Founders, Stop Getting Interrogated by VCs: 8 Questions Every Founder Must Ask VCs
Flip the fundraising script, qualify investors in minutes, and turn every call into mutual diligence.
Every week, I sit through about twenty calls with startup founders. In almost every single one, I’m the one firing questions while the founder politely stays in the hot seat. That dynamic might feel normal—after all, you’re the one who needs the cheque—but it’s a missed opportunity.
A venture investor isn’t a talent scout handing out jobs. We back only the companies that match our mandate: stage, geography, sector, ticket size, fund‑cycle timing, and return profile.
Unless you’re pitching a spray‑and‑pray micro‑fund, fit is everything.
Yet I can count on one hand the number of founders who have ever flipped the script and interrogated me back. Out of twenty calls, maybe one founder digs in to learn how our capital actually works.
Why you should ask questions
1 — Save time. In five minutes you can discover whether I can even write the ticket you need.
2 — Signal confidence. Great CEOs interrogate money as rigorously as money interrogates them.
3 — Build partnership. The fastest way to learn my playbook is to ask about it.
The 8 questions that separate pros from tourists
What is your current fund thesis, and how does my company fit?
How much dry powder is left, and over what time horizon are you deploying it?
Do you typically lead rounds or follow?
What cheque size do you reserve for follow-ups?
Which sectors are you doubling down on this year?
What traction benchmarks matter most when you issue a term sheet?
How long does your IC process take from first call to approval?
After investing, what tangible value‑add do you provide—customers, talent, downstream capital?
Feel free to riff on these, but cover the basics. The goal isn’t to grill your potential investor; it’s to find out whether we can do real work together.
How to weave these questions into a call
Prep. Research the fund’s last three deals so you can reference them intelligently — instant credibility.
Keep it conversational. Slip questions in naturally rather than firing them off like a checklist — real dialogue beats Q&A drills.
Listen actively. The answers reveal how decisions get made behind the curtain — deeper insight into the firm’s process.
Follow up. If the answers sound promising, ask for the next step before you hang up — momentum matters.
Capital is abundant—alignment is scarce
Fundraising calls should be a mutual diligence sprint, not a one‑way interrogation. Treat them that way and you’ll save yourself months of chasing the wrong cheques while signalling to the right investors that you run the show.
Vai, it would be better if you talked more about each questions. Like, why to ask this question, how this question help the founders and how the investors see those questions. Btw, I read all of your writings and they're helpful