Why did Stripe happen in 2010 and not 1999? Why did Column happen now vs 10 years ago? It feels like the use cases where already there - what was missing? TAM?

Does anyone know about this?

https://web.archive.org has the answer.

Re Stripe, compare any website 1999 vs 2010.

The web was basically homepages trying to figure out why they existed.

But Amazon/Viaweb/etc. showed ecommerce was a real thing, right?

They were gaining steam, but the small business/services thing just wasn’t tenable. Most hadn’t used a cc on the internet yet, and were  generally uncomfortable doing it.

bingo

it was budding, but concentrated and still a blip relative to retail

3PL and card networks opening up to smbs may have played the larger role... https://i.imgur.com/LWDr3oA.jpg

not explicitly, but finalizing a contract with a merchant acquirer was (and maybe is) a multi-month ordeal