I think it was pdubya that asked how I carved an arrow in a sheath. I did this project yesterday, and took a few photos to show you how. This happens to be for a West Virginia fan, but WV, arrow, initials, it doesn't matter, all done the same way.
I hope this helps some here.
First, draw out your design on cased (dampened) leather. Draw very lightly, and use a knitting needle or other semi-sharp object. A ball point pen will be perfect IF you disable it and keep it from writing.
Then make cuts in your design. I am using a simple and inexpensive knife for leather. The swivel knife shown on the table is better for curves, I prefer the red handled simple knife for straight cuts.
Here is the design, with all cuts made.
Here are three very basic stamping tools. The tool to the right is used at the edge where you cut, to make the design stand out. The little texture tool is for textured background and the rounded pear is to give some depth to overall carving.
My bad on these next crappy photos, hard to do it yourself. I am taking the angled tool, holding straight up and down, put the deepest part of the tool next to the carving (outside the carving), and tap. Move around the carving, it mashes down the leather outside the carving and leaves the inside raised. Tap, don't whack, with your hammer. Some use leather mallets, some use wood hammers or sticks, I use a dead blow. I like to tap and not whack.
I got inside the logo with the little texture tool. It is not always necessary to tap with hammer, these little tools can simply be pushed with your hand and make an impression. I think they call it finesse.
Last thing I do is go around the whole carving with the pear tool, which smooths out the tool marks around the carving and gives it more depth.