Once a year or so, everyone at our company gets together for a week to hang out, work together, and socialize. Because 37signals consists of 28 people located in nearly 20 cities around the world, these get-togethers are rare—and important.

Before our most recent get-together, in the summer, I wanted to focus on improving our products. I felt we were getting a little complacent. Sales were rising, and customers seemed happy, but it seemed as if it had been a long time since any of our products had gotten materially better. We weren't adding as many killer features as we used to.

A couple of days before the crew arrived in Chicago, I found myself watching a celebrity roast on Comedy Central. The guest of honor was Joan Rivers. One at a time, comics like Carl Reiner, Gilbert Gottfried, and Tom Arnold took the stage and just ripped poor Joan to shreds. "When Joan was born, the doctors took a look at her and said, 'Holy shit. We're going to make a fortune on this one,'" quipped the show's host, Kathy Griffin. "And then they got on the Mayflower and set sail for America." The camera cut to Rivers, who was laughing just as raucously as her tormentors and the live audience.

That's when it hit me: What 37signals needed was a roast.

We wouldn't be ripping on any individuals. Instead, we would roast one of our products. I figured the best victim would be Basecamp, our project management and collaboration software. Basecamp has long been 37signals's most popular product—and as a result, it was also the most sacred. Of course, because every employee works on Basecamp in one way or another, we'd also be roasting ourselves. It wouldn't be as racy, or nearly as funny, as the filleting of Joan Rivers, but discussion would be no-holds-barred.