Most of us aren't in the position to make that bet. The most I can afford to do usually is "leave this role because even though the press and investors are sti

Most of us aren't in the position to make that bet. The most I can afford to do usually is "leave this role because even though the press and investors are still on board, I don't think it's a good bet anymore." I've done it a few times, I've even been right about whether they'd make a good ROI on those new funds... and so I made modestly more in the new role than I would've by vesting more pointless options or whatever... but I couldn't really short those startups or subdivisions to make a fortune by them failing. While their founders/CEOs made a (small) fortune by failing, but in a big enough way.