Two Minds

Posted on September 18, 2013. Filed under: startups, venture capital |

I talked with a friend recently who is self-defined as a “creative.” He lives product. He thinks about people. He approaches every interaction as a human being first, and a business man a distant second. He hates paperwork. He hates contracts. He hates thinking with the part of his brain that calculates…he wants to take people at face value. He hates deals. He hates strategic thinking…he just wants to create and connect with people…both through his product and through his real life interactions. He is sensitive…

There is something very pure about this mind…something that doesn’t “take,” that isn’t transactional…that is how you would want a friend to be when interacting with you. My friend that I mention is on one end of a spectrum that I could call the empathy-ruthlessness spectrum. I have this mind that he expresses so fully…it leads me at times…but I am not as pure an expression of it as he.

The other mind…the ruthless mind…is also very present in our world. Just as we praise the pure creator…much praise is given to the pure executor. You may have heard the phrase “he’s an absolute killer” when discussing a founder that get’s shit done at all costs…the killer exercises his strategic mind…he dehumanizes the people behind his business interactions. He acts on perfect logic. He moves through people to get to his goal, and as long as he acts in accord with proper business logic, he is true to himself. He is not amoral, although there is a degenerative form of him that can be…he is simply mechanical. In fact he can be perfectly moral…extremely disciplined when it comes to behaving on the right side of ethical lines…but as long as he exists within them…any decision that is to teh advantage of his business or enterprise is the correct one and will be made. He presumes that everyone else acts the same, he anticipates and analyzes the intention of all those around him…he is Machiavelli. I have this mind as well.

If you were to put these two minds at either end of the empathy-ruthlessness spectrum…I believe most fall somewhere in the middle. Personally, I don’t feel that I am in the middle, but rather I jump from one end of the spectrum, over the middle, to the other…depending on the context of a given moment. I have deep, deep expressions of both minds…which has conflicted me for as along as I can remember…both minds can be so powerful in making progress and living the life you are trying to carve out for yourself…what I have learned with age and experience, is that the empathetic mind is beautiful, the ruthless mind is ugly, and both can be necessary when interacting with a world that is made up of people ruled by both. I try to exist in the beautiful as much as possible. and sometimes it takes the help of a another to remind me when I fall too deep into the ruthless. There are…however…times where living exclusively in the empathetic mind can be detrimental…I wish you could make it through a venture financing without exercising the ruthless mind…at least a little…but you can’t. At some point, when the rubber hits the road, and you move from product and love and relationships and communication to hard numbers, cap tables, and liquidation preferences…it does not benefit you to remain empathetic…even the purest of heart on the other side is excercising something other than pure empathy…there is self interest…business interest…and it is a function of the choice we have made to create within the business realm…as opposed to the arts, or the literary…or the natural…that we must deviate from the precipice of the empathetic mind, on occasion, to move through it. It hurts my heart to live in this reality but we must.

Only recently have I realized that one of the few pieces of true value that I try to share with my friends and founders that I have been lucky enough to invest in over the years is that I can move between these two minds seamlessly, and yet am governed at my core by the empathetic…it is often helpful to analyze the world through the ruthless mind, but communicate the conclusions with a compass  that’s true north is empathy.

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Having a ruthless mind is like keeping a gun in the house.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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