Another example is Chris Sacca, who burned through $16 million - $12 million in paper gains, and $4 million in borrowed money. From [1]:
Starting with around $10-$20,000 in what were college loans, Sacca realized that brokers weren’t accounting for margin usage on a real-time basis. The result was that even though firms were only allowing 50% margin, as long as a customer closed a trade before the trade settled, T+3, and showed proper equity in the account, positions larger than 50% margin usage could be opened.
Picking winners of stocks that by Sacca’s account had risen 40x, and betting with positions well above his margin requirements, his account grew to $12 million in 18 months. But, as we all know, the record levels of the Nasdaq and the dot com bubble of that time eventually burst....When it did burst, and even though the damage was from holding just two stocks, Sacca found himself in the hole with a $4 million negative balance.
Not if you're leveraging! For an extreme example, this guy lost $210k of borrowed money: https://www.bogleheads.org/forum/viewtopic.php?f=10&t=5934&s...