Illegitimi non carborundum: Don’t Let Investors Control Your Meeting

There’s a well-documented dynamic in fundraising that most founders feel long before they ever read about it.

Research (including a now widely cited Harvard Business Review article) shows that women and underrepresented founders are far more likely to be asked downside-focused questions—about risk, competition, defensibility, and failure—while white male founders are more often asked upside-focused questions—about scale, vision, and growth potential.

I’ve seen this play out in real life for more than 20 years as a venture capitalist, especially in public pitch forums and live Q&A settings. And while investors rarely think they’re doing this intentionally, the effect on the founder across the table is very real.

The Trap: Treating Every Question as Sacred

One pattern I see over and over is that female and underrepresented founders tend to be extremely conscientious in how they answer questions. They take each one seriously. They assume it deserves a direct, precise, fully reasoned response.

That instinct makes sense.

There’s a real power dynamic at play. Capital feels scarce. Access feels fragile. And if you don’t often feel like you’re in the driver’s seat in rooms like this, the natural reaction is to respond exactly as asked—carefully, thoroughly, and defensively.

The problem is that if you do this for the entire pitch, the conversation slowly drifts away from the most important thing: why this company could be big.

Pre-WritE the Storyline

The founders who navigate this best don’t wait for the Q&A to define the conversation.

They come in with a clear storyline they intend to deliver—and they return to it no matter what they’re asked.

That doesn’t mean dodging questions. It means answering them through the lens of the upside.

For example, let’s say your core thesis is that once customers adopt your product, expansion revenue is the real unlock.

An investor asks:

“This market is crowded. How are you going to cut through?”

A literal answer might spiral into a long explanation of competitive dynamics and go-to-market risk.

A stronger answer sounds more like this:

“We’ve already cut through—we’re seeing strong early adoption and unusually sticky usage. What’s exciting about that is what it enables: once customers are in, we see clear expansion paths that meaningfully grow revenue per account over time.”

You’ve answered the downside question. But you’ve ended on the upside.

Do this consistently and something interesting happens: by the time you’re done reinforcing your growth narrative, the original risk-framed question often fades away. Many of those questions aren’t deeply held objections—they’re habits. If you don’t linger there, neither will the investor.

Stop Trying to Prove You Belong

There’s another pattern that quietly eats up valuable pitch time: founders trying to establish that they deserve to be in the room.

Here’s the reality most people don’t internalize.

Investors see thousands of companies a year. They only take meetings with a small fraction of them—often 10–20%, sometimes less. If you’re sitting in that meeting, you have already cleared an initial bar.

Investors are not in the business of giving pitch practice. They are looking for companies that could return their fund. If they truly believed you were unqualified to build this business, you wouldn’t be there.

Which means this: you do not need to over-qualify yourself at the start of the meeting.

Unless your prior $500M exit is literally the hook, spending your opening minutes walking through a respectable but non-extraordinary career is usually a mistake. That early window is short. That’s where the hook belongs.

Assume you’re qualified. Act as if you belong. Start with the story.

Once you’ve hooked them—once they’re leaning in—that’s the right moment to talk about the team, the capabilities you’ve built, and what you’ll need to add next.

You can’t control the questions you’re asked. But you can control what the investor remembers.

For founders who disproportionately receive downside-focused questions, the goal isn’t to fight the dynamic head-on. It’s to redirect the energy of the conversation—again and again—back to the opportunity.

Write the story in advance. Return to it relentlessly. And don’t spend your limited time in the room trying to prove you deserve to be there.

If you’re in the meeting, you already do.