001 | Building a Startup in 2025

The best way to learn about what you're capable of is to push yourself far, far out of your comfort zone.

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I always wanted to be a film or video game composer. Then I had the sinking realization that I didn't like doing client work, so I decided to make my own films! However, most paid work was client work anyway. 

In 2024 I obtained my Masters in Fine Arts in filmmaking with a concentration in Film Music Composition — which is just a fancy way of saying an MFA in Film Music Composition. While I was at the program and my first semester, I used to play DND with some of my Film Music Composition students. It was there that I noticed that dungeon master Caleb Cannon (he's important, we'll return to him in a bit) was finagling with YouTube and Spotify playlists, which I inquired about. Surely a hobby like DnD has better tools for music playback than Spotify or YouTube?! He responded that there weren’t many and the ones that existed cost money without adding much functionality; he had subscriptions with both, so why not use them?

See, Dungeons & Dragons (D&D) Has been around for over 50 years now and almost every video game RPG or role-playing game has been influenced by the minutia of D&D. Everything, from the concept of classes to leveling up, to hit points and experience points, originated in D&D. Over the years as computers got faster silicone got cheaper, Graphics got crispier, file sizes got larger and as a result, games got better, D&D has remained largely the same.

As a composer and amateur D&D player, I realized two things:

1. Video games had gotten a lot more immersive over the years, largely due to advances in storage, graphics, sound design and music. Video game music unlike film and TV music is dynamic in nature. It scales up and down with gameplay, depending on factors like mood, story, setting, location, and the intensity of combat. Do you know what else has all these factors? Tabletop games!

   
   

2. A key aspect of tabletop role-playing games or TTRPG's Is their social nature. TTRPG's are most fun when players are interacting with each other and bouncing ideas stories and characters off of each other. Adding screens and bringing tech into the mix, runs the potential of breaking the immersion of the experience.

So If I was going to create a solution that played music and sound for Tabletop games, it would need to address those two points:

1. The music would have to be scale with respect to the situation or combat scenario. I.e. the music would have to have layeeerrs, like a video game score.

   
   

2. Users would need to have minimal interaction with this solution.

So in December of 2022, without really asking anybody’s permission or doing enough research, I got to work writing some epic D&D music for use in our campaign. After a week of writing I had written the first track and it sounded awesome, at least to me.

One of the things that I wanted the app to be was to feel 3-dimensional. The idea at the time was that as you moved your phone, so too would the lights and the shadows. So I created a mockup of the app on Blender 3D.

Then, I proceeded to show it off first to my roommate and long-time collaborators and close friend, Dmitri Dyó, who suggested the awesome name, Dungeon Maestro. I also created the app icon in Blender.

Next I presented it to my cohort during one of our Seminars at the Film Music Program at UNCSA. I distinctly remember my classmate, David J. Atkins' (he's important too. we'll return to him shortly) extremely vocal and emotional reaction to the presentation. Due to schoolwork and other miscellaneous projects that demanded my immediate attention, I focused my energies away from this  music app idea until the summer of 2023. 

I knew that I did not want this app to be limited to just Dungeons & Dragons or other RPGs. What if you wanted really cool music for your Wargaming sessions, like Warhammer 40k? The name “Dungeon Maestro” was too… Fantasy. I needed a more neutral name. So I began working on a new logo and running it by Caleb and brainstorming names with Dimitri again. There were two key objectives this time:

1. The app name needed to contain an element pointing to the words ”play” or “game”. 

2. Its music also needed to be memorable and catchy. They needed to be “hits”.

   
   

You see, a lot of tabletop games involving combat require characters to have health bars, populated by “hit" points. And if you wanted to increase your immersion with the battle, you’d want to hit "play" on some nice catchy music…

Hit play on the music…

HitPlay…

 HitPlay. It was f**king perfect!

The app icon needed to be easily recognizable and stand out from any and all other competitors. It needed to be easily visible when shrunk down or seen from a distance. It also needed to be visually distinct to people with partial or total colorblindness. Through sheer coincidence, I realized that a 20-sided dice (a D20) showed a play icon on the side when it caught the light. After a days of iterating, this was the first proper icon I settled on. 

I also started working on a new app UI mockup, in Blender and two more tracks. Things were starting to look… tasty.

When our new cohort assembled during the Fall of ‘23, I showed off the new assets and the music in an ungodly long 8-minute presentation. Again, David’s reaction to the whole thing was strongly positive. He assured me that he would follow up with me on its progress so that I would not lose track of it again.

Well… He kept his end of the deal, but I didn’t as other more immediate projects took over and the concept went into my very large ideas graveyard.

Fast forward to February of 2025. A months-long, very unsuccessful job search (involving over 1500+ applications!) had made me lose faith in ever getting a job. That and my ever-increasing appetite for entrepreneurship had lit a fire in me that I never knew I had. So I rang David up and asked if he wantd to join me in starting up a new company to create the app.

He said yes!

And so with David becoming COO and I becoming the CEO, we started a company. But what was this company to be called? We were going to go with HitPlay, but we did not want to be a one-trick pony, we had more ideas in the pipeline. We were going to have to call ourselves something else.

I’d like to tell you an awesome story of how our crack team of two wandered through a psilocybin-induced delirium in brainstorming the name of our company. But the truth is, the two of us got on a Zoom meeting and used ChatGPT as a bounce-board to come up with the name Tickle Engine. Naturally we needed to stick a feather into a Check Engine light for the logo:

Tickle Engine. We’re going to be a design company first and foremost. We are going to do things differently; we are going to carefully read through the rules and then burn the rulebook, and we don’t want to be another company that rose and fell and brought nothing of value to the world. 

Cool story bro, so how are weu gonna build HitPlay?

Having acquired a lot of skills in life, I realized that my days of doing everything were coming to a close. My Dad had taught me the importance of being an entrepreneur vs being self-employed. I wasn’t going to be a one-man army anymore. As I’ve gotten older, burnout has become a real thing. We needed a very talented and skilled Developer. We needed… a CTO

After over a month of searching, using Y-Combinator’s Co-Founder matching app (think Tinder, but for entrepreneurs) looking for the perfect team, we hit a dead end, until we spoke to our very own, Caleb Cannon. But hold up, Caleb wasn’t an app developer. See, the thing is, ever since Caleb joined our team in April 2025, he's actually built an app. It’s also quite simple. Caleb is the subject matter expert when it comes to board games. You can be damn well sure, if anyone is going to cook up an awesome app, it’s going to be him.

So, we got the team, we’re building our first product. All is well...