from me as a founder?
This is the question that surfaces the expectations nobody wrote into the documents.
How often do they want updates? Do they expect a board seat? How involved do they intend to be in decisions that are, technically, yours to make? What happens the first time you disagree?
Better to know this before you sign than to discover it in month three.
8. How do you think about exits?
Investors don’t invest in companies. Not really. They invest in outcomes.
Ask: “What does a successful exit look like to you?” IPO, strategic acquisition, secondary sale, founder buyout, long-term dividends — the answer tells you a lot.
Then ask the harder question: “How do you think founders and investors should work together to get there?”
I don’t believe exits happen by accident. I believe they are engineered, quietly, over years, by the founders, investors, employees and customers around a business, long before anyone shows up with an offer letter. That conversation should start now, not the day the offer arrives.
9. Who else is investing alongside you?
Do you invest alone? Are there other decision makers? Who are the other investors, and what role will each of them actually play? Strategic, financial, or simply passive? Who holds information rights? Board rights? Who has the standing to influence your next round?
You are not choosing one investor. You are choosing the whole ecosystem that will sit around your company for years.
10. Can I speak to some founders you’ve invested in?
Not the highlight reel. Ask for the founders whose companies struggled.
The real test of an investor is not how they behave when a company is winning. It’s how they behave when it’s losing. Ask those founders about communication, pressure, disagreements, and what actually happened when the money got tight. An investor who trusts what they’ve built with their portfolio won’t flinch at that request.
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Fundraising isn’t really about convincing someone to write you a cheque. It’s about deciding whose cheque you’re willing to take, and everything that comes attached to it.
Don’t cram these questions and pour them out verbatim. You should know better. Be subtle, gentle, and kind. But still ask.
Money always has a price. Capital has terms. And investors arrive with more than money — they arrive with expectations, networks, influence, temperament, and sometimes, quiet constraints they won’t mention until you’re already in business together.
So the next time someone across the table asks, “Do you have any questions for me?” — don’t say no.
Pull out your list. You are interviewing them too.
A fundraising meeting is not an audition where the founder waits to be chosen. It’s a courtship. Both sides are deciding whether they actually want this relationship.
The cheque may be coming from the investor. But the company is yours
