There were a lot of lottery winners who lost everything in the first tech bubble. Mark sold his company for billions then locked in his fortune using put and call options. Pretty smart if you ask me. Though, I do not agree with this article
It's easy being smart with billions of dollars, since you have access to the best financial advisors in the world.
Very few if any won the lottery like he did. Yahoo never made money on broadcast.com and eventually shut it down after buying for many billions of dollars.