Not necessarily, there are plenty of examples where earlier success did not lead to future success. A recent example that comes to mind is CloudKitchens? I could be wrong about CK, so happy to learn differently.
I am not sure why you're stipulating that there needs to be a threshold of minimal examples to present a contradictory pov, or why you need those counter examples to be greater in number. Most mammals don't have bills, but platypuses exist. Should we not describe a paltypus as a mammal simply because there are not enough examples of this type of animal? Or maybe I misunderstand your point.
Yes, they said "more likely", so I think what I said still works because just because you were successful in the past doesn't mean you're more likely to succeed in the future in all circumstances, i.e., if you extrapolate an infinite number of scenarios then your likelihood of success doesn't remain constant in each and every single one of them. If that were the case, then we wouldn't have Lehman brothers or Polanski (filmaker) or SBF.