I have also learned - discovered - that gambling on ideas is by far more interesting and, in the long, rewarding than betting the financial market.
I enjoy reading stories like yours where a personal leap back in history make it so clear just how far we have come in such a short timespace. Startups back then was groundbreaking and have more than one resemblance of the old wild west, not just location.
Recently I took the MOOC How to Build a Startup at Udacity. Even though I had a fair idea of it since before, that course was brilliant to watch and really helped laying out the framework in a forward thinking way.
I'm beginning to think of startups as just that, forward thinking with a great belief in that their idea will work out in the future. In relation, historically business have been, still are to much degree, about cashing in on already created results.
Maybe that is also making the sharing economy harder to grasp, because it so radically different?