The Perfect 2nd Investor Call

How to maintain control during investor meetings

September 19, 2022
min read

Welcome back, storytellers.

This week has been a great one for me. I talked to an amazing group at Stanford University about the massive funding gap for founders who don't look like me. I also started sharing my own personal journey on LinkedIn, including this video on making the decision to stop practicing law.

My hope in speaking about these things is that it will inspire others to take the leap—to speak to a new generation that will tackle big issues and live their passions out every single day.

That's also the goal of this newsletter. I want to give you the skills necessary to be a world-class storyteller and encourage you to make your dreams a reality.

Today, we're going to talk about running meetings, and how they can make or break your relationships with potential investors.

Let's take the leap.

DEEP DIVE: The Driver's Seat

Here’s the scenario:

Your first call with a potential investor went really well, and now it’s time for the second meeting. But when you sign on, another, new VC is sitting there as well.

What do you do?

Most founders I know would handle this situation in one of three ways:

1 - They run through their initial pitch from start to finish, essentially repeating the same points they went over in the first call;

2 - They assume the new investor is up to speed and skip all of the previous material;

3 - They ask the investors what they want out of the meeting with a line like “what would you like to talk about today?”

From the outside, any of these options seem reasonable, but they all have the potential to torpedo your chances of getting the investors to bite. With the first two options, you’re gambling on an assumption—either the second VC is up to speed or they’re not. And you know what happens when we assume.

The third choice is by far the most damning, because the moment you ask your audience to set the meeting’s agenda, the power dynamic fully shifts in their favor. Your meeting has now become an interrogation.

I can’t stress this enough: how you come across in meetings is CRITICAL to your success. I don’t care whether it’s your first or 300th meeting, whether it’s in a boardroom or the tiki bar on the corner, VCs are like Sting: Every breath you take, every move you make, they’re watching you.

Don’t Be a Passenger

Successful meetings are all about control. I’m not talking about in some weird, 50 Shades of Grey way—I mean that as the founder, you’re expected to be in the driver’s seat. VCs aren’t just evaluating your product and market when you’re talking to them—they’re assessing YOU. Do you have what it takes to steer this ship to the Promised Land?

“When placed in command, take charge,” General Norman Schwarzkopf once said. Of course, you’re not leading troops into battle, but the sentiment should remain the same.

Often I see founders who are content to let their audience drive because they don’t feel like they deserve to be there. As a result, they don’t think or act clearly. This impostor syndrome—the internal fear in which you doubt your skills or accomplishments—plagues nearly 85 percent of business professionals and entrepreneurs, according to a 2020 Kajabi study.

It also might come from a desire to please or be liked, which, as I wrote about a couple of weeks ago, is a death knell to your pitch. You owe it to yourself to be steadfast in what you value and believe in.  

Often, these feelings manifest in passive or passenger language, which looks like the “what do you want to talk about?” phrase from above.

If you find yourself slipping into that passive talk, remember that you’re in the room for a reason. VCs WANT you to succeed, and they want to see you demonstrate your confidence, ability to connect, and leadership. In short, all the qualities that make a great founder.

The Right Way to Run a Second Meeting

Let’s go back to that meeting scenario, where you got Pearl Harbored by a new potential investor. What’s the right way to handle it?

The trick is finding the balance between understanding how much everyone knows without ceding control. It’s absolutely possible. How to do it is pretty simple:

First, start the call by gathering the needed information, something like: “Great to meet you, (new investor). How much context did (first investor) give you about our story and what we’re building?”

By phrasing the question in this manner, you are still the guardian of your information, and thus you can control your own talking points without being repetitive.

But before you begin filling in the gaps, pull back for a moment. This looks like: “It was nice getting to know (first investor) on the last call, and it would be great to hear your story about how you got to where you are today. Then, I’m happy to dive into more about us.”

This tactic serves two purposes. One, it solidifies that YOU are the one running the meeting. You’re setting an agenda and controlling the flow of the conversation.

Two, asking for the new VC to share a little bit about themselves helps you get a feel for how you should tailor your pitch when it’s your turn. Having the investor tell their story is a recon mission—you’re listening for their tone, their values, and their approaches. Are they a buttoned-up professional, or more of a casual conversationalist? Are they more analytical or creative in their thought processes? Establishing rapport is a critical first step in any pitch meeting, and letting the investor go first will help you to assess and match their energy and needs.

With just that little tweak to your language and agenda, you are putting yourself into an excellent position to slay the second meeting—the driver’s seat.

RESOURCES for Founders and Storytellers

We’ve all sat in meetings where we’ve wanted to gouge our eyes out. What’s the difference between a good meeting and a bad one? This New York Times article lays out 14 great tips and strategies to running any kind of meeting—and all of them can be applied to an appointment with a potential investor.

Impostor syndrome is real, and you shouldn’t be embarrassed about it. In fact, as entrepreneur Max Friedman writes in this Fast Company article, it can actually be used to your advantage. “With the right mindset and support system in place, being an imposter is actually sometimes the best thing you can be,” he writes.

On that note, here is one of my favorite videos on the subject from Michelle Obama.

Tech Crunch reported this week that EU lawmakers are moving in on the metaverse and making it clear that whatever virtual worlds the term may refer to, these next-gen virtual spaces won’t escape regulation. Internal market commissioner Thierry Breton said this week the EU believes the profits made in an immersive software space should flow to network providers needed to host them. Cue the net-neutrality pearl clutchers.


Some big news coming in the next few weeks. Excited to share with you all soon.

See you all next week.

We work with a small handful of founders looking to fundraise large seed rounds through series C. There is currently a waitlist to join. If you're interested in learning more you can apply at the Founder Fundraising Program. Or you can always reply to this email.

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