To a large extent, Amazon got lucky by raising a ton of money right before the market crashed, giving the company the cushion it needed to ride out the turmoil of the early 2000s.
Isn't there an element of survivor balance there though? It worked for amazon but how many dozens of companies raised heavily and still failed to "capture the flag" on the other side?
It doesn’t matter - if you’re the founder of a company and you were able to convince investors (equity) or banks (debt) that your money losing venture can eventually make money, why not continue taking money from them? If the venture fails, your investors and/or bank loses money and you go out there and either start another business or get a job.
On the other hand, if it’s your own money, don’t get caught up in the sunk cost fallacy.