Missed opportunities

I've been at the right place at the right time with the right idea, but for one reason or another didn't act on it or execute. Here are a few of those missed opportunities in startups and investing:

  • Yahoo IPO, Apr 1996. I was ready to put all my money into this. Granted, I was 16, so not a lot of money, maybe ~7K. I had been on the Internet pre-Web and really thought they were onto something. I got talked out of it and didn't do it. Of course, I could have been wrong and lost it at all too!

  • Posterous, 2001-2003.  I had a thesis (which still seems true) that email is perhaps the easiest path to virality and mainstream adoption of Web services. I had three different projects around that time where you could send an email to an address, and then the service would auto-create an account and auto-publish content. I wasn't thinking big enough though (mine were too nichey) and I didn't have enough staying power. I did ride the same email thesis through my last successful company, but it had very little to do with publishing content. 

  • Bitcoin, 2010. I was following this closely and ready to pull the trigger here, but just didn't because I thought it would take a lot of time and I'm so busy with DuckDuckGo and other things. I didn't think hard enough about it to realize I should have just bought coins instead of doing calculations around mining for them.

  • Angel Investing, ongoing. As like probably most investors, I've already passed on several things that are doing awesome. Now they stare me down every day! 

I can't say I have any regrets though, and that's my central point. I like to think about startups as a career path. There are many apt analogies here, but along such a path there will be bumps, ups and downs, many at-bats with swings-and-misses. That's just the nature of the game.

If you don't have your fair share of failures after a while, then you're probably not trying hard enough, or at least not exposing yourself to enough opportunities. Nobody's perfect so to have captured opportunities you need missed ones too.


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I'm the Founder & CEO of DuckDuckGo, the search engine that doesn't track you. I'm also the co-author of Traction, the book that helps you get customer growth. More about me.