It’d been a few months since I’d left Compuware and set out, once again, on my own. Shirt Pocket was initially formed to create products for PDAs, a market segment that I’ve always found interesting… hence the name.

I was still working on a PC—an IBM ThinkPad T23—and while I had some good ideas, I was having a lot of trouble getting going. The design part was relatively easy—I knew what I wanted to achieve—but transitioning to coding was going poorly.

Our dog Ketzl needed TPLO (Tibial Plateau Leveling Osteotomy, pretty radical stuff) surgery to recover from a torn anterior cruciate ligament (Skier’s Knee for Dogs—who knew?), and that required an extended rest-and-recovery period: a time where she required near constant nursing. Since I work at home, I got to be the “dog nurse” as well.

Ketzl needed attention fairly often—a constant interruption. I’m usually pretty good with that kind of thing, but I was finding it difficult to keep focused on the task at hand: coding the new product.

Just. Wasn’t. Happening.

I put the whole thing to the side for a while and focused on Ketzl. And read. And listened to music. And got frustrated with my CDs. It was just too hard to find the music I wanted to listen to.

While I’d spent a little time ripping some CDs to my computer, it was clear that the PC-based music players just didn’t have what it took to be usable. I tried all of them, even wacky and obscure ones like B&O’s BeoPlayer (stylish, but absolutely horrific usability): they just weren’t working for me. It was too difficult to find music, even with a modest amount encoded, and I’m not of the type to shuffle everything… I know what I want to hear, and that means I need to find it.

Years ago, we’d used the Macintosh at UnderWare to do our in-house email and various other things that Macs were good at, but after Zabeth had a horrific experience with a 6300CD (from the Dark Days), we stopped buying Macs here (and tossed that one off the roof, which was strangely satisfying). And when the Newton was discontinued, I stopped following what Apple was doing very closely. While there was a lot to admire in Mac OS, it seemed to be maturing poorly, and OS9 just didn’t do it for me.

The introduction of OSX, though, piqued my interest. I’d had a NeXT cube back in the day, and did a lot of Track Record’s design—and nearly all its internal documentation—on it. Although its screen eventually became too dim to use and the whole thing was sent to the Computer Museum (aka the basement), it served me well for years: it was even UnderWare’s mail server back when we were “uw.com”. And now, it was back—sort of—on the Mac. And, when I went to take a look at it, I saw one other thing, too: the Mac had iTunes.

One quick look at iTunes made it clear that it was an excellent application. It organized things well, presented a simple and logical UI, and excelled at searching. Clearly great stuff. OSX looked good too: it felt less polished than iTunes—less well thought out—but had potential.

So, I made my very first computer decision as a user, as opposed to as a business owner. I bought an iBook. And, while taking care of Ketzl, I started ripping my CDs.

I outgrew the iBook really quickly: it was almost disturbingly obsolete, for my use, in days. Sold it and bought a PowerMac G4, then a Powerbook… an obsession had well and truly started. And OSX was better than I’d hoped. It was terrific. I was enjoying using my computer again. It’s good to be a user!

As the time taking care of Ketzl went on, I’d managed to rip about 2000 CDs (don’t ask—I’ve been collecting music for a long time), and had begun to realize one big problem with digital music: sure, I could use it on the computer, and on an iPod (or whatever), but it didn’t connect very well to my “real” stereo. And here I have a whole-house system that was crying out for that connection.

That wasn’t so easy! The main receiver was in a totally different part of the house. Running an audio cable was out of the question… but I could network up there, and attach another Macintosh, and share the disk that has the music library…

So, that done, another problem reared its ugly head: the computer playing the music was far away from where I was listening, and heading over there every time I wanted to find music was no fun at all. I tried using Apple Remote Desktop and VNC, but they were awkward (at best)—I didn’t want to take over the whole computer, I just wanted iTunes.

And that’s when I came up with netTunes. I just wanted iTunes, remotely. Exactly iTunes. So, that day, I became a full time Macintosh developer: learned Cocoa, designed and wrote netTunes, released it… and haven’t stopped—or developed for the PC—since. (More about the design process in a future post.)

Not where I expected to be when I set out again in this business. But I’m awfully happy I’m here!