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Keith Rabois, what was the most important decision you've ever made?

I'm reposting this from Quora.  I'm not sure who the Rabois Fanboy is that keeps asking Keith personal questions.  But I'm beginning to like it.  Here's Keith's answer (republished without permission):

In February of 2000, I agreed to leave the safety and security of large law firm life for the wildnerness of Internet startups.  The market crashed less than a month after I started my job at, a hot startup funded by over $15 million from CRV, Sigma Partners and Bessemer.  Our CEO was a 22-year old Harvard graduate.  

This decision would eventually alter my entire identity.   Until that moment, I had followed the most predictable, well-established paths and chased the most well-established credentials (Stanford poli sci, HLS, federal appellate clerkship, S&C etc).  I eschewed risk.

I had never even used an Internet browser until one year before that decision.  We were not even allowed to have an external email address at work until 1998.   I spent nearly all of my life with people from the same educational backgrounds and pursuing identical professional aspirations.

I jumped into a world I knew nothing about, with no real life-line.  I needed to learn everything on the fly, forge a completely new network, and navigate people who were unreliable, even willing to lie or betray you in a second.  We had to fire a guy on my team who would frequently show up for work drunk; this did not happen at Sullivan & Cromwell.

The first month was rough.  But by the third month, I was hooked.  Fortunately, Geoff Donaker was able to teach me the fundamentals of Internet BD and Excel-modeling quickly.  I mastered the BD part, and could at least fake a decent model (although Geoff always barfed on the formatting.)  I received a promotion in my fourth month.

If I had not quit the law before the market collapsed at the end of March 2000, I never would have been able to.

To quote a friend of mine from Stanford from the mid 1990's:  "Rabois, you went from the most risk averse person I knew"....  to someone who intentionally embraces risk.

Reader Comments (1)

I anonymously posted (just) 1 personal question to Rabois so I think it might be kind of a Quora phenomena now that is perpetuated by the community.

May 24, 2010 | Unregistered CommenterAlex Le

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