Failed Ventures & Missed Opportunities

As a maverick investor and entrepreneur, Alex has recorded many failures along with his successes, gleaning more valuable lessons from the former. Alex assesses that there are many reasons that appropriated his failures, many an underestimation of the time and money needed to implement the projects, as well as the level of commitment and abilities of the companies’ management.

According to him, the hardest part about losses is learning to when to cut them off and admit to mistakes. It all came full circle when the sage advice, "A focused mind is one of the most powerful forces in the universe" came to Alex through a fortune cookie while at a local eatery in Manhattan. He realized that some of his lessons took 20 years to learn.

Alex’s Own Firms, 2008
As the recession hit, Alex’s decision to leverage two of his ventures with debt turned disastrous as his lenders refused to be patient. He lost all his equity in one of the ventures as the other got refinanced. His takeaway from that event was to never put debt into early stage growth companies.
US Housing Market, 2006
Alex had a good intuition prior to the housing market collapse and finally decided to bet against it by shorting the home builders. He lost money in all of 2006 as the housing market continued to do well at that time, and eventually he decided to cut his losses early in 2007.He then went to watch home builders lose over 70% of their value in the following twelve months. He had failed to make the connection between the home builders’ collapse to the collapse of the banking and financial system which followed.The lesson he learnt was to stick to his guts, especially when one has a track record of being right.
Twitter, 2004
Alex knew there was going to be a better way to publish new information on the internet so he wrote a patent for publishing information in real-time to a list of followers.At the same time, he had also started working on GroundLink and had to make a choice between the two ventures. He chose GroundLink while the other idea turned into what came to be known as Twitter.
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Novocure, 2004
Alex had the opportunity to invest in this revolutionary cancer treatment process but decided it was too revolutionary.
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Skype, 2002
Alex had received a call from a VC asking about his opinion on a small startup doing a VOIP product. Since he knew the space too well, he decided the prospects for the firm were not good and passed on it.
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ICG, 1999
Alex was the seed investor in Arbinet at the time and he received an invitation to purchase pre-IPO equity for ICG. However, he wired the money too late to participate and ICG stock subsequently soared from $7 to $212 in six months.
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Google, 1998
Alex was introduced to Sergey Brin by Ester Dyson, and after listening to his presentation of ‘how a link-based algorithm could provide better search results,’ he regrettably said, "Who needs another search engine? We have AltaVista!"
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Tradeum, 1998
Alex was contracted to buy software at this firm. He even went on to negotiate the equity upside and co-investment possibilities but he switched his mind at the last minute and the firm went on to be sold for $1.2 billion the next year.
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ICQ, 1996
Yosi Vardi offered Alex equity in his company as barter for bandwidth from Arbinet but he declined the exchange and ICQ went on to sell to AOL for $450 million a mere eight months later.
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VocalTec, 1996
Alex had the opportunity to invest in the company twice before their IPO but passed on the opportunity both times.
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