[adrr]

Sell them to who? Are there any secondary market sites still running. Otherwise, you're cold calling investors. I tried to sell my shares in a startup to cover my six figure tax bill and couldn't find a buyer even with the company's CFO helping me.

[bogomipz]

The OP I was responding to was clearly talking about a publicly traded company - "the stock was at $50/share" and "Took years for the stock to recover." They could sell them to anyone who wanted to buy them and clearly people did if it was going up.

To answer your question, yes there are still companies that facilitate the secondary market for pre-IPO options, Forge/Sharespost is the one that immediately comes to mind.

[dominotw]

All those markets are currently dead. Been searching high and low on all those sites for my options but all the sites went completely quite last 3 months.

[pfarrell]

In this case, the company had gone public, so they could have sold. Bolt is a wholly different story. I think the employees back in 2000 had one window where they could sell where the stock was at a high value. Many of them passed it up, expecting it to go to 70.

In 2015, I talked to ESO fund for some fintech options I had where I couldn’t cover the tax when I quit (stock wasn’t public). I was very satisfied with my dealings with them. Ultimately, they pulled out on the deal. That was a pretty strong signal because, low and behold, that pre-ipo stock tanked in a month too. Luckily, the lessons I’d learned from the earlier stories helped me to walk away from those options. It was a tough, but ultimately good decision.

[adrr]

It's all luck and timing. The company I couldn't sell the shares to cover my tax bill was acquired for nine figures a year later and I had all my stock because I couldn't sell it.