By 1999 when blogging became more popular, DDS (the unfortunately unappealing acronym for my first startup) had grown so much that I had to split it into two companies with a total of perhaps 60 employees. I was also an executive board member and CTO of a venture backed online mortgage company. In retrospect, I probably would have both enjoyed and benefited from starting a blog at that time. But I was too busy, or at least that is what I told myself.

Which leads us to the question, “How far ahead of the chasm am I?” I am speaking of Geoffrey Moore’s chasm, of course. Am I an enthusiast or a visionary? Or (shudder) am I part of the early majority (the first post-chasm group).

My wife would like to peg me as the earliest of enthusiast adopters, always trying out the newest and uncertain technologies. As evidence, she would present the very nature of Blir, one of my more successful (prior) companies.

Blir was a custom software development and technology strategy consulting firm. For clients such as Albertson’s, Exodus Computing, and Bain & Company, we cut deep into the bleeding edge of technology to find ways to improve performance or create new business opportunities. The technologies we used were typically so new that our clients had very few people to turn to for implementing them. It was, of course, a critical part of the way we won business against the much bigger players in the market.

In response, I would point out that while we used cutting edge technology, our goals were eminently practical. Enthusiasm for the technology itself was far less important than excitement about what it could do for a company. In 1996-97 I had failed with an angel backed e-commerce marketplace. That (hard) lesson taught me to think twice about technology opportunity. Part of Blir’s marketing was that we could leverage our past failures to benefit our clients. The web, after all, was still a very woolly and frightening place.

By now, I can tell far too many stories about how uncertain web technology and startup businesses can be (mine included). Have these experiences changed me? Made me more reluctant to jump into new technologies? For example, I have put off purchasing an iPhone until version 2 comes out (I want 3G support). Also, I’m rarely the one playing with the latest nightly builds of an open source project. I go straight to the most stable release, and stick with it until there’s a reason to change.

As a serial entrepreneur (and sometime venture capitalist), it is my job to keep abreast of the latest technology. I like to think that I’m in the “visionary” bucket of adopters, which is where I think people such as I belong. But are hard knocks pushing me back along the adoption curve? Am I becoming a part of the “early majority” of adopters? My wife would tell you no, but it’s definitely something I’m keeping an eye on.

Readers, where are you on the adoption curve? Where do you think entrepreneurs should be?