I&#x27;ve worked at both startups and big companies since I first came to SV in 1999.  And some startups that became big companies.  For me, there&#x27;s much more than the practical &amp; financial considerations laid out here.  Deep down I know that I enjoy taking risks -- I like the roller coaster ride, and having a very real and visible impact on whether the company as a whole sinks or swims.  Know yourself and don&#x27;t ignore your intuition.<p>Also, while &quot;rand(100)&quot; might be an accurate characterization of the returns of all employees over all startups, it is not entirely a game of chance.  There is skill involved in picking the right startup to join: being proactive in your search, building a personal network, finding founders with track records, considering enterprise startups.  You can learn to improve your odds -- a bit like learning to count cards.