I'll nominate GoPro as case where bootstrapping's quirky virtues helped make everything click. Doug Woodman's basic idea dates back to 2002 or maybe earlier. His early iterations of ultra-mobile cameras were slightly successful but not yet the winning version.
By poking around, subject to the uniquely loose/tight constraints of what he could fund selling beads (!) and early prototypes, he bought himself a lot of time to try to get it right. Perhaps it was a case of available technology needing the better part of a decade to catch up to his vision.
With a big, impatient burst of SV funding at the start, version 1.0 of GoPro might have been a Segway-like flop.