[joshjkim]

This is a copy/paste from a prior HN discussion that I had:

[it's definitely true] that employees are discouraged from seeking buyers because there is an unspoken implication that this means the employee is "losing faith" or "believes less" in the company, or is getting ready to leave.

If the party line is: "hey, we are going to be a billion dollar company!" and then one employee says "hey, I want to sell at this $100M valuation", even if the $100M is a solid upside from the employees strike price the next natural question for the founder is: "hey, why would you sell at this valuation if we all know we are going to unicorn?" Lots of people are reasonable and could understand many good reasons to sell at that point, but in high-growth culture those are not always appreciated. Sure, employee can/should suck it up, but it still makes it more challenging.

Generally, I think this is why company's should more regularly organize secondaries, it removes this dynamic to a certain extent.

[bogomipz]

And with each round of financing your equity is likely getting diluted. If you are a good employee and sell some shares on the secondary market and continue to do a good job and remain at the company I don't think anyone can equate that with losing faith or imminent departure.