How did you end up working at Microsoft?

It was my first job out of college. I did a summer internship at Microsoft before my senior year. Didn't like it. Went back full time, didn't like it. [Laughs] Got transferred to Microsoft in New York. What I didn't like was living in Seattle -- I wanted to be on the East Coast. I transferred back to New York, spent another summer in Seattle working on MSN 1.0. Didn't like it. Eventually realized that I was just not going to like living in Seattle, and gave up on Microsoft.

I spent a few years on Excel when it was really sort of at the peak. It wasn't like the early days of Excel when they didn't know what they were doing. They had learned all the good tricks, and they were performing at their peak. And of course after I left everything went downhill, because it always does. The Excel team at some point decided they didn't really need to hog all the good people, and so they started farming out some of the best people to other teams. Once you have 100 percent market share, there's just really no point.

Because there's some point at which you have a product that does what people want it to do, and you've basically solved all the difficult problems?


Joel on Software

By Joel Spolsky

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Or you've completely hypnotized yourself into believing that you can't solve the remaining problems, such as the limit on the number of columns that Excel has, the fact that cut and paste doesn't work right -- all those little problems.

So you say, "Those will never be solved -- let's do something else"?

Exactly. It's kind of weird but everything that's happened in Office since about 1995 has been more or less user interface churn. Oh, let's put in the paper clip! Let's take out the paper clip! Or slightly redoing the toolbars, and then you have to do it for every single product. There's all this flotsam that's not the actual core functionality of the product but just crap on top of it. It's good crap, but once you get to 100 percent crap ...

Have you been writing all along in your career, or is it something new?

Only for four years. Joel on Software started in summer 2000 or so. I'd written papers in college.

You weren't writing away on the side and at some point decided to go public?

No. My job at Microsoft was program manager, and I was told my job was to write the spec, and I didn't realize that I could have, like many other program managers, found various excuses to not actually write a spec. So I did it. It was long and detailed. What I was doing there was really writing to a large extent. I got a lot of practice with the use of the typewriter.

Your company makes a content management system and a bug-tracking tool. Which came first?

We really started three companies: a consulting business, where we made a lot of money in the first two months, then that market just completely collapsed in November 2000, and we were back to just the two founders working on the software side. We produced CityDesk, which did OK, nothing to laugh at, but it wasn't a megahit, it wasn't really on fire. It had some design decisions which I wouldn't have made today, necessarily, and I still feel like there isn't a heck of a lot of money to be made from blogging tools, basically.

The bug tracking, however, became enormously popular. We sort of had a way of doing it that resonated with people. We were very high on the usability score; we had a ready-made audience in the Joel on Software audience of people that might consider using it to spread the word. So we put most of our effort into that, and we consider that to be our lead product right now. We're about to come out with the first beta of version 4.0.

There are so many stories of software start-ups that set out to make one thing and then find their real product in a different direction. And there are so many people making tools for developers.

That's a common mistake I never would have made, and that's why this was our lowest-priority thing. The mistake comes from the fact that you say, "I would want this, I would buy it -- surely everybody else would buy it!" And you don't realize quite how exceptional you are. And there's never that large a market for development tools, although there seems to be a pretty big market for FogBugz.

I keep hearing that the market for small or medium-size independent software vendors -- anyone besides Microsoft and open-source providers -- is dead.

Rubbish. Completely not true, because I sell software to all those companies. There's actually lots of software companies out there that nobody's ever heard of because they're in a niche. You ever heard of Blackbaud? I think it's a couple of hundred people; they're in, like, South Carolina. And they do software that you use for fundraising, if you're a charity or a charitable organization. And they're making piles of money selling to charitable organizations. They're the No. 1 package in that particular market -- Microsoft's never going to go into it. There's tons of good software businesses out there. Besides which, for all the fear of Microsoft, they've not really demonstrated the ability to move into a new market since the days of Office. How long has it taken them to get anything out of MSN that works?

Eight, nine years?

And the strategy changes every single year, and it's never very good. You probably remember when Microsoft was trying to do content.

You mean, when was it, 1997, and they were doing "shows"?

Yeah, shows. And they were all terrible. You know why they were terrible? They were tone-deaf. It was like they knew that there should be some kind of creative person. And a creative person should generate something called content that could be thrown up on a Web site, throwing in some advertising. But they just had no ability to generate that stuff.

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