Ask HN: How do I quit my own startup?

Hi,

I have done the same as you are planning to do. I was also the CTO (and founder), while my cofounder was for the sales side. However my company was already more advanced I assume and I had already done a partial exit. I left after about 10 years of having founded the company, and don't regret it. Sure, I might not ring the bell later when we IPO, but I don't need this. That's just an ego thing, but that you have to accept :).

My cofounder didn't like so much that I was leaving, reasoning that the company would be worth less later, wouldn't grow so fast, or engineers or others employees would leave. I stayed another 1 year working 50% until I left completely (They still though tried to retain me later on, but I declined). At the end no one of the employees left, as they all understood why I was leaving.

Just talk to your cofounder and explain him why you are leaving. I assume if you haven't yet exited, and that he would request some parts of your shares to be given to a replacement CTO. I think this is fair. In my case, the replacement CTO was a internal engineer I hired 8 years ago, and I was free to leave already years before. At the end, a new person can also bring in new ideas, sometimes better, sometimes worse. And it's also great if employees see that they can progress in the company.

I still very much care though about my former company and still have lots of friends there (not just IT), and I'm still a large shareholder.

This is probably a bigger deal to you than it is to the company. Your CEO may have an emotional attachment to you, as you do to them and the company, but your presence is not going to make or break the company, at this point.

Be straight forward with the CEO, or a trusted board member, and tell them it's time. You're not in a rush to leave, and can work with them, within reason, but it's time for you to move on. Then, see where it goes.

Staying, when you don't want to be there, is going to damage you and everyone around you. You are doing the right thing, but that doesn't mean it's not difficult.

Best of luck.

First question would be whether you ultimately want to transition to a clean break or just want a lot more time to do other things, because if it's the latter "stepping back to a more advisory role" is perfectly normal and need not be seen by anyone as a negative judgement of the company. Otherwise the tactful explanation for your decision is the other pursuit(s) that you want to focus on for the next year or two, coupled with the suggestion a new CTO more accustomed to the stage your startup is at might actually benefit them .

i would say have an open and honest conversation with your co-founder where :

- talk about your feelings, aspiration, what is your long-term plan and why you are leaving (avoid discussions on whether your reasons are valid or not, make it more of a statement rather than a top to discuss)

- agree on a timeline with your cofounder, something that is workable for both of you. it could take 3-6 months where every month you lower your commitment hours to the company.

- prepare an exit plan with your co-founder (in exchange with some shares or reward),together prepare a replacement plan, delegate some of your responsibilities that can be delegated to your team members/cofounder, find a replacement for things that can't be delegated.

- find the right time, angle to raise this to the board.

I quit a startup I co-founded. It was emotionally draining, but the right thing to do (for everyone). The startup survived and is doing quite well. Here are my tips.

   * Review your founders agreement and understand what the financial/vesting implications are.
   * It sounds like you have a team in place, which is great. Identify gaps where you need to do more docs or train someone up. This will be good even if you don't leave.
   * Write up why you are leaving. You don't need to share it with anyone, but writing it down will be clarifying.
   * Review your financial situation and make sure you can take some time off or sustain yourself (and family, if any) for a few months. You don't want to jump into a new job right away.
   * When you are ready, sit down with your co-founder face to face and share your decision. Offer to help with the transition in any way you can and let them own the messaging. When a co-founder leaves, this can shake a company to its core. If you want the company to continue (as I've inferred) then you want to let the co-founder message it as they see fit. (Don't lie, of course.)
   * Offer to contract back for a while. But don't make it perpetual; 3 months tops. The team needs to learn they can make progress without out. I was surprised how quickly my knowledge of the system became irrelevant.  
   * They may want to buy you out but don't agree or disagree with this out of hand; give it some analysis.
   * Realize when you pull the trigger that the closing of this door will be painful too. But that there will be other adventures in the future.
   * Stop paying attention to the startup after you have left. After pouring your life into it, this may be hard to do (it was for me) but some separation is what all parties need.

Hire someone else for the role. If you're still in the vesting period, there should be some spare shares to tempt them. If not, you could probably sell a few shares.

It's normal to swap out a founder for a CEO as the company scales, why not the CTO?

Delegate?