Back in 1986, I ran a top 20 Inc. 500 merchant payments company and executed what became the first documented Internet transaction.

Before Apple Pay even launched, I built PayFinders—a location service that could map Apple Pay-accepting merchants better than Apple's own infrastructure could. Got into early meetings with Apple and flagged the gap in their merchant discovery system.

The irony: a third-party tool was outperforming Apple's native merchant database before the product even hit the market. Classic case of external developers understanding real-world payment infrastructure better than the platform holder.