Treat Your Business Like a Hackathon

One of the constants in life is that you will always make mistakes, so here I reflect on both the good/bad easy/hard fun/scary lessons I learn. I do NOT try to find a solution, but rather a different path forward with my new knowledge. When I try to find solutions, I tend to believe that I cannot make the same mistake again. This space allows mistakes to exist so long as I continue to try different paths rather than claim solution over them.

What Happened

I spent the last few months in 2025 reading about how to start a company in a different way than I had been trying. In doing so, I realized it was similar to how I started, but much more focused and pragmatic. However, over those years, I developed a bad habit: Build First Mentality.

Especially for engineers who can build, this habit is destructive.

I thought that reframing how I was building and what I was building towards would change everything, but I just ended up having a Build First Mentality pop up in other places.

In three separate pet project/solopreneur ideas, I carried a build first mentality even though I was absolutely not trying to follow my previous start up methodology.

In these cases I built too big for a first pass, built without confirming my demand hypothesis, and built without confirming founder fit.

These were all pretty hard to admit, but everything is a learning process so I'm going to do my best not to be so hard. I'll go into more depth in each of the respective articles.

What I Noticed About Myself

I don't know why I still found myself 'building first', but I can say for sure that I need to rebuild my comfort zone/habit. The best way I've always found to do that is with structure.

I'm going to start a structured flow diagram that I keep updated for all of my endeavors and see where it leads me in a few months.

What I’m Sitting With

Where did I go wrong with these projects?

Each of them had different issues, but all of them resulted in me building big even if I reduced the size of the problem. I jump too quickly to coding as a solution.

Why did I still make the wrong choice?

I think it's probably just where I'm comfortable because I want things to just work. Often the opposite of a build first mentality is a 'do it by hand until you can't' mentality. This inherently means, building and tearing down again and again. I don't think I'm deeply comfortable with this and so even when I'm consciously trying not to, I end up doing it.

Why was I so confident in making that wrong decision?

I didn't have good systems in place to challenge the way I was building. It wasn't until weeks into all these projects did I really pick my head up and evaluate if I was going in the right direction.

How I’ll Hold This

I've started a live document to give myself better structure when pursuing ideas: Selling Something That Doesn't Exist.

Effectively, treat your business like a hackathon. What I mean by that is try to build it all in 24 hours. If you can't, make it smaller. If it isn't crystal clear, get more clear. I do not mean go insta-build and grind all-night to get some localhost demo. I'm really just referring to the 24 hour constraint of some hackathons. Maybe this isn't the best phrasing. It feels like it will be misunderstood in a few years 🫤.