It's very difficult, and not recommended unless they are ESO fund style loans, where you don't pay anything if the stock goes to zero. People did similar shit

It's very difficult, and not recommended unless they are ESO fund style loans, where you don't pay anything if the stock goes to zero. People did similar shit as getting HELOC loans in the dot com bubble, and it did not turn out well for them at all. Cash is cheap for a few large banks and other organizations rolling in money. Not for the middle class / upper middle class employee. Capital losses are only allowed to offset your normal taxes by a small amount in the USA. Also companies drag their feet in getting you the proper documents that you might be missing. It can take months and those 2-3 months later, ESO isn't interested anymore. It's happened to me.