This problem with the IRS seems to have influenced his life direction quite a bit judging from his blog. Transferred assets to a charity; acquired foreign citizenship; renounced US citizenship; moved to a country where foreign-sourced income is tax exempt. Guess it really stung!
Check sivers.org. He has blogged about this pretty extensively. I want to say it was 2010-2011 when he posted it, but my memory is failing. I came away from reading the blog thinking something was going on that he wasn’t mentioning in his blog. He generally posts in a positive tone but some of his choices seemed at odds with the tone of his blog. Namely, sell the business and put the money into a charitable trust, renounce citizenship and move abroad. I also seem to remember that the folks left holding the bag at cd baby weren’t exactly thrilled with his management style.
Not here to throw shade at the dude and I think he definitely has some gems in his blog, but it’s also showing the best self and not necessarily the real self.