10 years of entrepreneurship

I recently passed my ten-year anniversary of becoming an entrepreneur. I almost didn't realize it, but there's no escaping the math. In the summer of 1999, I started working on a startup from my college dorm. I'd eventually take a leave of absence from school and pursue it full-time, making just enough progress to catch the tail end of the dot-com bubble - and all of the dot-bomb crash. As we say, it was a "good learning experience."

Since then, entrepreneurship has occupied me in one form or another pretty much full-time. Much of what I've learned over the years has been invested in this blog, and that makes creating a sweeping summation challenging. I'm honored to be advancing the work of putting entrepreneurship on a more rigorous footing. But that's still in the future. Looking back, what strikes me the most is not how much I've learned - it's how much time I wasted on stuff that turned out to be utterly unimportant.

I pretty much missed all the trends. I'd been on the internet since I was playing MUDs as a kid, but by 1999 I felt I'd already missed the boat. All the good domain names were taken, all the good ideas were being implemented. If I'd bought just a handful of the "best of the rest" domain names that were available at the time (for a whopping $70 each), I probably could have just retired right then. And the great ideas that became today's successful tech startups dwarf anything that had been done to that point. I just couldn't imagine what the next ten years of innovation would look like. Yet my feeling of having missed out prevented me from experimenting with ideas that might have worked.

Nonetheless, my first startup was a tool for college students from elite colleges to create resumes and help them find jobs. Getting students to create their online profile was easy, but getting employers to pay for access proved difficult. Unfortunately, we were fixated on "building a real business" and never noticed that maybe students would want to share their profiles with each other. Could we have built the first college-based social network five years before Facebook? Maybe, but the thought never even entered our minds. (You can even see the humiliating evidence of my smug incompetence in this absurd article from 1999.) We were focused on revenue, but we didn't understand that revenue is not important for its own sake in an early stage company. Instead, we should have thought of it as an indication of validated learning.

And speaking of Facebook, I definitely didn't think it was a good idea when I first heard about it. Heck, I'd already seen Friendster flame out. What was different this time? And Google? No business model, either. I turned down two opportunities to interview at Google in its pre-AdWords days. It seemed like just a bunch of research-oriented PhD's. Oops. And then, at my first Silicon Valley startup, I watched friends get laid off in successive waves as it started to fail. Almost all of them got scooped up by pre-IPO Google this time. I was "lucky" to not be laid off, or so I thought. Yet, as it turns out, the earlier you got laid off, the earlier you got your Google options. That year, right before the IPO, those months mattered a great deal in terms of financial outcomes.

And while I'm confessing, let me add that I knew Matt Cohler way before he was famous. When he left his consulting job to join LinkedIn (whatever that was), I didn't think twice about it. In fact, I remember sending him and his obscure-to-me co-founder (aka Reid Hoffman) a bug report early-on, instead of taking them up on their offer of an in-person meeting. Doh! And when Matt left LinkedIn to take the reins at Facebook; once again, it didn't register. I was much more focused on other transient success stories of the day. I managed to be envious of dozens of other companies, founders, and colleagues who seemed to be having tremendous success but later turned out to be a mirage. If you'd asked me to rank the top most important people I'd met that year, I doubt it would look very impressive in retrospect.

I'm confident of that last statement, because I made the same mistake again a few years later, when I won an award in 2007. BusinessWeek named me one of the top young entrepreneurs in tech, based on my work at IMVU. Being called a techno-wonderboy in front of everyone I knew was pretty strange, and it felt stranger still to be taking credit for the hard work of the many people who really made IMVU a success. But they were very supportive, and the experience was a good one. Trying to take full advantage of the opportunity, I even reached out and met a few of the other award winners. But, looking back, was it obvious which of the other winners were destined to create world-changing companies? Nope. I completely missed Twitter, for example, which was just one more company to me. Oops.

And yet, missing out on these trends wasn't the end of the world. If I had joined Google early, I'd never have had the opportunity to be part of the founding of IMVU. Then I wouldn't have the chance to work with the incredible employees and mentors from whom I learned so much. And, as I've said many times on this blog, if it weren't for those colossal failures and embarrassing missteps, I'd never have learned anything of significance. So, looking back, I'm grateful for the failures and missed opportunities, embarrassing though they are.

One thing really stands out to me today. I wasted a lot of energy, time, and passion on trend-spotting and trying to compare my success with others. Is it really worthwhile spending time and money trying to impress each other with our supposed successes, especially in a business where real feedback can take five or ten years? We go to mixers, buy fancy offices, focus on PR, and try to one-up each other. I think it's wasteful. Instead, let's focus on building companies that matter, on creating real value for customers, and learning. In time, success will come. And if it doesn't, at least you'll have spent your time doing something intrinsically worthwhile.

In the meantime, don't worry if you can't spot the trends. Neither can the rest of us (well, except for Matt Cohler).