Introduction to Jay Cover Photo

046 – Painting Dice Boxes, Designing Merch & Managing Online Stores with Jay of 88Riddles


Today we get the pleasure of hearing from Jay, the owner and designer behind 88Riddles. You may have seen Jay for his painted dice boxes, as part of an add-on to several Kickstarters, or maybe for his t-shirt and hoodie designs. Jay is a super talented artist who has a lot of great wisdom to share on running a plethora of online shops.

If this is your first time tuning in to Roll Play Grow, hello! This podcast is a part of Lightheart Adventures, which is a small company I co-founded with my husband. We also do blogs, one-shots, and maps that you’ll find over on our website,

Today’s affiliate is one for my fellow entrepreneurs out there, who may be looking to upgrade your email marketing. FloDesk lets you make gorgeous emails that are completely automated, and I cannot speak highly enough of them. You can see an example of this by going to If you have popups enabled, within a few seconds, you’ll see a sign-up show up for a free D&D one-shot, or you’ll find other ways to get that sign-up throughout the website if you have pop-ups blocked. That sign-up is powered by FloDesk, and then it will email you a free one-shot and add you to an automated email workflow that I set up long ago. It’s very user-friendly to make new, gorgeous emails, and it’s very simple to schedule individual emails or create a workflow that messages your contacts week after week. If you use my affiliate link, you’ll get 50% off your first year. Go to to learn more about FloDesk and our other favorite things.

Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.

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Time Stamps & Screenshots

  • 00:00:00 Introduction
  • 00:02:09 Jay Introduction
  • 00:08:50 Starting his design shops
  • 00:11:35 How painting dice boxes turned into a business venture
  • 00:14:45 Collaborating with other TTRPG creators & pricing considerations
  • 00:27:03 Selling on Etsy
  • 00:36:26 Using pre-orders to balance inventory
  • 00:44:43 Streaming on Twitch: Watching Paint Dry
  • 00:54:13 What has been the most rewarding part?
  • 00:55:44 Upcoming projects
  • 00:57:40 Where can people find you?
  • 00:58:31 Wrap-up

Find Jay & 88Riddles at:

Show Affiliates / Some of Courtney's favorite things

  • FloDesk Easily create gorgeous emails. Get your 1st month free & 50% off for your first year.

  • Found Familiar Delicious coffee meets Dungeons & Dragons artwork. Use code lightheartadv for 10% off your order.

  • Friday Afternoon Tea Grab a cup of tea with blends based on your favorite nerdy series. Use lightheartadv for 10% off

  • Dice Envy creates beautiful dice in a variety of materials. Use lightheartadv for 10% off your order

  • Buzzsprout is my fabulous podcast host! Try it for free & receive a $20 Amazon gift card if you sign up.

Thanks for dropping by! We would love to know who would like us to interview, so please drop a comment here on the blog, on Twitter, Facebook, Instagram, or Discord to let us know who your favorite creators are! If you’d like access to more maps and content, including downloadable PDFs of our adventures, check out our Maps Patreon or Podcast Patreon. We’re able to do what we do because of all our amazing Patrons!

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