In 2012, my friend invited me to his birthday party at Michael Minna in San Francisco. Now, this quickly became a shitshow as it was not a crowd of people who normally went to such an establishment and we all drank like fish. Since I was dressed appropriately and me being me, I grabbed the waiter and kind of took control of the situation and made sure everyone got drinks, ordered some appetizers for the table, and generally managed things so it didn't get too out of control lest we get kicked out. At the end of the night, the waiter quietly slipped me the bill. It was $8,000. Now, the wealth disparity at this table was huge. There was a couple that had split one beer all night and another couple that had ordered filets and multiple bottles of very expensive wine. I asked how many cards we could split this between. Four. And these were the days before Venmo, Cash App, etc.. I quickly started doing some math but realized it was fruitless as people were already leaving since we were late to "the club" and no one seemed to care about paying or had cash. I grabbed the affluent people at the table and got them to contribute as much as possible, but at the end of the night, I ended up paying more than half the bill myself. In the end, my friends bought me dinners for months and were very appreciative and I enjoy giving so I wasn't annoyed.
But it got me thinking: there has to be a better way. So I build an app based around scanning a QR code on receipts, getting your receipt on a web app, and splitting your bill in real time. It worked really well and was actually quite more advanced than even today's solutions like Toast's.