Saving over $300k is sizable, but selling $10M in stock seems pretty risky. Wouldn't this be a huge red flag, especially for someone who works at the company? Seems to be lots of risk and not that much (comparatively) saved.
Or perhaps this was his strategy in flying under the radar, since it didn't net him that much on a percentage basis?
But most importantly, if you have ten million dollars in AAPL (and a job that pays you more besides) why on earth are you taking risks like this?