Step 1: Design in VCarve, Cut on the Shopbot.
TechShop already had the demitasse cups, so I set them up in a pleasant arrangement and made some measurements.
Using VCarve Pro, I drew a 7.5" by 13" rectangle, rounded off the corners and added 8 circles for the cups. Using the pocket function, I made a path to cut a .25" deep pocket for the cups to sit in, and then did profile to cut out the plank.
I tested it on some cheap wood (not shown) and then cut the Real Thing in some bamboo plywood I found in the scrap pile.
Step 2: Label It With the Laser Engraver
Once in Corel, I added some labels to enumerate the cups and added a TechShop logo and "Coffee Flight Deck" to the end.
After the first one took more than 20 minutes to engrave, I optimized the process by engraving "Coffee Flight Deck" in one pass and the numbers and logo in a second pass, reducing the engraving time to 13 minutes.