Post Written by Vasily Alekseenko

Investor meetings are part of the founder journey, but let’s face it: they can be downright bizarre. For anyone trying to raise funds, there’s always a chance you’ll walk into a meeting that feels less like a pitch and more like a test of your patience (and sanity). Let me share some of the worst experiences I’ve heard about, and more importantly, the lessons they teach us.

Imagine waiting an hour to pitch a big international fund—only to enter the room and find the investor barefoot, casually picking his feet while eating lunch. He smokes a cigarette mid-meeting, snuffs it out in his food, and pours his coffee over the mess. Power play or performance art? Who knows. But one thing’s clear: that was not someone worth doing business with.

Or take another founder who flew across the country for a meeting, only to discover none of the actual decision-makers showed up. They pitched to junior associates who had no authority to write checks. The result? A waste of time, energy, and airfare.

And then there’s the investor who spent the first five minutes of a pitch testing the founder’s ability to speak Chinese—ignoring the startup entirely. Spoiler: it didn’t lead to a deal.

These meetings, while extreme, highlight a crucial point: investor interactions can be unpredictable. But instead of letting them discourage you, use them to set realistic expectations. Fundraising is hard, time-consuming, and sometimes downright weird, but keeping your focus is key.

Here are some takeaways:

1. Respect is Non-Negotiable

Investors who waste your time or treat you poorly during a meeting won’t magically change after writing a check. Walk away if the vibe is off.

2. Control the Narrative

Always have a clear story about your business. Even if an investor gets distracted, you should remain sharp and professional.

3. Don’t Chase “Bad Money”

A great investor moves quickly, respects your time, and doesn’t micromanage. A bad one? They create more problems than they solve. Choose wisely.

4. Stay Grounded

Raising money isn’t your end goal—building a great business is. The right investors will see that, and they’re the ones worth working with.

Remember, fundraising isn’t about pleasing everyone. It’s about finding the right partner to help build your vision. Stay focused, and don’t let a wild investor meeting shake your confidence.

What was your wildest experience at investor meetings?

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