Couple of thoughts as a founder and investor: 1) The company is disincentivized to help you sell your stock/options because it will create a new valuation of common stock. Companies use the lure of a low 409a to attract employees, especially savvy executives, with equity packages. Doing anything to set a higher future strike price is not in their interest. 2) Your NDA almost certainly prohibits you from communicating…
You advice was great up until this bit, at which point you are completely wrong.
The best time to sell shares is on an up round. There will be people who didn’t get in who want to. It’s perfectly common that they’re underallocated to a company that you’re overallocated. That’s not a fire sale it’s just a deal that make sense.