Why Your Investor Meetings Suck

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I've had about a dozen calls with founders raising money over the past month, and I keep hearing the same frustrations.

"I can't even get VCs to take meetings with me."

"They seem completely uninterested when I pitch."

"I had a great first meeting, but then... nothing. No follow-up, no second meeting."

Sound familiar?

Fundraising is like sales—it’s not exactly the same because fundraising is much more tied to how much FOMO you can create, but that’s a separate conversation. You don't nail it on the first try. You iterate, you improve, you figure out what works.

The founders who raise successfully are those who iterate on their pitch. They record their calls. They analyze what worked and what didn't. They adjust their approach weekly based on real feedback from real investors.

If your VC meetings aren't going well, the problem (probably) isn't that you're a bad founder or that your startup idea sucks. You just need to do some debugging.

Here's how to debug your investor meetings and actually close your round.

The VC Meeting Funnel: Where Things Go Wrong

Like in sales, fundraising has a funnel, and prospects can drop out at different stages.

1. Top of funnel: Getting the initial meeting

2. Middle of funnel: Keeping investors engaged during the pitch

3. Bottom of funnel: Converting interest into follow-up meetings and due diligence

Most founders know something's wrong when they're not getting results, but they can't pinpoint exactly where they're losing people. The key is diagnosing which part of your funnel is broken so you can fix the right problem.

Here are the three most common issues I heard in the last month’s worth of founder coaching calls:

Top of Funnel: Can't Get Meetings

The problem: It’s hard to get meetings. You're sending dozens of emails and filling out applications, but VCs aren't responding.

What's really happening: You're relying on cold outreach, which should be an absolute last resort.

Cold emails and website applications have terrible conversion rates. You might spend 3 hours drafting and sending 100 cold emails to secure just one meeting.

Instead, spend those same 3 hours finding warm introductions to 10-12 different VCs, and you’ll probably get 4-6 meetings.

The number one way to secure meetings with VCs is—and will likely always be—warm introductions. Find someone you know, or someone that someone you know knows, who can introduce you to the investor. It takes longer, but the goal is to actually get the meeting.

Middle of Funnel: No Interest During Meetings

The problem: You get the meeting, but investors seem distracted, checking their phones or giving you polite but lukewarm responses.

What's really happening: You're not getting them excited about your vision quickly enough.

I had this exact experience when pitching Chezie. I was leading with our metrics (around $100K ARR at the time), but investors were mentally checking out. In one meeting in particular, all three investors on the other side of the call were doing different things instead of listening to me pitch.

It took me 30 meetings to realize I needed to lead with the big vision instead. Once I started opening with how employee resource groups could become business resources—conducting product focus groups, marketing case studies, etc.—investors perked up.

Within the first minute, you need to capture an investor’s attention with how your company will become a billion-dollar business. If not, you'll lose them to their phone.

Bottom of Funnel: Can't Close the Deal

The problem: You get first meetings, maybe even second meetings, but you can't get investors to actually commit. The process drags on for weeks, with investors asking for updates without providing a firm yes or no.

What's really happening: They're giving you mixed signals because they want to see who else invests before they commit.

This is one of the most frustrating parts of fundraising. You'll hear things like:

• "Let me know when you get a lead"

• "You're a bit too early, but keep me posted"

• "How's the round going?"

• "We're interested but want to see more traction"

These are all ways for VCs to skate around making a direct investment decision. Many are just looking to see if anyone else bites first because they're 50% of the way there, but not 100% committed.

This one is tougher to handle because there is a legitimate chance that if you get a lead, the investor who is 50/50 would actually commit. At the same time, if you’re consistently following up and providing materials that the investor asks for, that’s time that you could be spending targeting new investors or talking to folks who are genuinely interested.

My general rule for sales and fundraising is that if you follow up three times and don’t get a firm decision, keep it pushing.

In other words, if you send that “any updates?” email and the investor consistently has only excuses for you, you can move on.

