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I'm still curious how this is supposed to work for early investors in startups that don't succeed, but post impressive numbers. Say I'm a founder (I'm not) with no other major assets and for one year my share of my startup gets valued at $200M, which triggers this unrealized gains tax. Even if I get this "illiquid" status, I'm going to be assessed a 25% ($50M) tax bill. It's not uncommon for startups, even hugely publicized "unicorns" to fail completely. If the company is forced into a down round next year, and my share drops to $50M, where do I get the funding to pay my tax bill? Is the government going to take my entire stake? What if the company folds and I end up with nothing: do I still owe $50M? Is that a thirteenth amendment violation?
If the answer is "yes" here, I really can't let my assets be illiquid and volatile, lest I find myself unable to pay the tax man at some later date. It's also potentially concerning that triggering Mugabe-esque hyperinflation suddenly becomes a positive (real) revenue stream for the government when every asset is worth $200M or more and gets a 25% annual wealth tax.
And it probably pushes investors into infrequently-valued investments: buy a one-of-a-kind Renaisance masterwork, and how does the government handle that valuation? Supposedly my jurisdiction assesses my real estate property values annually, but I can tell you I've seen pretty substantial divergence between actual sale prices and assessed values over the last few years.
Due to tax treatment of certain types of options, there were a number of early failed-startup employees in the dot-crom crash who were left in insurmountable debt by tax bills for gains they never actually received (the options vested in the money, which was a taxable event, but the value of the stock cratered before they were allowed to sell it). I believe their options were 10 years of debt slavery to pay as much as they could (living on what the IRS would allow them), or suicide (since bankruptcy does not relieve you of tax debt). Since they were not sympathetic to the media, no one cared; the same will go for early investors who end up in the same sort of hole.
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