Running Investor Meetings Without Losing Yourself

Hello friends,

Investor meetings can feel like the most nerve-wracking part of fundraising. You’re in the room (physical or virtual), face-to-face, where the questions start flying and the dynamics can quickly shift.

It’s normal for that to stir up anxiety or self-doubt. I’ve certainly been there myself MANY times! The good news is that you can prepare for these meetings in a way that helps you feel grounded and confident, no matter who you’re looking to build a relationship with.

This chapter is all about giving you practical tools to run your meetings. We’ll look at common formats, how to prepare for each, and ways to gently guide the conversation so it works for you.

If you’d like to read the full chapter now, there is still time to apply to become a beta reader!

Running the Meeting – Adapting to Investor Preferences

You’ve practiced your pitch. You’ve tailored your delivery for the setting. Now comes the part that’s harder to control: the meeting itself.

Even if you’ve given your pitch a hundred times, each meeting will feel different depending on who you’re speaking with. Investors come with their own preferences, expectations, and communication styles. Some want structure. Others prefer casual conversation. Some want to be led. Others want to take the wheel. 

That unpredictability can feel frustrating or intimidating, especially if you're coming in with less fundraising experience or are used to environments where expectations are clearly laid out. There’s no need to guess in this case. You can learn to read the room, steer with empathy, and still show up as yourself. 

The more meetings you take, the more you’ll notice a pattern: investors aren’t just evaluating your business, they’re evaluating what it’s like to work with you. The ability to adapt while staying grounded in your own communication style is one of the most powerful signals you can send.

Angel Investors need help, too

By the way, investors are also adjusting on the fly based on the founder’s needs and preferences. Angel investors aren’t usually professional investors, and many of them who are newer to the game are just as nervous, if not more, than you for the 1:1 meeting.

In a recent conversation I had with someone who is “angel curious,” they had watched the founder’s pitch video, reviewed the deck, even had a virtual meeting with the founder, and still she shared:

“I don’t know what else to ask…and I don’t want to look like an idiot.”

I talk to a lot of people who are interested in angel investing but hesitate to act. They’re smart, accomplished, and financially ready, but unsure how to engage in a meaningful way. They’re afraid of asking the wrong question. Or sounding inexperienced. Or wasting a founder’s time.

Founders often assume these investors know how to evaluate their opportunity, and when a check doesn't come through, they take it as a sign of misalignment or lack of conviction.

The reality is often that they just don't know how to talk to each other. Founders aren’t taught how to build relationships with first-time or nontraditional investors. Investors aren’t taught how to build trust with early-stage founders.

How It’s Different for The Rest of Us

Investor meetings often come with an added layer of performance, whether anyone acknowledges it or not. You’re not just pitching your company, you’re pitching through a filter of bias and unfamiliarity, and you may not be given the benefit of the doubt that others receive automatically.

Here’s what that means in practice:

You might feel pressure to over-prepare, but also not come off too polished. To be confident but not "too confident." To be personable but not overly casual. This balancing act isn't imaginary; it's a very real survival skill for founders navigating rooms not built with them in mind.

When I was fundraising the $10M for my last company, I had to make a snap decision every time I entered a pitch meeting: do I talk about my kids, or not? When you’re a woman, you’re judged at every age, so you often need to decide what’s the lesser risk based on who’s in the room. I look younger than I am, so when I didn’t bring up my kids, I was usually called “young lady” and perceived as determined but inexperienced. When I did mention my kids, I was no longer too young, but now I was a mom, and therefore risky because my family obligations would supposedly be prioritized. I have yet to meet a dad who ran into this dynamic while pitching or running a startup.

Remember that you don’t have to mold yourself into what you think someone else wants. Your unique background, voice, and lens are valuable. The more you own your delivery style and practice it with intention, the more control you’ll gain in how others receive it.

That’s it for this week. Next time, we’ll talk about how to handle investor feedback. How to take what’s useful, leave what isn’t, and not let it shake your confidence.

Thanks for reading, and as always, I’m glad you’re here!

-Allison