He also acquired a second nationality, renounced US citizenship, and moved to a country that doesn't tax foreign sourced passive income. It's the most extreme example I've seen of planning your whole life around tax optimization.
Understandable though if you've read his book because he's had big problems with the IRS in the past and probably really wanted to show them his "FU money."
(I'd just like to acknowledge that my parent comment is pretty lousy. I don't know Derek and I'm making assumptions about his motives. I feel like it's fair game after his article "Why I gave my company to charity [1]" but I'm not proud of casting aspersions on internet celebrities. I have a jaded view of philanthropy and philanthropists that may be totally off in this case.)
It doesn't but all that means is the form for renouncing has a checkbox asking "are you doing this for tax reasons"? And you check "no". Then during the consular interview you spew some line about how you no longer have attachments to the US -- "I haven't been back in over 3 years, own no property, let my driver's license expire" and you do have attachments in your new country "All my friends are here and I even spend Christmas here!"
It is more of a retroactive "if we find out later you lied we now have a legal basis to add extra penalties" but in practice nobody is really checking or cares. The underfunded IRS doesn't care about the tiny number renouncing and the consular officials doing the interview certainly don't care.
Understandable though if you've read his book because he's had big problems with the IRS in the past and probably really wanted to show them his "FU money."