Tim... What led you to build Web Crossing?
We did a consulting project for The WELL back in 1994/1995 that introduced us to online communities. The WELL was started by Stewart Brand, and was one of the first large online communites, with over 10,000 members, mostly from the SF Bay Area. We learned a lot from the project, and when it was wrapped up we decided to work on an online community server for the Web. Netscape had just released their browser, and the Web looked like a big winner, doing away with the need to write custom programs to talk to a server. We build our first version of Web Crossing in just over 6 months, and launched in Nov 1995.
What were some of the greatest challenges in the early years?
How did you meet those challenges?
One of the challenges was figuring out where the market was. My background includes developing mass-market software; I was the lead developer for Microsoft Works for the Macintosh, which sold millions of copies and was targeted at an easy-to-use, low-cost market. As a result of this background, our initial direction was to build a low-cost, high-volume product, one that everyone would license and run on their own server. It turned out we were way ahead of the curve -- there are a lot businesses running their own communities today on PHP/MySQL/etc -- but back then, the main customers were large companies and the market for online community software was not large. So a $400 product was not a big revenue generator :-)
We scrambled to increase the feature set, to add the ability to customize and interface with a large customer's existing web site, scale our service to very high traffic levels, and increase the revenue per customer. We provided community for Excite, at the time a big deal, running a cluster of servers for them for a very large community. We provided software for CNN, with over 100,000 posts made the day the Princess Dianna died in a car crash.
The Linux motto is "ship early, ship often", and we lived by that and still do. In today's environment, as a software/services provider, you are in much closer contact with your users than ever before; it is like being immersed in a sea of customers. So it is always a problem to sort out what is important from this ocean swell of feedback and respond to what is really important.
What led you to your interests in online communities?
Were there specific people, events, circumstances that influenced you to go in this direction?
Serendipity -- we were looking for a project and the WELL needed a team of good developers. Once we got started, some of the key people early on were Dan Shafer, the webmaster at Salon, who picked us to replace a home-grown solution that wasn't working, and worked with us closely to add key features. Bruce Katz, who owned the WELL, was an inspiration, with his belief that community was an important service, both to make the world a better place and as a viable business. Bruce was became a friendly competitor when he started Prospero and helped keep us working hard. Sylvia Marino has been one of our top (outside) community managers for a long time, and has helped us keep the product moving in the right direction with a number of customers.
How did your Mathematics degree prepare you for software development, and eventually life as an entrepreneur?
I was in the Math PhD program at UC Berkeley for a year, which is how I got out to the SF Bay Area. I found I was spending all my time programming instead of doing math, so took that as a sign that I should change direction. Math is fascinating, and the "aha" experiences you get from math are rewarding, but it isn't particularly useful for what I ended up doing. I am not convinced that formal education is that useful for being an entrepreneur: it seems to be more experiential learning, social/teamwork skills, improving your judgement over time. I read a lot, and there are a lot of good books available today, but a lot of the reading just helps organize things I already know to make it more accessible and useful, rather than being totally new ideas.
Was there any particular experience early in your professional career that provided that aha! moment indicating you were on the "right" career path? Or did your direction and interests gradually develop over time?
Funny, I was just talking about "aha" and math :-)
I've always liked to build things, and software development is like building things with thousands of moving parts that all have to work together. I had a minor in Computer Science at MIT, and would have had a double-degree if I had written an undergraduate thesis in CS. So making the change from math to software was pretty natural. Besides, I had to pay my bills...
What do you see as one of the more promising web innovations that has arrived in the past year?
The obvious thing is the use of Ajax and dynamic pages. This allows you to build a much better user experience, and to build real applications in a browser. The result is freedom from the tether to your desktop environment.
I also just got an iPhone, and it is an awesome device. Incredibly well done, with the potential to revolutionize the way people work and communicate. Being able to use a touch interface in a natural way, with immediate response, bright/clear/high-resolution screen, and small form factor, is incredibly exciting. I'm looking forward to building some really good interfaces from it to our software.
That's interesting what you say about Ajax being revolutionary for software development.. As a non-developer I didn't know that it was such an important breakthrough.
Yes, the combination of Ajax and dynamic html/javascript lets you modify a portion of the current page based on a query to the server, so you can have user interactions without having to reload the entire page. It changes the entire scope of what you can do with a browser.
Last year Web Crossing launched Web Crossing Neighbors, your software for building and fostering social networks. I understand recently you added video capabilities to this year's Neighbors 2.0 release.
I'm probably going to see the movie Sicko! this weekend, and so I have healthcare on the mind...
How do you think an offering like Neighbors 2.0 could help in the healthcare industry? Are there any examples of a Neighbors implementation with respect to healthcare?

Social networks are going to turn out to be an important way for people to help themselves. When you are sick, particularly with a chronic condition, emotional support makes a big difference, both in terms of feeling better and in terms of outcomes. Having a group of people working together to find solutions also helps treatment evolve and can find effective treatments that wouldn't otherwise come to be widely used. Social networks have a good set of tools for providing personal connection and helping develop the best treatments.
We see a lot of this with already with our existing community tools at places like WebMD, and we have a number of social networking instances coming up as well; I think they will be a big help.
For your line of work, if there is an annual meeting or conference that you cannot miss...
What is it? and why?
I always go to Forum One's Online Community Summit in Sonoma, CA held in Oct every year.
This is an invitation-only conference limited to about 65 people, and is always a good cross-section of the online collaboration space. For me, it is a chance to catch up with people I don't get to see very often, a chance to talk about trends, new technology and business models, and is a great time to reflect on what we've accomplished and where we need to go over the following year.
Forum One runs a number of other conferences during the year, and they are also highly recommended from our experience.
July 18, 2007