"Where do you think Anderson was during that hearing? Probably knocking back his third mai tai, on an island so exclusive that neither you nor I have ever heard of it" i'm not sure this is 100% right. Maybe Tom was having huge FOMO pains not being "in the game". It reminds me of the song "Watching the Wheels":
People say I'm crazy
Doing what I'm doing
Well, they give me all kinds of warnings
To save me from ruin
When I say that I'm okay, well they look at me kinda strange
"Surely, you're not happy now, you no longer play the game"
Maybe Tom still wanted to play the game and watching the wheels was boring?
Being "in the game" is a tradeoff. The CEO of Twitter and Facebook undoubtedly wield a lot of power and money. But they're also very high profile individuals because of that power - they have to spend every waking moment making tough judgment calls and answering for their decisions, and they're under constant scrutiny and endless criticism from the public, the media, and all manner of bureaucrats and officials.
Tom managed to hit the sweet-spot of being just successful enough to retire to a life of luxury, while not being so successful that a low-profile lifestyle is impossible.
People say I'm crazy
Doing what I'm doing
Well, they give me all kinds of warnings
To save me from ruin
When I say that I'm okay, well they look at me kinda strange
"Surely, you're not happy now, you no longer play the game"
Maybe Tom still wanted to play the game and watching the wheels was boring?