Welcome to another edition of the What If? blog, where we delve into the minds behind the games and tools we love. Today I’m joined by Gil, a game designer who turned his frustration with prototyping tools into something remarkable. We’ll explore how the pain of creating card games with inadequate software sparked the creation of Dextrous, a purpose-built tool that’s changing how designers bring their ideas to life. From his early days making games for siblings to building a thriving community of designers, Gil’s story is one of persistence, adaptation, and finding joy in the journey. Let’s dive in!
Joe: Welcome to the What If blog, please introduce yourself to the readers, what brings you to the world of table top games design?
Gil: Thanks mate. For me it’s the usual story of playing classics like Monopoly and Risk and then eventually stumbling into gateway games like Catan and Citadels etc. When I was 13 or 14 my friend and I started making our own game, and after that I had the design bug and never looked back. Because I’m one of the eldest of 6 kids, I was always making up games for my siblings anyway, so discovering the hobby felt like a perfect fit for me. As I’ve gotten older I’ve realised game design is actually just like a game on super hard mode. It’s wonderful.

Then nearly 4 years ago I was working on a game idea with a friend and was frustrated by how long it took to make our first prototype (at the time I was using an InDesign data merge). In the end we decided to start a ‘small project’ of making our own prototyping tool. 4 years later, we’re still working on it (Dextrous) and trying to make our own games on the side too.
Joe: I’ve felt that frustration too, and what you’ve created with Dextrous is such a good tool. Would you be able to explore the challenges you were having with prototyping? And perhaps a bit about what drove you to decide to make the tool (many would just put up with the difficult methods).
Gil: Ha, I think I’m just a bit of an impatient person to be honest. I was facing a few problems, one of which was just that the tools I was using (InDesign, Word, PPT etc.) weren’t actually designed with board game components in mind in the first place. For example, I have some old Word docs now with so many images in them they are basically unusable because of the lag. And then when I had to make a change that rippled across multiple cards, that was always super painful because the smallest mis-click could bump other elements, or make a card break across pages etc.
I wanted something that would let me smash out a first prototype quickly, and then continue to update it easily if the idea turned out to be good.
I initially thought the InDesign data merge approach would solve all these problems, but it ended up being much more rigid than I wanted it to be – It was hard to have one card with a different font size or style etc. and features I really wanted like inline icons or responsive elements (auto-sizing zones, icons sliding into position if space allows) were seemingly impossible. I wanted something that would let me smash out a first prototype quickly, and then continue to update it easily if the idea turned out to be good. For me, it’s all about getting this iterative cycle as quick as possible, because I find that if it takes me too long to make the prototype I start to lose enthusiasm and momentum.

Joe: Having the right tools for the job is so important for being able to iterate quickly, and you’re so right about the rigidity of other tools, they were never designed for a speedy iterative approach, so they just don’t work.
I’m intrigued, did the game that created the frustration which inspired the project ever come to life? What was it?
Gil: Not yet! It was part of a few designs we worked on where we wanted to have a game like an MTG cube but more accessible, and that was also different every time. Essentially like an inbuilt meta that evolves every time you play. That’s the goal for a lot of my designs to be honest – something that gives you a fresh puzzle every game.

Joe: I’ll keep my eyes open for future games then, they sound super interesting.
OK so you’re scrabbling around getting frustrated with the tools at hand, so much so that you built your own. How was that process? I’m assuming that web development is well within your skills, how do you go about building such a great tool?
Gil: Actually when we started out we were pretty green. We’d done some online projects before but nothing quite so big. We’ve learned a lot along the way and this has been partly down to our approach. Doug (my Dex partner) and I have taken a pretty unconventional MVP approach to building the app where we:
- Release new features and try out new ideas quickly
- Listen to feedback from our users and make changes accordingly
In a way it’s exactly the same as our approach to prototyping a game – fail faster and adapt accordingly I guess. The downside is there’s a lot of change – the upside is people feel like their contributions are heard and reflected in the product (at least that’s my hope!). Just like you have to trim rules where possible in a game, sometimes we have to refactor old pieces of the app – which can be painful, but it’s how we learn and evolve, and at the end of the day everyone wins because of it. We’ve still got a long way to go and more features coming, but it’s also encouraging to see how far we’ve come – and most of that is directly tied to suggestions from our users.
In a way it’s exactly the same as our approach to prototyping a game – fail faster and adapt accordingly
Joe: Wow that’s impressive – it shows where you can get if you have the right team and support working in the same direction. What do you feel has been the biggest frustration during the development? And how did you learn from it and overcome it?
Gil: Hmm good question. Look at the start, it was a bit of a ghost town honestly. It’s definitely hard developing when you don’t have many people using the tool, or giving feedback.
Another big and ongoing challenge is balancing new features with stability (people get change fatigue) and as part of that, knowing what things to pursue and what to leave. We want to cover the whole gamut of idea to prototype to professional production, so as you can imagine, there’s a fair bit in that space especially when you’re considering digital platforms like TTS as well as print-ready PDFs.

