The Dark Side Of Entrepreneurship

This hurts

I’m going to get vulnerable here

Over the last month, I have been trying to clean up a big problem and a big miss in one of my portfolio companies.

The short version of the story is that I invested in a person who has not lived up to the expectations I had in my head. When I first met him, I’m embarrassed to admit I put him on a pedestal. He had achieved amazing success in his life, and I convinced myself that he knew how to make big things happen. I told myself that if I leveled up my mindset and went big alongside him, I could make big things happen too. Instead, the project has turned into a disaster, and it is likely my entire investment will go to zero.

As I was wrestling with this situation, I came across a soundbite from an interview with Jensen Huang, the CEO of NVIDIA.

As of this morning, NVIDIA is the most valuable company in the world. You would think Jensen Huang is flying high, right? Not necessarily.

In this interview, you can see that even at the highest levels of business, the pain of failure cuts deep.

Hearing him speak reminded me that no matter how successful you become, the shame and embarrassment of failure never fully goes away. I can relate to this so much.

Obviously I am not the owner of the world’s most valuable company. Nonetheless, entrepreneurship is the game we both play. For whatever reason, in business the losses hurt so much worse than the wins feel good.

Still, I try to remind myself of the bigger picture. When I look at everything objectively, I can accept that the loss I am taking on this investment is small compared to the wins I have had over the last ten years. Not to mention the future is still bright, and the decisions I have made will continue to bear fruit over the next five, ten, or even twenty years.

All is well and I am blessed.

But this failure has caused me embarrassment and has made me second guess myself. That tension is what makes entrepreneurship so difficult, because what I know in my head does not always match what I feel in my gut.

Knowing and feeling are two separate things.

I know that if this is the life I want to live, then I am going to take some losses and that is just the way it goes. But it feels like I ignored all the warning signs, like I was overconfident, arrogant, and like I am a big fat loser.

But when I zoom out, I remember this is simply the price of admission. That is the game we play. That is what I signed up for.

I do not regret anything, but I am wise enough now to let myself feel the pain of the failure and continue moving forward regardless.

Love you guys. Talk to you tomorrow.

Tim

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