So what superlative do we use when the entity you are borrowing money from is the same company you are investing that money back into!?!?? Most worst? überbad? Ponzi?
Their last Uber investment is under water... wouldn't be surprised if the $2b in WeWork stock they purchased is crushed as well at IPO time -- but at least they didn't follow through with the $8b they initially promised to Adam.
During private fundraising, investor (vs founder) stock generally has preferred rights when the company is sold and/or liquidated. There might also be restrictions on who and how someone can sell their common shares. This depends on the investors and the terms that were negotiated during fundraising.
So common stock generally is sold at a discount because it doesn't have any of these protections, and it's basically last in line to receive any payout.
However during IPO, often preferred stock converts into normal common stock so that it can be sold to Joe Smuck (or their pension fund institutional) investor.
Hence it's an arbitrage play; you purchase common at say a 30% discount in a late round and then sell it on the market for full price.
Unless Softbank is willing to lend said money unsecured to a limited liability SPV without a personal guarantee. I can't imagine that all these people are taking on personal debt to invest in the vision fund.
Worse idea: Also investing in that same company's highly risky VC fund.
Worst idea: Borrowing money to do so.