Get your game face on and run through the finish line in every meeting to find your greatness

Yesterday I had a conversation with a founder about meetings between entrepreneurs and VCs. We talked about the process of a meeting, the preparation that goes into it on both sides and the hardest parts of the process for me as an investor and for him as an entrepreneur. As in most conversations with founders, I learned a lot and one thing that I came away with is the importance of both people (founder and VC) running through the finish line in every meeting.

Watching the Olympics this year, the thing that stood out the most was the leaders coasting to the finish in the preliminary rounds and even in a few finals once the outcome of the event was clear. I saw this in other sports as well — diving for example — where the medal order was set and the athletes mailed in the last dive. I see the same thing in meetings with founders sometimes — and I have been guilty of pulling up and coasting to the end of the meeting once I feel like First Round is not a good fit as an investor. I shouldn’t do this and if I have done it to you, I am sorry.

As a VC I know I will be wrong a lot and I accept that. It is humbling to see founders realize a vision that I could not see or understand months/years earlier — and I always wonder what questions I could have asked to help me see what they saw and understand what they knew. I have also had the opposite experience where a founder will follow-up weeks or months after a meeting and let me know that one of my concerns about their business turned out to be a significant hurdle that they spent resources against only to end up validating my concern and needing to adjust in a way I had suggested. In this case I wonder what I could have done to help them see what I saw and understand what I knew in our first meeting.

I think it always comes back to not taking the easy way out, to asking the follow-up question and pushing back on conclusions in order to close the gap in understanding — on both sides. With every meeting I try to uncover the fact pattern that you are working off of, the conclusions you are drawing from those facts and the actions you will take based on those conclusions. I do this by studying the materials you send prior to the meeting and building a point of view on where we agree and where there are gaps. I view the meeting as an opportunity to fill those gaps with learning on both sides and the structure this takes is questions…lots of questions.

Everyday in the start-up industry thousands of people stand at the edge of the high dive, take a deep breath and jump. Everyday these people have decided to look for their greatness and I think the investor’s job is to help them find it – sometimes with an investment but always with deep engagement, tough questions and an honest, best effort to both understand and evolve the founder’s vision.

I never question the decision to jump but I am always trying to understand where you think you will land.