Where is the Logical Fallacy?

Now you seem to be equivocating. In your OP, “starting a business venture or career” wasn’t what you apparently meant by “winning”, nor “failing to start a business venture or career” what you apparently meant by “losing”. So I must ask at this point, what are your intended definitions for “winning” and “losing” for this thread?

As far as I can tell, this conclusion fails to hold for at least two reasons:

  1. “Nearly always” isn’t the same as “always”.
  2. More importantly, starting a business venture or career isn’t the same as succeeding in said business venture or career.

A deterministic assertion means that there can be no other way. Even one outlier is enough to cast the entire assertion into doubt. While you claim that your assertions in the OP are deterministic, you have not yet demonstrated this logically. Empirical evidence doesn’t matter here.