My Greatest Sadness

The cost of a startup is hard to measure, calculate, or even prepare for when you first begin your long and difficult quest. It’s more closely akin to preparing to summit Mt. Everest as a first-time adventurer but without a lot of good advice and no roadmap.

Yeah. It’s most-definitely like that. But this is as it should be because if we knew what all of this would cost us we’d never, ever, do it.

You see, we start the journey full of hope and we believe that we will be statistically-different than what the history books tell us. We believe that our startup will not fail even though we know that the vast majority die quiet, lonely deaths. In fact, many of us privately understand that we’d also statistically make more money if we got a full-time, “normal” job in our industry of choice.

And some of us try — I know I did.

My greatest sadness in the failure of my most recent project — in our attempt to reach product-market fit before running out of funds — is not that the product failed to achieve those quantitative and qualitative ends. Rather, it’s relationship-centric as I no longer have a functional relationship with my brother, in any way, shape, or form.

In fact, I haven’t spoken to him in years, since he left the project in early-2019. YEN did that. I did that. We did that.

There are no words to describe the pain because it is unlike anything I have ever experienced in my life and my heart still aches, desperately, but the sharp edges have been slightly dulled as time seems to salve and smooth all rough edges as a natural consequence of erosion, distance, and — eventually — acceptance.

The million (billion?) dollar question would be this: Would I have started this project knowing that I’d lose my best friend? It all feels upside-down and right-side wrong.

This is my greatest sadness.