ITR #014: The Silent Risk in Follow-Up VC Meetings

Welcome to the latest edition of “Into the Ring” - my biweekly newsletter on how to successfully plan & execute on your startup fundraise. As a reminder, I’m Jorian Hoover and I’m a Startup Fundraising Sparring Partner. I guide Pre-Seed thru Series A founders through their fundraising process, and you can check out how to work with me here. And a warm welcome to the new subscribers for this edition! If you were forwarded this newsletter, you can subscribe here.

First - congrats to my HBS sectionmate Abdul Al-Asaad who publicly launched his company Basic Capital last week. Basic Capital’s aim is to give power to the American worker by enabling them to dramatically increase their 401(k) contributions through leverage. I’ve been hearing Abdul talk about this since before we graduated in 2022, and it’s very cool to see this come to fruition. He’s got great backing from Lux Capital and industry titans such as Bill Ackman. And he even got featured in Matt Levine’s daily newsletter, Money Stuff.

Congrats, Abdul - here’s to an exciting journey ahead!

…now on to today’s newsletter topic around what happens when your cofounders aren’t prepared for VC meetings, and what you can do about it.

The Silent Risk in Follow-Up VC Meetings

A second meeting with a VC is usually something to celebrate. It means the investor is intrigued, your pitch landed, and they want to go deeper. But there’s a hidden danger lurking in these follow-up meetings that too many founders overlook: misalignment within the founding team.

Here’s how it often plays out:

In the first meeting, you present solo as the CEO or fundraising lead. You’re confident, polished, and clear on your narrative. Then the VC asks to meet your co-founders. You agree. You join the Zoom call. And halfway through the session, your technical co-founder casually contradicts a core point from the first meeting. Once is forgivable. Twice is a warning sign. By the third time, the investor is quietly closing the door on the deal.

This kind of internal contradiction is almost never intentional. Most of the time, it comes down to a simple problem: only one founder prepared for the fundraise.

Why It Happens

In most fundraises, there’s one co-founder who takes the lead. That’s a good thing. It gives VCs a single point of contact, a clear message, and a consistent narrative.

But follow-up meetings are different. When investors ask to meet the team, they’re not just looking to verify domain expertise. They’re assessing something deeper: how you operate as a unit.

Do you share the same vision? Are you aligned on where the company is going and how you’ll get there? Does the team dynamic suggest stability or chaos?

In a high-stakes fundraising environment, even small contradictions raise big red flags. Investors are wondering, If the founders can’t agree on the basics now, how will they scale a company together later?

What VCs Are Really Evaluating

When a VC brings your cofounders into the mix, they’re not just checking off a box. They’re gathering signal in a few key areas:

• Team chemistry: Do you collaborate well? Does the energy feel cohesive or disjointed?

• Clarity of vision: Are you all pointing in the same direction? Or do answers diverge under pressure?

• Communication patterns: Who talks over whom? Who dominates? Who supports?

• Competency and confidence: Even if they’re not the primary fundraiser, can your cofounders hold their ground and convey conviction?

They’re not expecting everyone to speak like a polished operator. But they are expecting you to be on the same page.

The Prevention Plan

So how do you make sure your cofounders don’t accidentally derail a raise? It comes down to three things:

1. Create a Shared Talk Track

Before any follow-up meetings happen, spend time writing down the core messages of your fundraise. What’s your story? What’s your differentiation? What are the 3–5 reasons a VC should invest?

This becomes your shared narrative. Everyone on the team should be familiar with it. You don’t need to memorize lines, but you do need to agree on the fundamentals.

2. Draft the 15–30 Most Common VC Questions

Every fundraise has predictable moments: What’s the business model? How are you thinking about go-to-market? Why now? Why you?

Make a list of the most common investor questions. Then add in the tricky ones specific to your business (e.g., defensibility, regulatory risks, or founder backgrounds).

Share this list with your cofounders and talk through answers together. Even just reviewing this for 30 minutes can eliminate major missteps.

3. Brief, Align, and Rehearse

Don’t assume your cofounders know what to expect. Brief them before the call. Share the context of the investor, their style, what they asked in the first meeting, and what your goals are for the next one.

If possible, rehearse together. This doesn’t need to be a formal pitch practice—just a run-through of the conversation flow and who might answer what. It’s especially important to clarify handoffs and avoid overlap.

Final Thought

It takes hours to secure a second meeting with a VC—and only a few minutes to lose the thread. The good news? This is totally preventable.

A few hours of prep with your cofounders can turn a potential liability into a strength. When you show up aligned, confident, and complementary, you send the clearest signal of all: this is a team that knows how to win.

Don’t just prepare yourself. Prepare the team. Investors are watching.

👉Want a sparring partner to help you prepare you & your cofounders? I would love to help.

Thanks for stepping Into the Ring 🙏

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👉 I’ve helped 40+ founders raise over $160M. Curious to work with me? You can learn more about what that looks like on my website.

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