Dylan Kapoor

Dylan Kapoor

Published April 24, 2024

 • 2 min read

Last Updated April 24, 2024

The story of Ridella

The origins of Ridella, a riddle-solving game designed by Dylan Kapoor. Because after all, what is up with the obsession with riddles?

What is the goal of Ridella?

My mission is to create the best riddle for every common word in English and become the greatest riddle master of all time.

But why the obsession with riddles?

I have always been a huge fan of puzzles and riddles. When I was in college back in 2016 I co-founded Escape 45, Baltimore’s first escape room.

Escape 45 founders
Escape 45 founders

I designed the rooms myself, and found it rewarding to see guests solve the challenges and have “ah-hah!” moments. Since then, Escape 45 has closed, but my love for riddles stayed strong. When I proposed to my now-fiance Ella, I took her on a scavenger hunt where she solved five different riddles I wrote which led her to the location where I popped the question.

handwritten riddle with a drawn map
handwritten riddle with a drawn map
Dylan proposing to Ella
Dylan proposing to Ella

In my time solving and writing riddles, I have noticed problems that make them unappealing for many players. For one, there can be a big gap in skill levels between players, making it difficult to write a riddle that is appealing to everyone. Second, quality riddles are hard to find, with many having the same repetitive solutions (like “The letter E”). Ridella addresses the first issue by revealing the lines one at a time - an experienced solver may only need 1-2 lines to solve the riddle, while a new solver may require all 4. The second problem is more challenging to address, and relies on me iterating and learning what makes a riddle good or bad.

The idea to create a daily riddle game with consistent, high-quality riddles has been floating around my head for a while. But the thought of writing a new riddle every day was daunting. Luckily, I was laid off from my software engineering job at Slack in Feb 2023 and thus had way more time to devote to writing riddles!

So I programmed a rough version of the game as Daily Riddle in around a week. It was only family and friends who played it initially. Then, I posted the game to Reddit and was blown away by the response - over 10,000 people played in one day! At that point I decided to work on improving the game and renamed it to Ridella - after my fiance Ella.

A good riddle is challenging, yet fair. It is a fine line to walk, and I know that not every riddle lives up to my standards. But as I collect statistics about solve rates for the riddles, I can identify the riddles that need improvement and rewrite them.

Anyways - Thanks for reading this and playing Ridella! It has been truly rewarding seeing how many people across the world are enjoying the game. Want to get in touch? Use the contact form here to drop me a note.

Dylan Kapoor