Tonight I attended a panel of INSEAD internet entrepreneurs talking about their experiences, the future of the internet, etc. and one story stood out.

Kevin Ryan (easily INSEAD’s most successful Internet entrepreneur) was talking about how he was able to recognize the Dot Com Bubble.  At the time, he was the founder and CEO of DoubleClick and was taking a week off to ski in early 2000.  While he was away skiing, the company’s valuation went up by $1 or 2 billion dollars - from $8 to 9 or 10 billion or so.  This was about 50x revenue (and they were still losing money) and he couldn’t think of why it had, so he figured it must be a bubble.

So what was his response?  Raise more money.  He went out and did a secondary offering of $1 billion for “confidential purposes” - and that money saved the company during the bust.  Lesson learned.