Not everyone will have this privilege, but if you have the choice of which investors to take money from, wouldn’t you want to take it from someone who has conviction in your business rather than someone who needs to see other people come in before they invest?

The exception: If you reach actual due diligence but can't close, that's different. At that stage, investors typically provide more direct feedback about why they're not investing, such as market concerns, team experience, the competitive landscape, or your go-to-market approach. Use that feedback to improve future pitches. Suppose they haven't provided you with direct feedback after conducting due diligence. In that case, you have every right to ask specifically why they're choosing not to invest, preferably over a call instead of email.

The key is recognizing the difference between genuine due diligence (with specific requests and timelines) and investors who are just keeping you warm while they wait to see what everyone else does.

A Framework for Iterating on Your VC Meetings

Most founders treat their pitch as if it were carved in stone, meaning that they build it and then never change it.

The best founders do something different: they treat every VC meeting like a learning lab. They record everything, analyze what worked, and constantly iterate their approach.

If I were raising today, here’s the exact 5-step process I would use to go from rejections to checks.

Step 1: Record Every Meeting

Start recording every single VC call. I use Fathom, but Granola or Otter.ai work just as well.

When it comes to recording, ask for forgiveness, not permission. Start recording as soon as you join the call. If they ask you to stop, you can turn it off. However, in my experience, most investors don't care—many of them record meetings as well.

Step 2: Upload Transcripts to AI

Let your recording tool auto-generate transcripts.

Every Friday or Sunday, copy all the transcripts from that week and dump them into ChatGPT. If you had a meeting-heavy week, copy the transcripts for just 3 meetings:

1. Two meetings that didn’t go well

2. One meeting that went very well

Step 3: Get Two Types of Feedback

Part A: Let AI Coach You

Upload your transcripts to ChatGPT with this exact prompt:

Consider uploading your pitch deck too, so ChatGPT has full context on your company.

Part B: Watch Your Best and Worst Meetings

Select your strongest and weakest meetings from the week (the same three that I mentioned above). Watch the actual video recordings, not just the transcripts.

Pay attention to the investor's body language. Most VCs stay pretty even-keel, but you can catch the subtle signals: eyes opening up when they get interested, leaning forward, putting down their phone, nodding their heads, asking follow-up questions.

Step 4: Iterate

Based on your analysis, make changes:

• Add slides to your appendix for commonly asked questions

• Update slides that consistently cause confusion

• Reorder your deck if certain sections generate more excitement

• Build a repository of questions that investors frequently ask, so you’re ready with responses next time they come up

• Adjust your talk track to lead with an attention-worthy detail

Don't overhaul everything weekly, but make meaningful tweaks. After 5-6 weeks of this process, your presentation should land significantly stronger.

Step 5: Repeat Weekly

Implement your changes in the following week's meetings, then repeat the entire process.

Track whether you're getting more second meetings and better engagement. Keep iterating until you hit a consistent rhythm—for me, that took about 30 meetings.

Dedicate just 90 minutes each week to this process—one hour for analysis, 30 minutes for updates. When you're in the heat of fundraising with 15-20 meetings weekly, this systematic approach ensures you're improving instead of just grinding.

Fundraising is a muscle you have to build. Eventually, you get to the point where everything is rinse and repeat, and you know your talk track forward and backward. But you have to take your lumps first.

The Bottom Line

Fundraising is no different from any other aspect of running a company. It's by no means a "set it and forget it" thing—you should always be iterating, changing your pitch, and tweaking your presentation to figure out what lands best with investors.

Eventually, you'll reach a point where it's much more rinse and repeat, and you're not making any changes. However, for your first 30 or so meetings, you should consistently change how you talk about your company.

The difference between founders who close their rounds and those who don't isn't always the quality of their business. It's whether they treat fundraising like a skill to be developed rather than a lottery ticket to be hoped for.

Use this framework to debug whatever challenges you're having with your VC meetings. Record everything. Analyze what's working and what's not. Make changes weekly. Keep iterating until you find what resonates.

Catch you next week 🤝🏾