When I first started pitching to investors, it felt like high school all over again. You’d think I’d say college, but no, in college there was clique for every imaginable combination. If you were an athletic nerd you had ultimate frisbee or competitive quidditch (that’s an actual college activity by the way, I’m not just making that up). There was an accepting group for everyone. There were also clear expectations for what you should study and skills you needed to hone or possess in order to do well on an exam. In high school, you more or less had to just do your homework and you’d rank well. From a social perspective, there was less variety in high school and everyone is basically looking for the cool kid to support.
A part of the investor pitch process for me was doing a post mortem after each one, figuring out what I thought I did wrong, and then moving to the next one. In essence, I tried to figure out how to adjust each pitch so I would be deemed the “cool kid” to these investors. Here’s where that becomes a problem, by overfitting (the process of adjusting for each data point on a graph) the line you can become unattractive to nearly everyone. Frankly you also lose your sense of identity because you’re constantly trying to match for the last person you spoke with. Imagine going to a speed dating event and after each momentary interaction you’re adjusting your personality to match for the last person you met. That’s bonkers.
One of my best friends and I have a phrase we tell each other when we share that we are nervous about an upcoming meeting or presentation — “You’re best at neutral.” Neutral means you’re not there to impress anyone. You’re there to be there and be you. Neutral means you’re not adjusting yourself for the sake of the audience, it means you are genuine in your presentation of yourself. It means you are vulnerable as far as you’re comfortable being.
When I brought this concept up with another friend that is a bit older, he told me “I’ve now learned after all these years and having kids, is that when you’re a really young kid you don’t care what others think. You’re just you. Then you get a bit older and gain this sense of self and outward facing view of yourself. You learn to be embarrassed and then all you want to do is fit in. Hide in the crowd. Then as you get older you vacillate between figuring out how to stand out while not being noticed.” As is with most things in life, it sounds like equilibrium is somewhere in the middle. Somewhere neutral.
As a bit of an aside while we’re on the topic of overfitting versus being neutral is an additional concern I have as it relates to pitching to investors. It encourages disingenuous behavior because people think they need to signal certain values — even if those values don’t actually align with the person that is pitching. I wouldn’t blame people for doing this either, since many founders and even investors I’ve spoken with have told me that I needed to adapt to pitching for VCs. I never really conformed to what people thought being a lawyer or an engineer was, so changing myself for the sake of asking for investments doesn’t make sense to me. It especially doesn’t make sense, since those that have tried to start similar ventures like mine in the past have failed or are failing. In a world where they seem to be championing diversity and inclusion, the VCs (perhaps unsurprisingly) have ended up training and encouraging a homogenous startup profile — over sell, go wide, bloviate, create hype, let cash be someone else’s problem. It encourages a mentality of get rich quick schemes. Overfitting to the model I just described (because it yields the highest returns when it comes to pitching investors) is incredibly dangerous both for the startup and the community at large. That’s just a thought. I don’t have any solutions for it at the moment.
