In 2015, as I was starting Laconia after five years of being an angel investor, I wrote this blog comparing a first pitch meeting with a VC to a first date. The parallels are uncanny—from the nervous anticipation to the delicate balance of making a great first impression without overdoing it. Now, as Laconia celebrates its 10th year, I pulled the blog back up, and it still holds true today. I decided to slightly update it and republish it—let me know if you disagree.
A warm introduction has been made. You’ve been wanting to meet this investor for a while, and now it’s finally happening. Thanks to the internet, you dive deep into your research. You check out their LinkedIn, scroll through their tweets, read their blog posts, listen to their podcast appearances, and see what deals they’ve done recently. The sheer amount of information can feel overwhelming, but being prepared is non-negotiable.
Everyone feels a little nervous before a first date—or in this case, a first investor meeting. It all starts with how you present yourself. You want to strike the right balance between professional and approachable. The last thing you want is to walk into the meeting feeling either over or underdressed. Read the room before you enter it.
On the way to the meeting, your mind is racing. How do you kick things off? Do you break the ice with small talk? What if they’re not a sports fan, or they don’t care about the latest tech trends? You remind yourself that both of you know why you’re here—the key is making that connection in an authentic way.
Then comes the chemistry test. Will they get you? Will they see the vision? Will they find you compelling or tune out after five minutes? You need to strike the right balance—confident but not cocky, passionate but not overwhelming, engaging but not dominating the conversation. This isn’t about a one-sided pitch; it’s a two-way street. You’re evaluating them just as much as they are evaluating you. Would they be a good long-term partner? Do they align with your values? Can they help you fill gaps where you need support?
Now, the conversation. You sit across from them with so much to say. You focus on making your points clearly and succinctly, avoiding rambling. You make eye contact, sit up straight, and try not to fidget. You know this isn’t their first pitch meeting, and it’s not yours either, but they hold the power of whether there will be a second meeting. You want to leave them with just enough intrigue that they want to continue the conversation, but not so much that you overwhelm them with every single detail about your business.
Then, just like a date, the meeting comes to an end. Did you make a strong enough impression? How do you follow up without coming off as too eager? Is a thank-you email enough? Should you send over a thoughtful note summarizing the conversation? Should you play it cool and wait for them to reach out? You remind yourself that if this doesn’t go anywhere, there are plenty of other investors in the sea.
Every meeting is an opportunity to refine your approach. Just like dating, you learn from each experience, adjust your strategy, and improve over time.
The analogy may make you laugh, but it holds true. A first meeting with a VC is just like a first date. Treat it that way—from how you dress to how you communicate and listen. Don’t push for a close; that’s not how venture investing works. Just like in dating, both sides need time to get to know each other, understand if there’s a real fit, and determine if this is the beginning of a long-term relationship or just a one-and-done meeting.
