The more successful and the bigger the investor, the bigger you roll the dice.
Once you have a bunch of unicorns and a few decacorns, you bet bigger and bigger. It’s OK to lose $50m on a deal or two if you made $20b on WhatsApp. It really is. Scale that up or down to the specific VC firm and/or individual partner.
But even with the deepest pockets, bad money doesn’t go after good forever. Once the bet clearly won’t pay off, there isn’t another check.
And the checks ended for Quirky.
If you ask for a third check, you better be killing it. Not on your last breath.