The cereal box sold by Team AirBnB to raise money to fund the company

You can really pass on a great deal based on how you think. Here is a great post by Fred Wilson with the title “You can do too much Due Diligence“, it is a classic case of mea culpa and analysis paralysis. I really admire Fred for coming out and admitting his mistakes, he did that with AirBnB as well. In the last couple of weeks, there have been many people who have reached out to me and do the same about CLARA. As I have mentioned before, we were very lucky to find Team CLARA and the work that we were able to do get the deal done. That being said, I am sure if me and my partners had put on the hat of figuring out what could go wrong with our investment and done too much due diligence we may have passed on the deal. Here is an excerpt from Fred’s post:

So what did I learn from this lesson? First, trust your gut. I was using Feedburner and knew it was a very useful service. I felt that others would see that too. They did, but it took some time. Second, I learned that a service can get traction with the little guys and in time, the big guys will come along. I have seen that happen quite a bit since then. And finally, I learned that you can do too much due diligence. It’s important to talk to the market and hear what it is saying. But you have to balance that with other things; the quality of the team, the product, the user experience, etc. You cannot rely alone on due diligence, particularly early on in the development of a company and a market.

I can relate to what Fred is talking about, I have really had to change my thinking to trust my gut. Our understanding of the world is very limited, we fool ourselves into talking and thinking ourselves into not following our heart or our gut. These tools have been given to us through the ages, over millennia of evolution. I surprise myself how we use our epistemological arrogance to suppress our primal instincts… there are times we need to do that, but not when it comes to investing in people or ventures. You need to take chance and work to mitigate the risk. All things are risky but the tricky part is no-one knows what is risky … that being said I would not do what Tom Hanks and Shelley Long did either 🙂