Microsoft Money 2.0 dropped in 1992 for Windows 3.1, and if you remember using it, you were probably the “finance person” in your family before anyone called it that. It was Microsoft’s big step up from the original 1991 release, adding easier checkbook balancing, basic budgeting tools, and the ability to track investments—game-changing stuff if you were tired of doing math on paper. Back then, importing bank data was almost sci-fi, so most of the time you were typing in transactions by hand. Updates through the early ’90s refined the interface and added small automation features, but the real hook was that Money 2.0 made personal finance feel accessible on a beige desktop running Windows 3.1. It wasn’t flashy—but for anyone managing bills in the ’90s, it felt like the future.