This video walks through the ten most important questions startup founders should ask their potential investors. Each question helps improve your chances of closing a deal and building a stronger relationship with your investors.
1. Why asking questions matters
The video opens with a familiar scenario: after a successful pitch meeting, the investor asks, "Do you have any questions for me?" Most founders freeze and say, "No, I'm good" — missing a golden opportunity.
Host Brett emphasizes that fundraising is ultimately a sales process, and to close big deals, you need to overcome objections. Asking the right questions is how you do that.
2. Five questions to ask during the pitch meeting
1) What concerns do you have about investing in our company?
Brett's favorite question. It surfaces the investor's real worries so you can address them on the spot. If they say they have no concerns, you can half-jokingly respond: "Great — so when can I expect a term sheet?"
2) Who else on your team is involved in this decision?
VC firms typically make decisions as a group. This question helps you understand how many meetings remain, who else you need to win over, and what the approval process looks like.
3) What does your investment process look like?
Every firm has a different process. Simply asking this reduces confusion about next steps. Some VCs decide after just three short meetings; others take much longer.
4) How do you work with founders when things go well — and when they don't?
Startups inevitably face unexpected problems. This question reveals whether the investor will actively support you through tough times and whether they're likely to participate in follow-on rounds.
5) What are the next steps?
Always close the meeting with this. Most investors will say they need to discuss with partners — at which point you should offer to provide additional data or materials to help advance the deal.
3. Five questions for the due diligence stage
Once the conversation gets serious, Brett advises asking these at the right moment:
6) Can you introduce me to CEOs you've previously invested in?
Just as investors do reference checks on founders, founders have every right to do the same on investors. A good investor will gladly connect you. If they hesitate, treat it as a red flag.
7) How have you supported portfolio companies during a crisis?
Brett shares his own experience: some investors walk away during tough times while others stay and fight alongside you. This question helps gauge an investor's true commitment.
8) Where are you in your current fund cycle?
Most venture funds operate on a 10-year lifecycle and concentrate new investments in the first 3–5 years. Knowing where they are in the cycle tells you about their capacity to invest and provide ongoing support.
9) How does our company fit into your overall portfolio strategy?
Most investors focus on specific verticals and avoid backing direct competitors. This question helps you understand whether you're a strategic fit and what role they see your company playing.
10) What are your reporting and communication expectations?
Most investors require quarterly reports and board participation, but some have demands that can drain a founder's time. Better to clarify expectations upfront than to be surprised later.
4. The real role of questions — and a final tip
Brett reminds founders that questions only work if the investor is already impressed by your pitch and materials. No amount of clever questions can make up for a weak presentation.
He closes with additional resources:
- Direct consulting via QR code
- Free startup pitch deck template
- Founder community (Zero to Pitch)
- 20-minute free pitch training video
Takeaway
These ten questions are powerful tools for building trust, communication, and deal momentum with investors. The key to successful fundraising starts with well-prepared questions and a genuine effort to understand your investor's real intentions.