Most of what I have learned over the years came primary due to my failures. Looking back at the decisions I have made in both selecting ideas to work on and deciding how much to invest in them it is painful to see how many times I have repeated the same mistakes.

It all comes down to decision making and the ability to predict the future and the timing of when things will take off. It is also critical to either do it yourself or only entrust a person who is more passionate than you about the subject.

While most of the projects I failed in where good ideas I usually dramatically underestimated how long it will take for adoption to take place or how much money will be needed. I also have discounted the level of commitment and ability management have presented thinking I could solve things later.

The hardest part I had to deal with was learning to cut my losses and admit my mistakes quickly. Again and again I tried to save these ventures and paid the price of being distracted and drained of resources to only prolong the inevitable.

A focused mind is one of the most powerful forces in the universe my fortune cookie read in a recent trip to a local eatery in Manhattan and I could not agree more.

It is amazing how some lessons take 20 years to learn.

Here is a list of my most spectacular failures and misses. I review them again and again to see what else I can learn and each time as I visit them in a new context a new side of this learning process reveals itself.

May 2008

• Novacure 2004 – had the opportunity to invest in this revolutionery cancer treatment process but decided it was too revolutionary.
• Skype 2002 – I got a call from a VC asking about my opinion on a small startup doing a VOIP product, since I know the space too well I did not think they prospects were good.
• ICG 1999 - ICG was the seed investor in Arbinet and I got pre IPO equity but wired the money too late to participate. Stock went from $7 to $212 in 6 months.
• Google 1998 – I was introduced to Sergey by Ester Dyson and after listening to his presentation of how a link based algorithm would provide better search results I said "who needs another search engine, we have AltaVista"
• Tradeum 1998 – I contracted to buy software and negotiated equity upside and co-investment but I switched at the last minute to another firm. Tradeum got sold for $1.2b just one year later.
• ICQ 1996 - Yosi Vardi offered me equity in his company as barter for bandwidth from Arbinet. I said no and ICQ was sold to AOL for $450m a mere 8 months later.
• Vocaltech 1996 – I had the opportunity to invest in the company twice before their IPO.