So often I feel like the entire pitching discussion revolves around one thing: how to pitch your startup in 3 minutes, on stage.

In reality, most deals (almost all of them actually) don’t happen this way.

They happen behind closed doors, in a 1-on-1 meeting. You and the VC you’re speaking with. That’s it.

So when I hear the word “pitching,” I don’t think of those 3-minute stage pitches. I think of the entire long-form meeting. An actual conversation, with questions and answers, where you build a relationship with the other party. The stage pitch? It’s a very limited use case, and not the one that’s ultimately going to get you funded.

So today, I want to share my experience with pitching, after listening to thousands of pitches and sitting through hundreds of 1-on-1 investment meetings with founders.

How a First Meeting Usually Plays Out

The first meeting is typically online, around 30 minutes. You’ll meet with an associate or principal. If you’re lucky or have a warm intro, a partner.

This first meeting is about setting the context and building rapport.

You should have shared your deck before the meeting. It gives investors the info they need so you don’t spend the entire call walking them through it slide by slide.

What the Meeting Looks Like, Step by Step

It starts with the warm-up. Hi, how are you, I think you know a friend of mine, you invested in so-and-so. Build the relationship.

Next, don’t just pull up the deck and start presenting. Involve them. Do they prefer to go through the deck together? Or would they rather hear the story first? Maybe they’ve already looked at it and have questions? Be prepared for all options. And keep in mind, this is a conversation, not a one-direction broadcast.

If you do share the deck, do not spend more than a third of the call on it. In any case! Leave plenty of time for discussion.

At the end, ask them about their fund and about what comes next in their process. Show that you care about understanding how they work, not just whether they’ll give you money. And most importantly, do not end the meeting without being crystal clear on the next steps!

What to Focus On During the Pitch

Win them with your story. How you started, why this problem is what keeps you up at night. Founders who can explain their “why” in a way that feels real always stand out.

Educate them about the market. Don’t assume they know anything! It’s your job to convince them this is an exciting opportunity worth their time and capital.

Make them believe in the problem. If the problem doesn’t feel urgent and real, the solution won’t matter.

Include your traction. Whatever you have: early revenue, pilots, LOIs, user growth. It’s your strongest proof.

And above all: treat pitching as a conversation. You want it to flow naturally. You want to build rapport. The best pitch meetings feel like a good discussion between two people who are curious about each other’s world.

The worst pitching mistakes I've seen

• Being super vague. Not quoting any facts, just throwing around empty statements.
• Avoiding or not answering questions when asked. VCs are incredibly BS-proof.
• Forgetting key numbers from your own business. MRR, churn, runway… you have to know these by heart.
• Not knowing anything about the VC you’re talking to. I actually got asked “So, what do you invest in?” Literally the first thing you’d see if you had opened our website.
• Reading from a script. It shows, and it feels very unnatural.
• Coming off as totally unconfident. I know it’s hard for many founders, but you need to practice until you can present with conviction.
• Becoming overly defensive when challenged. VCs will push back on your assumptions. That’s their job. How you handle pushback tells them how you’ll handle tough situations as a CEO.
• And the opposite, agreeing with absolutely everything. Sometimes you need to stand your ground.
• Going into too much detail about features without covering the business as a whole. Investors want to understand the big picture first. Feature deep-dives come later.
• And finally: if after the entire pitch, I still don’t understand what the company actually does, that’s obviously an issue. Investors should be able to grasp what you do in 30 seconds or less.

Now, I have a gift for you. It was originally built for an actual client of mine.

I built an entire checklist to help with the Investor Meeting preparation, covering before, during, and after the call.

You can access it here: The Investor Meetings Checklist​

Pitching is a huuuuge topic. I’ve talked about it in previous posts. You can check some of them here:

​As a founder, you should never let anybody else pitch to investors on your behalf. Ever.​

​Investors drown in generic pitches!​

​Being conservative in your pitch can kill investor interest.​

And finally, here’s a great video by Andrew Lee, partner at a16z Speedrun, on common mistakes he’s seen:

​10 things investors hate about your pitch​

P.S. Hope you learned a few things from this! And if you did please consider sharing this with a founder who could benefit!

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Ciao,

Geri