Founders, listen. I’m not sure where you picked up the habit of trying to interview the investors instead of actually pitching your startup, but it’s time to break it. I see an average of 10 startups a day, six days a week, and sometimes twice on Sundays. You get my drift? My schedule is tight, and your first impression is the only one you get.

So, when a founder starts the conversation with, “Tell me about CitySide Ventures,” or, “What is your check size?”… Well, you’ve lost me right there. I’m gone. I’m mentally checking out, taking a break, maybe going for a walk. Seriously? We built a website that spells it all out: who we are, what we do, our investment mindset, our guidelines, everything beside my favorite cigar (it’s a Montecristo Espada Maduro, if you really must know). You have all the information you could possibly need before we even hop on a call.

When you ask these foundational questions, you aren’t demonstrating curiosity; you are signaling laziness. It tells me you haven’t done your homework. It tells me that if you can’t bother to read a few pages on our website before asking for money, you probably aren’t doing your due diligence on competitors, markets, or product-market fit either. And that is a red flag the size of a billboard.

Do your homework for the sake of your own fundraising efforts. Start the conversation with value. Start it with, “I see you’ve been investing in MedTech, and here’s why we will be a perfect fit,” or, “We’ve reviewed your investment guidelines, and our roadmap aligns with your thesis,” or, “Here is exactly why we will be a great addition to your portfolio.”

Just so you know, we do significant screening on you and your company before we agree to take the call. We expect you to do the same. We are looking for partners who are precise, prepared, and professional.

Do you want the capital, or are you looking for a friendship? Because let’s be clear: we are not a social club. We are a firm looking for high-growth potential and serious operators. If you treat our time with respect, we’ll treat your pitch with attention. If you don’t, we’ll see you at the door.

Fundraising is a test of your ability to convince someone that you are worth their capital. That test begins the second you send the intro email or pick up the phone. Don’t fail it by being unprepared. Show me that you understand who we are, why you’re here, and what value you bring to the table. Anything less is just noise, and I have far too many startups to review to listen to noise. 

Come prepared, or don’t come at all.