Some time during my Junior year at Stanford, I got an email out of the blue from Dave Weekly. I had never actually met Dave, but he pointed out that we seemed to know the same people (the hip CS crowd, if I do say so myself)and have similar interests (I don’t remember exactly which were cited, but possibly Macs or startups or something like that). He suggested that we get together for coffee some time to chat.

I don’t remember exactly why that never happened back then. I think we agreed to meet, but never actually set up a time. I distinctly remember going through a phase back then when I was very wary of classmates who were starting companies. It seemed to me (rightly so) that startups were becoming too prolific at Stanford and the notion of leaving school and starting a company became almost hackneyed. I didn’t believe that any of my classmates would succeed in building a company right out of school so I guess I tended to shy away from the people who were most likely to attempt this.

Regardless of the original reason for our non-meeting in college, I recently started seeing Dave’s name on some blogs I read. I’m a big fan of boingboing, which listed Dave as a contributor several times. He also showed up on slashdot for his new venture, imsmarter. So with this reminder of the meeting that never took place, I emailed Dave (now about 5 years after the original exchange) and asked if he wanted to get together for coffee.

We talked a bit about imsmarter and Dave’s future plans for it. I’m not a super-active IM user, but I have to admit that some of the ideas for what you can do with an IM proxy seemed pretty neat. We also talked about Google and the general topic of regret over not jumping on that and other bandwagons. When we were in school, many of our peers (the aforementioned hip CS crowd) were joining Google. I never interviewed there, but I’m pretty sure I could’ve gotten a job. And that means that if I weren’t so stubborn over not following the herd, I’d be pretty wealthy right now.

I wanted Dave’s opinion on “Google Regret” because he has a roommate who works there so I suspect that he’s well aware of exactly how much one could have benefited by going there. Dave seemed to see the question coming and immediately said that he doesn’t spend any time at all thinking about it. He has no regrets, despite the fact that working for a year at Google could’ve given him the financial flexibility to do his own thing for the foreseeable future. For Dave, Google simply wasn’t the right place because he wanted to do his own thing from the get-go. This was takeaway #1: If you’re doing what you want to be doing, you haven’t made the wrong choice. I suppose this is something I already knew, but my reluctance to change my career situation when I knew that it wasn’t right demonstates that I hadn’t really taken this point to heart.

Dave spent about 20 minutes trying to convince me that I should start a company. Clearly, he has found it to be a rewarding experience. He extolled the ease and affordability of starting a web service company. He made a good case, and this is takeaway #2: getting started is easy. In software, the are few barriers to entry. I’ve thought a lot about this in the past, and my approach has always been to tinker with side projects while keeping my day job. Dave isn’t a fan of this approach — he thinks you need to either work on a project full-time or it won’t ever take off. I guess I tend to be a bit more conservative.

Another thought that arose out of that conversion, though I’m not sure exactly how it came about, is that I’ve found my notion of what it means to have a “successful” software company have changed. A few years ago, if you didn’t have a home run, you were nothing. Given the lowered barriers to entry these days, I think it would be possible and highly rewarding to maintain a small company, run by a few trusted friends, that is privately-held, cash-flow positive, and a great place to work.

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