What's interesting is that he could have cashed out after Twitter and led an incredibly entertaining and enjoyable life, but still chooses to push on further for more success, more challenges, etc to the extent that such a huge portion of his waking life is taken by "work" like this.

I could understand it (and put in a lot of hours myself) driving to get that first home run, but less so afterwards. I'd struggle to sit idle and travelling non-stop isn't the holiday everyone thinks it is, but my dream lifestyle definitely wouldn't involve 16 hour days once I had the means to pursue all my interests to a desired extent.