Dwight Beebe wrote: "...I used a feather file, more typically used to sharpen
Japanese dozuki and ryoba saws.  I used a Starrett punch for the
center dimple.  I also tried a very fine triangular saw file, but it was too
much of an angle...  Lots of trial and error, followed by grinding down to clean
metal and having a go at it again, and again, and again."

I've cut a lot of bookbinders' finishing tools, pretty much the same thing but
in brass and with different shapes. And at one time a lot of leather stamping
was done with simple shop-cut stamps rather than the complex Craftool-type ones.

Give the triangular file another chance. You can't go as deep with it, but you
don't need much depth for stamps, and a tool with the 60 degree spread from the
face is a lot less fragile than a tool with deep narrow cuts. Also, with a
triangular file you can correct mistakes by filing down the face just a little
bit, which will spread the lines and narrow the counters (the areas that will
print white), allowing you to correct without going all the way back to the
beginning. Most typographic punchcutting was done with small triangular files
and burins, and with shaped counterpunches (like your Starrett) for the
counters. For most designs one would work in at an angle from the side, as I see
you're doing on some of your stamps, not flat to the face, which is a lot
trickier.
A good-quality set of needle files is extremely helpful; you need jeweler's
files with sharp arrisses, though, not the hardware-store Chinese-made ones,
which don't come down to a sharp edge. Or, failing that, get a thin chainsaw
file, say 1/16", which will give a lot of scalloped-edge possibilities. Binders
used to use a lot of little leaves in left-and-right pairs, and closely related
pairs of tadpole shapes. Less common, but very useful, are little single flames.
Small simple stamps are more versatile than complex ones.

I find that files and burins are much more useful than a Foredom or Dremel tool.
The files help to guide your hand and create the shapes, and they cut at a
comfortable rate. The power tool doesn't actually speed things up very much, but
you have much less control and you have to bring your shapes out of your eye,
not out of your hand.

The radiating-line shapes are, in my experience, among the most difficult to
cut: for some reason the slightest irregularity shows and looks bad. On the
other hand, one of the most useful stippling tools is a simple circle like an
"o"; make the counter of the o with a punch or a drill and then file the outside
with about a 45 degree spread. It's surprisingly easy, especially by comparison
with radiating lines.
I was first taught to have the tool (i.e. the stamp) I was cutting upright in a
small machinist's vise, holding the files with both hands, even for the fine
lines. I later learned to use a jewelers' birdsmouth, that is a board with a
small v-cut in its end sticking over the edge of the bench, preferable set on a
high support or sitting in a low chair so that the birdsmouth is close to the
eyes without stooping over. The stamp being cut is held in the left hand and
braced against the birdsmouth, and the file is held in just the right hand. Even
if you like a birdsmouth it is easier to square the face and rough in using a
vise.

Some of the older leatherworking books have designs for shop-made stamps, and
suggested patterns for combining them. If you can find a copy of John W. Dean's
"Leathercraft: Techniques and Designs" (Bloomington: McKnight and McKnight,
1950) there is a particularly good section on shopmade stamps on pp. 60-65.

Tom ConroyBerkeley