Depends how you define insider. Employees were subject to a 6 month lockup and during that time the price dropped dramatically, but they still had to pay taxes on the $80 IPO price. Execs and institutional investors that were able to sell at IPO made out quite well though.
It's really not. Let me know if you find any lenders that will let me pay off a mortgage with a capital loss.
At least in the startup narrative that circulates on HN, most early employees at a company with that kind of IPO would hope to have a lottery like level of financial windfall. Now their upside is if they manage to get luck a second time they get to offset their winnings? :/
Not great for investors, but insiders benefitted a lot!