TGiR

One of the reasons I ended up at Stripe was Alyssa Henry. Square had recently purchased Caviar, the food delivery service, and Caviar ran payments on Stripe. A group of us thought this was silly. A fantastic PM (Jess) and an EM (JAW) found me to ask what legal things they needed to build a set of payment APIs and make Caviar the first customer. The good news was that we had all the things they needed in-house. We just needed to sort out some PCI things (easy for us because Square had world class experts here) and do some online terms (easy for me). They took it to Alyssa and the project got vetoed. In her mind this was a simple buy vs. build decision. Stripe worked. We should put the resources elsewhere. She focused on the micro — what does Caviar need — vs. the bigger macro opportunity — online commerce was growing 3x faster than in person retail (Square’s core business) and we didn’t have a product. A recruiter from Stripe called me a few months later. It was a no brainer to do the interview. Alyssa Henry had basically told me (and a group of other people) that the Stripe product was so good there was no reason to move off of it. If another payments company like Square purposely chose Stripe, that felt like the place I — a payments attorney — should be. Square did eventually build that API and made Caviar one of its first customers (I was at Stripe when they asked for our help to migrate all the tokenized card numbers). But it was too late. Adyen ate European omni-channel enterprise retail and Stripe was eating everything else. I bet someone out there has a similar story for why Toast was able to outflank Square on restaurants. Alyssa has a great resume and has seen some fantastic things, but I’m shorting PayPal if this is who they’re bringing in as advisors.

Back to the Stone Age.