If you’re an investor, have you ever gone through this:

You meet an entrepreneur and go over their startup idea. As he’s talking, your mind starts racing ahead and imagining all the wonderful places this startup will grow to be. The entrepreneur continues his demo of the site, faithfully calling out how great his features are, and how the visual design is awesome. But you’re only half listening; your brain is thinking about all the possibilities and how big this is going to get. You voice some of them; the entrepreneur nods and you see his nodding as “Yes I agree with this sage of an investor before me!” He continues onwards with his pitch, noting all the awesome features one by one but you’re still thinking about the $100M opportunity. At the end, he asks for your measly $100K to join him on his journey, him working on his nice product, and you living out your version of his startup along with your awesome vision of where it will go. You sign on the dotted line, transfer the money, and you’re on your way.

As he works on his coding and congratulates himself on his 100th user signup, you start chatting about how he’s going to achieve your ideas and your vision. He nods sometimes, but slowly but surely he starts talking as if he doesn’t have any idea what you’re talking about. He’s got a product to build, dang it! He’s got 100 users who are emailing him and making him think he’s the most awesome guy in the world! He needs to take care of them! You continue to talk about your vision, and he continues to move nowhere near where you’re talking about.

After about a year of this, you realize that the entrepreneur isn’t really listening to you. Instead, he’s been giving you grinfucks; you thought that you were convincing him that there was a better way but in actuality, he’s been thinking that his way was the only way, thank you very much.

In the end, your startup dies a miserable death. The entrepreneur got some awesome lean startup experience, and you (and your buddies too) have wasted $100K. He’s off to raise money on his next big feature for the web, and you’re still not recovered from a year of frustration that someone didn’t listen to your investor awesomeness.

In my early years as an angel investor, I fell into this trap several times. And this trap has many elements to it.

It is sometimes indeed possible that you really do have some investor awesomeness – call it life and work experiences as well as experience in spotting opportunities as an investor in many startups. And sometimes you are probably right in thinking that an entrepreneur should take his startup in some direction or another. The trap you have to watch out for is investing into his startup when you imagine and do not have actual verification that he believes in the vision or direction in the same way you do.

This is not about whether he may be right in the end, or you may be wrong. Or even if the outcome is awesome despite either or both of you being right or wrong. What I’m talking about is thinking you’re investing into a project of a certain nature when it’s actually not – you’re only wishing and imagining it to be something but it wasn’t real.

In many ways, it’s like meeting your perfect significant other, but that perfection is in your mind and you think he/she has the perfect traits for you, but in reality they are someone else and can never be that fantasy significant other for you.

A lot of this is about the fact that it is nearly impossible to transfer your idea to someone else. There can be many reasons for this. You and the other person simply have different viewpoints and experiences. When you say something, they may totally interpret that in a way that you didn’t mean for them to interpret it. Or they may not even know what you’re talking about. If you make a suggestion for a direction, it may be that, given your experiences and skills, you are the only one who can execute that direction and they may not be able to do it at all.

Today I was talking about this very thing with one of my entrepreneurs. Two weeks ago I pushed them on generating a big vision out of what they were working on. We went like this for several days. But they could only come up with something that I considered too likely to produce a small outcome for me to invest in. I sent them an email to that effect and then I went off on vacation.

However, we caught up today after I got back and spoke live about my email. I basically explained to him that I needed to hear that they were on board with some big vision. I had already come up with some possible big vision directions in my mind, but having some experience now I did not imagine them to also have the same visions; I wanted and NEEDED to hear them say it to have confidence that they understood and internalized whatever big vision there was, and were really on board to execute against that, versus what they presented to me two weeks ago. Given my desire for investing in big ideas with world dominating plans, I needed to hear them telling me the plan and not me telling them what the plan was.

To re-emphasize, this is not about who’s right or who’s wrong. It is entirely possible that in my investor awesomeness (in my own mind) that I am totally wrong on whatever vision I am imagining for a startup – and I’ve definitely been wrong many times. It’s all about making sure that you have comfort in whatever you and the entrepreneur can see eye to eye on, or lack thereof, and then making the investment decision based on that reality and not just what’s in your imagination.

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