I’ve been listening to a lot of pitches this past week, and I’m always shocked at the airs that founders will try and put on to impress you. I cannot speak for other investors, but for me that doesn’t do it. I am too old. I am cynical. I see too many pitches.
These founders are trying to convince you, almost will you, into an investment. While I appreciate the enthusiasm, I get a viscerally negative reaction.
I would advise founders to just be the best version of you. Be authentic.
Instead of trying to convince me to join your view of the world, tell me your story, and then listen to mine. Get real with me. From there, if I invest, you know I am all in and we can start building a healthy relationship. If not, then we both get to know each other as people and perhaps there are other ways we can help each other.
For instance, one entrepreneur pitched me on his previous rounds, raising a significant amount of capital from some top investors. He name dropped his A-list undergrad and MBA credentials. Finally, he told me about his current raise which was effectively a down round of about 75%.
I was puzzled, and then I asked, “May I ask a risky question? Why are you here? Specifically, where did you go wrong?”
The moment stopped him dead. He paused for a long while, slamming his back into the chair. He actually thanked me for the opportunity to get real with him. He described how they overbuilt their product and didn’t test enough. He talked about the internal power struggles between him and his co-founder.
While I probably will not invest in that company, it was the best meeting I had last week. It was the most authentic. He saw me, and I saw him for exactly what we were trying to do. I may not invest, but I am helping him with some product advice and connecting him to other product people in his field. And who knows, I may invest in his next startup because of the relationship he invested his vulnerability in last week.
My takeaway from this is to reorient your pitch. The goal is not always to “just win,” and try and get a commitment. An alternative is to think:
The right investor will be excited about this. Especially at the pre-seed stage, where we are looking for founder-market fit. Self-awareness, vulnerability, and grit are key characteristics we look for and authenticity is a prerequisite for all. Besides, once that authentic connection is made your ability to ask for advice (and get REAL answers) gets way easier.
While these may seem squishy, I wanted to offer a couple tactical ideas on how founders can optimize “speed to authenticity versus speed of investment.”
I admit, this post is touchy-feely, but one thing that founders should know is that investors are people, too. We are not just checkbooks. We want to back founders we connect with and understand us as human beings and business partners.