Ask HN: CTO wants me to leave

Being asked to "leave in 3-6 months" is the new CTO's opening gambit in the negotiation you're about to start.

Your _worst_ negotiating option will be to say "OK, bye".

Work out what you want.

Work out your best idea of what the CTO/company wants (depending on what you want, the first step here is most likely to be asking them outright - if what you want most is to get rid of this CTO, this step will need to be approached much more subtly and delicately, and probably with someone much more experience helping you out).

Work out some "next best alternatives" to your optimal outcome, and what you'd accept as compensation for agreeing to those non-optimal alternatives.

Mostly though - work out what _you_ want - and why, and once you've done that, look at it with the most objective view you can and determine if it's actually plausible and realistic. (To be honest, a guy who wasn't even writing tests a few months ago _isn't_ going to be the technical lead or chief architect of an enterprise software startup - at least not a startup with a high chance of succeeding or getting serious funding. Be realistic here.)

If it's just the vesting(/money) - you'll negotiate one way. It's it's actually an ego/ownership/founderdhip issue for you, then acknowledge that (at least to yourself) and work out how to negotiate your desired outcome while keeping that perspective firmly in mind (and seriously, think about whether you need to rethink that - if it's mostly an ego thing).

But if he actually is asking you to leave the company? He can fuck himself. But seriously, if it is clear that you are hurting more than helping by writing code, please stop. Keep learning, and ease into contributing again slowly.

Then you are in a relatively strong bargaining position now, but it will probably get dramatically weaker very soon if you do not act.

I agree with those who said you need to take proper legal advice about how secure whatever stake you have in the company really is if they try to take it from you. For example, it is surprising that you mentioned any problems with vesting; as a co-founder, do you not have a certain share of the equity outright? Remember that you are wearing at least two hats here, one as co-founder/investor/equity holder and the other as original chief geek, and hopefully these are completely separate.

In any case, if they need you to get to the big time, then you are in a good position to negotiate mutually acceptable terms for your future and should take immediate steps to do so. It sounds like the best outcome might be a (hopefully amicable) separation, if the professional relationship doesn't look like it has a future, but in that case you're well within your rights to expect fair compensation for anything you're giving up.

But before you do anything else, talk to a lawyer who specialises in this kind of subject, discuss the details of your exact situation, and take advice accordingly.

1) Ask yourself these questions:

* Did I get into this for a quick payday or to build a business?

* How could I best contribute to the business if I stayed? Is that something I want to do?

* Are these people I'd want to stay and work with indefinitely?

* If I had to walk away today and give up all my stock, what dollar value would I put on my contributions (both assets and effort) to date?

* If I had to walk away today, how much cash would I need to comfortably cover the downtime until I find what's next?

2) Talk to a personal attorney who has some experience working with start-ups, fundraising, etc. Someone who's negotiated founder contracts and separation agreements.

3) If you know them well enough, talk to the board, advisors, and/or investors who participated in your last round and ask their advice.

If they want you to leave after the next round, then that probably needs to be part of the conversations with potential investors. If you're a founder and have a large chunk of stock, it's not unlikely that they'd want to buy most or all of it back from you with proceeds from the next round.