It was 20 years ago today …

It’s easy to take for granted the mature tools available for music creation, and forget their history and the folks who made them real. While today it’s one of the biggest music software developers in the world, Cakewalk’s first sequencer of the same name started as a college project for a Philosophy major. Cakewalk founder, CEO, and original author of the Cakewalk sequencer Greg Hendershott was that student. For the twentieth anniversary year of the founding of his company (then known as 12 Tone Systems), Greg sat down with me in their Boston headquarters.

This was a personally meaningful meeting for me, as Cakewalk 4.0 for DOS (pictured above) was the first software sequencer I ever used — and remained my favorite some time after going to Windows. In those days, programmer’s names were front-and-center more than they are now, and so Greg’s name popped up every time I sat down to work. Greg also studied with Gary Lee Nelson, who was my first electronic music instructor (albeit for me at a summer camp). Of course, part of the reason it’s meaningful is that I’m far from alone — over 1,000,000 users have used Cakewalk’s software. A look at Cakewalk is also a look at the computer music software industry’s brief but fast-moving development, and the design of the tools that have evolved alongside it.

This winds up being a huge interview — you’ll believe me when I say this is basically a transcript of what Greg said. But it’s also a genuine slice of history, and also a glimpse into what the industry’s next 20 years might be like, so we’ll have at it.