The Art of a First Conversation

Reframe your pitch; why a conversation is so much better

I talk to entrepreneurs for a living. Between Stanford-StartX and now at Prime Movers Lab, I have spoken with 2,500+. There is a lot to be said for pattern matching in venture, looking at hundreds of market sizes, business plans, technical rollouts and teams. But what I have noticed is a much simpler pattern emerges in that very first conversation and how it is structured. The best entrepreneurs have the best first conversations, because they are not coming at it with an explicit Pitch mentality. Pitching can often manifest in a feeling of “I want something from you” versus a conversation which carries a feeling of “I want to share something with you”. In a conversation, you ask questions, you engage, you jump-around and volley back and forth. It is infrequently linear, but an intentional conversational style can convey even more information than the most well crafted of formal pitches.

Last week I spoke with an entrepreneur who was particularly gifted in the art of a first conversation. She is a serial entrepreneur who has raised venture capital money before and this is not her first rodeo, that was clear. There were some simple questions she asked upfront that would serve more entrepreneurs to ask. It truly sparked a wonderful discussion.

“Is [Company Name] something within scope for your fund? What else have you looked with in this space? When you haven’t gotten there, why? “

We talked about the market, the product, capital needs — all the things you would expect. But we didn’t start there. We started with core beliefs and a conversation about them. The first questions she brought up helped frame this discussion and she circled back to the information I had given her. Which of my core beliefs about the market were aligned with hers? Which were not, and why?

The undeniable fact is the vast majority of first conversations with an investor are not going to lead to an investment. But all first conversations can be a source of valuable information for the entrepreneur and should not just be a one sided exchange of knowledge. The market, the business model, the competitive landscape, any perceived skill gaps on the founding team. Engage the investor in that conversation and you, the entrepreneur, walk away with far more intelligence than you would using a traditional formal pitch format.

It is like the difference between sitting in a lecture hall with 500 other students, all watching a professor, versus an intimate class with a vigorous exchange of ideas. You can absorb information in both of those formats, but absorbing is not the same thing as engaging. I can absorb what you are doing, understand the vision and maybe agree with it, but if I don’t engage emotionally with it then it is very unlikely it makes sense to move forward. I believe it is always well intentioned, an entrepreneur is eager to communicate what they are doing and why it is going to be world changing, but a scripted pitch does you no favors. It is very ineffective to be talked at which is the unintentional side effect of pitching.

As VCs we have to do the very same thing when we go out to limited partners to raise our funds. I do have great empathy for sitting on the proverbial other side of the table. Narrative, core beliefs, emotions — all of these get woven together into a powerful communication tapestry. Being practiced is not the same thing as being scripted.

And like everything, this is just a skill that can be worked at and developed. Next time you find yourself pitching step back and ask yourself how you can create a two way conversation.

Prime Movers Lab invests in breakthrough scientific startups founded by Prime Movers, the inventors who transform billions of lives. We invest in companies reinventing energy, transportation, infrastructure, manufacturing, human augmentation, and agriculture.

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