[throwaway52]

Thanks for the experience based insight. I've had that nagging worry all along.

Part of me has wanted to be a bit more trustworthy as they've shown themselves to be very friendly people -- I regularly go to bars with the CEO outside of work, the COO and I share interests and talk about them/engage in them (being vague here), etc. But I think your point is pretty clear and well thought out. And pretty much not arguable. Thanks for that.

[gaius]

Sorry to be so blunt but in this setting, friendly and manipulative are synonyms.

[baguasquirrel]

I couldn't agree more, and add one to the folks who've been in the "when we become revenue neutral". The funny thing is that in my case, the entire company bought into the founder's line on that (well, only about 12 people), because none of us had done a startup before and we didn't know better. In any case, that's not how it works in the startup world. There's a reason why over the years, companies adopted vesting schedules.

edit: I should add that in my case, the stock options were left out more out of ineptness than maliciousness. Either way it's a bad sign. The company imploded after a year and a half, but not before one of the employees mentioned the options in a disgruntled tone. In short, we wondered if the founder really cared about our contribution.

[gaius]

I've been promised stock options that never materialized too. If it ain't on paper it don't exist, and if your boss is truly honest he won't pretend that it does.

[trevelyan]

I agree this guy should be looking for other work, but disagree that working relationships are always inherently manipulative.

The big problem here is the bloated management structure, pre-launch vacations and failures to meet targets, all of which are strong signs the decision makers in the company are bad at their job. This implies that decisions about this person's future compensation and role in the company will be made by a committee that does not understand his value. I think that is the problem more than anything else.

[gaius]

This is not a healthy working relationship - he is being manipulated. The equity participants are on vacation while the sole employee does all the work because they've made vague, non-specific promises that someday maybe he too can join them.