Comment by devoutsalsa

I had no idea how preferred shares actually worked, so I went down a rabbit hole looking it up. That "always get 1x back" thing you mentioned is called a liquidation preference, which means preferred shareholders get their money back first before anyone else sees a dime.

Turns out there are different flavors too. "Non-participating" means preferred gets their original investment back, then common stock splits whatever's left. "Participating" means preferred gets their money back AND also gets to participate in splitting the leftovers with common shareholders. No wonder investors are willing to pay up for these late-stage rounds when they've got that safety net.