Pocket gun is all you need!
I have always wondered about the veracity of that ad.
The Colt 1908 is 4.5" long which makes that bear somewhere around 2 feet or slightly longer.
That's awful small for a "300 pound bear".
I suspect what happened is that the gun looked small enough actual size lying on the bear as to be barely visible.
So they made the gun picture bigger and pasted it on the bear (which now makes the bear look smaller).
The gun and the bear were obviously photographed at different times and places.
My in-laws had a Browning .25 and it was so small my finger would barely go in the trigger guard.
I'd rather be toting a .22 LR any day over those things.
American Handgunner .25 ACP Ragtime Wonders - American Handgunner
Colt Model 1908 Vest Pocket - Wikipedia
I don't have a 296 but do carry a 396 quite often when the 696 would be too heavy over the long haul on my belt.
The 44 special with either Elmer's bullet or one of Veral Smith's is a good choice if one is not stricken with magnumitis
(which I'll admit to contracting occasionally).
It's all about what you are confident in and practice with.
My BIL in northern Wisconsin does get black bears visiting their back porch.
He keeps a 9mm near the back door because that's what he is good with (ex Navy pilot).
Way better than nothing.