Let Your Guard Down

One of the most important things I learned this week is to be more open with people and let my guard down more often. I’ve been told that I might seem “guarded” at times, and there’s probably some truth to that. However, it is by no means intentional. There are a myriad of reasons for “why” I think I often struggle with maintaining a consistently high level of confidence and feeling like I “belong,” and I think a lot of has to do with my childhood.

In comparison to those around the globe, and even most people in America, I live a very good life. But it wasn’t always like that and it has taken many years to psychologically adjust to it. Over the last 10 years of my life I have had the opportunity to work with and surround myself with very motivated and successful people. In fact, in my line of work, very rarely do I meet people that aren’t this way. For example, every entrepreneur I meet and work with is ambitious, motivated, and hungry. Our investors are smart, successful, and wealthy. It’s truly exciting to get to work with people like this every day.

Putting into practice the things I see successful people do is a conscious decision I make daily. As a youth I was a really good artist (pencil was my favorite medium). My best talent was being able to study and then draw – with great accuracy – very detailed works of art. I believe the skill of closely studying and then drawing was developed by growing up as a kid in a very poor and unstable environment. In my home life I was surrounded by poor role models in an environment of severe lack. I would look at those around me and make an effort to do the positive opposite. This was how I trained myself to think for many years, and I believe it negatively affected me when I became an adult. Instead of thinking about who or what I wanted to be in life, I only thought about who or what I didn’t want to be. This is not a healthy way of thinking as it can be severely limiting. Fortunately, I’ve learned to not think like this anymore and have used that skill of “studying” and “drawing” to model my life after those that I want to be like. It has also been a great skill to have when studying businesses and people in general.

I rarely talk with people about my childhood for fear of judgment, lack of relate-ability, or maybe because my background is just so different from the backgrounds of nearly everyone I know. Perhaps being guarded is my form of protecting myself or perhaps it’s a necessary measure for operating in a world where failure and excuses are not acceptable – only success and successful people are. And this leads me to my next point about how guarded entrepreneurs can be with me and with other investors. Every time I meet a new entrepreneur looking for capital, they only tell me the good things about their company, themselves, and why they’re the next big thing. While I think that’s fine and dandy, I also think it’s necessary (especially when I ask) to talk to me about the areas of their business that they’re not as thrilled about. From an investor’s perspective, I think it’s important to know about the struggles and difficulties of the business and how they plan to work through that. I purposely challenge entrepreneurs about their market or their team or their thesis because I want to see how they respond. If they respond by completely ignoring what could be a potential weakness and only tell me about how great they are and how great their business is, it immediately raises a red flag. Being somewhat guarded as an entrepreneur is probably not a completely bad characteristic. However, if entrepreneurs refuse to ever let their guard down and only talk about the good, then I feel like they’re doing their investors a disservice. Strategically, I think it makes more sense for entrepreneurs to talk about their issues and how they’re overcoming them to get better, then it does to not talk about them at all. As I give advice, I myself will also follow it.


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