The answer to both of these challenges ended up being the same: to listen to, and serve our existing designers. If they’re happy, they’ll eventually tell others, and we grow organically from there. It has been a long game though. It took 3 solid years of turning up to the Discord almost every day and making tutorials to get where we are now.
Joe: There’s plenty of similarities there to game design. That process of listening to and then integrating feedback has clearly been crucial in your process. When you’re designing and getting feedback you listen to many ideas of playtesters, then you need to work out what’s important and what doesn’t actually fit. How have you approached that process in the development of Dextrous, how do you decide which avenues to pursue, and which get left behind?
Gil: We tend to have an approach where ‘the squeaky hinge gets the oil’ as the saying goes. If lots of people request something we bump it up in priority and try to make it happen sooner. On the other hand, if a feature request is super niche it gets a lower score. We’d love to say yes to everything, but the reality is the needs of the many outweigh the needs of the few, and sometimes this leads us to places we didn’t anticipate. One example is we now have a lot of folks making TCGs who want a ‘deck builder’ tool for organising different mixes of cards like boosters etc. This is kind of outside the scope of Dextrous currently, but we’ve had enough requests for it that it’s now become one of our priorities.
The needs of the many outweigh the needs of the few, and sometimes this leads us to places we didn’t anticipate.
Joe: Listen out for those squeaky hinges! It’s great that you’re so community focused on what you’re developing. I suppose that’s in part because you’re looking to develop a useful tool that people will quickly realise is well worth using, but also paying for.
I’m currently using it for some development work and I wonder if I may briefly describe why I find it such an asset to my design toolbox.
Firstly, it’s incredibly intuitive to use, things feel like they’re in the right place, and alongside your tutorials, I got up to speed with “how the hell do I drive this thing?” incredibly fast.

For me though, the real beauty is the speed at which I can now iterate. Things can be shuffled, adjusted, scrapped and redrawn with so much ease. And then within moments, I’ve got the next iteration shooting out of the printer with crop marks and ready to slice. It’s taken so much of the pain away from the process that I can simply work faster and with less frustration.
Gil: Ha that’s good to hear! Making that playtest iteration loop as fast as possible has always been our main goal. As a designer it’s so easy to waste time between versions, which is frustrating because there’s such a sweet flow you can get into where you playtest, change a few cards, and go again etc.
Ultimately, speed and flexibility is really what the word ‘Dextrous’ is all about (that and a sneaky pun about cards of course). Once you start exporting to digital platforms (TTS, Screentop etc.) it becomes even faster too in terms of being able to playtest with people all over the globe very quickly.
Joe: Thanks for your insight in today’s blog Gil, what strikes me most is your dedication to a cause. In the blog, two final questions for you – with such a big project, what have you learned about yourself along the way, and what advice would you give others about to embark on their own projects?
Gil: I think I’ve learned I can be very driven, so it’s important to rest and also take time to make things sustainable too. I’m talking work hours and holidays, but also mentality. Sometimes it’s easy to focus on the destination and realise you haven’t been enjoying the journey as much as you could have.
I think my advice to others would probably be something similar – start that big project and if you keep chipping away at it you’ll get there – but follow the fun too. After all, why be in this industry if you’re not in it to bring more fun and joy into the world?
A huge thanks to Gil for taking the time to share his journey with us today. The parallels between game design and tool development are fascinating, and the community-focused approach behind Dextrous shows how listening to users can create something truly valuable. If you’re interested in exploring more about Gil’s work or trying Dextrous for yourself, you can find them on their Discord channel and website.
Don’t forget to subscribe to the What If? blog for more interviews with creators who are pushing boundaries in tabletop design.
I liked reading this blog.