Of course, for every Uber, there are many more failed companies. And for every investor who turns $5,000 into nearly $25 million, there are many more who decided to pass on the opportunity.

In the case of Uber, many early investors couldn't see how the product could go mainstream. It initially started upmarket with limousines, which was actually a clever way to hack the chicken-and-egg problem that plagues marketplaces.

Many also wondered how many metro areas outside of San Francisco had the kind of urban density and supply and demand drivers to support this kind of a service.

Today, some nine years later and many billionaires later, lots of people -- including myself -- are still wondering: Will Uber turn out to be a great (i.e. profitable) business? Hindsight is always 20/20.

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