Ask HN: Have you used a forward sale to avoid stock transfer restrictions?

I was an early employee at a reasonably successful startup company, and I have found myself in an awkward position. I have millions of dollars worth of stock that the company is not allowing me to sell citing transfer restrictions specified in the stock options agreement. I have multiple offers to buy my stock but the company won’t allow a stock transfer. It feels like such a hypocrisy, I “own” literally millions of dollars of stock which I had to purchase when I left yet I am not allowed to sell it. I’ve heard people mention that a “forward sale” is one way to get around this – they buy the shares now for a certain price and I transfer the shares later whenever it is possible. It seems like this would constitute a violation of the stock option agreement, but I’m also told that a company would never sue an employee to take their shares away because “that would look bad”. So I’m just curious, has anyone done this? How do you feel about the risk? I’m also just generally curious about the history / legality of transfer restrictions if anyone has any insights. Thanks!
Story Published at: May 21, 2023 at 06:58PM