Bad idea: Being dependent on a single company for your salary while also holding mostly that company's stock in your investment portfolio.
Worse idea: Also investing in that same company's highly risky VC fund.
Worst idea: Borrowing money to do so.
Worse idea: Also investing in that same company's highly risky VC fund.
Worst idea: Borrowing money to do so.
It didn't really make any sense to me, but I wanted to ask here:
Is there any truth to that? And if so how did it work?
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.