The story behind PickemSzn

I started developing PickemSzn all the way back in 2018. At my first job as a software engineer, every employee had their own plan detailing how they should develop their skills over the coming year or so. Some had courses they wanted to take, some had certifications they wanted to study for. Since I’m a learn-by-doing kind of person, I wanted to do a project. And that’s when the idea of PickemSzn was born. Or, well, it wasn’t really called that back then. The working name was simply Pick’em.

How I became an NFL fan

I’ve been a huge NFL fan ever since my brother introduced me to the Super Bowl back in the 2006 season. I was 14 at the time, and he used to watch it at our place. I stayed up for the first half or so of the Colts-Bears matchup. Then the next year came around: the infamous 2007 season, and the infamous Super Bowl between the 18-0 Patriots and the New York Football Giants. This is where I learned about the legend of Tom Brady. This is where I became a Patriots fan. Yes, you can hate me for it. I continued being a Super Bowl merchant for a couple of years, not really following along during the regular season or anything. I think the first year I got NFL Game Pass was 2014. That season I started following the NFL for real, and got hooked.

Why I wanted to develop PickemSzn

Combining my profession (software development) with my passion (NFL) in a side project I was basically paid to develop was a match made in heaven. But why a Pickem app, and not something else? Well, back to my brother again, the one who introduced me to the NFL. We used to pick the NFL playoff winners back in the day, put our picks in an urn, and look at them after the fact. I thought it would be fun to compete for real, across an entire season, with real odds. That’s why I wanted to build a Pickem app.

The early days of PickemSzn

Back in 2018, software development was quite different from how it is now, for obvious reasons. No Cursor or Claude Code to aid the process. Just a text editor and Google. That, combined with this being just a side project, is why it took me about three years to get to the first pre-alpha version. The first season I ran it on was 2021, when another NFL-interested software developer and I tested the app across the whole season. I’ve never been good at design or frontend development, so the website looked horrendous, but it worked quite well.

The advent of AI-assisted development

From 2021 to 2024, I basically only worked on fixing bugs and making the app’s features more robust. I didn’t do much about the design. In 2024, and especially 2025, AI-assisted development started to become a thing, and redoing the design with these tools was a perfect fit for me. That’s when the app started to become usable for the broader public. Before that, it had only been me and my brother playing, but for the 2025 season I started getting external people signing up. Retention and engagement were quite low, though, and that’s what I’m working on for the upcoming 2026 season.

So what is PickemSzn, actually?

If you’ve never played a pickem before, the idea is simple: each week you predict who wins every NFL game, you do it against real odds, and you do it for the whole season. Then you watch the standings sort out who actually knows ball and who’s just been riding luck. Basically the urn, except now it counts, and nobody can swap their paper scrap after the fact.

Come play

So that’s the story. From scraps of paper in an urn to an app I’m still building out season after season. 2026 is the one I want to get right: better retention, better engagement, and more people in the league than just me and my brother.

If any of that sounds like your kind of thing, come sign up at pickemszn.com and get your picks in before kickoff. Bring your friends. Beat your friends. That’s the whole point.

And yeah, you can hate me for being a Patriots fan. You can still pick against me.