In retrospect it makes perfect sense to not use an upcut bit with a masking film. 
As Jimmy DiResta says, “You go to school on the first one”.
EDIT: I made it work.
Happy making,
Nick
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Obligatory 20 Characters
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FYI, I use Oramask all the time with an upcut bit. You do have to make sure the mask is firmly attached to the surface of your material. I either use an old credit card edge or a brayer and roll the mask down. I also usually sand and seal the surface of the material ahead of applying the mask. Hope this helps. Better luck next time.
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I did some experimenting before running the clock in the video and learned the same things.
The stock for the clock was sanded-lacquered-sanded lacquered-sanded before being masked and a plastic squeegee was used to apply it. No bubbles!
I think my bit maybe sharp enough to cut wood but not sharp enough to cut plastic. It was also a 1/16-in bit so there’s not a whole lot of cutting surface there to start with.