How to have a coffee chat with a VC

What to talk about in your conversations

So, by this point you’ve hopefully fired off a bunch of emails and gotten to experience that electric hit of dopamine when your inbox shows a message of someone agreeing to chat. You responded to the admin that they copied in the thread, only after the obligatory “moving to bcc to spare your inbox,” and you now need to prepare for your meeting that they for some reason had to schedule for six weeks away.

You start to panic when you think about filling up 30 minutes of time with a complete stranger. At least on first dates you can kill time talking about some of your freezing cold takes like why New Girl is a better show than The Office.

Worse yet, you know they’ll inevitably start the conversation by asking you the infamous “what can I do for you?” question that you’ll have to answer in some way other than “give me a job.”

Alright, so let’s start with that first question: what can I do for you?

My strategy here is to frame my answer in a way that makes it seem like learning from them and sharing ideas/deals is the first priority of this call. And then afterwards mentioning, almost as an afterthought, that I’d also like to be considered for a job/introduced to someone that’s hiring. It might sound something like this:

“Your firm has done a lot of great deals in the education space, so I’m interested in learning a bit more about your investment strategy and about what you’re seeing in the space that has you excited… especially since I’ve come across a few deals recently that I think might be interesting.

And maybe I can also share a bit about myself just so you know a little more about me, because as you probably could have guessed, I’m trying to land a role in venture. So, if you think of someone else that I should be talking to hopefully you’ll be willing to connect us.”

From there, how do you ask questions that show you know what’s up?

You’ve now gotten that first curve ball of the conversation out of the way, so your goal is to spend the next 28 minutes showing that you’re knowledgeable about venture, thoughtful about trends, and in touch with the startup community. So, what does this look like in practice?

I usually start with a question about their personal path into venture just to get the ball rolling. I’ll focus on what I call their “last mile,” meaning the networking and interview process that led to the role they’re currently in.

From there, I’ll start to ask questions about their firm’s investment strategy to show a bit of knowledge. These are just a few examples of questions:

1. Does your firm typically source deals opportunistically or against thematics? Or is it some hybrid of the two and what does that look like?
2. How does your firm typically win deals/get an allocation in a round?
3. When evaluating deals, I always love to hear about investors’ ways for evaluating the team. What are some questions you ask or things you look for when speaking to the founders, aside from the usual relevant experience/network?
4. What are some categories that you’re currently excited about and why?

Lastly, you need to add your own personal touch that makes you memorable

Now that you’ve shown that you have a base level of knowledge about the core aspects of venture, it’s time to leave an impression by talking about some thoughts you have about the future of an industry or category. Have a point of view on emerging macro shifts in culture, technology, regulation, science, or the macro economy. For the purposes of this initial conversation, you don’t need to have a fully developed thesis, but you should be able to speak intelligently about an interesting trend you’re seeing and some companies that validate this trend/are positioned to win in this future world.

Very important: don’t start talking about a space that the individual has no interest in. If you’re speaking to an expert in enterprise SaaS, don’t start talking about a cultural trend that has you excited about food & beverage brands.

Here’s an example of something I put together for a quick call I had this past week.

Sample notes for my point of view on how cultural shifts would affect digital social interactions

Investors typically hone in on the companies you bring up, so be ready to discuss any of them in a bit more detail. By discussing the macro trends that led you to these companies, you’ll have already talked about the market (though you may want to throw in a quick figure for the TAM), so follow that up with a point or two on how the companies you named are differentiated in the market and what sustainable competitive advantages they have.

Bonus points: You’ll get bonus points for being able to introduce them to the founders of the highlighted companies, because it shows that you have what it takes to source. However, that’s not essential.

And hopefully the person you’re talking to reciprocates in this conversation by mentioning a couple companies of their own that they think you might be interested in (deals are the currency of venture, after all). You can then add these new deals that they mention to your list and trade them in future conversations. It all becomes a game of trading information.