Along with three partners, I started a business in 2004. From the outside, it looked like a trading firm, but from the inside, it was quite clearly a technology firm. We purpose-built a massive software system to realize our trading strategies. Our commitment to technology would be reflected in our employee rolls: on the day we sold the firm in 2009, we had two traders and seven technologists. This is common practice in this sector…what we do is so specialized and difficult that there really is no off-the-shelf product that works. Everyone builds.

The timing couldn’t have been worse when the markets fell apart in late 2008. We weren’t generating enough revenue to support our costs yet, and just as we were about to go out and try to raise more capital from our investors, they were watching their own personal fortunes crash. No one was in the mood to dump more cash into our fledgling, uncertain business as it was then structured. Our only choice was to sell the firm: the people, the assets, and especially the software. We did, and things worked out OK.

Recent events have given me reason to reflect on the business model and software system we built, still in use today. Steve Jobs’ passing adds a new dimension to my analysis / navelgazing.

What did we do right, especially from an Apple-ish point of view? Well, certainly, we focused on design. Elegance mattered. Doing it right mattered. It wasn’t a question of applying the Broken Windows Theory to our system flaws; it was about making those windows out of quartz in the first place. It was tight. Were there problems? Obviously. All systems have them. But I felt good (and still do) about the modularity of that design. As we identified weak spots, we could replace them on top of an infrastructure that made it possible without taking a backhoe to entire swaths of the codebase.

We also built a damn good team. Hiring well is the most important thing any business can do, and it’s that much more critical in a small business. We had a couple of misses, yes, but we also had a couple of rock stars. We all made each other better…no one wanted to be the derp fixing bugs in production. Great advice I once got from a manager of mine was to never be afraid to hire someone smarter than me.

We had a vision, technology-wise, and we followed it. We took our time and invested in the foundation. We sweat the details. We were all pulling the same way.

Now, don’t get me wrong; I would never dare to compare myself to Jobs in any way. I’m not sure we’re both Homo sapiens, and in terms of business sense, design ethic, marketing, and all the rest, the gap between him and me is measured in parsecs. Just saying: we did a few things Apple-ish, and these things I’m still proud of today. They are still working in production. Other systems I deal with aren’t close to that level of elegance or operational smoothness or extensibility.

But the business failed. So it couldn’t have been that awesome after all, right? I mean, some of it was due to market conditions, but ultimately the responsibility is mine. So, what I am wondering tonight is: what if we’d been more Apple-ish? In terms of our technical vision and our business plan and our relationships with investors? What if we’d been more committed and single-minded and confident? What if we believed harder in what we were doing and fought harder for the outcome we desired?

Where would I be driving to work tomorrow morning if I’d been just a tiny fraction more like Steve?