Let me give what I felt was a popular opinion when stripe launched: it seems like an iterative improvement with nice docs and a nice API - but what's to stop Braintree or anyone else from copying that tomorrow?

I think most investors would have claimed that Stripe would probably make money but would never get huge. Now they're pushing $2B - that is an extremely unlikely outcome and so fits sama's definition of black swan.

You should probably state what time period you are referring to when you recall hearing about Stripe..

I do not recall Stripe being positioned as a PayPal alternative really ever, but certainly not when it launched.

I also believe that Sam was first made aware of Stripe much earlier than most people and it probably did seem like quite a black swan at the time.

I know the very first time that I heard the idea for Stripe it was definitely considered a "crazy" idea. I would easily categorize it as a black swan investment.

The argument that Stripe was a black swan comes because getting into established industries with significant regulation used to be considered dead on arrival, now it's hip.

That's the heroic narrative used by investors like Sam, but I don't believe it.

Keep in mind Stripe's original name was /dev/payments. If you do some research you'll see they were in a pretty bad spot right until they opened publicly as Stripe.

Why?