You can crank out cutting boards like that with not much more than a bunch of clamps, a small drum sander, a miter saw, and a good vacuum cleaner - garage-friendly and under $2,000. The issue is the hours of manual labor you have to put into this, especially since people are not used to paying hundreds of dollars for a decorative cutting board.
There are custom cutting board businesses out there, but they just use a CNC mill to cut personalized shapes or messages in common stock. That's a larger capital investment but far less manual work.