Andy Trattner

September 29, 2022

I Suck.

I can't remember the last time I really beat myself up. It feels like I've received overwhelmingly positive feedback throughout life, so at this point I'm deeply confident and optimistic by nature. If I had to guess the last time I really let myself have it, this was probably in high school and likely chess-related.

Losing a game of chess can be an extremely emotional, self-flagellating ordeal. Years ago, when I beat little Hans Niemann in blitz, I recall he threw a serious tantrum—giving me a death stare, knocking over some pieces, and crying in the tournament hall. Based on this interaction alone, it did not surprise me to learn he has now become an infamously strong grandmaster.

My reaction to losing was generally mild. I felt bothered enough to improve, but at the end of the day, I didn't care that much. I went to college and plateaued, not only in chess but academically as well. I explicitly focused much more on socializing and accumulating "life experiences" by living spontaneously. My motivation was more curiosity than any sort of frustration with the status quo.

After five years of whimsy, external feedback had accumulated that something was missing in my life. I started blogging, which helped me take a hard look in the mirror. I discovered that I needed—and subsequently wanted—to get a job in tech. I became more open-minded and less self-confident, recognizing that although I had the right raw materials, I had a lot to learn in how to apply my skills professionally. 
Since working at Scale and ReadMe, I've continued to learn while shifting towards self-employment. There's a fine line between self-employment and self-indulgence. Now fully immersed as a startup founder, I'm encountering new challenges.

Recently, my company has felt a bit stagnant. At first, I couldn't articulate why. It's taken a couple months to let the situation sink in. Now I can articulate things more clearly, and although much can be said about the Latam fintech market etc, part of the issue seems to be me. 

I need to level up as a founder. I've been having trouble putting on my investor hat over my operational one, so our team has been strategically misoriented towards minor doing rather than major learning. A fever of to-do list thrashing is now coming to a head.

The worst part is—like many humans—I'm particularly slow at recognizing my failings. I have been bad at dedicating the requisite time for deep strategic reflection and work. I want to become more energetic and humble, fueled by intellectual curiosity and steered by focus down a road of proactivity. 

I'm excited to start with this blog post, my first in months (bad sign), and to continue by seeking some new form of accountability / coaching. I don't actually feel that I suck too much, but that's why this dramatic flag in the ground is necessary.

A friend reassuringly told me that founding a startup is a highly nonlinear process. Although I agree with this, I must not use it as an excuse for waiting around and hiding.

About Andy Trattner