And that's probably why they'll win. This generation of payment technology isn't going away in the next 12-18 months. I bet we won't see the next generation surpass this generation (in usage) for at least five years. During that time, someone like Square can build tremendous momentum and relationships that will allow it to much more easily transition to the next generation, because it has a strong brand, strong relationships with the marketplace, and corporate competency in the space.
For a fantastic example of what I'm talking about in another space, see Netflix.
Maybe. But relationships with whom? Why would a large retailer want to use Square? Why would a competing point of sale vendor with an enormous installed base want to work with Square?
Netflix isn't a very good analogy. The retail payment space involves a three-sided market: consumers, merchants and POS vendors. Netflix didn't even have to struggle with the complexity of a two-sided market. Though it's done well for itself, it also hasn't completed rendered the previous standard useless. Plenty of people use DVD and Blu-Ray today.
I think your view is possible but I'm not sure I understand the details. In contrast, I can answer both of those questions given the model for my company's technology.
I agree, Square has the best possible strategy -- they catch the laggard businesses who still don't have merchant accounts, individual people who have never had merchant accounts (i.e. everyone) and let them get away from PayPal, AND get a platform deployed which can handle NFC or some new payment/loyalty credential for early adopters on the merchant side.
On top of that, Keith Rabois is one of the top operating executives anywhere, and has extensive paypal experience.
NFC has been "the next thing" for years. I worked for an NFC reader company in ... 2003, which had been around for years. (ViVoTech). We don't even use chip and pin cards in the USA -- the magstripe is going to remain a major part of the market for the rest of the decade.
For a fantastic example of what I'm talking about in another space, see Netflix.