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Notes -
On the one hand, "purchased" should probably have scare quotes when applied to stock that isn't on the open market and that is being assessed at a 0.1-cent-per-share par value instead of anything an economist would recognize as value. Confinity might have been a gamble in 1999, but it was not a "the market cap would have been $62K" sort of gamble. Nobody gave Thiel 1.7 million shares of stock because its worth was anywhere near $1700, or because they really needed the cash for a new (but-not-top-of-the-line!) PC, and at anything like a real valuation he wouldn't have been able to squeeze more than a fraction of those shares under the IRA contribution limits. Under the spirit of the law this was a total scam.
On the other hand, I'd guess it was perfectly legal under the letter of the law, partly because there seems to be no limit to legislators' unjustified faith in their ability to write complex laws without loopholes or to fix the inevitable loopholes with more complex patches, and mostly because if "ha ha par value counts" wasn't a loophole in this case then by this point you'd expect Democrats would be prosecuting it, not writing whiny ProPublica articles about it.
On the gripping hand, this feels kind of like the cherry on top of the perfectly foreseeable karma for the "we need to protect the little guy from those conniving rich people" crowd. Public offerings are regulated out the wazoo, so a ton of stock changes hands at hard-to-quantify values before companies feel secure enough to brave the gauntlet of preparing for an IPO, so many of the opportunities for gains during that time are restricted to conniving rich people and kept out of the hands of the little guy. And even after the fact, are any of them complaining that we couldn't have gotten in on the earliest stage of the PayPal boom? Nah, just that the taxman couldn't. They only got $73.8 trillion dollars of revenue in the first quarter of the 21st century, when they should have gotten ... well, an extra $2 billion from Thiel still leaves us rounding to $73.8 trillion, but it's the principle of the thing!
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