This is a guide to the ten most important questions startup founders should ask investors after a pitch — questions that improve your chances of closing the deal and help you manage investor relationships more effectively. For each question, it explains how to use it in practice and why it matters.
1. Why Asking Investors Questions Matters
The video opens with a familiar scenario. After a successful IR meeting, the investor asks one final question:
"Do you have any questions for me?"
In that moment, many founders' minds go blank and they end up saying something like:
"No, I don't have any questions."
That's when you miss a golden opportunity to move the deal one step closer to a yes. The host, Brett, introduces his channel and explains that he helps early-stage startup CEOs with fundraising and growth. He emphasizes why asking questions at the end of an investor meeting matters so much:
"Fundraising is ultimately sales. To close a big deal, you have to overcome the other side's objections."
2. Five Questions to Ask During the Investor Meeting
1) What concerns do you have about investing in our company?
This is Brett's favorite question.
"What concerns do you have about investing in our company?"
This question gives you the chance to hear the investor's real worries directly and address or counter them on the spot. If the investor says they have no concerns, you can playfully respond:
"Really? So when can I expect to receive a term sheet?"
Said half in jest and half in earnest, this can naturally draw out any reservations the investor has been holding back.
2) Who else is involved in the decision on this investment?
Because most venture firms make decisions as a group of partners, you need to understand upfront whose approval is actually required.
"Who else on your team would need to be involved in this investment?"
This question helps you understand the road ahead — how many more meetings you'll need, and who else you need to impress.
3) What does your investment process look like?
Every firm has a slightly different process for making and executing investment decisions, and simply asking about it can save a lot of confusion.
"Can you walk me through how your investment process works?"
Brett shares from his own experience that some VCs can reach a decision after as few as three short meetings.
4) How do you support founders when things are going well — and when things get hard?
Startups inevitably hit unexpected problems, so it's worth understanding how actively an investor will help when it counts.
"How do you typically stay engaged with founders — both when things are on track and when they're going through a rough patch?"
This is also a good opportunity to gauge the investor's willingness to follow on in future rounds.
5) What are the next steps?
Always close the meeting by asking clearly:
"What's the process from here?"
Most investors will say they need to discuss it with their partners. At that point, Brett emphasizes that founders should be ready to provide additional information or stronger arguments to push the deal forward.
3. Five Questions to Ask During Follow-Up and Due Diligence
At the next, more serious stage of discussions, Brett advises bringing up the following questions at the right moment.
6) Can you introduce me to some of the CEOs you've backed?
Just as investors run reference checks on founders, Brett says founders have every right to verify the credibility of their investors.
"Is there anyone among the startup CEOs you've worked with who you'd be willing to introduce me to?"
A good investor will happily share that information. If they hesitate, treat it as a red flag.
7) How have you supported portfolio companies when they hit a crisis?
Brett shares a story from his own experience — when things went badly wrong, some investors walked away while others stepped up and helped until the end.
"When one of your portfolio companies faced a serious challenge, what did you actually do to support them?"
This question helps you gauge an investor's genuine commitment.
8) Where are you in the lifecycle of your current fund?
Most venture funds operate on a ten-year lifecycle, with new investments concentrated in the first three to five years. So timing matters enormously.
"Where are you in the lifecycle of your current fund?"
This question gives you real grounds to assess the likelihood of an investment and the prospect of continued support.
9) How do you see our company fitting into your overall portfolio strategy?
Most investors focus on specific sectors — AI, fintech, and so on — and typically won't back two companies competing directly against each other in the same space.
"What strategic role do you see our company playing within your portfolio?"
This helps you understand how well the firm is a fit for you and what role they expect your company to play going forward.
10) What are your reporting and information-sharing requirements for portfolio companies?
Most investment partners expect quarterly performance updates or board meeting participation, though some make demands that are excessive or burdensome.
"What level of reporting or meetings do you typically expect after an investment?"
Brett stresses the importance of checking upfront whether any requirements would consume a disproportionate amount of your time and energy.
4. The Real Role of Questions — and One Final Tip
As important as it is to ask the right questions, Brett reminds founders that it all starts with making a strong impression through your IR materials and pitch.
"Even the best questions are useless if your presentation and materials haven't already impressed the investor. Questions only matter once you've genuinely captured their attention."
Brett wraps up by pointing to additional resources:
- Reach out directly via QR code if you want to work with him
- Free startup pitch deck template available
- Invitation to join the founders' community (Zero to Pitch)
- Free 20-minute pitch training video
Closing
The ten questions Brett outlines are powerful tools for startup founders to build trust, improve communication, and advance the deal with investors. Remember: asking genuine, prepared questions to uncover what an investor truly thinks is the first step toward a successful fundraise. 🚀