Riddle Earth

I’ve reached peak nerd.

Today, in conjunction with a group of friends, I’m excited to launch Riddle Earth— a newsletter and website dedicated to original riddles. It’s in beta now, but it will continue to evolve over the coming weeks.

The origin of Riddle Earth can be traced back to the depths of Arizona’s Lava River Cave. After hiking the Grand Canyon last year, Kyle, Kevin and I ended up exploring Arizona’s longest cave.

Then this happened.

in the cave

A week later, Kevin followed up with this.

(I was right)

Like Bilbo and Gollum, we began creating our own riddles and challenging one another.

Sporadic riddle threads emerged over the course of a year. One day, I decided to pitch one of my riddles to colleagues over our weekly bagel breakfast:

I go bump in the night and also in the day.
I’m not necessarily broken, but if I appear, I need to be fixed.

Despite my name, you’ll never find me in the kitchen.

Stumped, my colleagues asked that I email them the riddle. I look around, and everyone has their day’s work on their laptops and my riddle on their auxiliary monitors.

After a couple hours, no one guessed the correct answer. So I added a new line upon request.

I can be shallow, but you really want to avoid me when I’m deep.

Within minutes, two correct answers were excitedly emailed to me. One came in all caps; it was the definitive answer.

This was the spark. I wanted to replicate what happened at work and create an email newsletter that would provide a riddle in the morning, allow people to guess the answer, and provide the solution in an afternoon email.

With a working concept, we now needed a name. Ideas we kicked around include Malcolm in the Riddle, Riddler’s List, Riddle House on the Prairie, and BetteRiddler.net.

Kyle then sent a text: Riddle Earth.

It has a tie-in to our origin story, and more importantly I imagine there is a 95% overlap of people that enjoy both riddles and The Hobbit. As a name for the site, it was perfect.


I did a bit of research, and the few riddle websites in existence today were either created in the 1990’s or rely on Microsoft clip art from the same era. There’s an opportunity for a modern riddle website, and that’s the goal of Riddle Earth.

Our riddles have three major tenets:

  • Original — You can’t Google the answer. There is no instant gratification — you have to use your brain.
  • 3-point shots — They aren’t layups. You’re not going to make every shot, but it’s more rewarding when you do hit it.
  • Definitive — When you get it, you know you got it.

In addition to Kyle and Kevin, my brother Zack helps craft and refine riddles, and my friend Christine is developing the website and tool.

We’ll send out new riddles by email every Monday and Friday. Check out today’s riddle here and be sure to sign up to receive our emails!

Over time we’ll include score tracking, a leaderboard, archives, an overhaul of the design, and more!

Welcome to Riddle Earth.


(As we’re in beta, please provide us with any and all feedback! You won’t hurt my feelings )

3 thoughts on “Riddle Earth

  1. Pingback: Parenting During a Pandemic | Mike Munsell

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