Why I Built ASCENDCHESS
Here I am driving around Lebanon, TN handing out flyers for the WilCo Chess Club I founded recently. I am completely immersed in chess at this point, and I am listening to an old podcast episode. I think it was the now defunct How to Chess podcast by Perpetual Chess host Ben Johnson. The guest, Hans Schut. Hans is talking about how he uses the 5 Whys framework with his students. Alarm bells in my head start ringing. For those that don’t know the concept, the 5 Whys was popularized by Toyota and westernized by “lean” management. I spent 18 years in supply chain management in manufacturing and healthcare before pivoting my career to tech. My day job is as founder of SEE/EYE, a continuous improvement and change management platform. Improvement is in my blood.
When I started studying chess seriously as an adult, I thought my problem was time.
Along with my founding duties, I have a family. I have the aforementioned chess club I run in Lebanon, Tennessee. The 1 hour or so I got to spend with my coach, Adam were the best 60 minutes I spent on chess during a week. The other six days were where things fell apart. Not because I wasn’t trying. Because I didn’t know what I was doing.
I had Chessable courses I was working through. I had books I was reading. I had games I was analyzing. I had puzzle ratings I was tracking. I had a coaching relationship that was giving me real feedback. What I didn’t have was any way to connect any of it together. My courses didn’t know about my games. My games didn’t know about my books. My weaknesses in one place weren’t visible in another. Every tool I used was a separate room, and I was the only person walking between them.
I kept thinking the problem was discipline. If I just studied more consistently, if I just reviewed my games more carefully, if I just spent my Chessable time better, eventually it would all come together. It didn’t. Not because I wasn’t disciplined. Because no amount of discipline can connect systems that weren’t built to talk to each other.
That podcast episode is where everything connected for me. I was approaching chess as a separate endeavor from everything else in my life, instead of connecting the dots. Who better than a guy who specializes in improvement methodologies to solve an issue improving at chess? SEE/EYE was an idea I had based on a similar problem; people who want to improve operations have to slog through 50 million different spreadsheets and tools to get the job done.
I looked at the software I was using, and I realized something that should have been obvious. None of these tools know me. Not one of them. Plus, I was using 50 million chess tools to get the job done. It was inefficient. For someone who is a bit ADHD like me, that’s an issue. Adam helped direct my focus. I needed a way to do that when he wasn’t around.
Chessable has 40,000 courses and no idea which one I should be doing today. My analysis tools know my rating but don’t know I played the Caro-Kann Fantasy last week and have no idea what I’m doing in the resulting middlegame. ChessBase has every game ever played and no idea that my real problem is that I drop pieces on move 34 when I’m winning, not move 14 when I’m preparing.
ChessBase is the 800 lb gorilla in this space. They have the database, the engines, the reputation, and the price tag to match. A full ChessBase setup runs hundreds of dollars. The interface looks like software designed in 1998 because it was. Every feature ever requested by a grandmaster is in there somewhere, buried four menus deep. You can learn to use it. Many people do. But you have to already know what you’re doing before the software becomes useful, which means it’s built for masters and tolerated by everyone else.
I had a conversation recently where someone told me no one will ever compete with ChessBase. My reply was that someone always rises up. That’s how free markets work. A dominant player gets comfortable. They add features for the top 1% of their users. They price for the users who have no choice. They stop building for the other 99% because the other 99% aren’t the ones complaining loudly. And then one day someone builds the thing those people actually needed and the dominant player wakes up to discover the ground has shifted.
I’m not claiming ASCENDCHESS is the thing that shifts the ground. I’m claiming the ground is going to shift and I’m working on what I think could move it. Those are different statements and I want to be honest about which one I’m making.
I am an efficiency and improvement focused individual building the tool I wanted to exist but didn’t. This was just supposed to be for me, but then I realized that it had potential for others. When I showed it to a guy at the club and he said, “I need this today, do I really need to wait 2 weeks to play with it?,” and he is about my skill level and has a similar dedication to chess study, it blew me away. I knew I had something that could help people make sense of a complex game and focus their attention.
Here’s what I decided to build.
A coaching platform that actually knows you. Not your rating band. You specifically. Your games. Your books. Your weaknesses. Your study history. Your style. The specific patterns you miss and the specific patterns you see. The games where you played well and the games where you fell apart. All of it, in one place, connected, with a coach that speaks to you about your chess, not chess in general.
The six months I’ve spent building this have been the most concentrated technical work of my career. I’m now a software developer by trade. I’ve shipped a lot of products. This one is different because I’m also the user. Every feature I build, I use. Every coaching voice I write, I read back to myself. Every metric I compute, I check against my own games. If something doesn’t help me improve at chess, it doesn’t ship. That’s the bar.
Working on it solo means it’s smaller than what a funded company could build. It also means it’s more honest. There’s no committee deciding what an adult improver needs. There’s me, my games, my club, my coach, and a growing handful of beta users at WilCo Chess Club who are telling me what’s working and what isn’t.
The platform is called ASCENDCHESS. It opens to beta users this month and to the public shortly after. If you want to know when it’s available you can subscribe to this Substack or sign up for the waitlist at
One last thing. I know this is a crowded space. I know there are a lot of chess improvement products. I know ChessBase has been the database of record since I was in grade school, and I know Chess.com has more users than the country of Norway. I’m not here to replace any of them. I’m building a thing that does what they don’t, for people they don’t serve well.
I’m a 1250 rated adult improver trying to get to master. I started building ASCENDCHESS because I wanted the tool that didn’t exist for people like me. Six months in, I’m convinced that tool should exist. Whether or not ASCENDCHESS ends up being it, someone’s going to build it. Free markets work that way.
I’d rather be the one who tried.