The opportunity from the early days of the American frontier is not typical. Instead, it's the brief burst of unrestrained growth as a better-adapted organization (the US, software companies) expands into, and expands, a niche--cannibalizing the previous occupant (Native Americans, older stagnant companies.) At times growth is so rapid that individuals are able to advance the frontier, but if the field stagnates, individuals will be outcompeted by corporations.
So, opportunity for individuals comes from disruption. Creative destruction is good up to a point, but it results from advancing capabilities. Technological advances compound and accelerate exponentially. Eventually we reach the point where any malcontent can destroy the world by snapping their fingers. At some point we need to place restrictions on the capabilities accessible to individuals. We have reached that point with nuclear weapons, and I think it is sensible to believe that AI is reaching that point as well.
Frontier mythology also hides quite a lot of tragedy and deaths too because of how many native Americans needed to die for it to be a frontier. It was not by any means unsettled land.
> Yes, but today a 16-year-old building a unicorn is about as likely as winning the lottery.
In today's world, a new digital service is more likely to be successful when attached to celebrities than from pure PLG / Marketing.