Honestly, I thought Square was kind of broke. Most of my contact with Square is in small cafes and restaurants, making this pivot kind of bizarre. Why would any food service company sign up for payment services with a company that's also competing with them? Stripe should be all over that angle.
I've also seen a long-term upward adoption trend for Square in small businesses in my area. Some of these are at their first-time accepting credit cards, especially at local farmer's markets where Square's adoption has increased from a fringe payments player to near ubiquity (>90%) over the past three to four years. It's also been interesting to see an increasing trend in businesses switching to Square from traditional wired or wireless credit card systems.
Every time I hear that Square isn't doing well financially, my heart sinks a bit. From my experience, it seems that they're nailing an underserved market and greatly improving the experience for these small businesses and their customers.
Go.com, Lycos, AltaVista, Excite, Yahoo!, Dogpile, Ask.com, Yandex and many other search engines existed before Google entered. Most were wildly profitable.
Sometimes it helps to read the articles you link to. None of them show that "Most were wildly profitable." In fact, those articles mention that search engines before google struggled to make money.
That's a good point, but Square and Stripe aren't really competitors, so I'm not sure what the opportunity is for Stripe (unless you are suggesting they launch a card reader).