Gracefully resigning from startup as cofounding CTO? (Lost passion) • Hacker News Board

Post by throwaway6794 » Sat, Apr 13, 2024, 3:44 PM UTC

Cofounded a software startup in grad school with someone I met on YC's cofounder match platform. Been working on the startup for 2 years, with the past year being full-time after graduation. We've raised just under $200k and the company remains just myself and my cofounder/CEO (plus a few part-time interns).

I'll keep the explanation short, but I've lost interest in the startup. Originally thought I was just severely burnt out and demoralized having faced ~70 pre-seed investor rejections, but we just secured our first true pre-seed check of $40k and secured a few paying customers, and I just returned from a 2.5 week vacation only to feel exactly the same as before I left. I've lost conviction in my cofounder as a CEO (he's a good person and we get along well, but he doesn't motivate or inspire me as a business leader) and have begun to find programming, technical leadership, and business pretty unfulfilling.

I need help thinking through how to leave gracefully at the current stage of the company. We still need to close out our pre-seed round, but we have enough runway to last until the end of the year. Customer traction is accelerating, and I think things are looking up for the company. I'm not necessarily in a rush to leave -- the career I'll be changing to will require a commitment by August, but I'll be able to stay working full-time until ~ May of next year. That said, I want to effectively spend my time at the company finding a replacement CTO. My cofounder deserves a better CTO and someone who is enthusiastic about the company.

If anyone has similarly resigned as a cofounder, can you provide some insights into:

* How can I best find a new CTO for the company? Should we be upfront and post on boards looking for a technical cofounder? Or should I hire an engineer under me and prepare them to take over?

* Whether we bring on someone directly as a new technical cofounder or as an engineer under me, how can I best prepare them to take over my role when I step away?

* Should the company buy out my vested shares (I would prefer they do)? We haven't run a 409A yet.

* Should I stay on part-time (<5 hours/week) as an advisor/expert in the systems and architecture we have already built? How do I determine what fair compensation for this would be?

Post by sirspacey » Sat, Apr 13, 2024, 6:13 PM UTC

I’m not sure any of what I’m about to say is good advice, but having been through a number of cofounder break ups (and helped others) here are my observations.

1) Have the conversation with your co-founder right away.

It sounds like you’ve already done this. People need time to process.

2) the new CTO will likely rewrite your app from the ground up.

This might not seem, or be, likely. But I’ve never not seen it happen eventually.

It’s more important to find someone you think could do that and then share your lessons learned. Smart people tend to make the same assumptions before they are knee deep in the problem.

3) You are the best recruiter for tech talent. Say you are looking to hire a founding engineer with the opportunity to become CTO. When you meet, let them know it’s a short trial period.

4) pick what you are going to demand on stock buyout and own it.

A solution is to have new investors buy your shares so the cap table stays open.

At the pre-seed stage there’s really nothing to buy your stock with but other people’s money.

To justify that to investors, you’d need to find a new hire that improved your ability to raise capital. That is straight-forward:

0. Lives where your HQ/investors live 1. Went to the right schools 2. Worked at the right companies 3. Was responsible for a project or team that was successful on solving a problem relevant to your value prop as a startup

Searching keywords on LinkedIn or GitHub is the best way to look, but posting for that explicitly here on HN and wherever your dev friends are is crucial.

Sum up: The best thing you can do is to find your team a founding engineer who is better than you & knows the space better. Buying out your stock so that person can have it is an easy decision.

If all the above seems challenging or not doable, you probably don’t have the network to safely launch startups. Build your network.

And good luck!