[Random_BSD_Geek]

This is unbelievable nonsense.

Your employees accrue PTO. If you can't handle them using their PTO, maybe you shouldn't have employees.

If three consecutive weeks is a lot to ask, what would you do when that same employee gets hit by a bus and is dead for even longer?

Oh right, you'd just replace them and the business would move on.

OP, this is the real answer to your question. The business doesn't care about you or your well being.

[foota]

I don't think you want your boss to replace you when you go on vacation.

[Random_BSD_Geek]

The point is that some arbitrary number of weeks of vacation isn't the business-destroying choice this founder makes it out to be. Use your PTO. You earned it.

[Clubber]

It depends on how important you are. If you are the director of sales, software architect, or something like that, it can be business destroying; particularly if some unforeseen emergency happens. An example is a new big client is suddenly requiring something happen before signing a contract and everyone needs to be on deck for that to happen.

If you are one of 100 CSRs, then it wouldn't be business-destroying obviously.

[id00]

Any serious business needs to have a continuity plan and can't depend on availability of a single person. What if the person you depend on will have a medical emergency or resign?

Business owners can take this risk but using "don't take more than 2 weeks of PTO" as a risk mitigation strategy is disingenuous and disrespectful to their employees.

[fnimick]

Startups running lean, which is what you need to do in order to maximize runway, don't have the money or time for "continuity plans".

Haven't you ever joked about the "bus factor"? All the startups I've worked at would have likely failed if any one of the core people had to depart, for any reason.

[bb88]

Then startups need to be honest about their needs up front, and stop using misleading terms like "unlimited" -- particularly early stage startups.

[Clubber]

You're not wrong, but early stage startups are a unique animal.

[frumper]

I've yet to see a job where hiring a new employee is more efficient than letting one have off 3 weeks instead of 2. There is a really good chance that a new employee wouldn't be working yet before they've returned.

[organsnyder]

The OP doesn't indicate how much vacation time they've accrued. Perhaps they get "unlimited" PTO, which makes things murky.

[paulcole]

If they had unlimited PTO it wouldn't be murky. The problem is that nobody has unlimited PTO, there's always a limit.

[samsolomon]

I gave a measured reply given what the poster provided.

"Unbelievable nonsense" is a pretty harsh response. If they are working for a 10-person business burning cash, that is very different than a profitable 1,000-person one.

The poster asked about etiquette. Personally, I'd be offended as a founder or employee at a 10-person company if someone asked for 3 weeks off at the last minute.