If you're confident that the company's eventually going to exit (obviously a big "if"), and you have the cash liquidity (which he obviously does, as one of the original co-founders of fb), is this essentially a method of getting compensation that isn't taxed as compensation? I'm trying to understand what the justification is for maintaining what looks like a fairly complicated transaction. It looks like they've done it a few times (2017, 2020 jan 2020 june). His entities also participated as investors in the Asana Series D and Series E rounds.
Not meaning to cast aspersions, just curious because I haven't seen these kinds of setups in S-1's before. But most S-1 companies don't have people with pre-ipo, >1bn net worth founder-CEOs, so it makes sense that this one might be a bit anomalous.