(My original intention was to also create chess pieces from his favorite video game, Skylanders, but with a little sense in my brain, I abandoned that part. Had i not started this 1.5 weeks before his birthday, I might have accomplished it. ;-)
Step 1: I started with a grid on Illustrator and created the squares at 1.5", then once I had created the board with 64 squares, I created a border to put his name on. You can download the file and change it, of course. I then added the center stars, selected all and used the Live Paint function for the color.
Step 2: Find some great wood for contrasting color. I went to a place called Rockler @ 7402 McKnight Rd, Pittsburgh, PA 15237 (pretty expensive, but worth it since I was a slacker and didn't buy my materials in advance enough to get a better deal). I used two pieces of 3"x24" for the squares and two 1.5"x48" pieces that were pre-milled and cut. It took me a while to settle on the colors that would suite the design I created, but I'm happy with my choices, 4 different wood colors in all. (This can, of course, be achieved cheaper with different wood stains on the same type of wood.)
Step 4: Created cutting templates for the Trotec using my original sketch. I used a total of 3 separate files. ( I combined the art boards below onto one file.) Make sure to change the color to 255 Red 0 Blue 0 Green and to make the stroke .001.
Step 5: Assemble pieces (interchanging the stars and letters with opposite wood) onto a 15"x15" board. I glued the border down first to create the frame, then the squares row by row alternating wood colors.
Step 6: I used a wood filler to fill in the separations and once dried I took a palm sander to sand the surface down to an even, clean and flat surface.
Step 7:Finish with a wood sealant like polyurethane or wax, and there you go!